The Twenty Minute VC

Jenna Brown is the Founder & CEO @ Shipamax, a data driven communications platform for brokers and operators. They recently raised their seed round from the likes of FF Angel, Y Combinator, Cherubic Ventures, and top angels including Lee Linden and my personal favorite, Andy Rankin. Prior to Shipamax, Jenna was Head of Global Expansion @ GoCardless, one of London’s leading Fintech players and before that was herself a trader at RWE Trading.

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In Today’s Episode You Will Learn:

1.) How Jenna made her way from ship broker to YC alum, changing the world of shipping with Shipamax?

2.) How does Jenna compare fundraising in the UK to Europe? Was it a challenge raising US funds, considering Jenna was operating outside of the valley? How did Jenna look to mitigate these concerns?

3.) How did Jenna experience both direct and indirect sexual discrimination throughout the fundraising process? Which form was harder to deal with? How did Jenna respond? In hindsight, would Jenna have done anything differently?

4.) What does Jenna advise founders in terms of taking operator VC money vs non-operator VC money? What differing questions must be asked? What should founders be wary of with both types of investors?

5.) Why does Jenna disagree with the commonly held suggestion that you must get people to pay for your product as soon as possible? Why is this not the case always? In what cases is it optimal to have a smoother and faster onboarding?

Items Mentioned In Today’s Show:

Jenna’s Fave Book: Hard Thing About Hard Things

Jenna’s Fave Blog: SaaStr

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

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

WePay helps online platforms increase revenue through integrated payments processing, helping platforms offer ROI-positive integrated payments to their users – within their UX and without taking on fraud & regulatory exposure. WePay also offers award-winning support and can even work with your team thru Slack or Zendesk. Get the payments revenue you want, without getting bogged down every time a user has a payments question. Simply visit wepay.com/harry

PipeDrive is the Sales CRM and pipeline management software to use, with the primary view being the pipeline a clear visual interface that prompts you to take action, remain organized and stay in control of a complex sales process. This is why sales pros and deal makers love it (my words, not Pipedrive’s). Plus it easily lets you find the stats you need and is fully customizable. Even better, you can signup for free on here it really is a must.

Jason Pressman is a Managing Director @ Shasta Ventures who have made investments in the likes of Nest, Dollar Shave Club, Smule, Class Dojo and more. With 10 portfolio company investments under his belt, Jason invests in both enterprise and consumer, currently serving on the boards of Crittercism, subscription billing unicorn Zuora, as well as Nextdoor and mobile music platform Smule. Prior to joining Shasta, Jason was Vice President, Strategy and Operations at venture-backed Walmart.com, where he took the online retailer from zero to large scale revenue in five years.

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In Today’s Episode You Will Learn:

1.) How Jason made his way into the world of venture from Walmart? What were the big takeaways from seeing Walmart enter their hyper-growth phase?

2.) Why does Jason believe it is bullshit to say, “you never regret paying a high price for getting into a good company”? How does Jason evaluate entry point? What makes one entry point attractive and another not?

3.) What does Jason see as the catalysts for the opening of public markets to tech companies? How long does he think this will continue? Is he concerned by the likes of Yext, IPOing with less than aggressive growth rates?

4.) Why does Jason believe there are only 2 price points that work in SaaS? What are they? How does this affect the structure and operations of your SaaS startup? What are the circumstances in which these price points do not apply?

5.) Why does Jason believe that eSports will be bigger than the NBA in 5 years? What are the catalysts driving this change? What needs to be formulated within eSports for this to happen?

Items Mentioned In Today’s Show:

Jason’s Fave Book: First, Break All The Rules

Jason’s Most Recent Investment: Plays.tv

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

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

WePay helps online platforms increase revenue through integrated payments processing, helping platforms offer ROI-positive integrated payments to their users – within their UX and without taking on fraud & regulatory exposure. WePay also offers award-winning support and can even work with your team thru Slack or Zendesk. Get the payments revenue you want, without getting bogged down every time a user has a payments question. Simply visit wepay.com/harry

PipeDrive is the Sales CRM and pipeline management software to use, with the primary view being the pipeline a clear visual interface that prompts you to take action, remain organized and stay in control of a complex sales process. This is why sales pros and deal makers love it (my words, not Pipedrive’s). Plus it easily lets you find the stats you need and is fully customizable. Even better, you can signup for free on here it really is a must.

