The Twenty Minute VC

Dylan Serota is the Founder & Chief Strategy Officer @ Terminal, the startup that helps you create world-class technical teams through remote operations as a service. They recently raised a phenomenal $13m Series A with some of the world’s most renowned names including Lightspeed, KPCB, Craft, Thiel, Atomic and Jerry Yang just to name a few. As for Dylan, he is also a Founder-in-Residence @ Atomic, one of the valley’s most exciting new institutions which both founds and funds companies and includes the likes of Hims, TalkIQ (acq by Dialpad) and more. Prior to Atomic and Terminal, Dylan was Head of Platform @ Eventbrite where he led platform product org, built third-party developer ecosystem and platform partnerships.

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In Today’s Episode You Will Learn:

1.) How Dylan made his way into the world of startups with Eventbrite and how that led to his realisation on the future of development operations with Terminal?

2.) Why does Dylan believe that it is important for startups to build distributed teams earlier in their growth curve than often suggested? What are the key aspects to making remote teams work well? Why does Dylan believe that “companies overvalue their culture”? How does Dylan assess culture across remote teams?

3.) Jason lemkin says “startups can either hire a stretch VP or a burnt out mediocre VP”, does Dylan agree with this? How does Dylan assess the balance between hiring functional specialists vs jack of all trades? When is the right time to make the transition from generalist to specialist?

4.) Hw does Dylan analyze and assess a startup leaderships team ability to adapt and prioritize speed? What is key to successful decision-making today in startups? How does Dylan think about the importance of speed when it comes to product ideation and iteration?

5.) What does Dylan believe is the biggest mistake many people make early in their career? What are the commonalities of the truly successful people in how they have structured their careers? How does Dylan think about the balance between title vs salary vs experience? What should one optimise for and when?

Items Mentioned In Today’s Show:

Dylan’s Fave Book: The Selfish Gene by Richard Dawkins

As always you can follow Harry, The Twenty Minute VC and Dylan on Twitter here!

Likewise, you can follow Harry on Instagram here for mojito madness and all things 20VC.

Are you told your standards are too high, well The League is the app that tells you to keep them that way, they know your time is valuable so simply tell them your preferences and they will handle the scouting and vetting for you. Plus even better, your profile will only ever be seen by people who match your preferences, matches expire after 21 days and so there are no drawn-out games and they even require LinkedIn to protect your privacy and block you from matching with co-workers and business connections. You can apply now by downloading The League on the app store or heading to The League.com

Zoom is the fastest-growing video and web conferencing service, providing one consistent enterprise experience that allows you to engage in an a variety of activities including video meetings and webinars, collaboration-enabled conference rooms, and persistent chat all in one platform. Plus, it is the easiest solution to manage, scale, and use, and has the most straightforward, affordable pricing. And you can see for yourself! Sign up for a free account (not a trial!). Just visit Zoom.us.

Culture Amp is the platform that makes it easy to collect, understand and act on employee feedback. From onboarding surveys to company-wide engagement, individual effectiveness and more, the platform manages multiple sources of feedback and connects the dots for you and that is why companies like Slack, Nike, Oracle and Lyft all trust Culture Amp. It enables leaders to make better decisions, demonstrate impact and turn your company culture into a competitive edge.  Find out more on cultureamp.com.

Jeff Fagnan is Founding Partner @ Accomplice, one of the East Coast’s leading early-stage funds with a portfolio including the likes of AngelList, PillPack (acq by Amazon), Freshbooks, Hopper, Secret Escapes and many more incredible companies. Accomplice is also unique as it is a platform builder creating incredible initiatives such as Spearhead, Maiden Lane and Boston Syndicates, really moving the needle in seeding local ecosystems. As for Jeff he is well known as a founding investor, working with most of his portfolio since inception, sometimes as a co-founder including Veracode (Sold to CA Technologies‍). Jeff also sits on the board of AngelList, PillPack, InsightSquared, Hopper, Freshbooks and more.

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In Today’s Episode You Will Learn:

1.) How Jeff made his way into the world of VC from consulting over 18 years ago? How did his experience of the bubble influence Jeff’s mindset and thinking?

2.) What did Jeff learn about building an optimal venture partnership with the transition from the 23 partner Atlas to the tight-knit Accomplice? Where does Jeff believe most venture partnerships go wrong today? What does Jeff believe is the right size partnership in venture? Why does Jeff believe that partners are there to save each other from themselves?

3.) How did Jeff’s experience with Atlas effect his views on portfolio construction? Why does Jeff advocate for the model of raising $200m every 2.5 years for a pure seed strategy? How does Jeff think about building an effective reserve strategy? Why does Jeff not believe pro-rata should be guaranteed? Why does Jeff believe force ranking a portfolio is dangerous?

4.) Jeff believes the best VCs are able to manage 2 things, what are those 2 things? From his 18 years on boards, what does Jeff believe makes the truly special board member? Who is the best he has worked with and why? How does Jeff look to gain the balance of being both proactive to opportunities and reactive to inbound?

5.) Accomplice has recently made it’s foray into the West Coast, what was the thinking behind that move? How does Accomplice think about establishing mindshare as a new entrant in a hotly contested environment? What does Jeff believe is the key to successful geographic expansion in venture?

Items Mentioned In Today’s Show:

Jeff’s Fave Book: Where The Wild Things Are 

Jeff’s Most Recent Investment: Perch

As always you can follow Harry and The Twenty Minute VC on Twitter here!

Likewise, you can follow Harry on Instagram here for mojito madness and all things 20VC.

Are you told your standards are too high, well The League is the app that tells you to keep them that way, they know your time is valuable so simply tell them your preferences and they will handle the scouting and vetting for you. Plus even better, your profile will only ever be seen by people who match your preferences, matches expire after 21 days and so there are no drawn-out games and they even require LinkedIn to protect your privacy and block you from matching with co-workers and business connections. You can apply now by downloading The League on the app store or heading to The League.com

Zoom is the fastest-growing video and web conferencing service, providing one consistent enterprise experience that allows you to engage in an a variety of activities including video meetings and webinars, collaboration-enabled conference rooms, and persistent chat all in one platform. Plus, it is the easiest solution to manage, scale, and use, and has the most straightforward, affordable pricing. And you can see for yourself! Sign up for a free account (not a trial!). Just visit Zoom.us.

Culture Amp is the platform that makes it easy to collect, understand and act on employee feedback. From onboarding surveys to company-wide engagement, individual effectiveness and more, the platform manages multiple sources of feedback and connects the dots for you and that is why companies like Slack, Nike, Oracle and Lyft all trust Culture Amp. It enables leaders to make better decisions, demonstrate impact and turn your company culture into a competitive edge.  Find out more on cultureamp.com.

Armon Dadgar is the Founder & CTO @ Hashicorp, the open-source software company that provides consistent workflows to provision, secure, connect and run any infrastructure for any application. To date, Hashicorp has raised over $74m in VC funding from many friends of the show including Scott Raney @ Redpoint, Glenn Solomon @ GGV, Semil Shah, True Ventures and Mayfield. As for Armon, today he leads the Hashicorp research group and focused on industrial research in the security and large-scale system management space. Prior to founding Hashicorp, Armon was a software engineer @ Kiip and Amazon.

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In Today’s Episode You Will Learn:

1.) How Armon made his way from intern at Amazon to founding Hashicorp and creating the game-changing suite of tools in the world of DevOps?

2.) Hashicorp has enjoyed success after success with new products, so what does Armon believe is the secret to continuous product innovation? What does Armon mean when he says “there are really 3 phases to product adoption”? How does Armon determine between vision for a product and the realism when it is not working, when launching products?

3.) Hashicorp only recently started generating revenue, why was now the right time? At what point does one go from building products for the community to building products people will pay for? How does Armon assess professional services today? What does Armon believe are the 2 foundational problems with “professional services”?

4.) Many VCs suggest it’s impossible to build big infrastructure businesses today given the commoditizing forces to open source and cloud computing. How have Hashicorp navigated that and bucked that conventional wisdom? How has Armon also bucked the conventional wisdom on the importance of focus? What core tenets must remain if one wants to go against this emphasis on focus?

5.) Armon and his co-founder brought on a CEO early, what was the realisation moment for the need to bring in an external CEO? How did Armon look to get comfortable with this transition? What advice would Armon give to founders contemplating bringing in an external CEO? With the benefit of hindsight, what would Armon do differently if he had the time again?

Items Mentioned In Today’s Show:

Armon’s Fave Book: To The Lighthouse by Virginia Woolf

As always you can follow Harry, The Twenty Minute VC and Armon on Twitter here!

Likewise, you can follow Harry on Instagram here for mojito madness and all things 20VC.

Are you told your standards are too high, well The League is the app that tells you to keep them that way, they know your time is valuable so simply tell them your preferences and they will handle the scouting and vetting for you. Plus even better, your profile will only ever be seen by people who match your preferences, matches expire after 21 days and so there are no drawn-out games and they even require LinkedIn to protect your privacy and block you from matching with co-workers and business connections. You can apply now by downloading The League on the app store or heading to The League.com

Zoom is the fastest-growing video and web conferencing service, providing one consistent enterprise experience that allows you to engage in an a variety of activities including video meetings and webinars, collaboration-enabled conference rooms, and persistent chat all in one platform. Plus, it is the easiest solution to manage, scale, and use, and has the most straightforward, affordable pricing. And you can see for yourself! Sign up for a free account (not a trial!). Just visit Zoom.us.

Culture Amp is the platform that makes it easy to collect, understand and act on employee feedback. From onboarding surveys to company-wide engagement, individual effectiveness and more, the platform manages multiple sources of feedback and connects the dots for you and that is why companies like Slack, Nike, Oracle and Lyft all trust Culture Amp. It enables leaders to make better decisions, demonstrate impact and turn your company culture into a competitive edge.  Find out more on cultureamp.com.

Nick Brown is Managing Partner @ Imaginary, founded alongside Net-A-Porter founder, Natalie Massenet, Imaginary invests in early–stage opportunities at the intersection of retail and technology. Included in their incredible portfolio is the likes of Glossier, Daily Harvest, Farfetch, Everlane and many more awesome companies. Prior to co-founding Imaginary, Nick was a Partner at 14W Venture Partners where he invested in the likes of Goop, Outdoor Voices, The Real Real and Business of Fashion just to name a few. Before that Nick was Head of New Media @ NV Investments.

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In Today’s Episode You Will Learn:

1.) How Nick made his way into the world of venture and consumer investing from the days of investment banking?

2.) We have seen an explosion in the world of consumer with regards to D2C brands, does Nick believe we are in a D2C bubble? There is a lot of skepticism around physical product companies being venture businesses, so what are the core considerations for Nick when investing in physical product brands today?

3.) Having backed the likes of Glossier, Farfetch, Everlane etc, what does Nick believe are some of the leading indicators from the early days whether a company has a sustaining and authentic brand? What does Nick believe is the future for direct to consumer of the next 24-36 months? What is he most excited by?

4.) How does Nick think about the interaction between D2C brands and wholesale and physical retail? When is the right time to pull the wholesale lever? What does Nick believe is a healthy ratio between paid to organic customer acquisition? What are the commonalities in the consumer brands that have broken out within his portfolio?

5.) In terms of character traits, what commonalities does Nick see in the most successful consumer founders he has backed today? We have seen a rise in the celebrity founder over the last few years, so what is the role of the celebrity founder? When does it work? When does it not work? How does the future of celebrity founder look to Nick?

Items Mentioned In Today’s Show:

Nick’s Fave Book: To Kill A Mockingbird

Nick’s Most Recent Investment: Fitplan

As always you can follow Harry and The Twenty Minute VC on Twitter here!

Likewise, you can follow Harry on Instagram here for mojito madness and all things 20VC.

Are you told your standards are too high, well The League is the app that tells you to keep them that way, they know your time is valuable so simply tell them your preferences and they will handle the scouting and vetting for you. Plus even better, your profile will only ever be seen by people who match your preferences, matches expire after 21 days and so there are no drawn-out games and they even require LinkedIn to protect your privacy and block you from matching with co-workers and business connections. You can apply now by downloading The League on the app store or heading to The League.com

Zoom is the fastest-growing video and web conferencing service, providing one consistent enterprise experience that allows you to engage in an a variety of activities including video meetings and webinars, collaboration-enabled conference rooms, and persistent chat all in one platform. Plus, it is the easiest solution to manage, scale, and use, and has the most straightforward, affordable pricing. And you can see for yourself! Sign up for a free account (not a trial!). Just visit Zoom.us.

Culture Amp is the platform that makes it easy to collect, understand and act on employee feedback. From onboarding surveys to company-wide engagement, individual effectiveness and more, the platform manages multiple sources of feedback and connects the dots for you and that is why companies like Slack, Nike, Oracle and Lyft all trust Culture Amp. It enables leaders to make better decisions, demonstrate impact and turn your company culture into a competitive edge.  Find out more on cultureamp.com.

Adam Goldberg is a Partner @ Lightspeed Venture Partners, one of the world’s leading funds with a portfolio including the likes of SNAP, Mulesoft, Max Levchin’s Affirm, AppDynamics and many more incredible companies. As for Adam, at age 13, Adam enrolled as a full-time student at UC Berkeley, where he studied pure and applied mathematics and conducted research in number theory and machine learning. He went on to work as a mathematician for the Department of Defense and as a researcher Berkeley, Wisconsin-Madison and Stanford. Following that, Adam worked as an engineer at Palantir and Dropbox and was an early product manager at Rubrik. In 2016, Adam left Rubrik to become a partner at Lightspeed where he has invested in the likes of Basis, Vector and Totemic Labs, just to name a few.

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In Today’s Episode You Will Learn:

1.) How Adam made his way into the world of venture from the department of defence and working at titans such as Palantir and Dropbox?

2.) Why does Adam believe the rate of founder learning is the most important skill that an investor can evaluate and assess? What does optimizing for learning really mean to Adam? In practice, what can one do to optimize for learning? What are the common traits and signs of those founders that do this well?

3.) Why does Adam believe that there remains today no mass market decentralised consumer product? What is needed for this to happen? How does Adam forsee the development of token economics over the coming years? What novel token financing solutions does Adam respect? What is required within token economics for Adam to gain real comfort?

4.) Why does Adam believe that the Telegram ICO got such attention? Why is Adam fundamentally bullish on the opportunity? What 2 core characteristics does Telegram have that are required for crypto projects to be successful? On the other side of the table, where is there cause for concern when reviewing the opportunity?

5.)How does Adam think about “betting on fundamental trade-offs in crypto”? What are the 4 key trade-offs that founders must contemplate? What are the trade-offs that Adam is willing to accept vs not accept? How does Adam envisage the willingness to accept trade-offs so widely, change over time in the space?

Items Mentioned In Today’s Show:

Adam’s Fave Book: Flowers for Algernon

Adam’s Most Recent Investment: Strangeworks

As always you can follow Harry, The Twenty Minute VC and Adam on Twitter here!

Likewise, you can follow Harry on Instagram here for mojito madness and all things 20VC.

Are you told your standards are too high, well The League is the app that tells you to keep them that way, they know your time is valuable so simply tell them your preferences and they will handle the scouting and vetting for you. Plus even better, your profile will only ever be seen by people who match your preferences, matches expire after 21 days and so there are no drawn-out games and they even require LinkedIn to protect your privacy and block you from matching with co-workers and business connections. You can apply now by downloading The League on the app store or heading to The League.com

Zoom is the fastest-growing video and web conferencing service, providing one consistent enterprise experience that allows you to engage in an a variety of activities including video meetings and webinars, collaboration-enabled conference rooms, and persistent chat all in one platform. Plus, it is the easiest solution to manage, scale, and use, and has the most straightforward, affordable pricing. And you can see for yourself! Sign up for a free account (not a trial!). Just visit Zoom.us.

Culture Amp is the platform that makes it easy to collect, understand and act on employee feedback. From onboarding surveys to company-wide engagement, individual effectiveness and more, the platform manages multiple sources of feedback and connects the dots for you and that is why companies like Slack, Nike, Oracle and Lyft all trust Culture Amp. It enables leaders to make better decisions, demonstrate impact and turn your company culture into a competitive edge.  Find out more on cultureamp.com.

Eddy Lu is the Co-Founder & CEO @ GOAT, the largest marketplace in the world for buying and selling authentic sneakers. To date, GOAT have raised over $97m in VC funding from some of the best in the business including Accel, Index, Upfront and include angel investments from Elad Gil, Ashton Kutcher and Alexis Ohanian. Prior to GOAT, Eddy enjoyed numerous different roles including founding a chain of Japanese dessert stores building a slew of different 99c apps and started on Wall St with Lehmann Brothers and Deloitte.

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In Today’s Episode You Will Learn:

1.) How Eddy made his way from Wall St to making 99c apps to creating a chain of Japanese desert stores to founding the world’s largest sneaker marketplace in GOAT?

2.) Pivoting from social dining to sneaker marketplace, how does Eddy determine between mission and passion for the vision vs when something is simply not working? What core metrics made Eddy realise this pivot was needed? How did Eddy communicate the pivot to the existing investor base? How did he get them on board for the next chapter?

3.) Over the years, GOAT has had many investors wanting to invest, how does Eddy approach investor selection? What advice does Eddy have on optimising for valuation and the terms that founders should really focus on? What have been the biggest lessons from having former Twitter COO, Adam Bain on the GOAT board?

4.) Does Eddy agree with Paul at Canvas that marketplace founders should give up if they do not have differentiated supply? What does Eddy believe is the core characteristic of the most successful marketplaces? To what extent does Eddy believe that early marketplaces must rely on existing distribution and offline activities to scale?

5.) Eddy took the decision to merge with Flight Club, what was behind the decision to open up the business to physical retail? Why does Eddy believe that physical retail does not affect the margin structure massively when compared to it’s online counterpart? How does Eddy assess the categories that make sense for physical retail between those that do not?

Items Mentioned In Today’s Show:

Eddy’s Fave Book: Crime and Punishment 

As always you can follow Harry, The Twenty Minute VC and Eddy on Twitter here!

Likewise, you can follow Harry on Instagram here for mojito madness and all things 20VC.

Are you told your standards are too high, well The League is the app that tells you to keep them that way, they know your time is valuable so simply tell them your preferences and they will handle the scouting and vetting for you. Plus even better, your profile will only ever be seen by people who match your preferences, matches expire after 21 days and so there are no drawn-out games and they even require LinkedIn to protect your privacy and block you from matching with co-workers and business connections. You can apply now by downloading The League on the app store or heading to The League.com

Zoom is the fastest-growing video and web conferencing service, providing one consistent enterprise experience that allows you to engage in an a variety of activities including video meetings and webinars, collaboration-enabled conference rooms, and persistent chat all in one platform. Plus, it is the easiest solution to manage, scale, and use, and has the most straightforward, affordable pricing. And you can see for yourself! Sign up for a free account (not a trial!). Just visit Zoom.us.

Culture Amp is the platform that makes it easy to collect, understand and act on employee feedback. From onboarding surveys to company-wide engagement, individual effectiveness and more, the platform manages multiple sources of feedback and connects the dots for you and that is why companies like Slack, Nike, Oracle and Lyft all trust Culture Amp. It enables leaders to make better decisions, demonstrate impact and turn your company culture into a competitive edge.  Find out more on cultureamp.com.

Jason Stoffer is Managing Partner @ Maveron, the consumer-only venture fund backing a new breed of brands. Their stellar portfolio includes the likes of eBay, Zulily, General Assembly, Allbirds and Dia&Co, just to name a few. As for Jason, Jason is the master of all things consumer education, e-commerce and marketplace businesses. He has been a Board Member of a number of category-leading consumer businesses, such as zulily (Nasdaq: ZU), General Assembly (acquired by Adecco), Common and more. Prior to Maveron, Jason was Senior Director of Strategic Operations at Career Education Corp where he saw the business scale to a market cap of over $4.5Bn.

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In Today’s Episode You Will Learn:

1.) How Jason made his way into the world of VC from the world of journalism? What were his biggest takeaways from seeing the boom and bust cycle of 2001 and 2008?

2.) Why does Jason believe that moats matter as much, if not more than brand today? How can founders look to create the strongest form of defensibility? How does Jason analyze the 2 paths for consumer businesses today; raise large amounts of capital and buy growth or raise little, grow slowly, understand unit economics and channels over time? Does Jason think we will see a graveyard of immensely funded consumer businesses?

3.) How does Jason view paid acquisition today? Does Jason agree with Peter Fenton. “there is a lack of free and open distribution in consumer today”? When does Jason believe that consumer founders should really focus on CAC/LTV? What metrics really matter in the early days for consumer? How does Jason analyse acquisition channel mortality? When does he mean when he says, “CAC works, until it does not”?

4.) Jason has said before that “VC is a struggle”. What elements does Jason find most challenging? How does Jason deal witht he shit hit the fan moments as a VC? Can VCs in this hyper-competitive world be openly vulnerable in Jason’s eyes? How has Jason seen his approach to hard and challenging situations in VC develop over time?

5.) Does Jason believe we are in a consolidatory environment today or will we see the next generation of mega consumer brands being built? When investing, does Jason ask, who is the potential acquirer? Why? What multiple is achievable? Would Jason agree with Kirsten Green that “Amazon does more to make the market than destroy it”? How does Amazon affect Jason’s investment philosophy and approach?

Items Mentioned In Today’s Show:

Jason’s Fave Book: 100 Years of Solitude

Jason’s Most Recent Investment: Imperfect Produce

As always you can follow Harry, The Twenty Minute VC and Jason on Twitter here!

Likewise, you can follow Harry on Instagram here for mojito madness and all things 20VC.

Are you told your standards are too high, well The League is the app that tells you to keep them that way, they know your time is valuable so simply tell them your preferences and they will handle the scouting and vetting for you. Plus even better, your profile will only ever be seen by people who match your preferences, matches expire after 21 days and so there are no drawn-out games and they even require LinkedIn to protect your privacy and block you from matching with co-workers and business connections. You can apply now by downloading The League on the app store or heading to The League.com

Zoom is the fastest-growing video and web conferencing service, providing one consistent enterprise experience that allows you to engage in an a variety of activities including video meetings and webinars, collaboration-enabled conference rooms, and persistent chat all in one platform. Plus, it is the easiest solution to manage, scale, and use, and has the most straightforward, affordable pricing. And you can see for yourself! Sign up for a free account (not a trial!). Just visit Zoom.us.

Culture Amp is the platform that makes it easy to collect, understand and act on employee feedback. From onboarding surveys to company-wide engagement, individual effectiveness and more, the platform manages multiple sources of feedback and connects the dots for you and that is why companies like Slack, Nike, Oracle and Lyft all trust Culture Amp. It enables leaders to make better decisions, demonstrate impact and turn your company culture into a competitive edge.  Find out more on cultureamp.com.

Fritz Lanman is the CEO @ ClassPass, the startup that provides the most flexible fitness membership ever. To date, they have raised over $154m in VC funding from the likes of Thrive, GV, CRV, Fifth Wall and Temasek just to name a few. As for Fritz, prior to ClassPass he was the Founder & CEO @ Livestar, a mobile recommendations startup that was acquired by Pinterest. Before that, he was a Senior Director in the Corporate Strategy Group @ Microsoft where he led several multi-billion dollar M&A evaluations and strategy projects including the Facebook investment and Yahoo deal. If that was not enough, Fritz is also a tremendously successful angel with a portfolio including the likes of Square, Pinterest, Wish, Flexport, Everlane and 75 or so more companies.

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In Today’s Episode You Will Learn:

1.) How Fritz made his way into the world of startups with Microsoft? How that led to angel investments in Wish, Flexport, Square and more? How he came to be CEO @ ClassPass?

2.) How did the $250m Microsoft investment in Facebook come about? What made Fritz so confident he told Steve Ballmer he was willing to bet his career it would be a $10Bn company? What was the decision-making process internally around that deal?

3.) How does Fritz assess his own asset allocation strategy? Why does Fritz not agree with thesis-driven angel investing? When starting angel investing, how did he approach portfolio construction? Why does Fritz believe it is immensely synergistic to be both an operator and angel? As a result, how does Fritz approach placing investors in a quadrant between helpfulness and high maintenance?

4.) Why does Fritz believe that your investor cannot be your recruiter? What have been Fritz biggest learnings on continuously attracting the best talent? Why does Fritz believe that it is BS that one should not celebrate fundraising? Ultimately, what does Fritz elieve fundraising signifies?

5.) ClassPass has expanded to 34 markets over the last few years, how does Fritz determine when is the right time to pour fuel on the fire? What are the 2 fundamental questions one must ask before you do? Does Fritz believe that aggressive growth and capital efficiency are mutually exclusive? How does Fritz think about capital efficiency with ClassPass today?

Items Mentioned In Today’s Show:

Fritz’s Fave Book: Endurance: Shackleton’s Incredible Voyage to the Antarctic

As always you can follow Harry, The Twenty Minute VC and Fritz on Twitter here!

Likewise, you can follow Harry on Instagram here for mojito madness and all things 20VC.

The reality is that hiring amazing developers is hard. Terminal.io is your dedicated partner in rapidly standing up world-class remote technical teams. How do they deliver both speed and quality? Terminal does this by focusing on everything necessary to successfully source, setup, and support these teams – from physical elements like beautiful workspaces and equipment to ongoing resources like HR, payroll, legal, professional learning and development. But don’t take my word for this, take the word of Eventbrite, former 20VC guest Hims, and Dialpad – all customers and lovers of Terminal. You can find out more today at Terminal.io.

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Elad Gil is the Founder @ Color, the startup that shows you your genes can help you make better health decisions. They have raised over $112m in funding from the likes of General Catalyst, CRV, 8VC, Aaron Levie and more incredible names. Elad is also an incredible angel, counting the likes of Airbnb, Stripe, Optimizely, Opendoor and Wish all in his portfolio. Now Elad is adding a new string to his very talented bow with the release of his book, High Growth Handbook, published by Stripe in which Elad interviews 14 leaders from the valley from Marc Andreesen to Reid Hoffman to Patrick Collison. Plus shares his own experiences from Google, growing from 1,500 to 15,000 and Twitter, growing from 100 to 1,500. High Growth Handbook is now available for sale on Amazon, Kindle, Kobo.

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In Today’s Episode You Will Learn:

1.) How Elad made his way into the world of startups, came to found 2 companies that sold to Twitter and Google and came to invest in Airbnb, Stripe, Wish etc?

2.) How does Elad define the role of the CEO today? What are the commonalities in those truly great CEOs? How do the very best CEOs hire the very best execs? How do they address role allocation internally? How do they determine between employees that do and do not scale with the firm? Where do CEOs make the most fatal mistakes in high growth startups?

3.) Why are pre-emptive rounds so common today? Why does Elad believe many people will lose a lot of money in them? What advice does Elad give to founders when they are an option? Does Elad believe the lack of liquidity is good for venture this cycle? How does Elad assess the emergence of megafunds? How does this alter and distort the market?

4.) With regards to market share, how should founders prioritise between pricing and market share? Is cash ever a defensible moat? What does Elad mean when he says that “too many people are stuck on Amazon as the winning model”? Why does Elad believe that margins and capital leverage are the unsung heroes of tech?

5.) Why does Elad believe we have seen such a reduction in M&A? Why do many founders not fully assess the financial benefits of being bought by a high growth startup?  What are the big questions founders should ask when an M&A opportunity does arise? What does Elad believe are the reasons to avoid IPOing? What are the inherent benefits of going public?

Items Mentioned In Today’s Show:

Elad’s Fave Book: Ben Horowitz, Andy Grove

As always you can follow Harry, The Twenty Minute VC and Elad on Twitter here!

Likewise, you can follow Harry on Instagram here for mojito madness and all things 20VC.

The reality is that hiring amazing developers is hard. Terminal.io is your dedicated partner in rapidly standing up world-class remote technical teams. How do they deliver both speed and quality? Terminal does this by focusing on everything necessary to successfully source, setup, and support these teams – from physical elements like beautiful workspaces and equipment to ongoing resources like HR, payroll, legal, professional learning and development. But don’t take my word for this, take the word of Eventbrite, former 20VC guest Hims, and Dialpad – all customers and lovers of Terminal. You can find out more today at Terminal.io.

Whether you’re starting your own small business or getting serious about making your small business more efficient, you need to invite FreshBooks to the table. FreshBooks makes cloud accounting software that’s so ridiculously easy to use and you’ll quickly understand why over 10 million people use it to radically streamline how they deal with their admin and paperwork. Plus, FreshBooks can handle a lot more than accounting related tasks. Using FreshBooks is kind of like having your own admin assistant who’s got your back, 24/7. To claim your 30-day unrestricted free trial, click here enter Twenty Minute VC in the “how did you hear about us section”.

Highfive makes meetings better for thousands of organizations with insanely simple video conferencing designed for meeting rooms. It’s the easiest-to-use solution, with all-in-one hardware and intuitive cloud software. Plus, it’s a high-quality experience with industry-leading audio powered by Dolby Voice. It’s so easy to use, that there’s no pin codes or app downloads. Just click a link in your browser, and you’re in the meeting. With customers in over 100 countries, Highfive is already trusted by the likes of Evernote, Expensify, and Betterment and you can learn more by simply heading over to highfive.com.

Rachel Blumenthal is the Founder & CEO @ Rockets of Awesome, the startup that is reinventing the way parents shop for their kids clothes. To date, Rachel has raised over $19m in VC funding from the likes of Kirsten Green @ Forerunner, August Capital, General Catalyst, Gwyneth Paltrow and Female Founders Fund to name a few. Prior to Rockets of Awesome, Rachel founded fashion jewelry brand, Rachel Leigh. Rachel scaled the business to being available in over 300 stores worldwide and being named one of Oprah’s “Favourite Things”. Before that Rachel began her career in the publicity department at Yves Saint Lauren.

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In Today’s Episode You Will Learn:

1.) How Rachel went from founding a company that created one of Oprah’s “favourite things” to reinventing the way parents shop for their children today?