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.

WePay helps online platforms increase revenue through integrated payments processing, helping platforms offer ROI-positive integrated payments to their users – within their UX and without taking on fraud & regulatory exposure. WePay also offers award-winning support and can even work with your team thru Slack or Zendesk. Get the payments revenue you want, without getting bogged down every time a user has a payments question. Simply visit wepay.com/harry

PipeDrive is the Sales CRM and pipeline management software to use, with the primary view being the pipeline a clear visual interface that prompts you to take action, remain organized and stay in control of a complex sales process. This is why sales pros and deal makers love it (my words, not Pipedrive’s). Plus it easily lets you find the stats you need and is fully customizable. Even better, you can signup for free on here it really is a must.

Max Levchin is the Founder & CEO @ Affirm, the company that aims to remake consumer finance from the ground up. They have backing from some of the best in the business with over $400m in VC funding from the likes of Founders Fund, Lightspeed, Andreesen Horowitz, Khosla Ventures and Spark Capital just to name a few. Prior to Affirm, Max held numerous exec positions including Chairman of Yelp for 11 years and sitting on the board of directors @ Yahoo. Before that, Max founded Slide, subsequently bought by Google and was the Co-Founder & CTO @ Paypal.

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In Today’s Episode You Will Learn:

1.) How did Max come to co-found Paypal and how did that serve as the foundations for his founding of Affirm today?

2.) Why does Max believe there is a crucial misalignment between service providers and consumers in financial services? Does Max agree with Bill Clerico that ‘we are still in the very early days for Fintech?’

3.) Having co-founded Paypal, Slide and now Affirm, how has Max changed as a leader and CEO? What does Max believe makes the truly great CEOs? Are there commonalities in how they operate and their skills?

4.) What does Max look for in all new hires or when evaluating founders for potential investment? Why is self-awareness so important for entrepreneurs to have? Why does Max want to be slightly terrified by how smart an individual is?

5.) How has having children changed Max’s perception of what is important and what he chooses to spend his time on? How does that reflect in his actions and self-discipline?

Items Mentioned In Today’s Show:

Max’s Fave Book: The Master and Margarita by Mikhail Bulgakov

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

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

eShares is the No 1 Cap Table Management platform, allowing for equity management, 409A valuations, and liquidity, all in one place. eShares is made for companies of all sizes with over 5,000 trusted customers including the likes of Squarespace, Kickstarter, and DoorDash just to name a few. To try out the must have service of the industry, simply head over to esharesinc.com it is a must.

Fond is the employee engagement suite with 3 core products, rewards: a recognition platform for rewarding achievements and milestones, perks: a premium corporate discounts program to show employees you care about them and then finally engagement IQ, a free employee engagement survey that allows you to measure the health of your organization. To check it out head over to fond.co

Roseanne Wincek is an investor with IVP, one of the leaders in growth financing with a portfolio including the likes of Snap, AppDynamics, SuperCell and Slack. At IVP, Roseanne focuses on investing in later-stage, high-growth consumer and enterprise companies, currently serving as a Board Observer for MasterClass and actively working with IVP’s investments in Compass, Glossier, and Qubole. Prior to IVP, Roseanne was a Principal with Canaan Partners where she completed transactions for Beckon, Metacloud, and Stayful, just to name a few. Prior to VC, Roseanne was a co-founder @ imthemusic working to built music apps on the early Facebook platform.

Mitch Lasky 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. As for Mitch himself, Mitch has made investments or is on the boards of Snapchat, Riot Games, Discord, Outpost Games and Cyanogen, just to name a few. Prior to Benchmark, Mitch was CEO @ JAMDAT Mobile where he led the mobile gaming company from a 10 employee startup to a 700 employee global business leading their IPO on the NASDAQ in 2004 and later negotiating their sales to Electronic Arts for $680m.

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In Today’s Episode You Will Learn:

1.) How Mitch made his way from leading a 700 person gaming company to IPO to being General Partner with Benchmark?

2.) What does the investment decision-making process look like at Benchmark? Why does Mitch believe small is beautiful when it comes to VC teams? What is it that makes the Benchmark partnership the very special partnership it is?

3.) What makes Mitch say that “venture is very much like Hollywood? What does he mean by this? How does he apply this to talent evaluation? The hits-driven nature of the business?

4.) Why is does Mitch struggle when analysing the future for VR? What is it about the current crop of innovation around VR that makes Mitch nervous? Where does Mitch see potential within the realms of VR & AR?

5.) How does Mitch view the continued rise of eSports? Does he believe that the industry will ever be as large as the traditional sports industry? What aspects of the industry does Mitch think is highly investable or not investable?

Items Mentioned In Today’s Show:

Mitch’s Fave Book: The Genius of System

Mitch’s Fave Blog: Above The Crowd

Mitch’s Most Recent Investment: Outpost Games

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

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

eShares is the No 1 Cap Table Management platform, allowing for equity management, 409A valuations, and liquidity, all in one place. eShares is made for companies of all sizes with over 5,000 trusted customers including the likes of Squarespace, Kickstarter, and DoorDash just to name a few. To try out the must have service of the industry, simply head over to esharesinc.com it is a must.

Fond is the employee engagement suite with 3 core products, rewards: a recognition platform for rewarding achievements and milestones, perks: a premium corporate discounts program to show employees you care about them and then finally engagement IQ, a free employee engagement survey that allows you to measure the health of your organization. To check it out head over to fond.co

Kim Scott is the Co-Founder @ Candor, the startup that allows you to become a better leader. Prior to founding Candor, Kim was a CEO coach at Dropbox, Qualtrics, Twitter and several other Silicon Valley companies. She was a member of the faculty at Apple University, developing the course “Managing at Apple,” and before that spent 5 years at Google on AdSense, YouTube, and Doubleclick Online Sales and Operations at Google. Previously, Kim was the co-founder and CEO of Juice Software, a collaboration start-up.

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In Today’s Episode You Will Learn:

1.) How Kim came to founder Candor and be an advisor to Twitter, Qualtrics and Dropbox?

2.) How did Kim’s interactions with Sheryl Sandberg while at Google shape how Kim views employee feedback? What is the most effective way for a superior to convey their feedback to their employee?

3.) What really is radical candor? How does it differ to more traditional “feedback”? What are the challenges of ruinous empathy? How does this play out in the work environment? How does this contrast to “obnoxious aggression”?

4.) Is this a gender issue? What makes it so difficult for people to be radically candid? Why is it a problem that people are told to ‘be professional’? How does that act to de-humanize people?

5.) How do males go most wrong when conveying feedback to their female counterparts? Why is this a problem for both the males and the females involved? What can the female do to ensure that she is not disadvantaged by this?

Items Mentioned In Today’s Show:

Kim’s Fave Book: Anna Karenina by Leo Tolstoy

Kim’s Fave Blog: Rands In Repose: Management

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

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

eShares is the No 1 Cap Table Management platform, allowing for equity management, 409A valuations, and liquidity, all in one place. eShares is made for companies of all sizes with over 5,000 trusted customers including the likes of Squarespace, Kickstarter, and DoorDash just to name a few. To try out the must have service of the industry, simply head over to esharesinc.com it is a must.

Fond is the employee engagement suite with 3 core products, rewards: a recognition platform for rewarding achievements and milestones, perks: a premium corporate discounts program to show employees you care about them and then finally engagement IQ, a free employee engagement survey that allows you to measure the health of your organization. To check it out head over to fond.co

Barry Schuler is a Partner @ DFJ Growth, the team that seeks out companies that have gone through the early stages of funding and are category leaders or are poised to be. Their portfolio includes the likes of Tesla, Twitter, Box, Unity 3D and more fantastic companies. As for Barry, he is credited with being one of the pioneers of the modern Internet as chairman and CEO of America Online and an entrepreneur for over 30 years. Today he serves on the board of some truly game-changing companies in the likes of Coinbase, Unity and Foursquare just to name a few.

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In Today’s Episode You Will Learn:

1.) How did Barry make his way from Chairman of Americal Online to Partner @ DFJ Growth, one of the leading growth funds?