2.) Why does Rachel believe that “fundraising is like dating”? What does Rachel mean when she says “you have to play the game”? What does this literally look like in practice? What works in generating investor interest? What does not? Where does Rachel see many make mistakes in the fundraising process?

3.) How does Rachel think about capital efficiency with the evolution of her business? What tips and suggestions does Rachel give to increasing burn flexibility when future growth is ambiguous? Why does Rachel disagree with the thesis of raise money when you don’t need it? What length of time does Rachel believe is the right time to raise for?

4.) Rachel has said before that, “the best investors are operators”. What makes Rachel believe this? What are the drawbacks to operator VCs? What are the benefits to non-operator investors? What makes the truly special investor? How can a founder stress test this prior to their investment? What advice would Rachel give to a non-operator VC to improve their empathy and experience with founders?

5.) Rachel previous sly said to me that “being a woman in this male-dominated environment is everything the stereotype suggests”, what moment or story particularly resonates for Rachel when saying this? How did she respond? How can less confident first time minority founders respond in these situations?

Items Mentioned In Today’s Show:

Rachel’s Fave Book: Fast Company, Inc

As always you can follow Harry, The Twenty Minute VC and Rachel on Twitter here!

Likewise, you can follow Harry on Instagram here for mojito madness and all things 20VC.

The reality is that hiring amazing developers is hard. Terminal.io is your dedicated partner in rapidly standing up world-class remote technical teams. How do they deliver both speed and quality? Terminal does this by focusing on everything necessary to successfully source, setup, and support these teams – from physical elements like beautiful workspaces and equipment to ongoing resources like HR, payroll, legal, professional learning and development. But don’t take my word for this, take the word of Eventbrite, former 20VC guest Hims, and Dialpad – all customers and lovers of Terminal. You can find out more today at Terminal.io.

Whether you’re starting your own small business or getting serious about making your small business more efficient, you need to invite FreshBooks to the table. FreshBooks makes cloud accounting software that’s so ridiculously easy to use and you’ll quickly understand why over 10 million people use it to radically streamline how they deal with their admin and paperwork. Plus, FreshBooks can handle a lot more than accounting related tasks. Using FreshBooks is kind of like having your own admin assistant who’s got your back, 24/7. To claim your 30-day unrestricted free trial, click here enter Twenty Minute VC in the “how did you hear about us section”.

Highfive makes meetings better for thousands of organizations with insanely simple video conferencing designed for meeting rooms. It’s the easiest-to-use solution, with all-in-one hardware and intuitive cloud software. Plus, it’s a high-quality experience with industry-leading audio powered by Dolby Voice. It’s so easy to use, that there’s no pin codes or app downloads. Just click a link in your browser, and you’re in the meeting. With customers in over 100 countries, Highfive is already trusted by the likes of Warby Parker, Evernote, Expensify, and Betterment and you can learn more by simply heading over to highfive.com.

Pete Flint is a Managing Partner @ NFX, one of Silicon Valley’s newest and most exciting funds with the recent announcement of their new $150m fund late last year. Prior to VC, Pete was a serial entrepreneur building one of today’s most successful marketplaces, as the co-founder of Trulia. Pete led the company from inception to more than 50 million monthly unique users, $250m in VC funding from the likes of Sequoia and Accel culminating in their merger with Zillow in 2015 that valued Trulia at $3.5 billion. Before Trulia, Pete was part of the founding team of lastminute.com, a leading European online travel site that was acquired in 2005 for over $1 billion.

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In Today’s Episode You Will Learn:

1.) How Pete made his way into the world of startups joining the founding team of lastminute.com and how that led to the founding of Trulia and entry into VC?

2.) Why does Pete believe that startup timing is so crucial? How does Pete analyze market timing risk when investing? What is the right way for investors to think about the innovation cycle we are in today? On review, what does Pete believe lastminute.com did most right? What would he most want to change?

3.) What are the leading indicators that suggest potential in a network effect business? Would Pete agree with Josh @ Jackson Square that not all GMV is created equal? How does Pete analyse the lack of free and open distribution today and how that affects marketplace scaling? Why does Pete still believe marketplaces are some of the most capital efficient businesses to grow?

4.) What has been Pete’s greatest time of failure in his career? What is the framework Pete uses to analyze and assess his own ego? What are the commonalities in how Pete has seen truly great founders overcome failure? How does Pete balance between realism when something is not working and the mission and vision of the founder?

5.) How does Pete think about optimizing decision-making, both in investing and operating? How does Pete approach the balance of head vs heart? When is the right time to decide with your head? When is the right time to decide with your heart? Why does Pete argue early-stage investing must be decided with your heart?

Items Mentioned In Today’s Show:

Pete’s Fave Book: Leonardo Da Vinci 

Pete’s Most Recent Investment: Ribbon

As always you can follow Harry, The Twenty Minute VC and Pete on Twitter here!

Likewise, you can follow Harry on Instagram here for mojito madness and all things 20VC.

The reality is that hiring amazing developers is hard. Terminal.io is your dedicated partner in rapidly standing up world-class remote technical teams. How do they deliver both speed and quality? Terminal does this by focusing on everything necessary to successfully source, setup, and support these teams – from physical elements like beautiful workspaces and equipment to ongoing resources like HR, payroll, legal, professional learning and development. But don’t take my word for this, take the word of Eventbrite, former 20VC guest Hims, and Dialpad – all customers and lovers of Terminal. You can find out more today at Terminal.io.

Whether you’re starting your own small business or getting serious about making your small business more efficient, you need to invite FreshBooks to the table. FreshBooks makes cloud accounting software that’s so ridiculously easy to use and you’ll quickly understand why over 10 million people use it to radically streamline how they deal with their admin and paperwork. Plus, FreshBooks can handle a lot more than accounting related tasks. Using FreshBooks is kind of like having your own admin assistant who’s got your back, 24/7. To claim your 30-day unrestricted free trial, click here enter Twenty Minute VC in the “how did you hear about us section”.

Highfive makes meetings better for thousands of organizations with insanely simple video conferencing designed for meeting rooms. It’s the easiest-to-use solution, with all-in-one hardware and intuitive cloud software. Plus, it’s a high-quality experience with industry-leading audio powered by Dolby Voice. It’s so easy to use, that there’s no pin codes or app downloads. Just click a link in your browser, and you’re in the meeting. With customers in over 100 countries, Highfive is already trusted by the likes of Evernote, Expensify, and Betterment and you can learn more by simply heading over to highfive.com.

Joe Fernandez is the Founder & CEO @ JoyMode, the startup that allows you to lend everything you need to have the experiences you want. To date, Joe has raised over $16m in funding for Joymode from friends of the show including Homebrew, Slow Ventures, Founder Collective, Scott Belsky, Collaborative Fund and Lowercase, just to name a few. As for Joe, prior to founding JoyMode, Joe founded Klout, one of the leading social media analytics platforms of the day and raised $40m in funding from Kleiner Perkins, IVP, Venrock, Greycroft and more. Klout was ultimately acquired by Lithium Technologies where Joe sits on the board.

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In Today’s Episode You Will Learn:

1.) How Joe made his way into the world of startups with the founding of Klout? Given his entrepreneurial start, would Joe say he is unemployable?

2.) Question from Craig Shapiro: What was your single greatest lesson from the Klout journey? How has that impacted how you operate JoyMode today? How has Joe approached fundraising fundamentally differently today than with Klout? How is Joe’s team building strategy today different to his with Klout?

3.) Why does Joe believe that “serial entrepreneurs are over-rated”? What does Joe mean when he says, “you have to know which hill you are willing to die on”? How does Joe look to accurately ego check today? What innovative methods does Joe employ internally to ensure that his views are validated and not submitted to?

4.) What does Joe mean when he says, “you have to make big bets to win”? How can you implement this risk-taking mentality in larger teams? What is the right way for both the team and investor base to respond? How does Joe use continuous iteration and data-centricity to test and validate these theses?

5.) How does Joe approach investor update emails? Why does Joe look to terrify investors with each update? Does Joe believe that it is right to thanks specific individuals in those emails? Does like like to select individuals and request their help in the emails? How can past updates be used to attain future investors?

Items Mentioned In Today’s Show:

Joe’s Fave Book: The Accidental Superpower

As always you can follow Harry, The Twenty Minute VC and Joe on Twitter here!

Likewise, you can follow Harry on Instagram here for mojito madness and all things 20VC.

The reality is that hiring amazing developers is hard. Terminal.io is your dedicated partner in rapidly standing up world-class remote technical teams. How do they deliver both speed and quality? Terminal does this by focusing on everything necessary to successfully source, setup, and support these teams – from physical elements like beautiful workspaces and equipment to ongoing resources like HR, payroll, legal, professional learning and development. But don’t take my word for this, take the word of Eventbrite, former 20VC guest Hims, and Dialpad – all customers and lovers of Terminal. You can find out more today at Terminal.io.

Whether you’re starting your own small business or getting serious about making your small business more efficient, you need to invite FreshBooks to the table. FreshBooks makes cloud accounting software that’s so ridiculously easy to use and you’ll quickly understand why over 10 million people use it to radically streamline how they deal with their admin and paperwork. Plus, FreshBooks can handle a lot more than accounting related tasks. Using FreshBooks is kind of like having your own admin assistant who’s got your back, 24/7. To claim your 30-day unrestricted free trial, click here enter Twenty Minute VC in the “how did you hear about us section”.

Highfive makes meetings better for thousands of organizations with insanely simple video conferencing designed for meeting rooms. It’s the easiest-to-use solution, with all-in-one hardware and intuitive cloud software. Plus, it’s a high-quality experience with industry-leading audio powered by Dolby Voice. It’s so easy to use, that there’s no pin codes or app downloads. Just click a link in your browser, and you’re in the meeting. With customers in over 100 countries, Highfive is already trusted by the likes of Warby Parker, Evernote, Expensify, and Betterment and you can learn more by simply heading over to highfive.com.

 

Joel Monegro is Founding Partner @ Placeholder.VC, one of the new venture capital partnerships that invest solely in crypto assets and more specifically in decentralized information networks. Prior to founding Placeholder, Joel spent three years at Union Square Ventures developing the firm’s blockchain investment thesis and portfolio. Before USV, Joel started the Digital Economy Department at the Ministry of Industry and Commerce of the Dominican Republic, a government office in charge of developing the country’s national and technology agenda.

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In Today’s Episode You Will Learn:

1.) How Joel made his way into the world of VC with USV and what created his love of crypto and led to his leaving USV to found Placeholder? What were some of Joel’s biggest investing lessons from his time with USV?

2.) How does Joel approach portfolio construction in building out a crypto portfolio? How does the use of reserves and building positions change when comparing VC to crypto? Why does Joel believe that the most interesting place to invest in crypto is in the assets themselves, rather than the companies?

3.) When does Joel think we will see institutional capital begin to move into the space in a meaningful way? What needs to happen/change for this institutional interest to materialize? How is the element of “custody” crucial to the entrance of institutions?

4.) In terms of fund construction, liquidity is often an attractive element to crypto, why does Joel believe that a traditional venture fund structure is necessary for Placeholder? What are the benefits both to the fund and the projects it backs? How do LPs both traditional and non-traditional respond to this?

5.) Joel has said before the 2 core elements are crypto economics and governance, why does Josh believe this? Why is governance the foundational layer where value will accrue in the space? How does the lack of defensibility of crypto projects make governance ever more valuable?

Items Mentioned In Today’s Show:

Joel’s Fave Book: Antifragile by Nassim Taleb

Joel’s Most Recent Investment: Decred Investment Thesis

As always you can follow Harry, The Twenty Minute VC and Joel on Twitter here!

Likewise, you can follow Harry on Instagram here for mojito madness and all things 20VC.

Whether you’re starting your own small business or getting serious about making your small business more efficient, you need to invite FreshBooks to the table. FreshBooks makes cloud accounting software that’s so ridiculously easy to use and you’ll quickly understand why over 10 million people use it to radically streamline how they deal with their admin and paperwork. Plus, FreshBooks can handle a lot more than accounting related tasks. Using FreshBooks is kind of like having your own admin assistant who’s got your back, 24/7. To claim your 30-day unrestricted free trial, click here enter Twenty Minute VC in the “how did you hear about us section”.

Highfive makes meetings better for thousands of organizations with insanely simple video conferencing designed for meeting rooms. It’s the easiest-to-use solution, with all-in-one hardware and intuitive cloud software. Plus, it’s a high-quality experience with industry-leading audio powered by Dolby Voice. It’s so easy to use, that there’s no pin codes or app downloads. Just click a link in your browser, and you’re in the meeting. With customers in over 100 countries, Highfive is already trusted by the likes of Evernote, Expensify, and Betterment and you can learn more by simply heading over to highfive.com.

 

Max Motschwiller is a Partner with Meritech Capital, one of the West Coast’s leading growth investment firms with over $150Bn in IPOs and a portfolio that includes the likes of Facebook, Salesforce, Snap, Box, Mulesoft and Cloudera just to name a few. As for Max, prior to Meritech he spent 3 years with Kleiner Perkins (KPCB) where he was actively involved with investments in Dropcam (Nest/Google), Duolingo, MyFitnessPal (Under Armour), RelateIQ (Salesforce.com) and Stance. Before joining KPCB, Max worked for 3 years at Summit Partners and was actively involved across Summit’s technology portfolio.

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In Today’s Episode You Will Learn:

1.) How did Max make his way into the world of VC with Summit and KP from University? What did that decision-making process look like for Max?

2.) As a career VC, would Max agree with Pat Grady @ Sequoia, “the rate of decay on operating experience has never been greater”? What would Max say are the biggest elements he missed through lack of operational experience? How do the skills required from early to pre-IPO change the type of background required?

3.) Max has said before, “to be a good VC you have to do 4 things well”, what are those 4 things? Why does Max believe that picking is the greatest skill to develop? At growth, what does Max mean when he says “the picking is around price”? How do the very best VCs approach price sensitivity?

4.) Question from Rob Ward: Max has mastered network development from an early age, what advice would Max give with regards to developing a network? What did he do well and works? What did he try and did not do well? How does Max think about depth vs breadth of network? How does he apply this to investing and due diligence?

5.) In a time of Softbank and Sequoia’s $7Bn fund, how does a firm like Meritech look to compete in such frothy environments? How has growth bifurcated into 2 clear stages? What are the advantages of being a small pure-play growth firm? How does the portfolio construction and return expectation change for you given the fund size and stage of investment?

Items Mentioned In Today’s Show:

Max’s Fave Book: Home Deus

Max’s Most Recent Investment: Amplitude

As always you can follow Harry, The Twenty Minute VC and Max on Twitter here!

Likewise, you can follow Harry on Instagram here for mojito madness and all things 20VC.

Whether you’re starting your own small business or getting serious about making your small business more efficient, you need to invite FreshBooks to the table. FreshBooks makes cloud accounting software that’s so ridiculously easy to use and you’ll quickly understand why over 10 million people use it to radically streamline how they deal with their admin and paperwork. Plus, FreshBooks can handle a lot more than accounting related tasks. Using FreshBooks is kind of like having your own admin assistant who’s got your back, 24/7. To claim your 30-day unrestricted free trial, click here enter Twenty Minute VC in the “how did you hear about us section”.

Highfive makes meetings better for thousands of organizations with insanely simple video conferencing designed for meeting rooms. It’s the easiest-to-use solution, with all-in-one hardware and intuitive cloud software. Plus, it’s a high-quality experience with industry-leading audio powered by Dolby Voice. It’s so easy to use, that there’s no pin codes or app downloads. Just click a link in your browser, and you’re in the meeting. With customers in over 100 countries, Highfive is already trusted by the likes of Evernote, Expensify, and Betterment and you can learn more by simply heading over to highfive.com.

Hemant Taneja is Managing Director @ General Catalyst, one of the world’s leading venture firms of the last decade with Airbnb, Stripe, Snapchat, Hubspot and Gusto all in their portfolio. As for Hemant, he has led investments at GC in Stripe, SNAP, Grammarly, Gusto, Livongo, Color Genomics, Class Dojo and more. He also directs the GC Stripe Platform Fund, a $10 million initiative to help start new ventures that are built on top of the Stripe Connect platform. On the educational front, Hemant holds 5 degrees from MIT and sits on the board of Khan Academy.

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In Today’s Episode You Will Learn:

1.) How Hemant made his way from 5 degrees at MIT and wanting to be an academic to pursuing startups in the world of VC with General Catalyst?

2.) Question from Sam @ ClassDojo: What were the hardest elements of establishing GC on the West Coast? With hindsight today, what would Hemant do differently given the chance? How does Hemant think about the development and ability to accelerate the creation of local reputation? What is crucial and works most effectively?

3.) How does Hemant respond to Elad Gil’s “everyone is looking for the next truly deep dein to explore”? Why is Hemant so bullish that we are in the “golden age of venture capital”? Why does Hemant believe that “scale” as a key measure has run it’s course? What does Hemant’s thesis of the future of “unscaling” really mean?

4.) How does Hemant analyse price sensitivity in todays forthy environment? How has his relationship to price changed over time? With regards to price, what have been some of his biggest regrets and learnings drawn from real-world examples? How does Hemant assess reserve allocation? Why does he think pro-rata is a lazy posture?

5.) Hemant has said on boards for over 1,800 hours, so what does Hemant belive makes the truly special board members? How does Hemant think about first building that rapport and “intimacy” with the founder? Secondly, how important does Hemant believe it is to build similar relations with other board members? Which founder exemplifies the best board management in Hemant’s mind?

Items Mentioned In Today’s Show:

Hemant’s Fave Book: Home Deus

Hemant’s Most Recent Investment: Spring Discovery

As always you can follow Harry, The Twenty Minute VC and Hemant on Twitter here!

Likewise, you can follow Harry on Instagram here for mojito madness and all things 20VC.

Highfive makes meetings better for thousands of organizations with insanely simple video conferencing designed for meeting rooms. It’s the easiest-to-use solution, with all-in-one hardware and intuitive cloud software. Plus, it’s a high-quality experience with industry-leading audio powered by Dolby Voice. It’s so easy to use, that there’s no pin codes or app downloads. Just click a link in your browser, and you’re in the meeting. With customers in over 100 countries, Highfive is already trusted by the likes of Evernote, Expensify, and Betterment and you can learn more by simply heading over to highfive.com.

Culture Amp is the platform that makes it easy to collect, understand and act on employee feedback. From onboarding surveys to company-wide engagement, individual effectiveness and more, the platform manages multiple sources of feedback and connects the dots for you and that is why companies like Slack, Nike, Oracle and Lyft all trust Culture Amp. It enables leaders to make better decisions, demonstrate impact and turn your company culture into a competitive edge.  So put your people and culture first and find out more on cultureamp.com.

Amanda Bradford is the Founder & CEO @ The League, the exclusive dating app that wants you to spend your time a little more intelligently when it comes to finding the perfect match online. They have raised funding from the likes of Aileen Lee @ Cowboy Ventures, Sherpa Ventures and Alex Rosen @ Ridge Ventures just to name a few. Prior to founding The League, Amanda spent time at Evernote as a Product Manager, as an investor with Sequoia Capital and started her career in the strategic partnerships team at Google.

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In Today’s Episode You Will Learn:

1.) How Amanda made her way into the world of startups and how she came to want to change the world of dating with The League?

2.) Why does Amanda totally disagree with the conventional wisdom that you cannot be a single founder? What are the benefits of being a single founder? How has Amanda used this to incentivize her team further? What are the core challenges that remain in being a single founder? What 2 reasons does Amanda feel 90% of startups fail?

3.) What does Amanda really mean when she says about “the art of the launch”? How can founders pre-game their launch to have existing users on day 1? What benchmarks does Amanda set when launching a new product, to determine the success of the launch? How core is the 7-day retention number to Amanda in her metric stack?

4.) How does Amanda think about the right time to turn on monetization? How can founders determine the level of consumer appetite for premium products, pre-developing them? What are the main challenges when turning on monetization? How does monetization affect investor appetite?

5.) Amanda has raised from Cowboy, Sherpa, Ridge, how was the fundraising process for Amanda? Why did Amanda choose to pursue the party round approach at seed? What are the core benefits of doing so? Has the lack of lead investor meant a reduced willingness to help from the investor base?

Items Mentioned In Today’s Show:

Amanda’s Fave Book: The Giver

As always you can follow Harry, The Twenty Minute VC and Amanda on Twitter here!

Likewise, you can follow Harry on Instagram here for mojito madness and all things 20VC.

Highfive makes meetings better for thousands of organizations with insanely simple video conferencing designed for meeting rooms. It’s the easiest-to-use solution, with all-in-one hardware and intuitive cloud software. Plus, it’s a high-quality experience with industry-leading audio powered by Dolby Voice. It’s so easy to use, that there’s no pin codes or app downloads. Just click a link in your browser, and you’re in the meeting. With customers in over 100 countries, Highfive is already trusted by the likes of Warby Parker, Evernote, Expensify, and Betterment and you can learn more by simply heading over to highfive.com.

Culture Amp is the platform that makes it easy to collect, understand and act on employee feedback. From onboarding surveys to company-wide engagement, individual effectiveness and more, the platform manages multiple sources of feedback and connects the dots for you and that is why companies like Slack, Nike, Oracle and Lyft all trust CultureAmp. So put your people and culture first and find out more on cultureamp.com.

Peter Parker is the Managing Partner @ BioInnovation Capital, the $130m fund transforming life science investing through backing companies based in shared laboratories in Cambridge, San Francisco, San Diego, Durham, and NYC. For the past three decades, Peter has devoted his life to venture and startups, starting in 1986 with his establishing Ampersand Ventures life sciences platform which he managed until 2006. During this period he was the first institutional capital and a Director to over 2 dozen life sciences startups and enjoyed more exits than I have done podcasts. He is also a co-founder of LabCentral, Inc, a not-for-profit shared facility for companies who need biolab space enables more than 75 companies to pursue their biotech start-up ambitions.

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In Today’s Episode You Will Learn:

1.) How Peter made his way into what was a very different VC industry back in 1986?

2.) Peter has seen the venture ecosystem develop enormously over the last 30 years, what have been the biggest changes and transformations? What are both the most positive and negative changes to hit venture? How has specialization changed the investing game? What would Peter like to change about the world of VC today?

3.) What does Peter mean when he says the best VCs understand the importance of process? What is the right way to construct your process in VC? How does this affect Peter’s thinking on functioning partnerships in venture? What can one do to optimise the quality of those relationships and conversations with partners?

4.) Peter has chaired over 25 boards over the last 32 years in VC, how has Peter seen his style of board membership fundamentally change over that time? What have been the inflection points in his learning? How do OKRs play a crucial role in how he drives board operations? How has Peter approached removing the CEO? What is the right way to do it?

5.) Peter’s most recent fund is a $130m seed fund, how was the latest fundraise for Peter? What drives Peter’s passion and enthusiasm for fundraising and LP communications? What makes the best LP meetings for Peter? How has Peter seen his presentation style to LPs change over time? What has Peter learned is crucial for LP conversion?

Items Mentioned In Today’s Show:

Peter’s Fave Book: The Barbarian: A Surfing Life

Peter’s Most Recent Investment: Graphwear

As always you can follow Harry and The Twenty Minute VC on Twitter here!

Likewise, you can follow Harry on Instagram here for mojito madness and all things 20VC.

Highfive makes meetings better for thousands of organizations with insanely simple video conferencing designed for meeting rooms. It’s the easiest-to-use solution, with all-in-one hardware and intuitive cloud software. Plus, it’s a high-quality experience with industry-leading audio powered by Dolby Voice. It’s so easy to use, that there’s no pin codes or app downloads. Just click a link in your browser, and you’re in the meeting. With customers in over 100 countries, Highfive is already trusted by the likes of Warby Parker, Evernote, Expensify, and Betterment and you can learn more by simply heading over to highfive.com.

Culture Amp is the platform that makes it easy to collect, understand and act on employee feedback. From onboarding surveys to company-wide engagement, individual effectiveness and more, the platform manages multiple sources of feedback and connects the dots for you and that is why companies like Slack, Nike, Oracle and Lyft all trust Culture Amp. It enables leaders to make better decisions, demonstrate impact and turn your company culture into a competitive edge.  So put your people and culture first and find out more on cultureamp.com.

Paul English is the Co-Founder of both Lola and Kayak. Starting on Lola, the company brings joy to business travelers by finding the best flights for busy schedules and perfect hotels that suit personal preferences. To date, Paul has raised over $44m with Lola from the likes of CRV, Accel, General Catalyst and GV just to name a few. Prior to Lola, Paul co-founded Kayak, the incredible success story that helps millions of travelers make confident travel decisions. Prior to their IPO, Paul raised over $229m in VC funding from Sequoia, Accel, IVP and General Catalyst before their reported $1.8Bn acquisition by Priceline. Paul is also a prolific philanthropist and due to his success has had much press attention including the Tracy Kidder book, A Truck Full of Money.

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In Today’s Episode You Will Learn:

1.) How Paul made his way into the world of startups from having his first taste of entrepreneurship buying and refurbishing air conditioning units?

2.) Paul is behind many groundbreaking ideas of the last decade, so what does the idea generation process look like for Paul? How does Paul determine between a good and a great idea? How has this process changed over time? How does Paul pull other individuals into validating ideas or not?

3.) Paul’s VCs stated “Paul is the best founder in the world for hiring”, how does Paul approach team building? What does Paul think is required to attract truly world calls talent? Can this skill be taught? Where does Paul believe so many founders go wrong in recruitment? What does Paul mean when he says you want to see “arrogant humility”

4.) Having raised from Sequoia, GV, General Catalyst and more, what has Paul found to really encapsulate the truly special VCs? What are Paul’s lessons on raising the highest quality capital possible? When is the right time to optimize for valuation and when is it not? What made Mike Moritz and Joel Cutler so special to work with on Kayak?

5.) How does Paul approach the aspect of board management? How has this changed over time for him? What relationship should founders desire with their VCs and then between the VCs themselves? How does one look to optimise for efficiency in board conversations? How does Paul look to handle board disputes?

Items Mentioned In Today’s Show:

Paul’s Fave Book: The Trumpet of Conscience

As always you can follow Harry, The Twenty Minute VC and Paul on Twitter here!

Likewise, you can follow Harry on Instagram here for mojito madness and all things 20VC.

Highfive makes meetings better for thousands of organizations with insanely simple video conferencing designed for meeting rooms. It’s the easiest-to-use solution, with all-in-one hardware and intuitive cloud software. Plus, it’s a high-quality experience with industry-leading audio powered by Dolby Voice. It’s so easy to use, that there’s no pin codes or app downloads. Just click a link in your browser, and you’re in the meeting. With customers in over 100 countries, Highfive is already trusted by the likes of Warby Parker, Evernote, Expensify, and Betterment and you can learn more by simply heading over to highfive.com.

Culture Amp is the platform that makes it easy to collect, understand and act on employee feedback. From onboarding surveys to company-wide engagement, individual effectiveness and more, the platform manages multiple sources of feedback and connects the dots for you and that is why companies like Slack, Nike, Oracle and Lyft all trust CultureAmp. So put your people and culture first and find out more on cultureamp.com.

Trae Vassallo is the Co-Founder and Managing Director @ Defy.VC, one of Silicon Valley’s newest and most exciting Series A funds with the announcement of their debut $151m fund in Sept 2017. Prior to co-founding Defy, Trae was a general partner at Kleiner Perkins Caufield & Byers where she invested in a number of leading companies including eero, Nest Labs, Dropcam, Aggregate Knowledge, and Opower. Before Kleiner, Trae founded Kleiner portfolio company, Good Technology which was ultimately acquired by Blackberry in 2015 for $425m. Trae is also the co-author of the incredible study, “Elephant in the Valley”, highlighting the underlying data around the experiences of women in technology.

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In Today’s Episode You Will Learn:

1.) How Trae made her way into the world of VC and Silicon Valley with a cold reach out to John Doerr and how that led to a role with Kleiner Perkins?

2.) What were Trae’s biggest learnings from having John Doerr on her board, as a first-time founder? What were some of the most memorable moments working with him? What was it about him that made him such a special board member? What was the moment that Trae realized what type of board member she is?

3.) What does Trae mean when she says “Kleiner taught me what a great investment looks like”? How does that affect her investing philosophy today? How did Trae’s investing learnings differ between John Doerr, Vinod Khosla, and Kevin Compton?

4.) Why does Trae believe that the venture industry is simply “overfunded”? If so, what was her reasoning for the founding of Defy? How does Trae see the expansion of multi-stage funds as presenting a market opportunity? Why are the larger players no longer incentivized to play at the Series A stage?

5.) How did Trae find the fundraising process? What were some of the core challenges in terms of the raise itself? Were there commonalities in the pushbacks that LPs had for Defy? How did Neil and Trae respond to the first time team question? How does Trae think about the infrastructure element of funds? Can it all be outsourced?

Items Mentioned In Today’s Show:

Trae’s Fave Book: Brotopia: Breaking Up the Boys’ Club of Silicon Valley

Trae’s Most Recent Investment: Owl Car Cam: The First Security Camera For Your Car

As always you can follow Harry, The Twenty Minute VC and Trae on Twitter here!

Likewise, you can follow Harry on Instagram here for mojito madness and all things 20VC.

Highfive makes meetings better for thousands of organizations with insanely simple video conferencing designed for meeting rooms. It’s the easiest-to-use solution, with all-in-one hardware and intuitive cloud software. Plus, it’s a high-quality experience with industry-leading audio powered by Dolby Voice. It’s so easy to use, that there’s no pin codes or app downloads. Just click a link in your browser, and you’re in the meeting. With customers in over 100 countries, Highfive is already trusted by the likes of Warby Parker, Evernote, Expensify, and Betterment and you can learn more by simply heading over to highfive.com.

Culture Amp is the platform that makes it easy to collect, understand and act on employee feedback. From onboarding surveys to company-wide engagement, individual effectiveness and more, the platform manages multiple sources of feedback and connects the dots for you and that is why companies like Slack, Nike, Oracle and Lyft all trust CultureAmp. So put your people and culture first and find out more on cultureamp.com.

Jack Groetzinger is the Founder & CEO @ SeatGeek, the world’s largest ticket inventory on the web serving more than 500,000 artists and teams in over 380,000 venues. To date, Jack has raised over $160m in VC funding with SeatGeek from the likes of John Locke @ Accel, Founder Collective, TCV and most recently a $57m Series D led by Glynn Capital Management. Prior to SeatGeek, Jack founded Scribnia, a web app that used collaborative filtering to recommend bloggers and blog content, sold to an ad network in 2009. Jack is also a Founder Partner @ Founder Collective and angel investor in Troops, Inc.

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In Today’s Episode You Will Learn:

1.) How Jack made his way into the world of startups and decided to reinvent the ticketing industry with SeatGeek?

2.) How does Jack think about the combination of technical vs commercial skills for founders today? Where has Jack struggled with this balance? What would his advice be to prospective founders? How does Jack use OKRs to drive efficiency at SeatGeek? How can OKRs be constructed the right way? What is a rate of failure that suggests you are being ambitious enough?

3.) Jack has raised multiple rounds and over $160m in funding, how have the rounds differed from round to round? How does what Jack wants from an investor differ with time? What one ability do truly unique board members have the ability to do? How does Jack think about board conflicts and the right way to communicate with boards?

4.) How does Jack determine when is the right time to raise big? What is the one core metric that says now is the right time? How does Jack think about both the diversification and mortality of customer acquisition channels? How have SeatGeek seen theirs fundamentally change over time?

5.) Jack led the $56m Toptix acquisition, how was the acquisition process for Jack? What were the big learnings for Jack in terms of buying something that is large? With the acquisition, how does Jack think about the balance between capital efficiency and aggressive growth? What would Jack have done differently with regards to their growth trajectory if he had his time again?

Items Mentioned In Today’s Show:

Jack’s Fave Book: Powerful: Building a Culture of Freedom and Responsibility

As always you can follow Harry, The Twenty Minute VC and Jack on Twitter here!

Likewise, you can follow Harry on Instagram here for mojito madness and all things 20VC.

Highfive makes meetings better for thousands of organizations with insanely simple video conferencing designed for meeting rooms. It’s the easiest-to-use solution, with all-in-one hardware and intuitive cloud software. Plus, it’s a high-quality experience with industry-leading audio powered by Dolby Voice. It’s so easy to use, that there’s no pin codes or app downloads. Just click a link in your browser, and you’re in the meeting. With customers in over 100 countries, Highfive is already trusted by the likes of Warby Parker, Evernote, Expensify, and Betterment and you can learn more by simply heading over to highfive.com.

Culture Amp is the platform that makes it easy to collect, understand and act on employee feedback. From onboarding surveys to company-wide engagement, individual effectiveness and more, the platform manages multiple sources of feedback and connects the dots for you and that is why companies like Slack, Nike, Oracle and Lyft all trust CultureAmp. So put your people and culture first and find out more on cultureamp.com.

Glenn Solomon is a Managing Partner @ GGV Capital, one of the world’s leading venture funds with  $3.8Bn under management across 8 funds and a portfolio including the likes of Airbnb, Xiaomi, Alibaba, Slack, Square, the list goes on. As for Glenn, since joining GGV in 2005 Glenn has helped 7 companies go public including Pandora, Zendesk, Square, SuccessFactors and more and has led investments in Airbnb, Slack, Opendoor, DOMO and Hashicorp just to name a few. Prior to GGV, Glenn was a General Partner with Partech and before that spent time with Goldman Sachs. You must also check out Glenn’s blog here.

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In Today’s Episode You Will Learn:

1.) How Glenn made his way from tennis at Stanford to the walls of Goldman Sachs before entering the world of VC with Partech and then GGV?

2.) Having been in VC for over 20 years, how has Glenn fundamentally seen the startup and VC landscape alter? How did advice from John Doerr alter his thinking on platform shifts? Does Glenn agree with Elad Gil that we are all looking for the next vein of innovation to explore? How must VCs respond?

3.) How has Glenn seen the development of himself as an investor over the last 20 years? What has he found to be the commonalities amongst the very best VCs? How does Glenn think about the importance of investor specialisation?

4.) How does Glenn think about price sensitivity? When has Glenn made his biggest mistakes with regards to price? How does Glenn’s opinions change with the differing insertion points from Series A to pre-IPO?

5.) What does Glenn believe makes the truly special board members? What does he mean when he says being on a board is a “full contact” sport? What are the foundational pillars that Glenn has learnt make the most productive and successful board meetings? What can both founders and VCs do to drive efficiency from their time in board meetings?

Items Mentioned In Today’s Show:

Glenn’s Fave Book: Shoe Dog, Born A Crime, Irena’s Children

Glenn’s Most Recent Investment: Unravel Data

As always you can follow Harry, The Twenty Minute VC and Glenn on Twitter here!

Likewise, you can follow Harry on Instagram here for mojito madness and all things 20VC.

Highfive makes meetings better for thousands of organizations with insanely simple video conferencing designed for meeting rooms. It’s the easiest-to-use solution, with all-in-one hardware and intuitive cloud software. Plus, it’s a high-quality experience with industry-leading audio powered by Dolby Voice. It’s so easy to use, that there’s no pin codes or app downloads. Just click a link in your browser, and you’re in the meeting. With customers in over 100 countries, Highfive is already trusted by the likes of Warby Parker, Evernote, Expensify, and Betterment and you can learn more by simply heading over to highfive.com.

Culture Amp is the platform that makes it easy to collect, understand and act on employee feedback. From onboarding surveys to company-wide engagement, individual effectiveness and more, the platform manages multiple sources of feedback and connects the dots for you and that is why companies like Slack, Nike, Oracle and Lyft all trust CultureAmp. So put your people and culture first and find out more on cultureamp.com.

Adrian Aoun is the Founder & CEO @ Forward, a health care system combining world-class doctors with advanced technology to empower patients to take control of their health. To date Adrian has raised funding from some of the true greats of the business including Marc Benioff, Eric Schmidt, Joe Lonsdale, Aaron Levie and Josh Kushner, to name a few. As a result of the incredible work at Forward, they were named to TIME’s Best Inventions of 2017. Before Forward, Adrian was the head of special projects for the CEO of Google/Alphabet and Adrian arrived at Google following the acquisition of his artificial intelligence (AI) company, Wavii. Adrian is also a prolific angel with the likes of WorkRamp, Atrium, Convoy and more in his incredible portfolio.

Dan Scheinman is one of the West Coast’s leading angel investors with a portfolio including the likes of Zoom.us, Tango.me, TomFoolery (acquired by Yahoo) and Arista Networks, where he also sits on the board. Prior to angel investing, Dan spent 18 years at Cisco in numerous roles including Senior Vice President of Corporate Development where he rebuilt corp dev as a growth enabler for Cisco. Dan was also the Senior Vice President and General Manager of the Cisco Media Solutions Group (CMSG), an internal startup which successfully developed and marketed a hosted software.

Seth Sternberg is the Founder & CEO @ Honor, the startup that provides homecare your family will love. To date Seth has raised over $60m in funding with Honor from the likes of Thrive Capital, a16z, Homebrew and 8VC. Prior to Honor, Seth was the Co-founder & CEO of Meebo, a web communications platform backed by the likes of Sequoia, Khosla and True Ventures. Meebo reached $50M in revenue and close to half of the US internet population before being acquired by Google for $100M in 2012. At Google, Seth became a Product Director working on the Google+ Platform and GoogleX. Seth is also a prolific angel investor with a portfolio including the likes of Fitbit and Gusto to name a few.

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In Today’s Episode You Will Learn:

1.) How Seth made his way into the world of startups with the founding of Sequoia backed, Meebo? How did he transition from social network to homecare provision?

2.) From his experience with Meebo, what are the biggest elements Seth has done differently with the building of Honor? What was successful the first time that he has carried with him to Honor? How does Seth approach the hiring process fundamentally differently the 2nd time around?

3.) Seth has worked with the likes of Sequoia, Khosla, Thrive and more, what are the commonalities that make the best VCs so special? Where does Seth believe VCs can add true value? Where do many seriously detract value? Why does Seth believe that 80% of VCs are actually detrimental to board meetings?

4.) What 3 questions must all founders ask when considering to take on a new investor? What is that investor-founder assessment structure? When there is a disagreement with investors, how does Seth approach this? What is the best method for doing this in as fast and efficient method as possible?

5.) Would Seth agree with David Barrett @ Expensify that we are going through a wave of founders creating companies for the quick flip? How does Seth’s 20-year time horizon with Honor affect how he both thinks about hiring and individual scaling within the firm? Why is he so jealous of Google and Facebook with regards to this?

Items Mentioned In Today’s Show:

Seth’s Fave Book: The Firm

As always you can follow Harry, The Twenty Minute VC and Seth on Twitter here!

Likewise, you can follow Harry on Instagram here for mojito madness and all things 20VC.

We also speak about Movidiam – as brands turn to smarter ways of creating video and digital content, the Movidiam platform offers faster turnarounds whilst maintaining or improving quality. They’re already working with some of the biggest, most innovative companies to help compare teams and freelancers across the global curated network of creative talent. Producers and marketers looking for the best creatives can get a shortlist from Movidiam’s account managers in hours – tailored to their project’s needs. Submit a brief or check out the platform at Movidiam.com.

Boris Wertz is the Founding Partner @ Version One Ventures, one of North America’s leading early-stage funds with a portfolio including the likes of previous guests Coinbase, AngelList, Shippo, TopHat, Polychain Capital and many more incredible companies. As for Boris, prior to VC, Boris was the COO @ Abe Books, where he led a team of 60 people until their acquisition in 2008 by Amazon. In addition to this, Boris is also a Board Partner with a16z and the lead independent director @ Ether Capital, a Toronto-based technology company aiming to become the central investment hub for the Ethereum ecosystem.

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In Today’s Episode You Will Learn:

1.) How Boris made his way from creating the largest European marketplace for used books to becoming one of North America’s leading investors with Version One?

2.) How does Boris analyze where we are at now in the development and hype cycle of crypto? How does it compare to the internet bubble of 99′? Does Boris get concerned by the amount of dumb money entering the space? What resources and tools does Boris advice for people looking to learn the foundations as quickly as possible?

3.) Why does Boris believe you have to apply a new mental model when investing in crypto? What do existing VCs need to do to ensure they are not left behind by the emerging world of crypto? What does Boris believe would need to happen for the existing institutional LP class to embrace crypto?

4.) Does Boris believe existing investors can transition into this space or will vertically specialised funds be the clear winner? If existing investors can, what is required within their partnerships to make this happen? What does Boris make of VCs investing in ICOs? How does Boris evaluate the Telegram ICO?

5.) How does Boris view the future of VC in tandem with the world of crypto and ICOs? What would VCs becoming small cap hedge funds mean for the industry? How would life change? What have been Boris’ biggest learnings from watching first hand a16z’s attempts to innovate the VC model at scale?

Items Mentioned In Today’s Show:

Boris’ Fave Book: Shoe Dog

Boris’ Most Recent Investment: Coinbase

As always you can follow Harry, The Twenty Minute VC and Boris on Twitter here!

Likewise, you can follow Harry on Instagram here for mojito madness and all things 20VC.

We also speak about Movidiam – as brands turn to smarter ways of creating video and digital content, the Movidiam platform offers faster turnarounds whilst maintaining or improving quality. They’re already working with some of the biggest, most innovative companies to help compare teams and freelancers across the global curated network of creative talent. Producers and marketers looking for the best creatives can get a shortlist from Movidiam’s account managers in hours – tailored to their project’s needs. Submit a brief or check out the platform at Movidiam.com.

Andrew Dudum is Co-Founder & CEO @ Hims, the fastest growing men’s health and wellness brand that has raised over $45m in VC funding from some of the best in the business including Thrive Capital, Forerunner Ventures, IVP, Redpoint and SV angel just to name a few. Andrew is also co-founder and General Partner at Atomic, a venture-builder backed by Peter Thiel, Marc Andreesen and many of the world’s best investors. Prior to Atomic and Hims, Andrew led Product at TokBox.com, the leader in web-based communication. In 2012 TokBox was acquired by the global telecommunications company Telefonica ($TEF).

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In Today’s Episode You Will Learn:

1.) How Andrew made his way into the world of startups, came to build a venture builder backed by Thiel and Andreesen before starting the fastest growing men’s health and wellness brand in Hims?

2.) How does Andrew view the world of online and offline marketing in today’s proliferated D2C space? What were the core elements that allowed Hims to achieve such success with their branding? How does Andrew respond to suggestions that there is a lack of free and open distribution due to incumbents paying up for traditional channels making CAC unachievable for startups? How does Andrew look to solve for this?

3.) What does Andrew believe it is that has allowed Hims to execute faster than any other D2C brand in history? How does Andrew distinguish between people and process when considering the scaling at different stages of the business? What are the pros and cons of having such constraints on headcount? When is the right time to pour fuel on the fire?

4.) Hims raised their last round at a $200m valuation in less than a year of operating, how did Andrew evaluate this one? Does this not effectively price Hims out of the majority of M&A?  What leads Andrew’s thesis with his suggestion that he thought the valuation was “quite frankly, a great price for investors”? What advice would Andrew have for founders entering the fundraising process?

5.) Andrew is also the co-founder @ Atomic, so what really is a venture builder? How have Atomic built a framework around idea generation? How do Atomic determine which ideas to pursue and which to disregard? How does data and benchmarking play a central role in this process?

Items Mentioned In Today’s Show:

Andrew’s Fave Book: Creativity Inc

As always you can follow Harry, The Twenty Minute VC and Andrew on Twitter here!

Likewise, you can follow Harry on Instagram here for mojito madness and all things 20VC.

We also speak about Movidiam – as brands turn to smarter ways of creating video and digital content, the Movidiam platform offers faster turnarounds whilst maintaining or improving quality. They’re already working with some of the biggest, most innovative companies to help compare teams and freelancers across the global curated network of creative talent. Producers and marketers looking for the best creatives can get a shortlist from Movidiam’s account managers in hours – tailored to their project’s needs. Submit a brief or check out the platform at Movidiam.com.

Andy McLoughlin is Partner @ Uncork Capital, formerly SoftTech and one of the leading early-stage funds on the West Coast. In their incredible portfolio, they have the likes of Fitbit, SendGrid, PostMates, Front, PoshMark, Eventbrite and many more. As for Andy, he loves to invest in “unsexy ideas” with stellar teams and has led deals in the likes of Postmates, LaunchDarkly, Human Interest (previously Captain 401), and Focal Systems just to name a few. Prior to VC, Andy co-founded Huddle, an enterprise collaboration platform which raised more than $80M in venture funding before its acquisition in 2017. Andy also has a stellar angel portfolio with the likes of Buffer, Intercom and Pipedrive all angel investments.

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In Today’s Episode You Will Learn:

1.) How Andy made the transition from Founder of one of the UK’s hottest startups to one of the leading early-stage VCs in Silicon Valley?

2.) Why did Softtech decide to make the big decision to rebrand to Uncork several years into the journey? What is core to successfully relaunching a VC brand to the ecosystem?

3.) Andy likes to back “non-obvious founders” building “non-sexy businesses”. What does Andy mean by “non-obvious founder”? How do they tend to behave differently to more seasoned serial entrepreneur founders from the valley? What does a “non-sexy business look like to Andy”? Why does he see such inherent opportunity within these segments?

4.) How does Andy evaluate the challenge of immensely long sales cycles within these industries? How can these be mitigated and measured against? How does this affect Andy’s thinking on the right amount of runway to raise for? How does Andy assess the often issue of regulation? How does Andy distinguish between viable/ non-viable?

5.) How does Andy assess VC value add? Where does Andy believe he can provide the most value to his portfolio? Why does Andy believe startups are not just competing against other plays in their space but every startup in the valley?

Items Mentioned In Today’s Show:

Andy’s Fave Book: Venture Deals

Andy’s Most Recent Investment: Fritz

As always you can follow Harry, The Twenty Minute VC and Andy on Twitter here!

Likewise, you can follow Harry on Instagram here for mojito madness and all things 20VC.

We also speak about Movidiam – as brands turn to smarter ways of creating video and digital content, the Movidiam platform offers faster turnarounds whilst maintaining or improving quality. They’re already working with some of the biggest, most innovative companies to help compare teams and freelancers across the global curated network of creative talent. Producers and marketers looking for the best creatives can get a shortlist from Movidiam’s account managers in hours – tailored to their project’s needs. Submit a brief or check out the platform at Movidiam.com.

Jesse Genet is the Founder & CEO @ Lumi, the startup that is used by thousands of e-commerce companies to get world-class packaging at unbeatable prices. To date, Jesse has raised close to $10m in VC funding from some of the best in the business and old friends of the show including Satya @Homebrew, Kirsten @ Forerunner, Spark Capital, Lowercase, Ludlow and more incredible names. Prior to Lumi, Jesse founded Inkodye, a bootstrapped business that Jesse scaled to 7 figures in revenue and was sold in retail stores around the world.

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In Today’s Episode You Will Learn:

1.) How Jesse made her way into the world of startups and VC having bootstrapped her prior business to 7 figures in revenue and being sold in 1,500 stores?

2.) Given that Lumi is Jesse’s first VC backed business, does this make Jesse a first-time founder? How did the bootstrapping to 7 figures in revenue with her last business, influence her philosophy and mindset with Lumi? What has Jesse done differently as a result? What are the dangers that Jesse was aware of and looks out for?

3.) What types of companies does an active content strategy make significant sense for? What are the core benefits of a well-executed content strategy? What have been the core pillars to Jesse’s success with content? Where does Jesse see many firms going wrong with their content strategy? How does Jesse look to measure the ROI from content?

4.) How was the fundraising experience for Jesse, given the “non-sexy” sector of packaging and supply chains? How did Jesse determine whether an investor was engaged or not? What does Jesse think she did well in the fundraising process? What would she like to improve for the next round? What is the common stereotype that VCs attribute to founders with bootstrapping experience?

5.) How does Jesse think about the benefits of her team being small vs her 10,000+ incumbent challenger teams? Why does this mean she has the advantage? How does Jesse manage the expectations of her employees when no one could do 1/10 of what Jesse does?

Items Mentioned In Today’s Show:

Jesse’s Fave Book: Gone with the Wind

As always you can follow Harry, The Twenty Minute VC and Jesse on Twitter here!

Likewise, you can follow Harry on Instagram here for mojito madness and all things 20VC.

We also speak about Movidiam – as brands turn to smarter ways of creating video and digital content, the Movidiam platform offers faster turnarounds whilst maintaining or improving quality. They’re already working with some of the biggest, most innovative companies to help compare teams and freelancers across the global curated network of creative talent. Producers and marketers looking for the best creatives can get a shortlist from Movidiam’s account managers in hours – tailored to their project’s needs. Submit a brief or check out the platform at Movidiam.com.

Jerry Neumann is one of New York’s leading angel investors with a portfolio including the likes of The Trade Desk (IPO: 2016), Datadog and Flurry (acquired by Yahoo) just to name a few. Prior to angel investing, Jerry built the first open market for the pricing and exchange of real-time consumer data in the form of Root Markets. Jerry was also the Managing Director @ Omnicom’s Venture Capital Division where he enjoyed an incredible 5 IPOs from the portfolio.

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In Today’s Episode You Will Learn:

1.) How Jerry made his way into the world of VC in the 90s and why it was difficult to lose money in venture at that time?

2.) Why does Jerry believe that the vast portfolio construction model is “wrong” and a “dead end”? In what circumstances does Jerry believe “spray and pray” investing can work? Why does Jerry believe you can only have as many companies as you can actively help? How does this lead Jerry’s thinking on his own portfolio construction?

3.) Why does Jerry believe that startups must have a board from Day 1? What are the inherent benefits of having a board so early? In the earliest of stages, how should those board meetings be run? Who are the best board members Jerry has worked with? Why were they so exceptional? How does Jerry think about building board intimacy?

4.) Why does Jerry disagree with the conventional wisdom of Silicon Valley that price does not matter because the exit will either be huge or a zero? How has Jerry seen the best firms in their thinking on market price vs indicated discount price? How has Jerry’s thinking on price sensitivity changed over the years?

5.) Why does Jerry believe that the follow-on investment is always a much better investment? How does the risk-reward ratio change from initial to follow-on investment? How does Jerry assess and prioritize future financing risk when investing in an opportunity? How does he mitigate that as much as possible?

Items Mentioned In Today’s Show:

Jerry’s Fave Book: Console Wars by Blake Harris

Jerry’s Most Recent Investment: Edmit

As always you can follow Harry, The Twenty Minute VC and Jerry on Twitter here!

Likewise, you can follow Harry on Instagram here for mojito madness and all things 20VC.

We also speak about Movidiam – as brands turn to smarter ways of creating video and digital content, the Movidiam platform offers faster turnarounds whilst maintaining or improving quality. They’re already working with some of the biggest, most innovative companies to help compare teams and freelancers across the global curated network of creative talent. Producers and marketers looking for the best creatives can get a shortlist from Movidiam’s account managers in hours – tailored to their project’s needs. Submit a brief or check out the platform at Movidiam.com.

James Reinhart is the Founder & CEO @ ThredUp, the world’s largest online thrift store, and consignment store. To date, ThredUp has raised over $130m in VC funding from many friends of the show including Tim @ Redpoint, Patricia @ Trinity, Eric @ Founder Collective and Ian @ Goldman Sachs just to name a few. As for James, prior to ThredUp he was a Goldsmith Fellow in Social Enterprise at HBS and a Bill George Fellow at the Center for Public Leadership at the Kennedy School. Before that, James co-founded Beacon Education Network, a charter management organization serving low-income students on California’s Central Coast.

Chris Olsen is the Founding Partner @ Drive Capital, the venture firm that believes the Midwest is the opportunity of our lifetime with more entrepreneurs building billion-dollar companies in the Midwest than in the last 50 years combined. Since inception in 2012, Drive have built an exceptional portfolio including the likes of Duolingo, FarmLogs, LeadPages and Udacity. As for Chris, prior to founding Drive he was a Partner @ Sequoia Capital on the West Coast where he learned the craft from some of the very best in the business. Before that he spent time at both TCV and UBS.

Marco Zappacosta is the Founder & CEO @ Thumbtack, the startup that allows you to find local professionals for pretty much anything. To date, Thumbtack has raised over $270m in funding from some of the very best including Sequoia Capital, CapitalG (Google Growth), Ali and Hadi Partovi, Scott and Cyan Banister and Jason Calacanis. Due to Marco’s incredible success scaling Thumbtack to helping millions of Americans today, he has been recognized by Forbes as 30 under 30 and Thumbtack was recently acknowledged as one of GlassDoor’s best places to work.

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In Today’s Episode You Will Learn:

1.) How Marco made his way into the world of startups and came to create one of the most prominent marketplaces of the day in Thumbtack?

2.) What does Marco mean when he says “founders must treat board members as employees”? How does Marco view the optimal structure for a board meeting? What are the core elements that founders must takeaway? Where do most first time founders go wrong with board management?

3.) Thumbtack has raised over $250m in VC funding, how can one look to achieve both operational efficiency and capital efficiency with such large injections of capital? What is core to maintaining this sense of frugality despite such large investments? How does Marco think about when is the right time to raise that war chest round?

4.) How does Marco suggest that marketplace founders can entice the supply side in the early days? How has Marco seen his supply-side acquisition change and develop with time? What has worked and what has not? Does Marco agree with Leah Busque that in marketplace, the NPS for one side will always be down?

Items Mentioned In Today’s Show:

Marco’s Fave Book: The Wizard and The Prophet

As always you can follow Harry, The Twenty Minute VC and Marco on Twitter here!

Likewise, you can follow Harry on Instagram here for mojito madness and all things 20VC.

Cooley is a global law firm built around supporting start-ups and the venture capital firms that fund them. Now we have spoken before about their forming the first venture fund in Silicon Valley, and forming more VC funds than any other law firm in the world but Cooley also represents more than 6,000 high-growth startups across the globe – through the full company life cycle. They are the #1 law firm for VC-backed exits (M&A and IPO) ranked by PitchBook, and since 2014 has represented more companies in their IPOs than any other law firm.  Simply head over to Cooley.com or you can check them out at Cooleygo.com.

 

Zal Bilimoria is Founding Partner @ Refactor Capital, one of Silicon Valley’s newest entrants to the early stage scene with a $50m fund looking to back founders solving fundamental human problems. Prior to co-founding Refactor, Zal was a Partner @ a16z where he co-led investments in Omada Health, Branch.co, AltSchool, Honor, and more, while helping to launch the firm’s Bio Fund. Before becoming an investor, Zal spent 10 years as a PM at Microsoft, Google, Netflix, and LinkedIn. He worked on emerging markets for Windows, became one of the first monetization team members at YouTube, and then  became the 1st Head of Mobile at Netflix and helped start the Sales Solutions business at LinkedIn.

Paul Hsiao is a Founding Partner @ Canvas Ventures, one of Silicon Valley’s leading and newer entrants to the Series A scene. At Canvas, Paul has made investments in the likes of Everwise, Fluxx Labs, Roofstock, Thrive Global, Transfix, and Zola. Before founding Canvas, Paul was a partner at NEA, where he led an early-stage investment in Houzz, as well as, had the privilege of helping eight companies go public on the NYSE or NASDAQ and seventeen companies with successful M&A exits during his 10-year tenure with the firm. Prior to VC, Paul was an entrepreneur with the founding of Mazu Networks, a pioneer in network security that was acquired by Riverbed Technologies.

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In Today’s Episode You Will Learn:

1.) How Paul made his way into the world of VC with NEA and got Scott Sandell as his first mentor in VC?

2.) Question from Oren Zeev: Having been a partner at both, how does Paul compare the culture and strategy of two such differing firms of Canvas vs NEA? How does Paul’s thinking on exit expectations and requirements change with the change of fund? How does a smaller fund fundamentally change the way you think about investing?

3.) What does Paul believe are the 5 fundamentals of building and scaling a successful marketplace? Why does Paul believe that it is the supply side that tells you if your marketplace is or is not working? Why does Paul believe stubbornness is good in marketplace founders?

4.) Why does Paul believe that raising $100m is critical for new companies if they want to go big? What does this mean for capital efficiency? What does this mean for ownership with multiple dilutive rounds impacting investor returns? How should founders then think about winning the “capital arms race”? What are the exceptions to these rules?

5.) Female founders receive 2.19% of VC funding, however, Paul has many more female founders in portfolio than the industry. Why does Paul think this is? What would Paul like to see change in the distribution of VC funds? What is the required steps to make this happen?

Items Mentioned In Today’s Show:

Paul’s Fave Book: The Innovator’s Dilemma

Paul’s Most Recent Investment: Thrive Global, Roofstock

As always you can follow Harry, The Twenty Minute VC and Paul on Twitter here!

Likewise, you can follow Harry on Instagram here for mojito madness and all things 20VC.

Cooley is a global law firm built around supporting start-ups and the venture capital firms that fund them. Now we have spoken before about their forming the first venture fund in Silicon Valley, and forming more VC funds than any other law firm in the world but Cooley also represents more than 6,000 high-growth startups across the globe – through the full company life cycle. They are the #1 law firm for VC-backed exits (M&A and IPO) ranked by PitchBook, and since 2014 has represented more companies in their IPOs than any other law firm.  Simply head over to Cooley.com or you can check them out at Cooleygo.com.

Darian Shirazi is the Founder & CEO @ Radius, the startup that provides you with not just data but truth allowing you to gain clarity to reach and convert your best B2B prospects. To date, Darian has raised over $105m in VC funding with Radius from some of the very best in the business including our friends at Founders Fund, 8VC, Salesforce Ventures and rockstars like Jared Leto and Charlie Songhurst. Prior to Radius, Darian has enjoyed roles such as first external engineering hire at Facebook and working on the “Sell Your Item” team at eBay. Darian has also made several angel investments in the likes of MessageMe, Sprig and Try.com just to name a few.

Jerry Chen is a Partner @ Greylock Partners, one of the world’s most successful VC funds with prior investments in the likes of Facebook, Instagram, LinkedIn, AirBnB, Dropbox, AppDynamics, Coinbase and many more incredible companies. As for Jerry, Jerry invests in entrepreneurs building new enterprise SaaS applications and in all aspects of AI and cloud infrastructure. Jerry currently sits on the Board of Docker, Cato Networks, Gladly, Rhumbix, Spoke, and Blend. Prior to joining Greylock, Jerry was Vice President of Cloud and Application Services at VMware where he was part of the executive team that scaled the company from 250 to over 15,000 employees and $5B in revenue. Check out Jerry’s recent writing on Risk: The Game of Strategic Investment here.

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In Today’s Episode You Will Learn:

1.) How Jerry made his way into the world of VC with Greylock from being on the exec team at VMWare, responsible for their scaling from 250 to over 15,000 people?

2.) What does Jerry believe are the different frameworks for how investors should measure risk? Why does Jerry believe to be a good investor, one has to be an optimist? What does Jerry find the most challenging element of risk assessment? What types of risk can Jerry tolerate and which can he not in a potential investment?

3.) How does Jerry break the theme of risk down into 2 very different categories? How does one define “uncertainty” in an investment? How does this compare to “probability”? How does both “uncertainty and probability” alter when comparing differing sectors? Does Jerry think that current pricing takes fair account of both “uncertainty and probability”?

4.) What does Jerry mean when he says, “you have to have product go-to-market fit”? Why does Jerry believe that platforms shifts are fundamentally distribution model shifts? Where does Jerry see an inherent opportunity within these net new nodes of distribution shift?

5.) How does Jerry evaluate the SaaS world today of bottoms up or top down? Why does Jerry believe that if you are budget additive, bottoms up with small ACVs is the current strategy? What does this mean for those that are budget replacements, both in sales model and ACV?

Items Mentioned In Today’s Show:

Jerry’s Fave Book: Skin In The Game 

Jerry’s Most Recent Investment: Blend

As always you can follow Harry, The Twenty Minute VC and Jerry on Twitter here!

Likewise, you can follow Harry on Instagram here for mojito madness and all things 20VC.