2.) Why does Barry believe we have seen a drought of tech IPOs in the last few years? What needs to be done to change this and generate the “200 IPOs a year that we need”?

3.) Why does Barry believe we are in a “bulge and not a bubble” in today’s current startup ecosystem? What does Barry suggest will happen to the many highly priced tech startups with lacking exit options?

4.) Why does Barry believe that companies are ‘bought and not sold’? How has Barry seen the growth and momentum patterns change for those in hypergrowth? How does that affect the IPO market and their price sensitivity?

5.) Why is Barry concerned that there is too much money chasing too few deals? What does that do to his funnel in producing 10m+ revenue scaling startups?

Items Mentioned In Today’s Show:

Barry’s Fave Book: Sapiens: A Brief History of Humankind

Barry’s Most Recent Investment: Unity 3D, Giphy

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

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

eShares is the No 1 Cap Table Management platform, allowing for equity management, 409A valuations, and liquidity, all in one place. eShares is made for companies of all sizes with over 5,000 trusted customers including the likes of Squarespace, Kickstarter, and DoorDash just to name a few. To try out the must have service of the industry, simply head over to esharesinc.com it is a must.

Fond is the employee engagement suite with 3 core products, rewards: a recognition platform for rewarding achievements and milestones, perks: a premium corporate discounts program to show employees you care about them and then finally engagement IQ, a free employee engagement survey that allows you to measure the health of your organization. To check it out head over to fond.co

Eric Feng is a Partner @ Kleiner Perkins, one of the world’s leading venture capital firms with prior investments in the likes of Google, Amazon, Snapchat, Uber, Twitter and more. At Kleiner Eric focuses on consumer and incubation with his current being his co-founding role with Packagd, the startup building a family of apps offering a new mobile shopping experience. Packagd recently raised a $6m Series A led by Forerunner and GV. Prior to KPCB, Eric held the role of CTO at both Flipboard and Hulu.

Ari Mir is the Founder @ Clutter, the startup that provides simple, painless solutions to your storage problems. They have raised over $90m in VC funding with their recent Series C round being a $64m round led by Atomico with participation from Sequoia, GV and the fantastic Brendan Wallace @ Fifth Wall. Prior to Clutter, Ari founded Gumgum, the world’s largest image ad network in the visual AI space and PocketChange, a startup backed by Google.

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In Today’s Episode You Will Learn:

1.) How Ari made his way into the world of early stage startups and came to found Clutter?

2.) Why does Ari believe that you should build a sports team and not a family, with regards to your team? What does that really mean? How does that affect both hiring, training and objective attribution?

3.) Why does Ari say ‘culture is not a happy hour’? How can one look to build a culture that is driven by humane performance management? Does this not instantly instill a culture of fear?

4.) Why does Ari believe that diversity of thought is so dangerous for early stage startups? How does this view change with the scaling of the team? What key inflection points has Ari noticed with the scaling of the Clutter team?

5.) Why did Ari only hire individuals with finance backgrounds in the early days of the company? What are the benefits of this, particularly for on-demand startups with a heavy focus on unit economics?

Items Mentioned In Today’s Show:

Ari’s Fave Book: Sam Walton: Made In America

Ari’s Fave Blog: AVC

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

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

eShares is the No 1 Cap Table Management platform, allowing for equity management, 409A valuations, and liquidity, all in one place. eShares is made for companies of all sizes with over 5,000 trusted customers including the likes of Squarespace, Kickstarter, and DoorDash just to name a few. To try out the must have service of the industry, simply head over to esharesinc.com it is a must.

Fond is the employee engagement suite with 3 core products, rewards: a recognition platform for rewarding achievements and milestones, perks: a premium corporate discounts program to show employees you care about them and then finally engagement IQ, a free employee engagement survey that allows you to measure the health of your organization. To check it out head over to fond.co

Ethan Kurzweil is a Partner @ Bessemer Venture Partners, one of the world’s leading venture funds with prior investments including the likes of Skype, LinkedIn, Yelp and Pinterest just to name a few. As for Ethan, he focuses on consumer facing technology and developer platforms having made investments in the likes of Twitch, Periscope and Dropcam on the consumer side and Twilio, Intercom and SendGrid on the developer platform side, just to name a few from his outstanding portfolio.