Cooley is a global law firm built around supporting start-ups and the venture capital firms that fund them. Now we have spoken before about their forming the first venture fund in Silicon Valley, and forming more VC funds than any other law firm in the world but Cooley also represents more than 6,000 high-growth startups across the globe – through the full company life cycle. They are the #1 law firm for VC-backed exits (M&A and IPO) ranked by PitchBook, and since 2014 has represented more companies in their IPOs than any other law firm.  Simply head over to Cooley.com or you can check them out at Cooleygo.com.

Rachel Drori is the Founder & CEO @ Daily Harvest, the direct-to-consumer brand that delivers real, unprocessed, unrefined foods in the most convenient format possible: frozen. To date, they have raised over $43m in funding from the likes of former guest Alex Taussig @ Lightspeed, Collaborative Fund and future 20VC guest Beth Ferreira who sits on the board. As for Rachel, prior to starting Daily Harvest, Rachel harnessed her skills as a customer-centric marketing executive, leading teams at Gilt Groupe, American Express, and Four Seasons Hotels and Resorts.

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In Today’s Episode You Will Learn:

1.) How Rachel made her way from the corporate world of American Express and The Four Seasons to founding Daily harvest, looking to change the eating habits of millions?

2.) Why did Rachel decide to deliberately raise small Seed and Series A rounds? What does Rachel believe these capital constraints allow companies in the early days? How did Rachel prioritize where to spend and where not to? How would Rachel advise emerging startup founders when it comes to capital efficiency today?

3.) Rachel recently raised $43m Series B, how did Rachel see the rounds differ from round to round? Why does Rachel believe it is imperative to VC date before the fundraising process begins? Why was Rachel’s Series A very unconventional in the modern world of fundraising? What did Rachel look for most in the investors she chose from round to round? How is that different considering her single founder status?

4.) Question from Alex Taussig: How has Rachel seen the NYC ecosystem develop and evolve since the founding of Daily Harvest? Would Rachel agree that there remains a lack of early stage conviction investors in NYC? What are NYC’s biggest strengths and then biggest weaknesses?

5.) Rachel has said before, “fake it till you make it” when was the last time Rachel did this and what was the outcome? Rachel also said previously, “ask for forgiveness not permission”, when was the most recent occassion of this and what did it result in?

Items Mentioned In Today’s Show:

Rachel’s Fave Book: Deep Nutrition: Why Your Genes Need Traditional Food: Volume 1

As always you can follow Harry, The Twenty Minute VC and Rachel on Twitter here!

Likewise, you can follow Harry on Instagram here for mojito madness and all things 20VC.

Leesa is the Warby Parker or TOMS shoes of the mattress industry. Leesa have done away with the terrible mattress showroom buying experience by creating a luxury premium foam mattress that is ordered completely online and ships for free to your doorstep. The 10-inch mattress comes in all sizes and is engineered with 3 unique foam layers for a universal, adaptive feel, including 2 inches of memory foam and 2 inches of a really cool latex foam called Avena, design to keep you cool. All Leesa mattresses are 100% US or UK made and for every 10 mattresses they sell, they donate one to a shelter. Go to Leesa.com to start the New Year with better nights sleep!

Zoom, fastest growing video and web conferencing service, providing one consistent enterprise experience that allows you to engage in an array of activities including video meetings and webinars, collaboration-enabled conference rooms, and persistent chat all in one easy platform. Plus, it is the easiest solution to manage, scale, and use, and has the most straightforward, affordable pricing. Don’t take our word for it. Zoom is the top rated conferencing app across various user review sites including G2Crowd and Trust Radius. And you can sign up for a free account (not a trial!). Just visit Zoom.us.

Dan Lewis is the Founder & CEO @ Convoy, the startup that really is the future of freight with trucking services powered by technology to drive reliability, efficiency and insights. To date they have raised over $80m in funding from some of the world’s best-known investors and individuals including Y Combinator Continuity Fund, Greylock, Jeff Bezos, Marc Benioff, Drew Houston, Kevin Systrom and leading angels, Ali and Hadi Partovi. Before Convoy, Dan served as general manager of new shopping experiences at Amazon and spent time at Google and Microsoft in a number of logistics-related roles.

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In Today’s Episode You Will Learn:

1.) How Daniel first fell in love with the logistics space as a little boy, made his move into the world of tech with Google and Microsoft and came to found Convoy?

2.) How does Dan truly define the differences between linear and non-linear businesses? Why does Dan believe that startup timing is like surfing? How must founders think about this through the different stages of the business?

3.) What was Dan’s strategy for choosing the right investors and how did he think about board composition? How can investors be used to build customer trust? How does Dan analyze and look to enhance board chemistry? What was a time for Dan when he actively went against the advice of the board? How did that play out?

4.) Why did Dan accept so many investors at the seed round? What changed between rounds that made Dan want to go big with the $62m Series B? Does Dan agree with Reid Hoffman, “if you can raise the money, do”? Why did Dan choose YC Continuity Fund as the lead growth investor of choice? What were the benefits?

5.) Why does Dan believe that scaling the first initial customers is the hardest of all? Why does Dan believe that a culture of experimentation is key across functions? How does Dan think about his own scaling as CEO? How has he seen his role change with the growth of the firm? What have been the biggest challenges of this personal learning?

Items Mentioned In Today’s Show:

Dan’s Fave Book: The Stranger by Albert Camus

As always you can follow Harry, The Twenty Minute VC and Dan on Twitter here!

Likewise, you can follow Harry on Instagram here for mojito madness and all things 20VC.

Leesa is the Warby Parker or TOMS shoes of the mattress industry. Leesa have done away with the terrible mattress showroom buying experience by creating a luxury premium foam mattress that is ordered completely online and ships for free to your doorstep. The 10-inch mattress comes in all sizes and is engineered with 3 unique foam layers for a universal, adaptive feel, including 2 inches of memory foam and 2 inches of a really cool latex foam called Avena, design to keep you cool. All Leesa mattresses are 100% US or UK made and for every 10 mattresses they sell, they donate one to a shelter. Go to Leesa.com to start the New Year with better nights sleep!

Zoom, fastest growing video and web conferencing service, providing one consistent enterprise experience that allows you to engage in an array of activities including video meetings and webinars, collaboration-enabled conference rooms, and persistent chat all in one easy platform. Plus, it is the easiest solution to manage, scale, and use, and has the most straightforward, affordable pricing. Don’t take our word for it. Zoom is the top rated conferencing app across various user review sites including G2Crowd and Trust Radius. And you can sign up for a free account (not a trial!). Just visit Zoom.us.

Leah Busque is a General Partner @ Fuel Capital, one of Silicon Valley’s leading seed funds with the most incredible portfolio including many previous 20VC guests Ryan @ Flexport, Florian @ Mesosphere, Alex @ Clearbit and Dan @ Convoy (episode Friday). As for Leah, prior to VC, she was a pioneer of the sharing economy with her founding of TaskRabbit, one of the leading online labor marketplaces in the US, raising over $37m in the process before their sale to IKEA last year. Due to this incredible success, Leah has been named to Fast Company’s “100 Most Creative People in Business”.

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In Today’s Episode You Will Learn:

1.) How Leah made her way from sitting on the couch discussing dog food with her husband to founding TaskRabbit and how that translated into the world of VC today?

2.) How did Leah’s time in operations affect:

• Question from Sean @ Shasta: the founders Leah backs and why she chooses them?
• Question from Craig @ Collaborative: the business models and unit economics Leah backs and why she backs them?

3.) Leah has said before that “authenticity and transparency between VC and founder are now table stakes”, what more can be done to improve the VC product? How did Leah select the investors she worked with on TaskRabbit? How can founders truly determine “founder friendly” VCs?

4.) What have been Leah’s biggest surprises on her move into the world of VC? What elements has Leah found most challenging? How has Leah looked to scale that learning curve?

5.) What does a successful marketplace look like? How does one know when is the right time to really scale a marketplace? What is the inflection point? How can marketplaces be efficient with their unit economics from day 1? How does one balance the NPS of the supply side with the NPS of the demand side?

Items Mentioned In Today’s Show:

Leah’s Fave Book: Founders at Work 

Leah’s Most Recent Investment: Bark: Parental Control Phone Tracker App

As always you can follow Harry, The Twenty Minute VC and Leah on Twitter here!

Likewise, you can follow Harry on Instagram here for mojito madness and all things 20VC.

Leesa is the Warby Parker or TOMS shoes of the mattress industry. Leesa have done away with the terrible mattress showroom buying experience by creating a luxury premium foam mattress that is ordered completely online and ships for free to your doorstep. The 10-inch mattress comes in all sizes and is engineered with 3 unique foam layers for a universal, adaptive feel, including 2 inches of memory foam and 2 inches of a really cool latex foam called Avena, design to keep you cool. All Leesa mattresses are 100% US or UK made and for every 10 mattresses they sell, they donate one to a shelter. Go to Leesa.com to start the New Year with better nights sleep!

Zoom, fastest growing video and web conferencing service, providing one consistent enterprise experience that allows you to engage in an array of activities including video meetings and webinars, collaboration-enabled conference rooms, and persistent chat all in one easy platform. Plus, it is the easiest solution to manage, scale, and use, and has the most straightforward, affordable pricing. Don’t take our word for it. Zoom is the top rated conferencing app across various user review sites including G2Crowd and Trust Radius. And you can sign up for a free account (not a trial!). Just visit Zoom.us.

Mike Silagadze is the Founder & CEO @ Top Hat, the market leader in student engagement software, and is used by millions of students at three-quarters of the top 1,000 colleges and universities in North America. To date, they have raised over $47m in VC funding from many friends and former guests on the show including Albert Wenger @ USV, Boris Wertz @ Version One, Uncork Capital, Felicis and Emergence just to name a few. As for Mike, prior to TopHat, he was a developer at MioVision Technologies.

Alex Taussig is a Partner @ Lightspeed Venture Partners, one of the leading firms of the last decade with a portfolio including the likes of Snapchat, Mulesoft, Max Levchin’s Affirm, The Honest Company and many more incredible companies. As for Alex, at Lightspeed, he has made investments in Zola, Daily Harvest, Vector & Poncho. Before moving to the West Coast, Alex spent 7 years at Highland Capital Partners, where, as a Partner, he made investments in thredUp, JauntVR and RentJuice (acq by Zillow) and was involved in several IPOs. Alex is also the writer of a fantastic newsletter: Drinking From The Firehose.

Leore Avidar is the Founder & CEO @ Lob, the startup that provides a powerful suite of API’s to deliver robust automation and scale for anything with a stamp. To date, Lob has raised close to $30m in funding from some of the greats of the investing world including Floodgate, Initialized, First Round and most recently YC’s Continuity Fund. As for Leore, prior to Lob he spent time in the technical business development team at Amazon Web Services and before that was a derivatives trader on Wall St with Citigroup.

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In Today’s Episode You Will Learn:

1.) How Leore made the move from the world of trading on Wall St to founding one the game-changing companies in the world of API’s, Lob?

2.) What does Leore believe are the 2 levers that founders must use when fundraising? How can founders create a sense of VC FOMO when raising their round? How can founders enter a round with leverage? What does always having the upper hand in fundraising look like?

3.) How does Leore define “sustainable growth”? Why does Leore believe that most fast-growing companies do go bankrupt? What is Leore’s biggest fear with regards to “sustainable growth”? How does Leore advise founders to think about macro funding conditions when operating their company and thinking about expenditure?

4.) How has Leore seen his role as CEO change with the scaling of the company? Why does Leore believe the main job of the CEO is to hire and replace yourself? What have been the biggest challenges for Leore in the scaling of himself?

5.) Leore wants to create a company where people stay for 30+ years, what are the foundations to a workplace culture with such deep routes? What must be done from management to ensure this? How does Leore approach accountability and responsibility amongst the team?

Items Mentioned In Today’s Show:

Leore’s Fave Book: Multipliers: How the Best Leaders Make Everyone Smarter

As always you can follow Harry, The Twenty Minute VC and Leore on Twitter here!

Likewise, you can follow Harry on Snapchat here for mojito madness and all things 20VC.

Leesa is the Warby Parker or TOMS shoes of the mattress industry. Leesa have done away with the terrible mattress showroom buying experience by creating a luxury premium foam mattress that is ordered completely online and ships for free to your doorstep. The 10-inch mattress comes in all sizes and is engineered with 3 unique foam layers for a universal, adaptive feel, including 2 inches of memory foam and 2 inches of a really cool latex foam called Avena, design to keep you cool. All Leesa mattresses are 100% US or UK made and for every 10 mattresses they sell, they donate one to a shelter. Go to Leesa.com to start the New Year with better nights sleep!

Zoom, fastest growing video and web conferencing service, providing one consistent enterprise experience that allows you to engage in an array of activities including video meetings and webinars, collaboration-enabled conference rooms, and persistent chat all in one easy platform. Plus, it is the easiest solution to manage, scale, and use, and has the most straightforward, affordable pricing. Don’t take our word for it. Zoom is the top rated conferencing app across various user review sites including G2Crowd and Trust Radius. And you can sign up for a free account (not a trial!). Just visit Zoom.us.

Anu Hariharan is a Partner @ Y Combinator’s Continuity Fund, the growth stage investing arm of Y Combinator that has made investments in the likes of Segment, Lob (coming on Friday), Convoy, where Anu is a board member and RazorPay. Prior to YC, Anu was an investment partner at Andreessen Horowitz, where she worked actively with the management teams of portfolio companies including Airbnb, Instacart, Medium, OfferUp and Udacity. Before that Anu was a Principal at The Boston Consulting Group’s Private Equity practice where she led multiple growth equity due diligences in the consumer and fintech sector.

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In Today’s Episode You Will Learn:

1.) How Anu made her way from engineer to consultant to Andreesen investment partner to now, one of the leading members of YC’s growth stage investing vehicle?

2.) How does Anu truly define “network effect”? Where does Anu think startups most commonly misunderstand network effects? Which form of network effect does Anu find most exciting? Why? How has this evolved over the years?

3.) What are the 2 core indicators that show the sustainability of network effect? Looking at past examples of products and founders, who has best executed on this? What are the signs that founding teams fundamentally analyze and optimize network effect virality?

4.) Why does Anu believe that growth teams will be a fundamental requirement for companies in the future? What are the 2 mistakes startups make when establishing their growth team? How does one know when is the right time to build their growth team? What are the core challenges in scaling growth teams? How does this drive decision-making?

5.) How does Anu describe “Phase 1” and “Phase 2” of company scaling? What transition must the CEo adopt when making this scaling transition? Comparing founders, what are the commonalities in those that succeed with the transition and those that do not?

Items Mentioned In Today’s Show:

Anu’s Fave Book: Grit by Angela Duckworth

Anu’s Most Recent Investment: Convoy

As always you can follow Harry, The Twenty Minute VC and Anu on Twitter here!

Likewise, you can follow Harry on Snapchat here for mojito madness and all things 20VC.

Leesa is the Warby Parker or TOMS shoes of the mattress industry. Leesa have done away with the terrible mattress showroom buying experience by creating a luxury premium foam mattress that is ordered completely online and ships for free to your doorstep. The 10-inch mattress comes in all sizes and is engineered with 3 unique foam layers for a universal, adaptive feel, including 2 inches of memory foam and 2 inches of a really cool latex foam called Avena, design to keep you cool. All Leesa mattresses are 100% US or UK made and for every 10 mattresses they sell, they donate one to a shelter. Go to Leesa.com to start the New Year with better nights sleep!

Zoom, fastest growing video and web conferencing service, providing one consistent enterprise experience that allows you to engage in an array of activities including video meetings and webinars, collaboration-enabled conference rooms, and persistent chat all in one easy platform. Plus, it is the easiest solution to manage, scale, and use, and has the most straightforward, affordable pricing. Don’t take our word for it. Zoom is the top rated conferencing app across various user review sites including G2Crowd and Trust Radius. And you can sign up for a free account (not a trial!). Just visit Zoom.us.

Mariam Naficy has pioneered consumer Internet models since 1998, when she co-founded the first online cosmetics retailer, Eve.com, which was sold for over $100 million. Today, Mariam is the Founder & CEO @ Minted, the startup that uses crowdsourcing and analytics to bring the best designs to market faster than anyone. To date, Mariam has raised &89m in VC funding with Minted from some of the best in the business including our favourites Floodgate, Benchmark, Menlo, Slow, Ridge Ventures and then prominent individuals such as Marissa Meyer and Jeremy Stoppelman. In addition, Mariam sits on the Board of Yelp and Every Mother Counts.

Steve Vassallo is a General Partner @ Foundation Capital where he sits or has sat on the boards of Pocket (acquired by Mozilla), PrivateCore (acquired by Facebook), Sunrun [RUN], Sentient Energy and many more. Prior to Foundation, Steve was Senior Vice President of Product and Engineering @ Ning, the social platform he helped launch in 2004. Before that, Steve was a project leader at IDEO, where he developed more than a dozen successful products for companies including Cisco, Nike, BMW and McDonalds. In addition, this year, Steve published The Way to Design, a guidebook for becoming a designer founder and building a design-centric company.

Chris Hutchins is the Founder & CEO @ Grove, the startup reinventing financial planning allowing you to reach your goals with personalized financial advice. Just last week they announced their seed round from some of the best in the business including First Round Capital, Lowercase Capital, Box Group and SV Angel. Prior to Grove, Chris was an Partner & EiR with Google Ventures and before that co-founded Milk (acq by Google) alongside Kevin Rose.

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In Today’s Episode You Will Learn:

1.) How Chris made the move from Google acquired Founder to Partner @ Google Ventures to now, founding First Round backed, Grove?

2.) What does Chris believe are the foundational elements founders must consider pre-fundraise? How does Chris suggest founders structure the process? How important is a fundraise deadline? How does Chris advise founders on getting warm intros, what is best?

3.) How can founders really optimise VC interactions? What is the biggest mistake founders make when meeting VCs? What should founders be looking to take from these meetings? How transparent should founders be about their meetings with other investors?

4.) What are Chris’ view on the rise of SAFE’s vs priced equity rounds? In what situations do SAFE’s make sense? How did Chris think about this with his own fundraise recently? Does Chris believe there is too much money in the ecosystem? Where are there gaps and where is there overfunding?

5.) Why does Chris think hiring is a “big data problem”? Where do many founders make mistakes in recruiting in the early days? What hacks can be done to ensure a quality stream of candidates continuously?

Items Mentioned In Today’s Show:

Chris’ Fave Book: Happy Money

As always you can follow Harry, The Twenty Minute VC and Chris on Twitter here!

Likewise, you can follow Harry on Snapchat here for mojito madness and all things 20VC.

Cooley are the global law firm built around startups and venture capital.  Since forming the first venture fund in Silicon Valley, Cooley has formed more venture capital funds than any other law firm in the world, with 50+ years working with VCs. They help VCs form and manage funds, make investments and handle the myriad issues that arise through a fund’s lifetime. So to learn more about the #1 most active law firm representing VC-backed companies going public. Head over to cooley.com and also at cooleygo.com.

Zoom, fastest growing video and web conferencing service, providing one consistent enterprise experience that allows you to engage in an array of activities including video meetings and webinars, collaboration-enabled conference rooms, and persistent chat all in one easy platform. Plus, it is the easiest solution to manage, scale, and use, and has the most straightforward, affordable pricing. Don’t take our word for it. Zoom is the top rated conferencing app across various user review sites including G2Crowd and Trust Radius. And you can sign up for a free account (not a trial!). Just visit Zoom.us.

Jeremy Liew is a Partner @ Lightspeed Venture Partners, one of the leading firms of the last decade with a portfolio including the likes of Snapchat, Mulesoft, Max Levchin’s Affirm, The Honest Company and many more incredible companies. As for Jeremy, he is best known for being the 1st investor in Snapchat and has also led investments in StitchFix, Affirm, Ripple, Giphy and Bonobos just to name a few. Previously, Jeremy was with AOL, first as SVP of corporate development and chief of staff to the CEO, and then as general manager of Netscape. Due to his incredible investing success, Jeremy has been featured on the Forbes Midas List multiple times.

Nadia Boujarwah is the Founder & CEO @ Dia & Co, the startup that provides premier plus size clothing and styling for women. To date they have raised over $20m in funding from some of the best in the business including the likes of Alfred Lin @ Sequoia and the team @ NextView Ventures. Prior to Dia&Co Nadia was the CFO and COO @ Frieda and Nellie and also enjoyed time in the marketing and strategy team @ Diane von Furstenberg.

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In Today’s Episode You Will Learn:

1.) How Nadia made her way from HBS grad to founding one of the hottest e-commerce companies of the day backed by Sequoia, Dia&Co?

2.) Why does Nadia believe that the biggest opportunity for value creation is through category creation? What does Nadia mean when she discusses category re-architecture? How does she think of the inherent cons (CAC, consumer education, distribution etc.)

3.) Despite the likes of Sequoia being invested now, the first year of Dia gained no institutional money. Why does Nadia think this is? What was the inflection point for VC interest? Is there anything that Nadia would change about how she has run the fundraising process?

4.) What does Nadia suggest as some core solutions to ensuring that more females become VCs? How does Nadia believe this will impact the types of companies that are being funded and built? What remain the core issues today?

5.) How does Nadia differentiate between customer centricity and customer devotion? Why is this so crucial in today’s proliferated world of e-commerce? How does Nadi and Dia determine with data, the extent to which they achieve their customer devotion targets?

Items Mentioned In Today’s Show:

Nadia’s Fave Book: Competing Against Luck

As always you can follow Harry, The Twenty Minute VC and Nadia on Twitter here!

Likewise, you can follow Harry on Snapchat here for mojito madness and all things 20VC.

Cooley are the global law firm built around startups and venture capital.  Since forming the first venture fund in Silicon Valley, Cooley has formed more venture capital funds than any other law firm in the world, with 50+ years working with VCs. They help VCs form and manage funds, make investments and handle the myriad issues that arise through a fund’s lifetime. So to learn more about the #1 most active law firm representing VC-backed companies going public. Head over to cooley.com and also at cooleygo.com.

Zoom, fastest growing video and web conferencing service, providing one consistent enterprise experience that allows you to engage in an array of activities including video meetings and webinars, collaboration-enabled conference rooms, and persistent chat all in one easy platform. Plus, it is the easiest solution to manage, scale, and use, and has the most straightforward, affordable pricing. Don’t take our word for it. Zoom is the top rated conferencing app across various user review sites including G2Crowd and Trust Radius. And you can sign up for a free account (not a trial!). Just visit Zoom.us.

Dick Costolo is the Chief Executive and co-founder of Chorus, a startup that is reimagining the path to personal fitness. Dick is also a Mentor @ Index Ventures, one of the world’s leading venture funds, which he joined in 2016. Costolo was most recently Chief Executive of Twitter from 2010 to 2015, where was at the forefront for their hypergrowth onto the main stage of tech. Prior to joining Twitter, Dick co-founded and ran three startups, including FeedBurner, which sold to Google in 2007. The former improv comedian has been a consultant on HBO’s “Silicon Valley” and currently sits on the boards of Patreon and IfOnly.

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In Today’s Episode You Will Learn:

1.) How Dick made his way from Improv Comedian to founding a startup acquired by Google and then becoming CEO of Twitter?

2.) Why does Dick believe that starting a company is like an improv stage? What were Dick’s biggest personal learnings from his drama career that he has applied to being a better leader today?

3.) Having given up the comedy dream for tech, how does Dick balance the entrepreneurial unwavering vision with a realism of when things are not working? What is the inflection point?

4.) What was the biggest challenge over the 5 years in scaling Twitter? What strategies did Dick utilise to combat this? How does Dick think about creating a culture of accountability without fear? How does this change the ownership of decisions?

5.) What is Dick’s biggest superpower and super weakness? Why must all entrepreneurs have to have a fundamental ability to compartmentalize? In terms of temperament, what were Dick’s biggest lessons from watching Youtube CEO, Susan Wojcicki, operate?

Items Mentioned In Today’s Show:

Dick’s Fave Book: Creativity Inc.

As always you can follow Harry, The Twenty Minute VC and Dick on Twitter here!

Likewise, you can follow Harry on Snapchat here for mojito madness and all things 20VC.

Cooley are the global law firm built around startups and venture capital.  Since forming the first venture fund in Silicon Valley, Cooley has formed more venture capital funds than any other law firm in the world, with 50+ years working with VCs. They help VCs form and manage funds, make investments and handle the myriad issues that arise through a fund’s lifetime. So to learn more about the #1 most active law firm representing VC-backed companies going public. Head over to cooley.com and also at cooleygo.com.

Zoom, fastest growing video and web conferencing service, providing one consistent enterprise experience that allows you to engage in an array of activities including video meetings and webinars, collaboration-enabled conference rooms, and persistent chat all in one easy platform. Plus, it is the easiest solution to manage, scale, and use, and has the most straightforward, affordable pricing. Don’t take our word for it. Zoom is the top rated conferencing app across various user review sites including G2Crowd and Trust Radius. And you can sign up for a free account (not a trial!). Just visit Zoom.us.

Brian Garrett is the Founding Partner @ Crosscut Ventures, one of LA’s leading venture funds today with a portfolio including Super Evil Mega Corp, The Black Tux and Mobcrush just to name a few. Incredibly during the early days of Crosscut, Brian went back into a full-time operating role with a Public-company turnaround at Quepasa.com before co-founding vertical eCommerce brand StyleSaint.com. After surviving with the equivalent of two full-time jobs for roughly 6 years, Brian the attention of institutional capital, which enabled CrossCut to scale into a fund with $75M raised for CrossCut 3 in 2015. This has snowballed to their latest fund raised in December being $125m.

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In Today’s Episode You Will Learn:

1.) How Brian made his way into the world of VC and came to found one of LA’s leading funds in the form of Crosscut?

2.) What does Brian believe are the 3 core components that make for a successful VC? How important is the presence of humility for VCs today? How does Brian look to balance between arrogance and confidence? How is this shown in the entrepreneurial class?

3.) Why does Brian believe that vulnerability is actually a strength today? How can entrepreneurs be honest and vulnerable without ruining market perceptions and future fundraising aspirations?

4.) How does Brian look to place his relationship with the entrepreneur at the very core of every investment he makes? What does this relationship onboarding process look like? Is this possible in the fast-moving world of US deals today?

5.) What was the most challenging fundraise for Brian? Why was this case? How has he seen the evolution of Californian tech over the last few years since Fund III? What was the most memorable LP meeting for Brian?

Items Mentioned In Today’s Show:

Brian’s Fave Book: The Alchemist

Brian’s Most Recent Investment: Fuzzy Pet Health

As always you can follow Harry and The Twenty Minute VC on Twitter here!

Likewise, you can follow Harry on Snapchat here for mojito madness and all things 20VC.

Cooley are the global law firm built around startups and venture capital.  Since forming the first venture fund in Silicon Valley, Cooley has formed more venture capital funds than any other law firm in the world, with 50+ years working with VCs. They help VCs form and manage funds, make investments and handle the myriad issues that arise through a fund’s lifetime. So to learn more about the #1 most active law firm representing VC-backed companies going public. Head over to cooley.com and also at cooleygo.com.

Zoom, fastest growing video and web conferencing service, providing one consistent enterprise experience that allows you to engage in an array of activities including video meetings and webinars, collaboration-enabled conference rooms, and persistent chat all in one easy platform. Plus, it is the easiest solution to manage, scale, and use, and has the most straightforward, affordable pricing. Don’t take our word for it. Zoom is the top rated conferencing app across various user review sites including G2Crowd and Trust Radius. And you can sign up for a free account (not a trial!). Just visit Zoom.us.

Andy Pflaum is the Founder & CEO @ Astro, the startup that brings email, calendar, and an AI-powered assistant together to help you focus on what’s most important. They have raised over $10m from leading West Coast investors such as Satish @ Redpoint, former guests Kent Goldman @ Upside and Michael Dearing @ Harrison Metal. As for Andy, prior to founding Astro, he spent 15 years in the valley, serving as the CMO @ Zimbra where he saw their immense scaling to their $350m acquisition by VMware where he then spent time on the other side of the table before moving to Chile to manage a family winery for 1.5 years.

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In Today’s Episode You Will Learn:

1.) How Andy made his way into the world of startups, made the transition to large corporates with VMware and Yahoo, came to run a Winery in Chile before founding Astro?

2.) Found a startup, work in early-stage startup or work at large incumbent; where does Andy believe young people today have the biggest growth opportunities? How does this mean emerging startups have to react to attain that talent?

3.) Why does Andy disagree with the notion that more and more incumbents are falling? Why is it harder than ever to compete against such a strong set of incumbents? What are the dangers of dependency on paid growth?

4.) How does Andy feel about distributed workforces? What is core to attaining the individuals and then scaling them successfully as a team, in a distributed fashion? How does Andy feel about hiring technical talent in the bay today?

5.) Why does Andy also argue, despite the incumbents, that it is also easier than ever to operate a business today What are the core changes that have allowed for this to happen? How does Andy break down the tech stack they use for Astro?

Items Mentioned In Today’s Show:

Andy’s Fave Book: The Wright Brothers

Andy’s Fave Blog: Tom Tunguz, Michael Dearing: Harrison Metal

As always you can follow Harry, The Twenty Minute VC and Andy on Twitter here!

Likewise, you can follow Harry on Snapchat here for mojito madness and all things 20VC.

NatureBox Unlimited snack plans offer all you can eat snacks for one fixed price per employee. Naturebox use simple ingredients you can trust to create bold flavors you can’t find anywhere else. All NatureBox snacks are free from artificial junk and variety is endless with options from sweet or savory to vegan or gluten-free. Simply choose the plan that fits your team’s unique snacking habits and select any of NatureBox’s time-saving add-on’s. And beyond Unlimited snacks, you’ll receive perks such as free kitchen setup, no contracts, a dedicated account manager and more. Simply click here to and use the offer code VC20 to get 20% of your first Naturebox month.