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In Today’s Episode You Will Learn:

1.) How Ethan made his entrance into the world of venture and came to be a partner @ Bessemer?

2.) What was the developer roadmap that Ethan established a couple of years ago? Why was it controversial at the time? How have we seen this play out and come into fruition? What is the next frontier in developer focussed businesses?

3.) Ethan has previously said, ‘history does not repeat itself but it does rhyme’. How does Ethan view pattern recognition? How does Ethan look to avoid biases and escape the echo chamber of Silicon Valley?

4.) How does Ethan see the world of eSports evolving? From an investment perspective, where does the equity value creation lie; the brands being built or the core underlying technology?

5.) Bessemer publishes their anti-portfolio, why is this? What does one need to take away when assessing the opportunities they have missed? How can one build a process of self-reflection around the anti-portfolio?

Items Mentioned In Today’s Show:

Ethan’s Fave Book: The Namesake

Ethan’s Fave Blog: Nuzzel

Ethan’s Most Recent Investment: Periscope Data

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

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

eShares is the No 1 Cap Table Management platform, allowing for equity management, 409A valuations, and liquidity, all in one place. eShares is made for companies of all sizes with over 5,000 trusted customers including the likes of Squarespace, Kickstarter, and DoorDash just to name a few. To try out the must have service of the industry, simply head over to esharesinc.com it is a must.

Fond is the employee engagement suite with 3 core products, rewards: a recognition platform for rewarding achievements and milestones, perks: a premium corporate discounts program to show employees you care about them and then finally engagement IQ, a free employee engagement survey that allows you to measure the health of your organization. To check it out head over to fond.co

Jeremy Levine is a Partner @ Bessemer Venture Partners, one of the world’s leading venture funds with prior investments in the likes of Skype, Shopify, LinkedIn and Twitch, just to name a few. As for Jeremy, 4 of the companies he has invested in with Bessemer have become $Bn companies with 2 of the above; LinkedIn and Shopify, in addition to Yelp and MindBody. If that was not enough, Jeremy is also on the boards of some phenomenal companies in the likes of Pinterest, Yelp and Shopify to name a few.

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In Today’s Episode You Will Learn:

1.) How Jeremy made his entrance into the world of venture and came to be a partner @ Bessemer?

2.) What are the 2 rules Jeremy has with every founder he invests in, prior to making the investment? Why does Jeremy have these rules? At what stage of the pre-investment process are they illustrated?

3.) What are the 2 main reasons that Jeremy believes we are entering a fallow period for the world of consumer? What elements of the incumbency advantages of Facebook, Apple and Google concern Jeremy most? Where does he also see great opportunity?

4.) How has Jeremy seen his style of board member change over the last 16 years? How does Jeremy believe founders can optimize their board through strategic positioning of the VCs they have and where they are placed?

5.) Why does Jeremy believe that it is bogus that operational VCs can provide more value than non-operational VCs? What is the thesis behind this? Where are the core strengths of operational VCs? Where founders must be wary of operational VCs?

Items Mentioned In Today’s Show:

Jeremy’s Fave Book: The Outsiders

Jeremy’s Fave Blog: Dan Primack

Jeremy’s Most Recent Investment: Toss

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.

eShares is the No 1 Cap Table Management platform, allowing for equity management, 409A valuations, and liquidity, all in one place. eShares is made for companies of all sizes with over 5,000 trusted customers including the likes of Squarespace, Kickstarter, and DoorDash just to name a few. To try out the must have service of the industry, simply head over to esharesinc.com it is a must.

Fond is the employee engagement suite with 3 core products, rewards: a recognition platform for rewarding achievements and milestones, perks: a premium corporate discounts program to show employees you care about them and then finally engagement IQ, a free employee engagement survey that allows you to measure the health of your organization. To check it out head over to fond.co

Bart Lorang is the Founder & CEO @ FullContact, the leading contact platform for professionals, teams and businesses. They have raised over $45m in funding from some of the best in the business and dear friends of the show in the likes of Foundry Group with Brad Feld, David Cohen and Techstars and Howard Lindzen at Social Leverage just to name a few. As well as being the rockstar founder @ FullContact, Bart has a unique position as he is also Managing Director @ V1.vc, a seed stage VC fund based in Colorado and San Francisco, providing Bart unique insight into both founding and investing in companies at the same time.