Leesa is the Warby Parker or TOMS shoes of the mattress industry. Leesa have done away with the terrible mattress showroom buying experience by creating a luxury premium foam mattress that is ordered completely online and ships for free to your doorstep. The 10-inch mattress comes in all sizes and is engineered with 3 unique foam layers for a universal, adaptive feel, including 2 inches of memory foam and 2 inches of a really cool latex foam called Avena, design to keep you cool. All Leesa mattresses are 100% US or UK made and for every 10 mattresses they sell, they donate one to a shelter. Go to Leesa.com to start the New Year with better nights sleep!

Andrew Parker is a General Partner @ Spark Capital, one of the best performing funds of the last decade with a portfolio including the likes of Twitter, Slack, Oculus, Medium, PostMates, Cruise (acq $1Bn) the list goes on. As for Andrew, he has led Spark’s investments in Carta, Kik, Panorama Education, Socratic, Splash, Particle and Quantopian. Prior to joining Spark in 2010, Andrew was a member of the investment team at Union Square Ventures. Before becoming an investor, Andrew did UI design and user-experience testing at Homestead Technologies and was a web developer at Groupspace.org.

Neil Young is the Founder & CEO @ N3twork, the next generation mobile games maker and publisher with their services already touching millions of customers. They have raised over $17m in VC funding from some of the very best in the business including Mike Maples @ Floodgate, Bing Gordon @ KPCB and the team at Google Ventures. Prior to N3TWORK, Neil founded ngmoco, a leading social mobile games company, acquired by DeNA for a reported up to $400m. Before ngmoco, Neil spent many years at Electronic Arts where he was responsible for producing some of EA’s most successful game franchises including: The Lord of the Rings, The Sims, Medal of Honor and Command and Conquer, among others.

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In Today’s Episode You Will Learn:

1.) How Neil made his way from telling his mother in the UK he was not going to university to producing world-leading games, to selling a company for a reported $400m?

2.) What are the 2 questions Neil believes everyone should ask when evaluating the potential of a new platform? How does Neil think about the platform shifts at present given his publishing to mobile? Where do most people make mistakes when assessing platform shifts?

3.) Peter Fenton stated on the show: “startups are starved of free and open distribution”. How does Neil think about incumbency advantages with regards to distribution? Would an open platform yield greater potential distribution? How does Neil view the world of paid and performance marketing today? How has his views changed on the space?

4.) What are the 3 things that Neil believes all founders must do in order to assemble and manage a board successfully? Why is it important to listen to board members on their own and as a group and compare? Where do most founders go wrong in board management?

5.) Neil sold ngmoco for a reported $400m, what does Neil believe are the 2 big questions that all founders must ask themselves when contemplating a potential sale? What are the 2 different types of acquisitions that exist today?

Items Mentioned In Today’s Show:

Neil’s Fave Book: The Second World War

Neil’s Fave Blog: Gaming Insiders

As always you can follow Harry, The Twenty Minute VC and Neil on Twitter here!

Likewise, you can follow Harry on Snapchat here for mojito madness and all things 20VC.

NatureBox Unlimited snack plans offer all you can eat snacks for one fixed price per employee. Naturebox use simple ingredients you can trust to create bold flavors you can’t find anywhere else. All NatureBox snacks are free from artificial junk and variety is endless with options from sweet or savory to vegan or gluten-free. Simply choose the plan that fits your team’s unique snacking habits and select any of NatureBox’s time-saving add-on’s. And beyond Unlimited snacks, you’ll receive perks such as free kitchen setup, no contracts, a dedicated account manager and more. Simply click here to and use the offer code VC20 to get 20% of your first Naturebox month.

Leesa is the Warby Parker or TOMS shoes of the mattress industry. Leesa have done away with the terrible mattress showroom buying experience by creating a luxury premium foam mattress that is ordered completely online and ships for free to your doorstep. The 10-inch mattress comes in all sizes and is engineered with 3 unique foam layers for a universal, adaptive feel, including 2 inches of memory foam and 2 inches of a really cool latex foam called Avena, design to keep you cool. All Leesa mattresses are 100% US or UK made and for every 10 mattresses they sell, they donate one to a shelter. Go to Leesa.com to start the New Year with better nights sleep!

Eurie Kim is a General Partner @ Forerunner Ventures, the early stage firm dedicated to investing in entrepreneurs defining the next generation of commerce. Fun fact, they are the only firm to have investments in both Jet.com and Dollar Shave Club, two of the biggest and highest-profile e-commerce exits in recent years. Forerunner also counts Birchbox, Bonobos, Glossier, Hotel Tonight, Warby Parker and Zola among its portfolio companies. Prior to Forerunner, Eurie was a consultant at Bain and before that an investor at Castanea Partners. Eurie currently sits on the boards of companies such as Away, MoveWith and The Farmers Dog, just to name a few.

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In Today’s Episode You Will Learn:

1.) How Eurie made her into the world of VC and investing in the next generation of commerce with Forerunner?

2.) How does Eurie look to argue that commerce deals do attain the same revenue multiple on exit as enterprise deals? Do Forerunner think about exit potential when investing in companies? How does this Eurie’s thesis on both ownership and price sensitivity? What are the required fund-returning ownership levels today?

3.) With the time it takes for brands to flourish, how does Forerunner think about reserve allocation? How does Forerunner determine which companies to double down on and which to constrain capital? Why does Eurie believe that it takes less time than ever for brands to flourish today? What is a good example of this?

4.) How does Eurie define the term “digitally native vertically integrated brand”? What are the core components that make those all star brands of today shine in the early days? What are the commonalities in those successful founders that build these mega brands?

5.) Given the rise of some prominent new brands eating incumbent market share, does Eurie believe this is a market of consolidation or new incumbents will be made? How does Eurie view the role of Amazon? To what extent does Eurie observe and analyse Amazon’s activity?

Items Mentioned In Today’s Show:

Eurie’s Fave Book: Blue Ocean Strategy 

Eurie’s Fave Blog: Business of Fashion

Eurie’s Most Recent Investment: Shop Shops

As always you can follow Harry, The Twenty Minute VC and Eurie on Twitter here!

Likewise, you can follow Harry on Snapchat here for mojito madness and all things 20VC.

NatureBox Unlimited snack plans offer all you can eat snacks for one fixed price per employee. Naturebox use simple ingredients you can trust to create bold flavors you can’t find anywhere else. All NatureBox snacks are free from artificial junk and variety is endless with options from sweet or savory to vegan or gluten-free. Simply choose the plan that fits your team’s unique snacking habits and select any of NatureBox’s time-saving add-on’s. And beyond Unlimited snacks, you’ll receive perks such as free kitchen setup, no contracts, a dedicated account manager and more. Simply click here to and use the offer code VC20 to get 20% of your first Naturebox month.

Leesa is the Warby Parker or TOMS shoes of the mattress industry. Leesa have done away with the terrible mattress showroom buying experience by creating a luxury premium foam mattress that is ordered completely online and ships for free to your doorstep. The 10-inch mattress comes in all sizes and is engineered with 3 unique foam layers for a universal, adaptive feel, including 2 inches of memory foam and 2 inches of a really cool latex foam called Avena, design to keep you cool. All Leesa mattresses are 100% US or UK made and for every 10 mattresses they sell, they donate one to a shelter. Go to Leesa.com to start the New Year with better nights sleep!

Florian Leibert is the Founder & CEO @ Mesosphere, the most flexible platform for containerized, data-intensive applications. They are trusted by some of the world’s leading companies from Yelp to Yammer to Verizon and have raised over $120m in VC funding from the likes of a16z, Kleiner Perkins, Khosla, Data Collective and then incumbents such as Microsoft and Hewlett Packard. Prior to founding Mesosphere, Florian spent time with Twitter and Airbnb, both as a tech lead and if that was not enough, Florian also has a stellar angel portfolio including the likes of Away, Cockroach Labs, Drift and Buoyant.

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In Today’s Episode You Will Learn:

1.) How Florian came to found Mesosphere? What were the big takeaways for him from his more formative years at Twitter and Airbnb?

2.) Why does Florian believe that sometimes “you should not listen to your investors”? What is the right way to communicate this disagreement to them? What supporting evidence is required to substantiate your thoughts? What method would Florian prefer to receive such feedback?

3.) What are the biggest benefits of having strategics such as Microsoft and Hewlett Packard on the cap table? What are some potential drawbacks? What advice would Florian give to founders contemplating taking strategic investment? When is the right time for these staretgics to insert themselves?

4.) With the scaling of Mesosphere, how have Florian’s thoughts and approach to sales execution changed? What have been the core struggles? Why does Florian think it is imperative to build the sales team slowly?

5.) At what point does Florian think that operational efficiency must be front and centre for founders scaling their companies? What has Florian found to be the most challenging personally in achieving such operational efficiency?

Items Mentioned In Today’s Show:

Florian’s Fave Book: Alchemist: A Fable about Following Your Dream

Florian’s Fave Blog: Seeking Alpha

As always you can follow Harry, The Twenty Minute VC and Florian on Twitter here!

Likewise, you can follow Harry on Snapchat here for mojito madness and all things 20VC.

NatureBox Unlimited snack plans offer all you can eat snacks for one fixed price per employee. Naturebox use simple ingredients you can trust to create bold flavors you can’t find anywhere else. All NatureBox snacks are free from artificial junk and variety is endless with options from sweet or savory to vegan or gluten-free. Simply choose the plan that fits your team’s unique snacking habits and select any of NatureBox’s time-saving add-on’s. And beyond Unlimited snacks, you’ll receive perks such as free kitchen setup, no contracts, a dedicated account manager and more. Simply click here to and use the offer code VC20 to get 20% of your first Naturebox month.

Leesa is the Warby Parker or TOMS shoes of the mattress industry. Leesa have done away with the terrible mattress showroom buying experience by creating a luxury premium foam mattress that is ordered completely online and ships for free to your doorstep. The 10-inch mattress comes in all sizes and is engineered with 3 unique foam layers for a universal, adaptive feel, including 2 inches of memory foam and 2 inches of a really cool latex foam called Avena, design to keep you cool. All Leesa mattresses are 100% US or UK made and for every 10 mattresses they sell, they donate one to a shelter. Go to Leesa.com to start the New Year with better nights sleep!

Sam Altman is the president of Y Combinator, the world’s most successful accelerator with alumni that includes the likes of Airbnb, Dropbox, Reddit, Flexport and many more incredible companies. Sam is also the co-chair of OpenAI, thenon-profit AI research company, discovering and enacting the path to safe artificial general intelligence. Prior to YC, Sam was co-founder and CEO of Loopt, which was funded by Y Combinator in 2005 and acquired by Green Dot in 2012. Sam also founded Hydrazine Capital, whose stellar portfolio included the likes of Zenefits, Flexport and Soylent.

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In Today’s Episode You Will Learn:

1.) How Sam made his way into the world of startups with Loopt and YC? How he came to invest with Hydrazine Capital and then rejoin YC as Partner and now President?

2.) Having watched and seen Paul Graham since Batch 1, what does Sam believe makes Paul Graham the special leader he is? What makes Sam and Paul such great Partners? How did they enact the transition of Sam to President? How did it change the relationship?

3.) What is Sam’s tactic that he uses to fully evaluate the skills and execution of a founder? When investing where did Sam make his most frequent mistakes? Why does Sam expect seed stage investing as a whole, will compress? Is Sam concerned of too much capital in the market at present?

4.) Question from Jack Altman: what is the main difference between a great seed investor and a great Series A investor? Sam has said before he likes to invest in messy, somewhat broken companies”. How does Sam determine between the fixable and the unfixable? How much of a role does price play in his evaluation of an opportunity?

5.) One of Sam’s recent goals was “figure out how to scale YC 2x”. How does Sam think about this in terms of stage? Will YC replace VC with lifecycle funding? How does Sam think about YC’s expansion geographically into China? How does Sam assess the vertical expansion of deep tech and bio tech that YC is going after?

Items Mentioned In Today’s Show:

Sam’s Fave Book: The Making of The Atomic Bomb

As always you can follow Harry, The Twenty Minute VC and Sam on Twitter here!

Likewise, you can follow Harry on Snapchat here for mojito madness and all things 20VC.

NatureBox Unlimited snack plans offer all you can eat snacks for one fixed price per employee. Naturebox use simple ingredients you can trust to create bold flavors you can’t find anywhere else. All NatureBox snacks are free from artificial junk and variety is endless with options from sweet or savory to vegan or gluten-free. Simply choose the plan that fits your team’s unique snacking habits and select any of NatureBox’s time-saving add-on’s. And beyond Unlimited snacks, you’ll receive perks such as free kitchen setup, no contracts, a dedicated account manager and more. Simply click here to and use the offer code VC20 to get 20% of your first Naturebox month.

Leesa is the Warby Parker or TOMS shoes of the mattress industry. Leesa have done away with the terrible mattress showroom buying experience by creating a luxury premium foam mattress that is ordered completely online and ships for free to your doorstep. The 10-inch mattress comes in all sizes and is engineered with 3 unique foam layers for a universal, adaptive feel, including 2 inches of memory foam and 2 inches of a really cool latex foam called Avena, design to keep you cool. All Leesa mattresses are 100% US or UK made and for every 10 mattresses they sell, they donate one to a shelter. Go to Leesa.com to start the New Year with better nights sleep!

Emilie Choi is Head of Corporate Development @ Linkedin where she has led 40+ acquisitions, acquihires or investments. In terms of acquisitions, Emilie led the acquisitions of Lynda, Bizo, Newsle, Bright, Pulse, SlideShare, and Rapportive just to name a few. On the strategic investment side, she led Linkedin’s investment in Cornerstone On Demand and G2 Crowd. Before Linkedin, Emilie enjoyed roles such as Director of Digital Business Strategy and Operations at Warner Bros, International Strategy and Ops @ MySpace and Corp Dev and Strategy @ Yahoo. Emilie has also sat on the Naspers board for the last 10 years.

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In Today’s Episode You Will Learn:

1.) How Emilie made her way into the world of M&A and came to lead over 40+ game-changing acquisitions for Linkedin?

2.) In 2016, M&A made up 95% of startup exits, how does Emilie evaluate the current state of exit environments? What 2 reasons have caused the drop in startup M&A? How does Emilie view the rise of PE and strategic investors to the acquisition markets?

3.) Paul Graham said ‘startups should only talk to corp dev when they are doing really well or really badly’. What are Emilie’s thoughts on when is the right time for startups to have conversations with Corp Dev teams? When does Emilie you most like to begin the relationship? How does Emilie like to work with VCs in this relationship building?

4.) Paul Graham also described the structure of M&A as “grueling”. Does Emilie agree with this? How does Emilie map out the structure of a typical M&A deal, from start to finish? How much of a role does price play in her evaluation of a deal? How does Emilie measure the success of an acquisition?

5.) Matt Switzer @ Hootsuite stated the biggest M&A risk to be integration. What does smooth integrations look like for both consumer vs enterprise? Why do they differ? How can this integration work be de-risked and front loaded?

Items Mentioned In Today’s Show:

Emilie’s Fave Book: The Bonfire of the Vanities 

Emilie’s Most Recent Investment: Heighten

As always you can follow Harry and The Twenty Minute VC on Twitter here!

Likewise, you can follow Harry on Snapchat here for mojito madness and all things 20VC.

NatureBox Unlimited snack plans offer all you can eat snacks for one fixed price per employee. Naturebox use simple ingredients you can trust to create bold flavors you can’t find anywhere else. All NatureBox snacks are free from artificial junk and variety is endless with options from sweet or savory to vegan or gluten-free. Simply choose the plan that fits your team’s unique snacking habits and select any of NatureBox’s time-saving add-on’s. And beyond Unlimited snacks, you’ll receive perks such as free kitchen setup, no contracts, a dedicated account manager and more. Simply click here to and use the offer code VC20 to get 20% of your first Naturebox month.

Leesa is the Warby Parker or TOMS shoes of the mattress industry. Leesa have done away with the terrible mattress showroom buying experience by creating a luxury premium foam mattress that is ordered completely online and ships for free to your doorstep. The 10-inch mattress comes in all sizes and is engineered with 3 unique foam layers for a universal, adaptive feel, including 2 inches of memory foam and 2 inches of a really cool latex foam called Avena, design to keep you cool. All Leesa mattresses are 100% US or UK made and for every 10 mattresses they sell, they donate one to a shelter. Go to Leesa.com to start the New Year with better nights sleep!

 

 

Henry Davis is the President and COO @ Glossier, a New York brand that has taken the beauty world by storm. To date they have raised close to $35m in VC funding from some of the best in the business including past guests on the show Kirsten Green @ Forerunner, Index Ventures, IVP and our friends at Thrive. As for Henry, prior to entering the world of beauty and brands with Glossier, he sat on the other side of the table as a VC with Index Ventures in London. Before that, for his sins, Henry spent time in the world of corporate finance with Citi Group.

Crystal Huang is a Principal @ GGV Capital, one of the world’s leading venture firms partnering with entrepreneurs in the world’s largest markets, the US and China. At GGV Crystal led the firm’s investment in Wigo (acquired by Cinemagram) and attends board meetings at Tile and Flightcar. Crystal is also a board member @ NextGen partners, the organization representing the future General Partners within the bay area. Prior to joining GGV, Crystal worked as an analyst in Blackstone’s Technology M&A Advisory Group and due to her immense promise and success already, Crystal has been named to Forbes’ 30 Under 30 Venture Capital.

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In Today’s Episode You Will Learn:

1.) How Crystal made her way into the world of VC from Tech M&A with Blackstone?

2.) How does Crystal view the ongoing debate of operator vs non-operator experience? Does Crystal agree with Pat Grady that the rate of decay on operating experience has never been greater? What elements of operational experience, applied to VC, do stand the test of time?

3.) What does Crystal believe are the 3 key differences when comparing the US and Asian tech markets? How do deal sizes change across geographies? What does this do to the unit economics of the businesses? How does vendor engagement and sales cycles differ?

4.) In a world of Baidu, Alibaba and Tencent quickly acquiring or copying innovative ideas, is there a market for true later stage VC in Asia? Where are the market opportunities? How does incumbent power in Asia differ to incumbent power in the US?

5.) How does Crystal fundamentally see distribution models vary between the US and Asia? Has Asia enjoyed the same rise of the “self-service model” enacted by many in the US? What does this mean for internal org structures and unit economics?

Items Mentioned In Today’s Show:

Crystal’s Fave Book: The Code Book

Crystal’s Most Recent Investment: BitSight

As always you can follow Harry, The Twenty Minute VC and Crystal on Twitter here!

Likewise, you can follow Harry on Snapchat here for mojito madness and all things 20VC.

NatureBox Unlimited snack plans offer all you can eat snacks for one fixed price per employee. Naturebox use simple ingredients you can trust to create bold flavors you can’t find anywhere else. All NatureBox snacks are free from artificial junk and variety is endless with options from sweet or savory to vegan or gluten-free. Simply choose the plan that fits your team’s unique snacking habits and select any of NatureBox’s time-saving add-on’s. And beyond Unlimited snacks, you’ll receive perks such as free kitchen setup, no contracts, a dedicated account manager and more. Simply click here to and use the offer code VC20 to get 20% of your first Naturebox month.

Leesa is the Warby Parker or TOMS shoes of the mattress industry. Leesa have done away with the terrible mattress showroom buying experience by creating a luxury premium foam mattress that is ordered completely online and ships for free to your doorstep. The 10-inch mattress comes in all sizes and is engineered with 3 unique foam layers for a universal, adaptive feel, including 2 inches of memory foam and 2 inches of a really cool latex foam called Avena, design to keep you cool. All Leesa mattresses are 100% US or UK made and for every 10 mattresses they sell, they donate one to a shelter. Go to Leesa.com to start the New Year with better nights sleep!

Hans Tung is a Managing Partner @ GGV Capital, one of the world’s leading venture firms partnering with entrepreneurs in the world’s largest markets, the US and China. Evident when looking at Han’s incredible investments in the likes of Wish, Poshmark, musical.ly, Slack and OfferUp in the US and then Xiaomi, Forgame, and Domob Ads in Asia. Previously, Hans was with Bessemer Venture Partners, where he helped global players such as Skype expand into China. Hans was also a founding member of two pan-Asian internet startups that were subsequently sold to telcos. Due to his incredible success, Hans has been ranked as a top VC on the Forbes Midas list since 2013 and was recognized by The Founder and CBN News magazines in the past as a Top 10 most entrepreneur-friendly VC in China.

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In Today’s Episode You Will Learn:

1.) How Hans made his way into VC with Bessemer having founded and exited 2 prior startups?

2.) Why does Hans believe that the globalisation of consumer mobile companies is the biggest trend in his career? Why is Hans still so attracted to consumer with lacking distribution channel availability and incumbents like Amazon? Have Amazon already won?

3.) What were Hans’ biggest lessons from investing in China that have allowed him to invest better in the US? How does Hans evaluate prior US companies entering strategies into China? How does he analyse Uber’s entering into China?

4.) Hans has backed some of the hottest companies in the business from Airbnb to Wish, how does Hans respond to price sensitivity and having to pay up to get into the round? How does Hans think about the opportunity cost of capital deployment?

5.) Why does Hans remain so bullish on the globalisation of tech? In a world of Trump and Brexit are we not in ever more atomistic times? How does Hans see the convergence of millenial consumers when comparing the US and Asia?

Items Mentioned In Today’s Show:

Hans’ Fave Book: The Information, Stratechery

Hans’ Most Recent Investment: iBotta

As always you can follow Harry, The Twenty Minute VC and Hans on Twitter here!

Likewise, you can follow Harry on Snapchat here for mojito madness and all things 20VC.

NatureBox Unlimited snack plans offer all you can eat snacks for one fixed price per employee. Naturebox use simple ingredients you can trust to create bold flavors you can’t find anywhere else. All NatureBox snacks are free from artificial junk and variety is endless with options from sweet or savory to vegan or gluten-free. Simply choose the plan that fits your team’s unique snacking habits and select any of NatureBox’s time-saving add-on’s. And beyond Unlimited snacks, you’ll receive perks such as free kitchen setup, no contracts, a dedicated account manager and more. Simply click here to and use the offer code VC20 to get 20% of your first Naturebox month.

Leesa is the Warby Parker or TOMS shoes of the mattress industry. Leesa have done away with the terrible mattress showroom buying experience by creating a luxury premium foam mattress that is ordered completely online and ships for free to your doorstep. The 10-inch mattress comes in all sizes and is engineered with 3 unique foam layers for a universal, adaptive feel, including 2 inches of memory foam and 2 inches of a really cool latex foam called Avena, design to keep you cool. All Leesa mattresses are 100% US or UK made and for every 10 mattresses they sell, they donate one to a shelter. Go to Leesa.com to start the New Year with better nights sleep!

Ben Marcus is the Founder & CEO @ Airmap, the startups that provides everything one needs to unlock and scale drone operations in the ever-changing world of airspace. They have raised over $40m in funding from industry heavyweights Sony, Rakuten, Qualcomm, Airbus Ventures and then also many friends of the show including Semil Shah, Lux Capital, Microsoft Ventures, General Catalyst, BullPen Capital and David Waxman at TenOneTen, just to name a few. Prior to AirMap, Ben co-founded and was CEO of the world’s largest light business jet sales company, Jetaviva and before that started his career as a flight instructor and later became a flight test engineer. Fun fact, Ben is also an FAA-certified Airline Transport Pilot and Flight Instructor with over 4,500 hours of flight experience.

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In Today’s Episode You Will Learn:

1.) How Ben made his way into the world of startups and drones from being a pilot and flight test engineer?

2.) What does Ben think is a strong investment strategy when investing in the drones? What 4 categories present nascent opportunities to Ben? What elements of the tech stack should potential investors further drill down on with potential investments?

3.) Question from Hemant Taneja: How does Ben assess the presence and desires of Amazon and Google with their pre-existing mission to win the airspace? Question from Semil Shah: Does this lead to a world of consolidation and startup M&A by incumbents?

4.) What does Ben believe are the core catalysts that will take drones to 100s of millions of people? How does Ben assess the similarties and differences in serving enterprise vs consumer drone markets? Does Ben agree with Jonathan Downey in his expression that enterprises like “boring” offerings?

5.) How does Ben evaluate the hardware vs software paradigm in the drone market? Does Ben see the commoditisation of drone hardware in the coming years? How does Ben evaluate the likes of DJI with their prominence? Does the weaponisation of drones cause significant alarm for Ben?

Items Mentioned In Today’s Show:

Ben’s Fave Book: The Wealth of Nations

Ben’s Fave Blog: Social Capital Newsletter

As always you can follow Harry, The Twenty Minute VC and Ben on Twitter here!

Likewise, you can follow Harry on Snapchat here for mojito madness and all things 20VC.

NatureBox Unlimited snack plans offer all you can eat snacks for one fixed price per employee. Naturebox use simple ingredients you can trust to create bold flavors you can’t find anywhere else. All NatureBox snacks are free from artificial junk and variety is endless with options from sweet or savory to vegan or gluten-free. Simply choose the plan that fits your team’s unique snacking habits and select any of NatureBox’s time-saving add-on’s. And beyond Unlimited snacks, you’ll receive perks such as free kitchen setup, no contracts, a dedicated account manager and more. Simply click here to and use the offer code VC20 to get 20% of your first Naturebox month. 

Leesa is the Warby Parker or TOMS shoes of the mattress industry. Leesa have done away with the terrible mattress showroom buying experience by creating a luxury premium foam mattress that is ordered completely online and ships for free to your doorstep. The 10-inch mattress comes in all sizes and is engineered with 3 unique foam layers for a universal, adaptive feel, including 2 inches of memory foam and 2 inches of a really cool latex foam called Avena, design to keep you cool. All Leesa mattresses are 100% US or UK made and for every 10 mattresses they sell, they donate one to a shelter. Go to Leesa.com to start the New Year with better nights sleep!

 

 

Kevin Thau is a General Partner @ Spark Capital, one of the best performing funds of the last decade with a portfolio including the likes of Twitter, Slack, Oculus, Medium, PostMates, Cruise (acq $1Bn) the list goes on. As for Kevin, he has led investments in Medium, LOLA, CTRL Labs, Aura and Haven. Prior to Spark, Kevin enjoyed an incredible 7 years at Twitter, when he joined they had less than 20 employees and 1m users and he carried roles such as Director of Mobile Products and VP of Business & Corporate Development. Before Twitter, Kevin was employee number 7 at Software.com (which became Openwave) where he helped ship the first mobile browser, mobile messaging services and mobile websites.

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In Today’s Episode You Will Learn:

1.) How Kevin made his way into VC with Spark having spent years in operations with Twitter and Silicon Graphics?

2.) What were Kevin’s biggest lessons from watching the hyper-scaling of Twitter? What are the most prominent challenges companies face at this stage? What were his takeaways from working with product visionaries like Jack Dorsey & Sonos’ John MacFarlane?

3.) As an operator turned investor, how does Kevin characterise his approach to working with portfolio companies? What were Kevin’s early VC learnings from his discussions with Fred Wilson and Bijan Sabet on VC profile and psychology?

4.) Why does Kevin believe that VC is a game of “maximizing serendipity”? How does Kevin assess personal time allocation, today as a VC? What has Kevin found most challenging since making the move to VC from operations?

5.) How does Kevin assess the consumer landscape at present? Does Kevin agree with Kirsten Green that “Amazon does more to make the market than crush it”? Why does Kevin find Instagram such a special tool for evaluating brands? What does he look for in the Instagram profiles of these emerging brands that really excites him?

Items Mentioned In Today’s Show:

Kevin’s Fave Book: Moneyball: The Art of Winning An Unfair Game

Kevin’s Most Recent Investment: CTRL-Labs

As always you can follow Harry, The Twenty Minute VC and Kevin on Twitter here!

Likewise, you can follow Harry on Snapchat here for mojito madness and all things 20VC.

NatureBox Unlimited snack plans offer all you can eat snacks for one fixed price per employee. Naturebox use simple ingredients you can trust to create bold flavors you can’t find anywhere else. All NatureBox snacks are free from artificial junk and variety is endless with options from sweet or savory to vegan or gluten-free. Simply choose the plan that fits your team’s unique snacking habits and select any of NatureBox’s time-saving add-on’s. And beyond Unlimited snacks, you’ll receive perks such as free kitchen setup, no contracts, a dedicated account manager and more. Simply click here to and use the offer code VC20 to get 20% of your first Naturebox month. 

Leesa is the Warby Parker or TOMS shoes of the mattress industry. Leesa have done away with the terrible mattress showroom buying experience by creating a luxury premium foam mattress that is ordered completely online and ships for free to your doorstep. The 10-inch mattress comes in all sizes and is engineered with 3 unique foam layers for a universal, adaptive feel, including 2 inches of memory foam and 2 inches of a really cool latex foam called Avena, design to keep you cool. All Leesa mattresses are 100% US or UK made and for every 10 mattresses they sell, they donate one to a shelter. Go to Leesa.com to start the New Year with better nights sleep!

Brian Armstrong is the Founder & CEO @ Coinbase, the startup that provides the world’s most popular way to buy and sell bitcoin, ethereum and litecoin. They have backing from some of the biggest and best in VC having raised over $215m from the likes of Andreesen Horowitz, IVP, USV, DFJ and many more incredible investors. As for Brian, prior to Coinbase he was a Software Engineer @ Airbnb and before that founded his own startup, Universitytutor.com

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In Today’s Episode You Will Learn:

1.) How Brian made his way from Airbnb to founding one of the early disruptors in the crypto space with Coinbase?

2.) Doing an 80/20 analysis, what are the 3 fundamental differences between Bitcoin and ethereum? What is Brian’s opinion on the scaling path ahead for ethereum? How do the teams behind ethereum and Bitcoin differ and what effect do these differing approaches have?

3.) What is an ICO? Does Brian believe ICOs will be a sustainable method of company financing in the future? What needs to take place to ensure for the continued momentum of ICOs? What have been the biggest surprises of ICOs for Brian?

4.) How does Brian view the regulatory stance around both ICOs and blockchain more generally? What is he concerned will happen? What would be the optimal regulatory framework for the theme to thrive?

5.) How does the rise of blockchain disrupt the VC industry? Why does Brian agree with Naval in stating the future will involve the unbundling of money, control and advice from the realms of VC?

Items Mentioned In Today’s Show:

Brian’s Fave Book: Surely You’re Joking Mr. Feynman

Brian’s Fave Blog: Week In Ethereum

As always you can follow Harry, The Twenty Minute VC and Brian on Twitter here!

Likewise, you can follow Harry on Snapchat here for mojito madness and all things 20VC.

Namely is the all-in-one HR, payroll, and benefits platform your employees will love to use. It’s as intuitive as social media, but powerful enough to support the complexity of today’s workforce. Namely’s mission is to help mid-sized companies build a better workplace. See how Namely can transform your workplace at www.Namely.com.

Eero is the world’s best-reviewed wifi. A system of eero and eero Beacons wirelessly connects to blanket your home in fast, reliable WiFi, so despite the increased number of devices with Christmas coming, you’ll still be able to get powerful mesh WiFi in every nook and cranny of your home, backyard included. No more dead spots, slow spots, drop-offs, or buffering — right out of the box. Eero is only available in the US and Canada and you can check it out here!

Kirsten Green is the Founding General Partner @ Forerunner Ventures, where she has raised over $250M from leading investors and has invested in more than 40 early-stage companies. Forerunner Ventures is the only VC firm to invest in both Dollar Shave Club and Jet.com, two of the biggest and highest-profile e-commerce exits in recent years, and counts Birchbox, Bonobos, Glossier, Hotel Tonight, Warby Parker and Zola among its portfolio companies. She’s been honored in Time’s 100 Most Influential People in 2017, named VC of the Year at TechCrunch’s 2017 Crunchies Awards, and is part of Forbes 2017 Midas List.

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In Today’s Episode You Will Learn:

1.) How Kirsten came to found one of the most successful early stage funds of the past decade in Forerunner?

2.) Question from Michael Kim @ Cendana: How does Kirsten view the optimal portfolio construction theory for a thematically specialized consumer fund? What is the one question Kirsten asks herself pre-investing in a startup?

3.) Question from David Pakman @ Venrock: Given the scope of consumer as a space, is Forerunner large enough to attain the required ownership levels? What does this mean for the future of Forerunner in terms of further funds, opportunity funds and entry points?

4.) What are the 3 core principles to developing an exciting investment opportunity in the consumer space? What commonalities do they have? What do you look for in a consumer brand founder that might be different from a software founder?

5.) Why does Kirsten believe that Amazon has done more to make the market opportunity than they have to crush it? What makes Kirsten believe we really are in the early innings for commerce? How will we see the notion of brand evolve over the coming years?

Items Mentioned In Today’s Show:

Kirsten’s Fave Book: Charlie and The Chocolate Factory

Kirsten’s Fave Blog: TheSkimm

Kirsten’s Most Recent Investment: Packagd 

As always you can follow Harry, The Twenty Minute VC and Kirsten on Twitter here!

Likewise, you can follow Harry on Snapchat here for mojito madness and all things 20VC.

Namely is the all-in-one HR, payroll, and benefits platform your employees will love to use. It’s as intuitive as social media, but powerful enough to support the complexity of today’s workforce. Namely’s mission is to help mid-sized companies build a better workplace. See how Namely can transform your workplace at www.Namely.com.

Eero is the world’s best-reviewed wifi. A system of eero and eero Beacons wirelessly connects to blanket your home in fast, reliable WiFi, so despite the increased number of devices with Christmas coming, you’ll still be able to get powerful mesh WiFi in every nook and cranny of your home, backyard included. No more dead spots, slow spots, drop-offs, or buffering — right out of the box. Eero is only available in the US and Canada and you can check it out here!

Peter Fenton is a General Partner @ Benchmark, one of the world’s leading VC funds with a portfolio including the likes of Twitter, Uber, Snapchat, eBay, WeWork, Yelp and many more revolutionary companies of the last decade. Peter himself sits or has sat on the board of Twitter, previous guest Cockroach, Optimizely, New Relic and ZenDesk just to name a few. Prior to Benchmark, Peter was a Managing Partner @ Accel. It is clearly not just me that has a man crush on Peter though as he has been named to Forbes Midas List for many consecutive years with the last list placing Peter as No 3 in the world.

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In Today’s Episode You Will Learn:

1.) How Peter made his way into the world of VC with Accel and came to be a General Partner @ Benchmark?

2.) How does Peter differentiate between the good and the great VCs? How can VCs use hyper-curiosity and hyper-competitiveness to improve their investing ability? Why does Peter not believe that operational experience is a necessity pre-VC?

3.) How does Peter view the importance of valuation in the investment decision making process? How much of a role does it play for him and what is his psychology around valuation, especially with regards to ownership levels?

4.) Why is Peter amused when he hears other investors say they must ‘invest in big markets’? What were his big takeaways from watching the investment and hyper-growth journey of Snapchat? How did that influence his view on markets?

5.) Peter has previously said that he is a ‘student of great board members’. What are the commonalities among the truly great board members? How do they engage and interact with the entrepreneur? How do they get the most out of their fellow board members?

Items Mentioned In Today’s Show:

Peter’s Most Recent Investment: Zen.ly

As always you can follow Harry, The Twenty Minute VC and Peter on Twitter here!

Likewise, you can follow Harry on Snapchat here for mojito madness and all things 20VC.

Namely is the all-in-one HR, payroll, and benefits platform your employees will love to use. It’s as intuitive as social media, but powerful enough to support the complexity of today’s workforce. Namely’s mission is to help mid-sized companies build a better workplace. See how Namely can transform your workplace at www.Namely.com.

Eero is the world’s best-reviewed wifi. A system of eero and eero Beacons wirelessly connects to blanket your home in fast, reliable WiFi, so despite the increased number of devices with Christmas coming, you’ll still be able to get powerful mesh WiFi in every nook and cranny of your home, backyard included. No more dead spots, slow spots, drop-offs, or buffering — right out of the box. Eero is only available in the US and Canada and you can check it out here!

Olaf Carlson-Wee is the Founder & CEO @ Polychain Capital, one of the world’s premier funds actively managing a portfolio of blockchain assets. Having founded the firm less than 2 years ago with their initial $4m fund, Polychain now has over $200m AUM with backing from the likes of Sequoia, Founders Fund, Andreessen Horowitz and USV just to name a few. Prior to founding Polychain, Olaf was the first employee at Coinbase serving as their Head of Risk and as product manager. In addition, Olaf has also been an active angel with a portfolio including the likes of Robinhood, Ethereum and Numerai.

Jyoti Bansal is the former Founder & CEO of AppDynamics, backed to the tune of over $350m in VC funding from the likes of Lightspeed, Greylock and Kleiner Perkins, just to name a few, before it’s ultimate acquisition by Cisco for $3.7Bn. Today, Jyoti is the Founder and CEO of BIG Labs, essentially a laboratory for creating, developing, and launching innovative ideas. The first of these ideas being turned into companies being, Harness.io the industry’s first continuous delivery as a service platform, where Jyoti is the Founder & CEO. As a result of his tremendous success, Jyoti has been a recipient of many leadership awards including, “Best Cloud Computing CEO to Work For,” “Best CEO” by San Francisco Business Times.

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In Today’s Episode You Will Learn:

1.) How Jyoti made his way from selling farm machinery with his father in India to founding and selling AppDynamics for $3.7Bn?

2.) How does Jyoti look to build world class teams around him? What are the core characteristics and profiles and seed success into an organisation? How does Jyoti look to optimise each individual function in the organisation?

3.) What did the sale process of AppDynamics look like? Did Jyoti and the team run a dual process of acquisition & IPO? How did the deal come about? What were the negotiations like? Why did Jyoti turn down the first two offers? What was critical to the successful deal?

4.) Jyoti has said before, “there are 3 simple things VCs look for”. What are those 3 things? How did the fundraising of AppDynamics go in the early days? What was it about the first 20 pitches that made VCs say no? What does Jyoti most look for now when choosing the VCs to work with?

Items Mentioned In Today’s Show:

Jyoti’s Fave Book: Crime and Punishment

As always you can follow Harry, The Twenty Minute VC and Jyoti on Twitter here!

Likewise, you can follow Harry on Snapchat here for mojito madness and all things 20VC.

Namely is the all-in-one HR, payroll, and benefits platform your employees will love to use. It’s as intuitive as social media, but powerful enough to support the complexity of today’s workforce. Namely’s mission is to help mid-sized companies build a better workplace. See how Namely can transform your workplace at www.Namely.com.

Eero is the world’s best-reviewed wifi. A system of eero and eero Beacons wirelessly connects to blanket your home in fast, reliable WiFi, so despite the increased number of devices with Christmas coming, you’ll still be able to get powerful mesh WiFi in every nook and cranny of your home, backyard included. No more dead spots, slow spots, drop-offs, or buffering — right out of the box. Eero is only available in the US and Canada and you can check it out here!

Jake Flomenberg is a Partner @ Accel, one of the top performing venture funds of the last decade with investments in the likes of Dropbox, Slack, Facebook, Deliveroo and Atlassian, just to name a few. As for Jake, at Accel he specializes on all things Big Data and has led investments in the likes of Demisto, Origami Logic, Sumo Logic, Trifacta, and Zoomdata.  Prior to Accel, Jake was director of product management at Splunk, where he was responsible for the product’s user interface and big data strategy. Before that, he worked at Cloudera where he helped the founding team tackle a broad array of sales, marketing and product issues.

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In Today’s Episode You Will Learn:

1.) How Jake made the transition from the world of operations with Cloudera and Splunk to the other side of the table, as Partner at Accel?

2.) Why does Jake believe a large element of his role is “how to make AI not BS”? How does he approach this from the three-legged stool of machine learning, data and workflow? How do each subsequently rank?

3.) To what extent is Jake concerned by the data incumbency advantages that are present in the market with Google, Amazon, Facebook and Apple (GAFA)? Where is the room for real opportunity and innovation? When should a startup be concerned about GAFA entering?

4.) How does Jake respond to Aaron Van Devender’s suggestion that the value of large datasets is overplayed? Where are the inflection points in dataset value? How does David compare the value of initial data vs derivative data and the subsequent value?

5.) How does Jake assess the current state of the cybersecurity market? Is this increased investment period sustainable or due to more macro attention and events? Where does Jake feel the real opportunity is in cyber today? Where is it overplayed?

Items Mentioned In Today’s Show:

Jake’s Fave Book: Ready Player One

Jake’s Fave Blog: The Morning Paper (Harry’s Favourite also)

Jake’s Most Recent Investment: Radar

As always you can follow Harry, The Twenty Minute VC and Jake on Twitter here!

Likewise, you can follow Harry on Snapchat here for mojito madness and all things 20VC.

Namely is the all-in-one HR, payroll, and benefits platform your employees will love to use. It’s as intuitive as social media, but powerful enough to support the complexity of today’s workforce. Namely’s mission is to help mid-sized companies build a better workplace. See how Namely can transform your workplace at www.Namely.com.

Eero is the world’s best-reviewed wifi. A system of eero and eero Beacons wirelessly connects to blanket your home in fast, reliable WiFi, so despite the increased number of devices with Christmas coming, you’ll still be able to get powerful mesh WiFi in every nook and cranny of your home, backyard included. No more dead spots, slow spots, drop-offs, or buffering — right out of the box. Eero is only available in the US and Canada and you can check it out here!

Rich Wong is a General Partner @ Accel, one of the world’s leading venture funds with investments in the likes of Dropbox, Slack, Facebook, Deliveroo and Atlassian, just to name a few. As for Rich, Rich has led investments in the likes of Rovio (IPO), SwiftKey, AdMob, MoPub and more incredible companies. Rich also sits on the boards of the likes of Checkr, Osmo, Rovio and Atlassian where he was first outside Board member and lead investor. Prior to joining Accel, Rich served as SVP of products for mobile pioneer, Openwave Systems and CMO of Covad Communications.

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In Today’s Episode You Will Learn:

1.) How Rich made his way into the world of VC with Accel from OpenWave and having been active in the mobile and broadband ecosystems?

2.) What does Rich mean when he states the rise of the “Globalisation of VC”? How does Accel both find and win deals in locations such as Australia, Finland? How do the founder’s mentalities differ to Bay area founder mentality?

3.) How does Rich think about price sensitivity when assessing opportunities? What would be considered a good return multiple when investing from the early stage fund? How does this differ from the growth fund?

4.) What is the internal structure of investment decision making at Accel? How does Rich analyze reserve allocation? How does initial to reserve decision-making differ? How does the Accel partnership determine the 10% of portfolio that are “winners”?

5.) Question from Manu Kumar @ K9: How does Rich decide when is the right time for a company to scale? What is the balance of not too early and not too late? How should unit economics play a role in this decision? What characteristic must be inherent within multiple functions of the business, pre-scaling?

Items Mentioned In Today’s Show:

Rich’s Fave Book: The Big Short

Rich’s Fave Blog: Wolf Street

Rich’s Most Recent Investment: Instabug

As always you can follow Harry, The Twenty Minute VC and Rich on Twitter here!

Likewise, you can follow Harry on Snapchat here for mojito madness and all things 20VC.

Namely is the all-in-one HR, payroll, and benefits platform your employees will love to use. It’s as intuitive as social media, but powerful enough to support the complexity of today’s workforce. Namely’s mission is to help mid-sized companies build a better workplace. See how Namely can transform your workplace at www.Namely.com.

Eero is the world’s best-reviewed wifi. A system of eero and eero Beacons wirelessly connects to blanket your home in fast, reliable WiFi, so despite the increased number of devices with Christmas coming, you’ll still be able to get powerful mesh WiFi in every nook and cranny of your home, backyard included. No more dead spots, slow spots, drop-offs, or buffering — right out of the box. Eero is only available in the US and Canada and you can check it out here!

Debbie Sterling is the Founder & CEO @ Goldieblox, an award‐winning toy company on a mission to “disrupt the pink aisle.” An engineer and entrepreneur, Sterling has made it her mission in life to tackle the gender gap in science, technology, engineering and mathematics. Sterling was named TIME’s “Person of the Moment” and Business Insider’s “30 Women Who Are Changing the World” and is regarded as one of the leaders of the movement toward getting more girls interested in engineering and technology. In January 2014, GoldieBlox beat out more than 20,000 businesses in a contest run by Intuit to become the first‐ever small business to air a commercial during the Super Bowl.

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In Today’s Episode You Will Learn:

1.) How Debbie overcame the “engineering boys club” at Stanford and the a-ha moment that led to the creation of Goldieblox?

2.) How does Debbie look to overcome those really tough times as an entrepreneur, from exclusion to the “engineering boys club” to a harsh reception at an accelerator, how did Debbie look to deal with that personally?

3.) Question from Kanyi Maqubela: Is the gender diversity issue primarily a pipeline problem? Where are the key cracks in the system? What does Debbie believe is the point of key leverage?

4.) Question from Harley Finkelstein @ Shopify: How does Debbie ensure that everyone of Goldieblox’s videos go viral as it does? What is both the content creation strategy? How does Debbie look to optimise distribution of their content to attain that virality?

5.) Why does Debbie believe that VCs are missing a massive opportunity by not investing in CPG and hardware? What single value add would be most attractive to Debbie for an investor entering the space? What must hardware and CPG founders really look for in their investor base?

Items Mentioned In Today’s Show:

Debbie’s Fave Book: The Brothers Karamazov

As always you can follow Harry, The Twenty Minute VC and Debbie on Twitter here!

Likewise, you can follow Harry on Snapchat here for mojito madness and all things 20VC.

Available in carry-on and check-in sizes, Raden is the case for better, smarter travel. By pairing the lightest and most durable materials with technology, travelers can charge their devices on the go, weigh, and track their cases. Visit Raden.com to use code 20VC at checkout. After purchase, you will receive $25 credit to Uber this Holiday season. If a UK listener, head over to Selfridges.com and/or Selfridges on Oxford St. and farfetch.com to shop Raden today.

The Simba Hybrid. The most advanced mattress in the world. With a unique combination of two thousand five hundred conical pocket springs and responsive memory foam, it offers the perfect support for two people. A mattress that responds to you and your partner’s sleeping patterns. Delivered free, with a one hundred night sleep trial, free returns and a ten year guarantee. Start your free trial at simbasleep.com

David Waxman is the Founding Partner @ TenOneTen Ventures, one of the leading new venture firms in the rising tide of LA tech. Their portfolio companies have enjoyed exits from the likes of Facebook, Google, Amazon Cisco, AirBnB and including companies like eCommerce pioneer and unicorn, Wish and the world’s leading airspace services platform, AirMap. As for David, prior to TenOneTen, David enjoyed an incredible career in operations starting with the founding of his first company, Firefly in 1995, an early pioneer in personalization and privacy technology which he sold to Microsoft in 1998. David then co-founded PeoplePC, a company dedicated to simplifying the process of joining the online world. The company went public in 2001 and was acquired by EarthLink in 2002.

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In Today’s Episode You Will Learn:

1.) How David made his way from selling a company to Microsoft and taking the next public to being one of the leading new managers in LA’s tech scene?

2.) Why does David believe that market sizing is a futile effort, or as he calls it “Tamfoolery”? What is the right way that founders should present the market to investors, both in discussion and visually? Why is it impossible for investors to foresee market magnitude?

3.) Why does David strongly dislike convertible notes? Why does he believe that they are worse for not only investor but founders too? In what rare cases do they make sense? Why are they completely ridiculous in multi-million $ deals?

4.) Why does David believe that pro-rata rights have become such a mess? How can founders honour the agreements with their early investors and satiate the ownership appetite of A funds? How would David navigate this if he were a founder today?

5.) Why does David believe the biggest asymettry in VC is the DD that founders engage with, in comparison to that of VC on Founder DD? How should founders structure this DD on investors? What is the right framework? What is the crucial question to ask?

Items Mentioned In Today’s Show:

David’s Fave Book: The Last Lion: Winston Spencer Churchill: Defender of the Realm

David’s Fave Blog: Strictly VC, Nuzzel

David’s Most Recent Investment: Velocity

As always you can follow Harry, The Twenty Minute VC and David on Twitter here!

Likewise, you can follow Harry on Snapchat here for mojito madness and all things 20VC.

Available in carry-on and check-in sizes, Raden is the case for better, smarter travel. By pairing the lightest and most durable materials with technology, travelers can charge their devices on the go, weigh, and track their cases. Visit Raden.com to use code 20VC at checkout. After purchase, you will receive $25 credit to Uber this Holiday season. If a UK listener, head over to Selfridges.com and/or Selfridges on Oxford St. and farfetch.com to shop Raden today.

The Simba Hybrid. The most advanced mattress in the world. With a unique combination of two thousand five hundred conical pocket springs and responsive memory foam, it offers the perfect support for two people. A mattress that responds to you and your partner’s sleeping patterns. Delivered free, with a one hundred night sleep trial, free returns and a ten year guarantee. Start your free trial at simbasleep.com

Bing Gordon is a Partner and Chief Product Officer @ Kleiner Perkins, one of the world’s most prestigious venture funds with prior investments in the likes of Google, Amazon, Twitter, Square and Airbnb just to name a few. At Kleiner Bing has either worked with or invested in the likes of Spotify, Zynga, Amazon, Twitter and Magic Leap, just to name a few. Bing also serves on the boards of Zynga, Zazzle, N3twork and until March this year, Amazon. Prior to Kleiner, Bing had been a long-time executive at Electronic Arts, beginning with EA’s founding in 1982 with initial funding from Kleiner Perkins. He was chief creative officer at EA from 1998 to 2008 and previously headed EA marketing and product development.

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In Today’s Episode You Will Learn:

1.) How Bing made the move from Chief Creative Officer at EA to Partner @ Kleiner Perkins?

2.) What were Bing’s biggest lessons from sitting on the boards of Amazon and Zynga and working with Jeff Bezos and Mark Pincus? What is the most important value-add that a VC should bring? What question must all new board members ask themselves?

3.) Why does Bing believe there are two types of investors in VC? How does Bing determine whether it is right to fix losers or ride winners? How does Bing look to balance between being the cheerleader or critical analyst to the CEO?

4.) What are the signs of truly great and productive board meetings? From Bing’s vast experience, which VCs does Bing most like to sit on a board with and why? Which board meeting sticks out in Bing’s memory as being of particular significance and why?

5.) What mentality do all great investors have when entering deals? What are the two commonalities of people that are largely right in their choices? How important a role does valuation play for Bing when evaluation potential opportunities?

Items Mentioned In Today’s Show:

Bing’s Fave Book: Dataclysm: Who We Are (When We Think No One’s Looking)

Bing’s Most Recent Investment: N3twork

As always you can follow Harry, The Twenty Minute VC and Bing on Twitter here!

Likewise, you can follow Harry on Snapchat here for mojito madness and all things 20VC.

Available in carry-on and check-in sizes, Raden is the case for better, smarter travel. By pairing the lightest and most durable materials with technology, travelers can charge their devices on the go, weigh, and track their cases. Visit Raden.com to use code 20VC at checkout. After purchase, you will receive $25 credit to Uber this Holiday season. If a UK listener, head over to Selfridges.com and/or Selfridges on Oxford St. and farfetch.com to shop Raden today.

The Simba Hybrid. The most advanced mattress in the world. With a unique combination of two thousand five hundred conical pocket springs and responsive memory foam, it offers the perfect support for two people. A mattress that responds to you and your partner’s sleeping patterns. Delivered free, with a one hundred night sleep trial, free returns and a ten year guarantee. Start your free trial at simbasleep.com

Chad Richard is the Senior Vice President of Business & Corporate Development @ Yelp, where he leads acquisition and investment activity. Yelp is one of the most active in the space having acquired both NoWait and Turnstyle Analytics, plus selling Eat24 to GrubHub for $287.5m, all in the past year. Prior to Yelp, Chad spent six years at Apple as Senior Director of Worldwide Product Marketing focused on Apple’s operating systems and internet services. Prior to Apple, he co-founded and was CEO of Simple Star, a photo and video software and services company that was acquired by Roxio. If that was not enough, Chad has also advised the likes of Flipboard, MoveWith and Curbside, just to name a few.

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In Today’s Episode You Will Learn:

1.) How did Chad make his way from startup founder to leading Apple’s M&A charge to today, running M&A with Yelp?

2.) What did the Apple M&A strategy look like when Chad was with the company? Why was Apple so keen to pursue a product focussed M&A strategy? What were Chad’s big learnings from that experience with Apple?

3.) How does Chad look to build potential startup pipe with Yelp? What attracts Chad to one startup over another? What does Chad wish that startup founders did and knew more about in the initial relationship building phase?

4.) Yelp also makes strategic investments, how does Chad ease founder and VC concern that a strategic investment is not an acquisition? Does a strategic investment prevent a startup from partnering with other firms? What should founders be aware of when accepting strategic investment?

5.) How does Chad analyse the compensation element? Why does Chad believe that valuing potential acquisitions is the hardest element of the process? How do acquirers determine whether to present a cash vs stock deal? What should founders consider with stock deals between private and public company stock?

Items Mentioned In Today’s Show:

Chad’s Fave Book: Disneywar

Chad’s Most Recent Investment: Turnstyle Analytics

As always you can follow Harry, The Twenty Minute VC and Chad on Twitter here!

Likewise, you can follow Harry on Snapchat here for mojito madness and all things 20VC.

Available in carry-on and check-in sizes, Raden is the case for better, smarter travel. By pairing the lightest and most durable materials with technology, travelers can charge their devices on the go, weigh, and track their cases. Visit Raden.com to use code 20VC at checkout. After purchase, you will receive $25 credit to Uber this Holiday season. If a UK listener, head over to Selfridges.com and/or Selfridges on Oxford St. and farfetch.com to shop Raden today.

The Simba Hybrid. The most advanced mattress in the world. With a unique combination of two thousand five hundred conical pocket springs and responsive memory foam, it offers the perfect support for two people. A mattress that responds to you and your partner’s sleeping patterns. Delivered free, with a one hundred night sleep trial, free returns and a ten year guarantee. Start your free trial at simbasleep.com

Mark Pincus is a serial entrepreneur and investor, best known for founding Zynga, the first company to introduce the mass market to social gaming. To date, more than one billion people around the world have played Zynga’s games, which include hits like FarmVille and Words with Friends. Mark is also known for his investments in some of the internet’s largest and most successful companies, including Facebook, Twitter, Airbnb, Snapchat and Xiaomi. One of the earliest pioneers in social networking, Mark founded multiple startups including support.com and tribe.net, before going on to create Zynga. A fun fact – recognizing the importance of social networking, in 2003 Mark teamed up with his friend Reid Hoffman, the founder of LinkedIn, to purchase the fundamental Six Degrees patent –  which broadly covers social networks – in order to keep it out of the hands of patent trolls and guarantee that all players could innovate on this technology.

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In Today’s Episode You Will Learn:

1.) Having founded one of the first social networks, Tribe and seed invested in Facebook, what convinced you that 2007 was the right time to start a social games company, Zynga?

2.) Having mastered distribution with Zynga, does Mark believe we are in a “fallow” period for consumer with a lack of distribution channel availability? If distribution is not the core problem, what does Mark believe is the fundamental issue?

3.) What have been Mark’s biggest lessons when it comes to assembling truly great teams? What does Mark mean when he says that he looks for people with “broken resumes”? Why is that so beneficial to potential candidates?

4.) When investing, how does Mark determine timing on when to ride winner and cut losers? What does Mark really mean when he says, ”you have to instill a mindset of expected value over loss avoidance”?

5.) What are the 2 biggest lies in Silicon Valley told by founders and VCs? How can founders truly test the alignment with their VC? How did Mark do this in pitches with Zynga? What were Mark’s learnings on optimising board composition and performance?

Items Mentioned In Today’s Show:

Mark’s Fave Book: Ready Player One

As always you can follow Harry, The Twenty Minute VC and Mark on Twitter here!

Likewise, you can follow Harry on Snapchat here for mojito madness and all things 20VC.

Available in carry-on and check-in sizes, Raden is the case for better, smarter travel. By pairing the lightest and most durable materials with technology, travelers can charge their devices on the go, weigh, and track their cases. Visit Raden.com to use code 20VC at checkout. After purchase, you will receive $25 credit to Uber this Holiday season. If a UK listener, head over to Selfridges.com and/or Selfridges on Oxford St. and farfetch.com to shop Raden today.

The Simba Hybrid. The most advanced mattress in the world. With a unique combination of two thousand five hundred conical pocket springs and responsive memory foam, it offers the perfect support for two people. A mattress that responds to you and your partner’s sleeping patterns. Delivered free, with a one hundred night sleep trial, free returns and a ten year guarantee. Start your free trial at simbasleep.com

David Barrett is the Founder & CEO @ Expensify, the startup relieving the world’s frustrations, one expense report at a time. With 35,000 companies and more than 5 million users, David has raised close to $30m from the likes of Redpoint, OpenView, Travis Kalanick, Baseline and SV Angel. However, David certainly does not have traditional views on funding, something we very much touch on in the interview today! Prior to Expensify, David built a peer-to-peer file transfer technology called Red Swoosh with Uber’s Travis Kalanick, which was acquired by Akamai in 2007.

Elizabeth Yin is the Co-Founder & Managing Partner @ Hustle Fund, as they describe, the ventue fund for hilariously early hustlers. Elizabeth is also the co-founder of HustleCon, a conference series for non-technical entrepreneurs to launch and scale their startups. Prior to Hustle Fund, Elizabeth was a Partner @ 500 Startups where she ran the 500 Startups seed program in Mountain View and where she and her partner saw over 20,000 startup decks. Before that Elizabeth was a successful operator, as the Co-Founder and CEO of Launchbit, an adtech platform that was acquired by BuySellAds.

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In Today’s Episode You Will Learn:

1.) How Elizabeth made her way from successful founder with LaunchBit to Partner @ 500 Startups to now founding partner of Hustle Fund?

2.) Why does Elizabeth believe that VCs fundamentally assess founders the wrong way? What is the right way to assess founders in such early stages? How can one really stress test the level of hustle from the founding team?

3.) How does Elizabeth assess innovation in the practice of venture capital? Why does Elizabeth believe that there has been very little creativity towards innovation? Who has innovatively addressed sourcing the best companies?

4.) In a world of noted rounds with a cap structure, how does Elizabeth feel about gaining the pro-rata in deals? Why does Elizabeth believe that ownership stake and portfolio size are not in conflict with one another?

5.) How does Elizabeth view the future of the VC industry? How can the early stage funnel be flipped on it’s head? Why does Elizabeth believe that SAFEs and convertible notes are the future of investing?

Items Mentioned In Today’s Show: 

Elizabeth’s Most Recent Investment: The Pill Club

As always you can follow Harry, The Twenty Minute VC and Elizabeth on Twitter here!

Likewise, you can follow Harry on Snapchat here for mojito madness and all things 20VC.

Available in carry-on and check-in sizes, Raden is the case for better, smarter travel. By pairing the lightest and most durable materials with technology, travelers can charge their devices on the go, weigh, and track their cases. Visit Raden.com to use code 20VC at checkout. With purchase, receive credit towards Tablet Hotels for the next year. If a UK listener, head over to Selfridge’s and shop Raden today.

The Simba Hybrid. The most advanced mattress in the world. With a unique combination of two thousand five hundred conical pocket springs and responsive memory foam, it offers the perfect support for two people. A mattress that responds to you and your partner’s sleeping patterns. Delivered free, with a one hundred night sleep trial, free returns and a ten year guarantee. Start your free trial at simbasleep.com

Alex Rampell is a General Partner at Andreessen Horowitz where he leads the firms fintech investments and serves on the boards of Branch, PeerStreet, Point, and Quantopian. Prior to joining a16z, he was the CEO and co-founder of TrialPay, a leading transactional advertising and payments company with 100 employees and over $300M in revenue. TrialPay was acquired by Visa in 2015. Previously, Alex cofounded FraudEliminator, the first consumer anti-phishing company, which merged into SiteAdvisor and was acquired by McAfee for $75M in 2006. Prior to joining the firm, Alex had been an active angel investor with the likes of Pinterest, Bloomreach, SiftScience among many others in his portfolio and served as an advisor to the SV Angel fund. He also co-founded three other companies: TXN, Point, and Affirm, with Max Levchin.