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In Today’s Episode You Will Learn:

1.) How Bart made his way into the world of early stage startups and came to found FullContact?

2.) Bart is also a VC with V1, how does being both a founder and a VC affect how Bart views startups and operates @ FullContact? What have been the key learnings for Bart with regards to capital allocation and portfolio construction?

3.) Bart has a CEO coach being the famous, Jerry Colonna, so what was the catalyst for Bart’s desire to have a CEO coach? What have been the inflection points in Bart’s journey with Jerry? Should every CEO have a CEO coach?

4.) What does Bart believe are the core tenets to successful negotiation? What can be done to ensure a win-win situation for both parties? From what mindset should this be approached? Does Bart agree that you should only monetise to 30% of your value?

5.) Why does Bart pay every employee $7,500 per year to go on holiday on top of their standard salary? Whare the the key rules to ensure this is successful? What are the key benefits that can be derived from this essential vacation?

Items Mentioned In Today’s Show:

Bart’s Fave Book: Jonathan Livingston Seagull

Bart’s Fave Blog: Abundance Insider by Peter Diamandis

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

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

eShares is the No 1 Cap Table Management platform, allowing for equity management, 409A valuations, and liquidity, all in one place. eShares is made for companies of all sizes with over 5,000 trusted customers including the likes of Squarespace, Kickstarter, and DoorDash just to name a few. To try out the must have service of the industry, simply head over to esharesinc.com it is a must.

Fond is the employee engagement suite with 3 core products, rewards: a recognition platform for rewarding achievements and milestones, perks: a premium corporate discounts program to show employees you care about them and then finally engagement IQ, a free employee engagement survey that allows you to measure the health of your organization. To check it out head over to fond.co

Elad Gil is the Founder of Color Genomics, however, Elad is also one of the most prominent angel investors in the valley with a portfolio including the likes of Airbnb, Stripe, Square and Pinterest just to name a few. Prior to founding Color Genomics, Elad was VP of Corporate Strategy @ Twitter where he ran various product teams including geo and search. Before that, Elad spent 3 years at Google where he started Google’s mobile team and was involved with 3 acquisitions including Android.

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In Today’s Episode You Will Learn:

1.) How Elad made his way into the world of angel investing and came to invest in Airbnb, Square and Stripe?

2.) Why does Elad take a very market-driven approach to investing? Does this go against the very founder-first approach taken by many in the valley today?

3.) Why does Elad believe that people totally mislead themselves when sizing up potential markets? How should markets be addressed and evaluated? What are the core elements to look for?

4.) Should VC services always be bundled together? Is there a smarter way to decouple these services to make the best products for founders? How could this look in reality?

5.) How does Elad approach valuation? Does Elad agree with Peter Fenton that ‘all best companies always seem expensive at the time and cheap in hindsight’?

Items Mentioned In Today’s Show:

Elad’s Fave Book: The Wind-Up Bird Chronicle

Elad’s Most Recent Investment: Checkr

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

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

eShares is the No 1 Cap Table Management platform, allowing for equity management, 409A valuations, and liquidity, all in one place. eShares is made for companies of all sizes with over 5,000 trusted customers including the likes of Squarespace, Kickstarter, and DoorDash just to name a few. To try out the must have service of the industry, simply head over to esharesinc.com it is a must.

Fond is the employee engagement suite with 3 core products, rewards: a recognition platform for rewarding achievements and milestones, perks: a premium corporate discounts program to show employees you care about them and then finally engagement IQ, a free employee engagement survey that allows you to measure the health of your organization. To check it out head over to fond.co

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.

eShares is the No 1 Cap Table Management platform, allowing for equity management, 409A valuations, and liquidity, all in one place. eShares is made for companies of all sizes with over 5,000 trusted customers including the likes of Squarespace, Kickstarter, and DoorDash just to name a few. To try out the must have service of the industry, simply head over to esharesinc.com it is a must.