Lloyd Tabb is the Founder & Chairman @ Looker, the startup leader pioneering the next generation of business intelligence (BI). They have raised over $175m from some of the best in the business including CapitalG, Kleiner Perkins, First Round, Redpoint & PivotNorth. As for Llyod himself, he has spent the last 25 years revolutionizing how the world uses the internet, starting with his founding of Commerce Tools, which was acquired by Netscape. At Netscape, Lloyd led several releases of Communicator and helped define Mozilla.org. Following Netscape, Lloyd later was CTO of LiveOps, co-founder of Readyforce and founder then advisor to Luminate.

Eric Ries is the author of International Bestseller, The Lean Startup, which changed the language of business introducing terms such as A/B testing, MVP and “pivoting”. The book has sold over 1m copies and been translated into over 130 languages launching a global “lean startup” movement. Eric is also the author of the recently released, The Startup Way, detailing transformations at tech titans such as Facebook and Amazon, providing a framework for entrepreneurial management. In addition, Eric is also the Founder & CEO of The Long-Term Stock Exchange and has served as an EiR at the likes of Harvard Business School, IDEO and Pivotal.

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In Today’s Episode You Will Learn:

1.) What is the origin story of “The Lean Startup” and Eric’s realizations for the importance of the methodologies presented in the book?

2.) What is the matrix management structure? In which cases does it work well? Where does the traditional structure fall down? How does this affect how startups should think about their structure from day 1?

3.) Why does Eric believe that “we have to create a new accountability paradigm”? Why does Eric believe that most organizations have a pathological fear of failure? How is this conveyed in their structure? What are the consequent dangers of this fear? What does a “productive failure” look like?

4.) How does Eric view the creation and maintenance of culture? How exactly does Eric define culture and what it is to a company? Why does Eric not believe in manifestos!

5.)How can employees determine how committed their employer is to enacting these policies? How can this be reflected in the company attitude to budget? Why does Eric believe that each element of the organization should have independent fluctuating budgets?

Items Mentioned In Today’s Show:

Eric’s Fave Book: Ancillary Justice

Eric’s Fave Blog: Kickstarter Blog

As always you can follow Harry, The Twenty Minute VC and Eric on Twitter here!

Likewise, you can follow Harry on Snapchat here for mojito madness and all things 20VC.

Available in carry-on and check-in sizes, Raden is the case for better, smarter travel. By pairing the lightest and most durable materials with technology, travelers can charge their devices on the go, weigh, and track their cases. Visit Raden.com to use code 20VC at checkout. With purchase, receive credit towards Tablet Hotels for the next year. If a UK listener, head over to Selfridge’s and shop Raden today.

The Simba Hybrid. The most advanced mattress in the world. With a unique combination of two thousand five hundred conical pocket springs and responsive memory foam, it offers the perfect support for two people. A mattress that responds to you and your partner’s sleeping patterns. Delivered free, with a one hundred night sleep trial, free returns and a ten year guarantee. Start your free trial at simbasleep.com

Oren Zeev is the Founding Partner @ Zeev Ventures, one of Silicon Valley’s most under the radar but high performing funds with a portfolio including the likes of Houzz, Chegg, Audible and recent guest with Adi Sideman @ YouNow. Prior to founding Zeev Ventures, Oren was a General Partner @ Apax Partners, as part of the founding Apax Israel team. Before VC, Oren was a founding team member of IBM’s chip design group in Haifa.

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In Today’s Episode You Will Learn:

1.) How Oren made his way into the world of VC as part of the Apax Israel founding team? What was the catalyst behind his decision to go solo with Zeev Ventures?

2.) What were Oren’s biggest lessons from investing in the up and down of the bubble with Apax? Why did this lead to Oren’s belief that “diversification does not work”? How does that play out in his portfolio construction?

3.) Why does Oren believe that “LPs are suckers for longevity”? How does that influence the partnerships that they generally back? How does Oren assess VC partnership dynamics? How should founders evaluate VC partner relationships?

4.) Oren has spent over 1,000 hours on the boards of some of the most transformational companies, how has he seen his style of board member change over the years? What has been his biggest lesson? What board member behavior does he dislike the most?

5.) Why is Oren skeptical of thematic investing? Why is this not optimal in producing funds that deliver out-sized returns? What examples does Oren have that prove adopting a generalist approach is beneficial from a returns standpoint?

Items Mentioned In Today’s Show:

Oren’s Fave Book: The Innovator’s Dilemma

Oren’s Fave Blog: AVC, The Twenty Minute VC

Oren’s Most Recent Investment: Next Insurance

As always you can follow Harry, The Twenty Minute VC and Oren on Twitter here!

Likewise, you can follow Harry on Snapchat here for mojito madness and all things 20VC.

Available in carry-on and check-in sizes, Raden is the case for better, smarter travel. By pairing the lightest and most durable materials with technology, travelers can charge their devices on the go, weigh, and track their cases. Visit Raden.com to use code 20VC at checkout. With purchase, receive credit towards Tablet Hotels for the next year. If a UK listener, head over to Selfridge’s and shop Raden today.

The Simba Hybrid. The most advanced mattress in the world. With a unique combination of two thousand five hundred conical pocket springs and responsive memory foam, it offers the perfect support for two people. A mattress that responds to you and your partner’s sleeping patterns. Delivered free, with a one hundred night sleep trial, free returns and a ten year guarantee. Start your free trial at simbasleep.com

Jack Altman is the Founder & CEO of Lattice, actually our partners for this month on the show and as you will hear, they are the #1 performance management solution for growing companies. Lattice have raised close to $10m in funding from some of our favourites in industry including the likes of Miles Grimshaw @ Thrive, Khosla Ventures, Elad Gil, Alexis Ohanian and YC’s Daniel Gross. Prior to founding Lattice, Jack was the Head of Business Development @ Lattice where he saw the firm move into hyperscaling. Jack has also build an incredible angel portfolio including the likes of Gusto, OpenDoor, Instacart, Zenefits and Soylent.

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In Today’s Episode You Will Learn:

1.) How Jack made his way from leading angel investor to Head of Business Development @ TeeSpring to the world of SaaS with the founding of Lattice?

2.) What does Jack mean when he says “founders must do what it takes to get the best people on board”? To what extent does Jack believe that great investors provide social validity to future hires?

3.) How does Jack think about really getting the best from his team? What is core to empowering them? Why does he believe that EQ is the most important skill for managers? What does Jack believe is the right way to give clear and direct feedback?

4.) Why does Jack believe that the best relationships with investors are less formal? What does Jack really look for in his relationships with investors? What does Jack mean when he says ”investor advice is right on valuation”?

Items Mentioned In Today’s Show:

Jack’s Fave Book: Meditations

Jack’s Fave Blog: SaaStr

As always you can follow Harry, The Twenty Minute VC and Jack on Twitter here!

Likewise, you can follow Harry on Snapchat here for mojito madness and all things 20VC.

Lattice is the #1 performance management solution for growing companies. With Lattice, it’s easy to launch 360 performance review cycles as often as you want. And you also get a continuous feedback system with OKR goal tracking, real-time feedback, and 1-on-1 meetings to make sure employees get feedback between reviews. Find out why the likes of CoinBase, PlanGrid, Birchbox and WePay trust Lattice as their performance management solution by heading over to lattice.com to start investing in your people. That’s Lattice.com.

Recurly, the company powering subscription success, with Recurly’s enterprise-class subscription management platform providing rapid time-to-value without requiring massive integration effort and expense and they have the ability to not only increase revenue by 7% but also reduce the all-important churn rate. That is why thousands of customers from Twitch to HubSpot to CBS Interactive trust Recurly as their subscription management platform. Check them out on recurly.com that really is a must.

Paul Buchheit is a Partner @ Y Combinator, the world’s most successful accelerator with portfolio companies including the likes of AirBnB, Dropbox, Stripe, Zenefits, Twitch, the list goes on. Before YC and starting from the beginning, Paul was the 23rd employee at Google where he created Gmail, developed the original prototype for Google AdSense and even suggested the company’s former motto, “Don’t Be Evil”. He then started FriendFeed in 2006 where he created the like button as we know it, the company was later acquired by Facebook where Paul worked until his move to Y Combinator in 2010, where he is a partner. Paul is also a prolific angel having created an immense portfolio with the likes of Gusto, Checkr, Optimizely and many more incredible teams.

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In Today’s Episode You Will Learn:

1.) How Paul made his way from creating Gmail in the early Google days, to founding the like button we know today, to being with Y Combinator currently?

2.) What does Paul believe it is that makes Paul Graham (PG) the special individual that he is? How has Paul seen the scaling of PG and Jessica Livingstone as leaders with the scaling of YC?

3.) Why does Paul believe it is fundamental to attain 100 happy users? How can one stress test levels of customer satisfaction accurately? How can founders determine which users and which advice to incorporate and which to disregard?

4.) Having worked alongside the likes of Mark Zuckerberg and Larry Paige, what does Paul believe makes the truly special founders? How does Paul assess the balance between stubbornness and vision? What is the telltale sign of stubbornness beginning?

5.) Question from Justin Kan: How does Paul look to determine the 10% that delivers 90% of the value? Where has Paul made mistakes and seen others make mistakes in trying to implement this level of focus?

Items Mentioned In Today’s Show:

Paul’s Fave Book: Eckhart Tolle

Paul’s Most Recent Investment: Greo

As always you can follow Harry, The Twenty Minute VC and Paul on Twitter here!

Likewise, you can follow Harry on Snapchat here for mojito madness and all things 20VC.

Lattice is the #1 performance management solution for growing companies. With Lattice, it’s easy to launch 360 performance review cycles as often as you want. And you also get a continuous feedback system with OKR goal tracking, real-time feedback, and 1-on-1 meetings to make sure employees get feedback between reviews. Find out why the likes of CoinBase, PlanGrid, Birchbox and WePay trust Lattice as their performance management solution by heading over to lattice.com to start investing in your people. That’s Lattice.com.

Recurly, the company powering subscription success, with Recurly’s enterprise-class subscription management platform providing rapid time-to-value without requiring massive integration effort and expense and they have the ability to not only increase revenue by 7% but also reduce the all-important churn rate. That is why thousands of customers from Twitch to HubSpot to CBS Interactive trust Recurly as their subscription management platform. Check them out on recurly.com that really is a must.

Ali Rowghani is a Partner @ Y Combinator, the world’s most successful accelerator with portfolio companies including the likes of AirBnB, Dropbox, Stripe, Zenefits, Twitch, the list goes on. At YC, Ali leads the Continuity Fund where has made investments in the likes of Segment, Convoy and Lob, where he also sits on the board of all 3. Prior to investing with YC, Ali spent 4 years at Twitter, starting as CFO before becoming COO. Whilst at Twitter, Ali saw the company scale from $0 revenues to over $2Bn and 20m users to close to 300m users. Before Twitter, Ali was the CFO @ Pixar Animation Studios.

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In Today’s Episode You Will Learn:

1.) How Ali made his way from CFO @ Pixar and COO @ Twitter to now leading YC’s continuity fund?

2.) Ali describes a story of his time at Pixar working with Steve Jobs? How did he carry himself both as a leader and an operator? What was it about Steve that makes Ali say he is the most impressive exec he has ever worked with?

3.) Having seen the likes of Steve Jobs, Ed Catmull, Jack Dorsey in action what have been Ali’s biggest takeaways with regards to what makes the truly great leaders? Why does Ali believe there are 3 traits all great leaders share? What are they?

4.) How does Ali look to bring that experience to his role now, investing with YC Continuity? How does that affect his mindset and evaluation when assessing investment opportunities today?

5.) Why does Ali believe that too many startups have been damaged by the amount of capital they have raised? As a former CFO, how does Ali analyze the capital being raised today and some of the burn rates in the valley?

Items Mentioned In Today’s Show:

Ali’s Fave Book: Theodore Roosevelt by Edmund Morris

Ali’s Fave Blog: Bill Gurley: Above The Crowd

Ali’s Most Recent Investment: Segment

As always you can follow Harry, The Twenty Minute VC and Ali on Twitter here!

Likewise, you can follow Harry on Snapchat here for mojito madness and all things 20VC.

Lattice is the #1 performance management solution for growing companies. With Lattice, it’s easy to launch 360 performance review cycles as often as you want. And you also get a continuous feedback system with OKR goal tracking, real-time feedback, and 1-on-1 meetings to make sure employees get feedback between reviews. Find out why the likes of CoinBase, PlanGrid, Birchbox and WePay trust Lattice as their performance management solution by heading over to lattice.com to start investing in your people. That’s Lattice.com.

Recurly, the company powering subscription success, with Recurly’s enterprise-class subscription management platform providing rapid time-to-value without requiring massive integration effort and expense and they have the ability to not only increase revenue by 7% but also reduce the all-important churn rate. That is why thousands of customers from Twitch to HubSpot to CBS Interactive trust Recurly as their subscription management platform. Check them out on recurly.com that really is a must.

Adi Sideman is the Founder & CEO @ YouNow. Since founding the company in 2011, Adi has grown YouNow to be a global social network with more than 100 million user sessions a month, and creators now producing more than 50,000 hours of original live content each day. They recently released PROPS (Telegram available here), the next generation platform that leverages the power of crypto economics & participation in digital media. To fund this growth, they have raised over $25m in funding from some of the greats of the investing world including Andy Weissman @ USV, David Pakman @ Venrock and future guest Oren Zeev. Due to this incredible progress, YouNow has been named one of the most innovative companies of 2016 by Fast Company and was a finalist for Fastest Rising Startup of 2016 at the Crunchies Awards.

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In Today’s Episode You Will Learn:

1.) How Adi made his way into the world of participatory digital content, came to found the world’s first online karaoke company and then found YouNow?

2.) Setting the scene now, where are we at with TV? What platform does Adi believe will rise formidably in it’s place? How does that affect the age-old industry of advertising? Why does Adi believe after so many years, now is the time for micro-payment content creation?

3.) Why does the digital media content landscape need to be decentralized? What is fundamentally broken with the current centralised networks? What are the benefits of such decentralization?

4.) How does Adi envision this decentralization to be? Does Adi believe we will build new decentralized protocols and exact the decentralized network through them or does he believe we will integrate new protocols into existing services?

5.) Why does this decentralized network be crypto-based? With centralized networks the value largely accrues to investors and founders, how does Adi sell the value of a decentralized network to an investor base with fiduciary responsibilities?

Items Mentioned In Today’s Show:

Adi’s Favourite Book: The Last Lion: Winston Spencer Churchill 

As always you can follow Harry and The Twenty Minute VC on Twitter here!

Likewise, you can follow Harry on Snapchat here for mojito madness and all things 20VC.

Lattice is the #1 performance management solution for growing companies. With Lattice, it’s easy to launch 360 performance review cycles as often as you want. And you also get a continuous feedback system with OKR goal tracking, real-time feedback, and 1-on-1 meetings to make sure employees get feedback between reviews. Find out why the likes of CoinBase, PlanGrid, Birchbox and WePay trust Lattice as their performance management solution by heading over to lattice.com to start investing in your people. That’s Lattice.com.

Recurly, the company powering subscription success, with Recurly’s enterprise-class subscription management platform providing rapid time-to-value without requiring massive integration effort and expense and they have the ability to not only increase revenue by 7% but also reduce the all-important churn rate. That is why thousands of customers from Twitch to HubSpot to CBS Interactive trust Recurly as their subscription management platform. Check them out on recurly.com that really is a must.

Nicole Quinn is a Partner @ Lightspeed, one of the world’s leading venture funds with a portfolio including the likes of Snapchat, Nest, StitchFix, AppDynamics and Max Levchin’s Affirm, just to name a few from their incredible portfolio. At Lightspeed, Nicole focuses on the consumer market having made investments in the likes of Cheddar, Zola and Rothy’s. Prior to Lightspeed, Nicole worked at Nutmeg, one of London’s leading fintech players and before that spent 8 years covering consumer, eCommerce and brands at Morgan Stanley on the equity sales and research side. At Morgan Stanley, Nicole worked on the IPOs for Facebook, Groupon and Pandora. Fun fact: Nicole is also a star of the big screen featuring on Apple TV’s Planet of The Apps.

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In Today’s Episode You Will Learn:

1.) How Nicole made her way from Morgan Stanley to a leading London Fintech player to now, a partner a Lightspeed in San Francisco?

2.) How does Nicole define “digitally native brands”? What are the core benefits of owning the entire customer journey? Why does Nicole believe that brand is a key network effect today?

3.) Why does Nicole disagree that we are in a fallow period for consumer? How does Nicole analyze the incumbent heavy competitive landscape? Does Nicole believe that Amazon does more to make the market than destroy it?

4.) Why does Nicole believe we are in a consolidatory environment? What about the current ecosystem makes now the most exciting time for M&A in a long time? How does Nicole analyze M&A’s ability to move the needle with transactions like Bonobos’ acquisition?

5.) Being a star of Planet of The Apps, how important does Nicole think it is for investors to have public brands today? How does Nicole view VCs and digitally native brands in the same way? How does this mean that VCs should act in market?

Items Mentioned In Today’s Show:

Nicole’s Fave Book: The Magic Faraway Tree by Enid Blyton

Nicole’s Fave Blog: Lean Luxe

Nicole’s Most Recent Investment: Rothy’s

As always you can follow Harry, The Twenty Minute VC and Nicole on Twitter here!

Likewise, you can follow Harry on Snapchat here for mojito madness and all things 20VC.

Lattice is the #1 performance management solution for growing companies. With Lattice, it’s easy to launch 360 performance review cycles as often as you want. And you also get a continuous feedback system with OKR goal tracking, real-time feedback, and 1-on-1 meetings to make sure employees get feedback between reviews. Find out why the likes of CoinBase, PlanGrid, Birchbox and WePay trust Lattice as their performance management solution by heading over to lattice.com to start investing in your people. That’s Lattice.com.

Recurly, the company powering subscription success, with Recurly’s enterprise-class subscription management platform providing rapid time-to-value without requiring massive integration effort and expense and they have the ability to not only increase revenue by 7% but also reduce the all-important churn rate. That is why thousands of customers from Twitch to HubSpot to CBS Interactive trust Recurly as their subscription management platform. Check them out on recurly.com that really is a must.

Semil Shah is the founder of Haystack, an early stage investment firm now investing out of it’s fourth fund, with previous investments in the likes of Instacart, DoorDash, Giphy, OpenDoor & Managed by Q. Semil is also a Venture Partner @ GGV Capital, one of the leading multi-stage funds and in the past he has also been a consultant to the likes of Kleiner Perkins, DFJ, General Catalyst and more. If that was not enough, Shah also has an extensive career in media having been a contributor for both TechCrunch and the Harvard Business Review in the past. Due to all of this, Shah is known for being on the speed dial of some of the industry’s most respected VCs with the likes of Marc Andreessen naming him one of his ’55 Unknown Rockstars in Tech’.

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In Today’s Episode You Will Learn:

1.) How Semil made the transition from the world of writing to investing alongside some of the best in venture with Haystack?

2.) Why do more and more managers want to introduce institutional capital into their LP base? What are the advantages? What are the drawbacks? Where does Semil see most managers going wrong when pursuing institutional capital for the first time?

3.) What does Semil mean when he states the importance of “pre-marketing”? How open is one in these pre-discussions with potential LPs? What is the right amount of time to be pre-marketing for? How does Semil determine whether to adopt a piece of LP advice and when not to?

4.) In the raising process, why does Semil never like to the use the deck when meeting in person? What core elements of the presentation did LPs always hone in on? What tips does Semil have to potential managers to ensure they can pitch at any time, not just the boardroom?

5.) How has moving from non-institutional to institutional fund, changed how Semil thinks about reserve allocation? Why does Semil believe that the majority of LPs have a wrong thesis to reserve allocation?

6.) Why does Semil believe the VC business model is severely constrained in terms of exits through IPO and acquisition? What does this mean for the use of secondaries? How will managers need to incorporate this into their strategy?

Items Mentioned In Today’s Show:

Semil’s Fave Blog: AVC 

Semil’s Most Recent Investment: Ironclad

As always you can follow Harry, The Twenty Minute VC and Semil on Twitter here!

Likewise, you can follow Harry on Snapchat here for mojito madness and all things 20VC.

Lattice is the #1 performance management solution for growing companies. With Lattice, it’s easy to launch 360 performance review cycles as often as you want. And you also get a continuous feedback system with OKR goal tracking, real-time feedback, and 1-on-1 meetings to make sure employees get feedback between reviews. Find out why the likes of CoinBase, PlanGrid, Birchbox and WePay trust Lattice as their performance management solution by heading over to lattice.com to start investing in your people. That’s Lattice.com.

Recurly, the company powering subscription success, with Recurly’s enterprise-class subscription management platform providing rapid time-to-value without requiring massive integration effort and expense and they have the ability to not only increase revenue by 7% but also reduce the all-important churn rate. That is why thousands of customers from Twitch to HubSpot to CBS Interactive trust Recurly as their subscription management platform. Check them out on recurly.com that really is a must.

Julia Hartz is the Co-Founder & CEO @ Eventbrite, the unicorn startup that is the world’s largest event technology platform, powering over 2 million events around the world each year. They have raised over $330m from some of the greats of industry including Roelof Botha @ Sequoia Capital, Jeff Clavier @ SoftTech, David Saks, Bebo’s Michael Birch, Tiger Global and many more. Under Julia’s leadership, she has taken Eventbrite to become the world’s largest event technology platform and has received multiple accolades for workplace culture, being named the best place to work in SF for 7 years running. Personally, Julia has won numerous awards including Fortune’s 40 Under 40, Inc’s 35 Under 35 and Most Powerful Female Entrepreneurs.

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In Today’s Episode You Will Learn:

1.) How Julia came to found Eventbrite with her husband Kevin from a small apartment in Potrero Hill and turned it into the unicorn it is today?

2.) How did Julia and Kevin meet? What was the meet-cute? How did that translate into the founding of Eventbrite? How did Julia think about partnering with her fiancee at the time, as a business partner? What made it also a great business partnership?

3.) Why does Julia believe that creating a company is like creating a family? How has Julia seen herself scale as CEO of the company, with the immense scaling and growth of the firm? What have been the challenges and how did she overcome them?

4.) What does Julia believe are the requirements for successful CEO transition? How can this be managed correctly both internally and externally? What other elements made last year a particularly momentus year for change at Eventbrite?

5.) How does Julia think about balancing the immediate elements of the present day with the long-term vision for the roadmap? What is the right mindset to adopt? How does one look to prevent “Innovators Dilemma”? How does Julia split her time?

Items Mentioned In Today’s Show:

Julia’s Fave Book: Overwhelmed

Julia’s Fave Blog: The Skimm

As always you can follow Harry, The Twenty Minute VC and Julia on Twitter here!

Likewise, you can follow Harry on Snapchat here for mojito madness and all things 20VC.

Lattice is the #1 performance management solution for growing companies. With Lattice, it’s easy to launch 360 performance review cycles as often as you want. And you also get a continuous feedback system with OKR goal tracking, real-time feedback, and 1-on-1 meetings to make sure employees get feedback between reviews. Find out why the likes of CoinBase, PlanGrid, Birchbox and WePay trust Lattice as their performance management solution by heading over to lattice.com to start investing in your people. That’s Lattice.com.

Recurly, the company powering subscription success, with Recurly’s enterprise-class subscription management platform providing rapid time-to-value without requiring massive integration effort and expense and they have the ability to not only increase revenue by 7% but also reduce the all-important churn rate. That is why thousands of customers from Twitch to HubSpot to CBS Interactive trust Recurly as their subscription management platform. Check them out on recurly.com that really is a must.

Sam Arbesman is the Scientist-In-Residence @ Lux Capital, the fund that supports scientists and entrepreneurs who pursue counter-conventional solutions to the most vexing puzzles of our time, the more ambitious the project, the better. Sam works with companies and founders that recognize the future happens at the boundaries of science and technology infusing computation into everything from biology to manufacturing.Sam’s scientific research has been published in everything from the Wall Street Journal to The New York Times and The Atlantic. Sam is also the author of the award-winning The Half-Life of Facts and the new book Overcomplicated: Technology at the Limits of Comprehension.

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In Today’s Episode You Will Learn:

1.) How Sam made his move from being a best-selling author to Scientist in Residence for Lux Capital? As Scientist in Residence, what does Sam do on a day-to-day basis?

2.) What does Sam mean when he says that startups need to embrace “radical interdisciplinarity”? What really is “radical interdisciplinarity”? What are the benefits it brings to an organisation? Does this go contra the importance of specialisation?

3.) How does Sam view the partnership between man and machine? Why does Sam believe we will see computational creativity in a way never seen before? How does Sam view the societal barriers to the embracing of this partnership?

4.) How does Sam view the promise of analogizing in the face of such complex systems? How does Sam assess the perils of such analogies? Does Sam believe that VCs of today are equipped to invest in such complex systems? What must they remember?

Items Mentioned In Today’s Show:

Sam’s Fave Book: The Baroque Cycle by Neal Stephenson, The Three Body Problem

Sam’s Fave Blog: Marginal Revolution

As always you can follow Harry, The Twenty Minute VC and Sam on Twitter here!

Likewise, you can follow Harry on Snapchat here for mojito madness and all things 20VC.

Lattice is the #1 performance management solution for growing companies. With Lattice, it’s easy to launch 360 performance review cycles as often as you want. And you also get a continuous feedback system with OKR goal tracking, real-time feedback, and 1-on-1 meetings to make sure employees get feedback between reviews. Find out why the likes of CoinBase, PlanGrid, Birchbox and WePay trust Lattice as their performance management solution by heading over to lattice.com to start investing in your people. That’s Lattice.com.

Recurly, the company powering subscription success, with Recurly’s enterprise-class subscription management platform providing rapid time-to-value without requiring massive integration effort and expense and they have the ability to not only increase revenue by 7% but also reduce the all-important churn rate. That is why thousands of customers from Twitch to HubSpot to CBS Interactive trust Recurly as their subscription management platform. Check them out on recurly.com that really is a must.

Aaron VanDevender is the Chief Scientist at Founders Fund, one of the world’s leading fund with investments in the likes of Facebook, Airbnb, SpaceX, Spotify and many more incredible companies. At Founders Fund, Aaron monitors the scientific impact of the portfolio, works with portfolio companies, assesses new technologies, and conducts his own research. Prior to Founders Fund, Aaron has designed single-photon and single-atom quantum computers in academia and government (NIST), advanced the quantum-mechanical theory for microscopic black holes, patented the fastest transparent optical switch, and is a co-inventor of yoctotechnology. He then developed next-generation DNA sequencing technology at Halcyon Molecular. His broad scientific interests encompass energy, biotech, nanotech, and computing.

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In Today’s Episode You Will Learn:

1.) How Aaron made his way from microscopic black holes and DNA sequencing to the world of Founders Fund? What does a Scientist-In-Residence do?

2.) Why does Aaron believe that AI is mostly a scam? Where does Aaron see and then want to see further progression in the field of AI and ML? How does Aaron distinguish between crazy and genius? What are the signs?

3.) Why does Aaron believe that the value of massive datasets is largely overplayed? What characteristics of datasets are exciting for Aaron to see when evaluating an opportunity? Where and how can datasets be misleading and lose their value?

4.) How does Aaron view the societal effects of 4m truck drivers being unemployed by the rise of self-driving? How does Aaron view trucking both as goods distribution and wealth distribution networks?

5.) How does Aaron view the implementation of universal basic income? Why does Aaron believe we have a challenge decoupling wealth and virtue? To what extent is this a core problem?

Items Mentioned In Today’s Show:

Aaron’s Fave Book: Tales From The Thousand & One Arabian Nights

Aaron’s Fave Blog: Slash Dot

Investment Aaron is Most Excited By: Ayar Labs

As always you can follow Harry, The Twenty Minute VC and Aaron on Twitter here!

Likewise, you can follow Harry on Snapchat here for mojito madness and all things 20VC.

Lattice is the #1 performance management solution for growing companies. With Lattice, it’s easy to launch 360 performance review cycles as often as you want. And you also get a continuous feedback system with OKR goal tracking, real-time feedback, and 1-on-1 meetings to make sure employees get feedback between reviews. Find out why the likes of CoinBase, PlanGrid, Birchbox and WePay trust Lattice as their performance management solution by heading over to lattice.com to start investing in your people. That’s Lattice.com.

Recurly, the company powering subscription success, with Recurly’s enterprise-class subscription management platform providing rapid time-to-value without requiring massive integration effort and expense and they have the ability to not only increase revenue by 7% but also reduce the all-important churn rate. That is why thousands of customers from Twitch to HubSpot to CBS Interactive trust Recurly as their subscription management platform. Check them out on recurly.com that really is a must.

Luis Von Ahn is the Founder & CEO @ Duolingo, the leading language learning platform with over 100m users. They have backing from some of the best in the investing world with over $100m in funding from the likes of USV, Kleiner Perkins, NEA, Google Capital and even Ashton Kutcher. Prior to Duolingo, Luis is known for inventing CAPTCHAs, being a MacArthur Fellow (“genius grant” recipient), and selling two companies to Google in his 20’s. Luis has been named one of the 10 Most Brilliant Scientists by Popular Science Magazine, one of the 20 Best Brains Under 40 by Discover.

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In Today’s Episode You Will Learn:

1.) How Luis, a man as he describes “never great at learning languages”, came to found the leading language learning app, Duolingo?

2.) Why do VCs generally believe Edtech to be such a “hard” space? Is that really a fair assumption? How does the role of government change the distribution and landscape of edtech? How does content creation play a pivotal role in edtech today?

3.) What role does Luis believe AI and ML will play for the future of edtech? Will the transition to bots represent a transformational shift in the interface paradigm? How does gamification and edtech integrate? Why does Luis always measure themselves against the most addictive of games?

4.) How has Luis seen himself scale and change as a leader with the scaling of the firm? What story shows an element that Luis struggled with and how did he overcome it? What were the major inflection points in the growth of the firm?

5.) Duolingo recently raised their $25m Series E, how did this round differ from prior rounds? Why did they want to negotiate down the figure they wanted to raise? How did Valley based VCs present herd mentality for the duration of the recent raise?

Items Mentioned In Today’s Show:

Luis’s Fave Book: Godel, Escher, Bach: An Eternal Golden Braid 

Luis’ Fave Blog: AVC by Fred Wilson

As always you can follow Harry, The Twenty Minute VC and Luis on Twitter here!

Likewise, you can follow Harry on Snapchat here for mojito madness and all things 20VC.

Lattice is the #1 performance management solution for growing companies. With Lattice, it’s easy to launch 360 performance review cycles as often as you want. And you also get a continuous feedback system with OKR goal tracking, real-time feedback, and 1-on-1 meetings to make sure employees get feedback between reviews. Find out why the likes of CoinBase, PlanGrid, Birchbox and WePay trust Lattice as their performance management solution by heading over to lattice.com to start investing in your people. That’s Lattice.com.

Recurly, the company powering subscription success, with Recurly’s enterprise-class subscription management platform providing rapid time-to-value without requiring massive integration effort and expense and they have the ability to not only increase revenue by 7% but also reduce the all-important churn rate. That is why thousands of customers from Twitch to HubSpot to CBS Interactive trust Recurly as their subscription management platform. Check them out on recurly.com that really is a must.

Michael Dearing has established himself as an icon of early-stage venture over the last decade. With his founding of Harrison Metal in 2006, he has backed the likes of AdMob, MoPub, Heroku, TellApart and Harry’s just to name a few of his incredible companies. Prior to being in VC, Michael spent 6 years at eBay across numerous roles and before that held positions at Shoe Warehouse as CEO, The Walt Disney Company in corporate strategy and then Bain & Co as a consultant.

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In Today’s Episode You Will Learn:

1.) How Michael made his way into the world of venture from selling shoes with Shoe Warehouse to eBay to founding his own fund?

2.) Michael has said before that he looks for “personal exceptionalism” within the teams he backs, what does that really mean? How does he distinguish brilliance from arrogance? What is the balance between vision and stubbornness?

3.) How does Michael think about price sensitivity? How does he use it as a determining factor to test his level of conviction in the deal? More broadly, how does Michael view pricing in the market today? Why are the convertible debt markets so toxic?

4.) How does Michael view strategy around reserve allocation? Why does Michael believe reserves are where he has made the biggest mistakes? What are his takeaways from those mistakes? Why does recycling not feature as a core tenet of his strategy?

5.) Why does Michael believe that “benevolent dictatorship” is a beautiful thing? Does this thesis change in the debate over founder vs company first? How does Michael use McCallum’s 5 key principles to assess founders and their ability?

Items Mentioned In Today’s Show:

Michael’s Fave Book: Confederacy of Dunces

Michael’s Most Recent Investment: Astro

As always you can follow Harry, The Twenty Minute VC and Michael on Twitter here!

Likewise, you can follow Harry on Snapchat here for mojito madness and all things 20VC.

Lattice is the #1 performance management solution for growing companies. With Lattice, it’s easy to launch 360 performance review cycles as often as you want. And you also get a continuous feedback system with OKR goal tracking, real-time feedback, and 1-on-1 meetings to make sure employees get feedback between reviews. Find out why the likes of CoinBase, PlanGrid, Birchbox and WePay trust Lattice as their performance management solution by heading over to lattice.com to start investing in your people. That’s Lattice.com.

Recurly, the company powering subscription success, with Recurly’s enterprise-class subscription management platform providing rapid time-to-value without requiring massive integration effort and expense and they have the ability to not only increase revenue by 7% but also reduce the all-important churn rate. That is why thousands of customers from Twitch to HubSpot to CBS Interactive trust Recurly as their subscription management platform. Check them out on recurly.com that really is a must.

Samir Kaji is what one might call, a master of all things seed stage and micro VC financing. Over his 18 years in venture capital, Samir has assisted or advised over 700 companies and 300 VC firms and has completed tech financing transactions totaling over $4.0 billion in committed capital. Today, Samir is the Senior Managing Director @ First Republic Bank where leads the technology banking team managing venture capital and startup company relationships. He joined First Republic in 2013 from Silicon Valley Bank, where he was also a managing director.

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In Today’s Episode You Will Learn:

1.) How Samir made his entry into the world of VC from the ground up and has come to advise and assist on over $4Bn worth of capital commitments?

2.) Where is the micro VC and seed market today? What is the overview? What has fundamentally changed over the last few years? Are all increases in capital supply good or is this too much? Why is Samir concerned by valuation bloat at seed?

3.) How are LPs reacting to this explosion in seed and micro fund managers? How does this differ when assessing the differing classes of LP from institutions to HNWs and family offices? What are the likelihoods of 1st-time funds attaining institutional capital?

4.) How should potential managers think about the right fund size to raise? How long a timeline should be given to the raising of micro and seed funds? What exceptions are there to this timeline? How does the role of multiple closings play into this timeline?

5.) How does Samir differentiate between raising a fund and building a franchise? What does this mean about how a certain set of anagers not only engages in the fundraising process but also depicts the narrative?

Items Mentioned In Today’s Show:

Samir’s Fave Book: Hard Thing About Hard Things

Samir’s Fave Blog: Strictly VC, AVC by Fred Wilson

As always you can follow Harry, The Twenty Minute VC and Samir on Twitter here!

Likewise, you can follow Harry on Snapchat here for mojito madness and all things 20VC.

Lattice is the #1 performance management solution for growing companies. With Lattice, it’s easy to launch 360 performance review cycles as often as you want. And you also get a continuous feedback system with OKR goal tracking, real-time feedback, and 1-on-1 meetings to make sure employees get feedback between reviews. Find out why the likes of CoinBase, PlanGrid, Birchbox and WePay trust Lattice as their performance management solution by heading over to lattice.com to start investing in your people. That’s Lattice.com.

Recurly, the company powering subscription success, with Recurly’s enterprise-class subscription management platform providing rapid time-to-value without requiring massive integration effort and expense and they have the ability to not only increase revenue by 7% but also reduce the all-important churn rate. That is why thousands of customers from Twitch to HubSpot to CBS Interactive trust Recurly as their subscription management platform. Check them out on recurly.com that really is a must.

Sami Inkinen is the Founder & CEO @ Virta Health, the startup on a mission to reverse type 2 diabetes for 100m people by 2025. They have raised over $35m in funding from the likes of Max Levchin, Ev William’s Obvious Ventures, Paypal, Ray Tonsing @ Caffeinated Capital and previous 20VC guest, Bob Kocher @ Venrock. Previously, Sami was a co-founder, COO and President of Trulia until it’s IPO and eventual sale for $3.6B. Sami, an avid athlete, is a triathlon world champion in his age group, and recently rowed across the Pacific Ocean from California to Hawaii unsupported with his wife at a record speed to raise awareness about healthy nutrition.

Bram Sugarman is the Director of Corporate Development & Strategic Partnerships at Shopify, the e-commerce titan that has over 500 merchants in 150 countries on their platform. Prior to joining Shopify, Bram was a venture capitalist with OMERS Ventures, the venture capital arm of one the largest pension funds in the world. As a VC, Bram worked on more than 20 transactions helping the OMERS Ventures grow from 1 investment to 24 investments. Bram helped lead and manage OMERS Ventures’ investments in Shopify (IPO), HootSuite, VidYard, PasswordBox (Acquired by Intel), BusBud, Hopper, League, and AppHero (Acquired by Fuse Powered).

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In Today’s Episode You Will Learn:

1.) How Bram made his way into the world of VC and then jumped to the other side of the table, buying startups with Shopify?

2.) What does using corporate development as a platform to accelerate product roadmap mean? How does this mean it differentiates from traditional M&A? How does Bram work with product team in the M&A process? What are the benefits of doing this?

3.) How does Bram assess the attractiveness of acquihires? What are the 2 differing types of acquihires? What are the essential characteristics of the individuals in those acquihire situations?

4.) With integration being the biggest risk of M&A, what does the ideal post-acquisition process look like? What must be done on both the side of the startup and the acquiror to make the process as smooth as possible?

5.) With regards to pricing and valuation, why does Bram urge founders to consider the long term and what does that mean? How can founders determine the truth with regards to long term objectives of their acquiror?

Items Mentioned In Today’s Show:

Bram’s Fave Book: Einstein by Walter Isaacson

Bram’s Most Recent Acquisition: Oberlo

As always you can follow Harry, The Twenty Minute VC and Bram on Twitter here!

Likewise, you can follow Harry on Snapchat here for mojito madness and all things 20VC.

If you are an early stage startup, the right infrastructure and support systems are critical, that is where First Republic is so good. First Republic’s resources network and expertise allow entrepreneurs to customise a solid foundation for their business. Why First Republic, well you get to leverage their incredible network of VC firms to prepare you for future fundraising events, you get to count on a single point of contact that will be there for you and your employees, you get access to exclusive events and networking opportunities. Their clients include the likes of Instacart, eShares and Wish just to name a few. Check it out by heading over to innovation.firstrepublic.com

Segment allows you to collect data from every platform (mobile, web, server, cloud apps) and load it into Segment. Segment then sends the customer data to your tools and destinations where it can be used most effectively, destinations include email, analytics, warehouses, helpdesks and more. With over 200 sources and destinations on the Segment platform that can empower your team, Segment really is the last integration you will ever do and that is why the world’s best companies use segment to drive growth and revenue including Atlassian, New Relic and Crate & Barrel. Simply head over to segment.com to find out more.

Matt Switzer is the Senior Vice President of Strategy and Corporate Development @ Hootsuite, the social media management platform that has raised venture funding from some of the best in the world including Accel, Insight Venture Partners and Fidelity. At HootSuite, Matt and his team have raised over $250m in funding, acquired 8 companies and launched 4 new products. Prior to Hootsuite, Matt was on the other side of the table as a VC, where he helped to establish a new fund and manage an incubator.

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In Today’s Episode You Will Learn:

1.) How Matt made his way into the world of VC and then decided to jump to the other side of the table as acquirer with Hootsuite?

2.) What is the build, buy or partner thinking process? When analysing markets, what does that deep dive and examination look like and entail? How does Hootsuite identify and select startups within the identified markets?

3.) How does Hootsuite most like to interact with startups in pipe? What does the relationship building look like? What platforms and tools are used to monitor those relationships post initial meeting?

4.) What does the internal conviction building process look like around a potential deal? What is the traditional structure of such a deal? How does Matt assess price sensitivity and it’s ties to product market fit achieved by the startup?

5.) From the other side of the table, when should startups look to be building their M&A pipe? In conversations with potential acquirers, what are the foundations for them to remember? What role do VCs play and value do they provide in these conversations?

Items Mentioned In Today’s Show:

Matt’s Fave Book: Red Notice

Matt’s Fave Blog: Tom Tunguz

Matt’s Most Recent Acquisition: AdEspresso 

As always you can follow Harry, The Twenty Minute VC and Matt on Twitter here!

Likewise, you can follow Harry on Snapchat here for mojito madness and all things 20VC.

If you are an early stage startup, the right infrastructure and support systems are critical, that is where First Republic is so good. First Republic’s resources network and expertise allow entrepreneurs to customise a solid foundation for their business. Why First Republic, well you get to leverage their incredible network of VC firms to prepare you for future fundraising events, you get to count on a single point of contact that will be there for you and your employees, you get access to exclusive events and networking opportunities. Their clients include the likes of Instacart, eShares and Wish just to name a few. Check it out by heading over to innovation.firstrepublic.com

Segment allows you to collect data from every platform (mobile, web, server, cloud apps) and load it into Segment. Segment then sends the customer data to your tools and destinations where it can be used most effectively, destinations include email, analytics, warehouses, helpdesks and more. With over 200 sources and destinations on the Segment platform that can empower your team, Segment really is the last integration you will ever do and that is why the world’s best companies use segment to drive growth and revenue including Atlassian, New Relic and Crate & Barrel. Simply head over to segment.com to find out more.

Roger Dickey is the Founder & CEO @ Gigster, the smart development service combining top developers and designers with artificial intelligence. They have raised over $30m in funding from the likes of a16z, Redpoint, Marc Benioff, Ashton Kutcher, Michael Jordan and then previous guests Rick Marini and Felicis Ventures. Prior to Gigster, Roger founded Mafia Wars, where he built the business to $1Bn in revenues and 100m users. Roger is also a prolific angel investor and LP in venture funds with a portfolio including the likes of Docker, ClassDojo and Addepar, just to name a few. If that was not enough Roger is also an advisor to 8VC, Lemnos Labs and OpenDoor.

Drew Oetting is a Founding Partner @ 8VC, one of Silicon Valley’s youngest and most exciting new entrants to the VC market with $425m for their debut fund. In just a few years they have built a portfolio including the likes of Oculus, RelateIQ, previous guest Elad Gil & Color, recent guest Mario @ Oscar and many more incredible companies. As for Drew, previously he served as Chief of Staff to fellow 8VC Founding Partner, Joe Lonsdale and was a two-time Bill Gates Investment Asset Management Fellow. Drew is also an advisor to Living On One, Rubicon Global and is a Founding Board Director @ Affinity Technologies.

Eric Vishria is a General Partner @ Benchmark, one of the world’s leading VC funds with a portfolio including the likes of Twitter, Uber, Snapchat, eBay, WeWork, Yelp and many more revolutionary companies of the last decade. At Benchmark, Eric has led deals and sits on the board of the likes of Confluent, Amplitude, and Bugsnag. Prior to being in VC, Eric was the Founder & CEO @ Rockmelt, the startup that sought to re-imagine the browser for the way people use the web today, the company was ultimately acquired by Yahoo in 2013. Prior to Rockmelt Eric held numerous different roles including VP of Products @ HP and VP of Marketing @ Opsware.

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In Today’s Episode You Will Learn:

1.) How Eric came to be one of the 5 GP’s at Benchmark following operational success with Rockmelt, HP and Opsware?

2.) Why does Eric believe the pendulum has swung too far to the operational route into VC? What are the under-appreciated benefits of career VCs and the perspective they bring? How does Eric expect the pendulum to swing in the coming years?

3.) What makes the best-performing venture partnerships? How does Benchmark think about partner composition and career pre-VC? How does Benchmark structure investment decision-making? Why do they favor advocacy over unanimity?

4.) What does Eric mean when he says we are at the beginning of an infrastructure renaissance? What opportunities does this create in the venture landscape? How does this lead Eric to consider the current state of the consumer landscape?

5.) How does Eric view multi-stage investing? Why does Eric and Benchmark favour stage specifity when it comes to investing? What are the dangers of larger stage funds investing in earlier rounds for optionality?

Items Mentioned In Today’s Show:

Eric’s Fave Book: Endurance: Shackleton’s Incredible Voyage To The Antarctic

Eric’s Most Recent Investment: Confluent 

As always you can follow Harry, The Twenty Minute VC and Eric on Twitter here!

Likewise, you can follow Harry on Snapchat here for mojito madness and all things 20VC.

If you are an early stage startup, the right infrastructure and support systems are critical, that is where First Republic is so good. First Republic’s resources network and expertise allow entrepreneurs to customise a solid foundation for their business. Why First Republic, well you get to leverage their incredible network of VC firms to prepare you for future fundraising events, you get to count on a single point of contact that will be there for you and your employees, you get access to exclusive events and networking opportunities. Their clients include the likes of Instacart, eShares and Wish just to name a few. Check it out by heading over to innovation.firstrepublic.com

Segment allows you to collect data from every platform (mobile, web, server, cloud apps) and load it into Segment. Segment then sends the customer data to your tools and destinations where it can be used most effectively, destinations include email, analytics, warehouses, helpdesks and more. With over 200 sources and destinations on the Segment platform that can empower your team, Segment really is the last integration you will ever do and that is why the world’s best companies use segment to drive growth and revenue including Atlassian, New Relic and Crate & Barrel. Simply head over to segment.com to find out more.

Mario Schlosser is the Founder & CEO @ Oscar, the startup that makes health insurance easy. They have raised over $700m in funding from some of the world’s best investors including the likes of Founders Fund, Google Capital, Thrive Capital, Lakestar, Khosla Ventures and Jim Breyer just to name a few. Previously, Mario co-founded the largest social gaming company in Latin America and held roles with the likes of Bridgewater Associates and McKinsey. Fun fact, as a visiting scholar at Stanford University, Mario wrote 10 computer science publications, including one of the most-cited computer science papers published in the past decade.

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In Today’s Episode You Will Learn:

1.) How Mario made his way into the world of healthcare and Oscar from founding Latin America’s largest social gaming company?

2.) Why is insurance one of the most complex spaces in tech? Why is there a chance for companies, not governments, to cut costs and innovate on the current system? Does Mario agree with Brian Singerman, “once we go to a single player, innovation ends”, thesis?

3.) Oscar has raised over $700m, to what extent does Mario believe that too high a valuation can be a liability? How did Mario look to select his investors? What are the challenges of raising funds for a category-defining opportunity?

4.) Oscar now has over 600 in the team, where have been the inflection points in the scaling of the company? Where have things broken? How does Mario look to rectify and observe these inflection points ahead of time?

5.) How does Mario look to optimise team composition? How does he look to balance athletes with heavy domain experts? Does Mario believe that too much domain expertise can prevent innovation due to a lack of naivety?

Items Mentioned In Today’s Show:

Mario’s Fave Book: Herr Lehmann

Mario’s Fave Blog: Spiegel

As always you can follow Harry, The Twenty Minute VC and Mario on Twitter here!

Likewise, you can follow Harry on Snapchat here for mojito madness and all things 20VC.

If you are an early stage startup, the right infrastructure and support systems are critical, that is where First Republic is so good. First Republic’s resources network and expertise allow entrepreneurs to customise a solid foundation for their business. Why First Republic, well you get to leverage their incredible network of VC firms to prepare you for future fundraising events, you get to count on a single point of contact that will be there for you and your employees, you get access to exclusive events and networking opportunities. Their clients include the likes of Instacart, eShares and Wish just to name a few. Check it out by heading over to innovation.firstrepublic.com

Segment allows you to collect data from every platform (mobile, web, server, cloud apps) and load it into Segment. Segment then sends the customer data to your tools and destinations where it can be used most effectively, destinations include email, analytics, warehouses, helpdesks and more. With over 200 sources and destinations on the Segment platform that can empower your team, Segment really is the last integration you will ever do and that is why the world’s best companies use segment to drive growth and revenue including Atlassian, New Relic and Crate & Barrel. Simply head over to segment.com to find out more.

Jeremy Conrad is a Partner @ Lemnos Labs, the fund that believes in the earliest stages of building hardware, every dollar counts, every hour matters and every decision is crucial to success or failure. Consequently, Lemnos invests in pre-seed and seed hardware startups encountering these very real challenges. Among their portfolio is the likes of previous guest Swift Navigation and Airware, just to name a few. As for Jeremy, prior to VC he was in the United States Airforce where he was in charge of an $80m tests and targets group and was also responsible for the BMC4I system of the Airborne Laser (ABL).

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In Today’s Episode You Will Learn:

1.) How Jeremy made his way from the United States Airforce to investing in the next generation of great hardware founders with Lemnos?

2.) Why does Jeremy believe that now is the time for robotics? What megatrends mean now is the right time? Why does Jeremy believe that core AI today is largely a bunch of nifty tricks?

3.) Why does Jeremy believe that Silicon Valley will dominate the future of robotics? What characteristics does the valley have that mean this is the case? What is the dirty secret of Silicon Valley?

4.) How does Jeremy view the funding environments for hardware? Where is there constrictions of capital for hardware startups? What must hardware founders have in place in order to raise a Series B?

5.) Why does Jeremy believe that consumer electronics is the hardest space for venture today? With the likes of Juicero and Pearl, is consumer still possible today? Are the likes of GoPro and FitBit merely anomalies in the dataset?

Items Mentioned In Today’s Show:

Jeremy’s Fave Book: The Better Angels of Our Nature 

Jeremy’s Fave Blog: Dan Primack: Pro Rata

Jeremy’s Most Recent Investment: Marble

As always you can follow Harry, The Twenty Minute VC and Jeremy on Twitter here!

Likewise, you can follow Harry on Snapchat here for mojito madness and all things 20VC.

If you are an early stage startup, the right infrastructure and support systems are critical, that is where First Republic is so good. First Republic’s resources network and expertise allow entrepreneurs to customise a solid foundation for their business. Why First Republic, well you get to leverage their incredible network of VC firms to prepare you for future fundraising events, you get to count on a single point of contact that will be there for you and your employees, you get access to exclusive events and networking opportunities. Their clients include the likes of Instacart, eShares and Wish just to name a few. Check it out by heading over to innovation.firstrepublic.com

Segment allows you to collect data from every platform (mobile, web, server, cloud apps) and load it into Segment. Segment then sends the customer data to your tools and destinations where it can be used most effectively, destinations include email, analytics, warehouses, helpdesks and more. With over 200 sources and destinations on the Segment platform that can empower your team, Segment really is the last integration you will ever do and that is why the world’s best companies use segment to drive growth and revenue including Atlassian, New Relic and Crate & Barrel. Simply head over to segment.com to find out more.

Charlie Lee is the creator of Litecoin, the most popular alternative currency to Bitcoin, which Charlie created as a side project in 2011 while working at Google. Today Litecoin has a market cap of $3.29Bn. As well as creating Litecoin, Charlie has also been the Director of Engineering @ Coinbase, working alongside recent 20VC guest and Coinbase founder, Brian Armstrong. Prior to this, Charlie held roles at Microsoft, Google and Guidewire.

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In Today’s Episode You Will Learn:

1.) How Charlie made his way from Google to Coinbase to founding Litecoin in his free time? What were Charlie’s biggest takeaways from being at Coinbase?

2.) What does Charlie believe is the biggest barrier to the world of cryptocurrency and BTC? What is the holy grail to securing this and the future of the space within mass consumer usage?

3.) How does Charlie think about the largest problem for crypto and BTC, scaling? Why does Charlie believe that Ethereum will have large problems scaling? How does Charlie assess the balance of centralization, scaling and transaction efficiency?

4.) Why is Charlie’s biggest concern the current ICO market? Why does he believe it is the “wild west”? What happens to alternative currencies when the ICO market crashes? Who are the ultimate winners in the ICO markets?

5.) How does Charlie analyse the differing communities when comparing ETH to BTC to LTC? Does community serve as a core form of IP for currencies and their stability moving forward?

Items Mentioned In Today’s Show:

Charlie’s Fave Book: Game of Thrones

As always you can follow Harry, The Twenty Minute VC and Charlie on Twitter here!

Likewise, you can follow Harry on Snapchat here for mojito madness and all things 20VC.

If you are an early stage startup, the right infrastructure and support systems are critical, that is where First Republic is so good. First Republic’s resources network and expertise allow entrepreneurs to customise a solid foundation for their business. Why First Republic, well you get to leverage their incredible network of VC firms to prepare you for future fundraising events, you get to count on a single point of contact that will be there for you and your employees, you get access to exclusive events and networking opportunities. Their clients include the likes of Instacart, eShares and Wish just to name a few. Check it out by heading over to innovation.firstrepublic.com

Segment allows you to collect data from every platform (mobile, web, server, cloud apps) and load it into Segment. Segment then sends the customer data to your tools and destinations where it can be used most effectively, destinations include email, analytics, warehouses, helpdesks and more. With over 200 sources and destinations on the Segment platform that can empower your team, Segment really is the last integration you will ever do and that is why the world’s best companies use segment to drive growth and revenue including Atlassian, New Relic and Crate & Barrel. Simply head over to segment.com to find out more.

Kathleen Utecht is a General Partner @ Core Innovation Capital, I would say one of the most under the radar but immensely exciting funds in market and they are looking to revolutionize financial services with their portfolio. With their portfolio are the likes of NerdWallet, PayJoy, fundera and Mayvenn just to name a few. Prior to Core, Kat was an investor at Comcast Ventures and WVP Ventures. Prior to her venture roles, Kath invested in and led Green Rock Entertainment, an online/offline commerce startup. Before that, Kat cut her teeth in the world of finance working as an investment banker at Raymond James.

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In Today’s Episode You Will Learn:

1.) How Kat made her way from car entrepreneur dreams to operator to now, General Partner @ Core?

2.) Why does Kat believe that “society is on a downgrade”? Does Kat agree with the Thiel thesis of “we expected flying cars and were given 140 characters”? Where does Kat most want to see entrepreneurs spending their time and skills?

3.) How does Kat view regulation with regards to startup operations and expansion? Why does Kat believe that “sector specific funds should be in every highly regulated deal”? What are the core benefits? How can VCs really aid with regulation?

4.) Kat has previously said that “VC is a lifestyle not a job”, what does Kat mean by this? How does this mean VCs should behave with regards to founder interactions and communications? How can entrepreneurs stress test whether a VC has this belief?

5.) How does Kat view the process of losing companies? What does her post mortem analysis look like? Why does Kat believe that if you do not lose companies, you are not taking enough risk?

Items Mentioned In Today’s Show:

Kat’s Fave Book: Atlas Shrugged

Kat’s Fave Blog: AVC by Fred Wilson

As always you can follow Harry, The Twenty Minute VC and Kat on Twitter here!

Likewise, you can follow Harry on Snapchat here for mojito madness and all things 20VC.

If you are an early stage startup, the right infrastructure and support systems are critical, that is where First Republic is so good. First Republic’s resources network and expertise allow entrepreneurs to customise a solid foundation for their business. Why First Republic, well you get to leverage their incredible network of VC firms to prepare you for future fundraising events, you get to count on a single point of contact that will be there for you and your employees, you get access to exclusive events and networking opportunities. Their clients include the likes of Instacart, eShares and Wish just to name a few. Check it out by heading over to innovation.firstrepublic.com

Segment allows you to collect data from every platform (mobile, web, server, cloud apps) and load it into Segment. Segment then sends the customer data to your tools and destinations where it can be used most effectively, destinations include email, analytics, warehouses, helpdesks and more. With over 200 sources and destinations on the Segment platform that can empower your team, Segment really is the last integration you will ever do and that is why the world’s best companies use segment to drive growth and revenue including Atlassian, New Relic and Crate & Barrel. Simply head over to segment.com to find out more.

Andy Weissman is a Partner @ Union Square Ventures, one of the world’s leading VC firms with investments in Twitter, Twilio, Zynga, Soundcloud, Tumblr, Lending Club and many more. At USV, Andy sits on the boards of YouNow, ScienceExchange, Figure 1 and previous guest, CircleUp. Prior to joining USV, in 2007 he co-founded betaworks, which both created and invested in social, real-time applications and services. You can also check out Andy’s fantastic blog here.

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In Today’s Episode You Will Learn:

1.) How Andy made his way into the world of startups and investing, came to found Betaworks and then made the move to USV?

2.) Andy has previously said the business “is more about luck than skill and process rather than foresight”. Why does Andy place so much emphasis on process? How has Andy seen his process evolve over the years? How does the process of an individual balance with the process of the firm?

3.) Why does USV not agree with voting as a method of investment decision making? How do Andy and USV approach reserve allocation? What model and simulators do they use to determine which companies receive follow on funding?

4.) Why does Andy believe that recycling cash from early exits is good for everyone? How has Andy found that LPs respond to this? What is the balance? What is the right amount for recycling, 110%, 120% or 130%?

5.) How does Andy view price sensitivity? To what extent does Andy agree with Peter Fenton that “valuation is a mental trap”? Has there been a time when Andy has lost a deal due to price? How has that changed his psyche and approach to the topic?

Items Mentioned In Today’s Show:

Andy’s Fave Book: On The Road by Jack Kerouac

Andy’s Fave Blog: Phish.net, Continuations, Radio Free Mobile

Andy’s Most Recent Investment: Flip

As always you can follow Harry, The Twenty Minute VC and Andy on Twitter here!

Likewise, you can follow Harry on Snapchat here for mojito madness and all things 20VC.

If you are an early stage startup, the right infrastructure and support systems are critical, that is where First Republic is so good. First Republic’s resources network and expertise allow entrepreneurs to customise a solid foundation for their business. Why First Republic, well you get to leverage their incredible network of VC firms to prepare you for future fundraising events, you get to count on a single point of contact that will be there for you and your employees, you get access to exclusive events and networking opportunities. Their clients include the likes of Instacart, eShares and Wish just to name a few. Check it out by heading over to innovation.firstrepublic.com

Segment allows you to collect data from every platform (mobile, web, server, cloud apps) and load it into Segment. Segment then sends the customer data to your tools and destinations where it can be used most effectively, destinations include email, analytics, warehouses, helpdesks and more. With over 200 sources and destinations on the Segment platform that can empower your team, Segment really is the last integration you will ever do and that is why the world’s best companies use segment to drive growth and revenue including Atlassian, New Relic and Crate & Barrel. Simply head over to segment.com to find out more.

Jon Callaghan is a founder of True Ventures, one of the West Coast’s leading early stage funds with a portfolio including the likes of Fitbit, recent unicorn Peloton, Automattic (makers of WordPress) and more amazing companies. Jon also led the deals and sits on the board of Fitbit, Brightroll, Peloton and Glu Mobile, just to name a few. Prior to True, Jon founded 3 of his own companies, the first being in 1986 with Mountain Bike Outfitters Inc. Following several years founding companies, Jon made his move into VC with Summit Partners and then enjoyed roles with AOL’s venture incubator, CMGi’s Venture group and Globespan Capital.

Phil Black is a founder of True Ventures, one of the West Coast’s leading early stage funds with a portfolio including the likes of Fitbit, recent unicorn Peloton, Automattic (makers of WordPress) and more amazing companies. Prior to True, Phil learnt the craft of venture at Summit Partners and at the predecessor firm to Lightspeed Venture Partners. However, it was in 2003 that Phil co-founded a small angel fund, Blacksmith Capital with the mission to prove his thesis that great founders of early stage technology companies can and often prefer to start their businesses and get a lot of traction with $2.5 million or less of initial funding.