Fond is the employee engagement suite with 3 core products, rewards: a recognition platform for rewarding achievements and milestones, perks: a premium corporate discounts program to show employees you care about them and then finally engagement IQ, a free employee engagement survey that allows you to measure the health of your organization. To check it out head over to fond.co

Nicolas Dessaigne is the Founder & CEO @ Algolia, the most reliable platform for building search into your business. Just last week they raised $53m in funding led by Accel with participation from Jason Lemkin @ SaaStr, Point Nine Capital, AppDynamic’s Jyoti Bansal, Intercom’s Des Traynor and InVision’s Clark Valberg and more incredible investors.

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In Today’s Episode You Will Learn:

1.) How Nicolas made his way from Paris to YC to founding one of the hottest SaaS startups of the day in Algolia?

2.) Tom Tunguz has said before that the Series B is the hardest to raise, having just raised his, does Nicolas agree with this? How did this round differ from others? How can founders know what is the right amount to raise? Is 18 months still the desired runway?

3.) Does Nicolas think he made the move to the US at the right time? Too early or too late? What advice would Nicolas give to founders making or thinking about making this move? What areas are Europe and vice versa the US better at hiring for?

4.) Which functional areas do both Europe and the US lead in their respective fields? Why does Nicolas think that it is harder to hire well in the US? Does Europe still have a fundamental lack of experienced sales and marketing professionals?

5.) How did Jason Lemkin train Nicolas to approach the fundraising process? What other than funds can founders gain from the process? How can these conversations be initiated?

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

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

Zoom is the No 1 Video and WebConferencing Service, providing one consistent enterprise experience that allows you to engage in an array of activities including online meetings, video webinars, collaboration-enabled conference rooms and business instant messaging. Plus, it is the easiest solution to use, buy and scale with the most straightforward pricing. Do not take our word for it, Zoom’s their partnership with Sequoia in their latest 100m funding round says it all. Zoom is a must for your business.

ViewedIt is a free video-recording tool that makes it easy for organizations to embrace the power of video for personalized communications. ViewedIt enables sales professionals, executive leaders and customer support teams to easily record personalized videos and add them to their email conversations. Plus, with built-in tracking powered by the Vidyard platform, video creators will know who is watching what, and which video messages resonate with viewers. They’ll receive immediate playback notifications that will eliminate the wondering of whether the recipient received or watched their content. Find out more and download ViewedIt for free at vidyard.com/viewedit.

Tony Conrad is a Partner @ True Ventures, one of the leading early stage funds on the West Coast with a portfolio including the likes of Automattic, Fitbit, Blue Bottle Coffee and recent unicorn, Peloton. Tony is also the Co-Founder & CEO @ About.me (acquired by AOL in 2010). They have since raised funding from some of our favourites in the industry including Brad @ Foundry, SoftTech and BullPen just to name a few. Prior to About.me, Tony founded Sphere (acquired by AOL) in 2008.

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In Today’s Episode You Will Learn:

1.) How Tony made his way from founding About.me to moving into VC with True Ventures?

2.) How has Tony’s investment mentality changed since being an incredibly successful angel to now writing institutional cheques with True? What has he learned about investing from the transition?

3.) Why does Tony look to straddle the divide between investor and founder? How does this help him to examine what true product/founder fit is? How does this affect his ability to source deals? Why should more investors look to do the same?

4.) How does Tony view party rounds/ why are they so dangerous? Why is it so wrong for founders to optimize for valuation? What are the later repercussions of doing so? What is a more effective way for founders to approach the raise?

5.) Having spent over 1,500 minutes in board meetings, what has Tony learned about what makes the beat board members? How can founders detect the board member that is truly aligned to them?

Items Mentioned In Today’s Show:

Tony’s Fave Book: Endurance by Shackleton

Tony’s Most Recent Investment: Teamable 

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

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

Zoom is the No 1 Video and WebConferencing Service, providing one consistent enterprise experience that allows you to engage in an array of activities including online meetings, video webinars, collaboration-enabled conference rooms and business instant messaging. Plus, it is the easiest solution to use, buy and scale with the most straightforward pricing. Do not take our word for it, Zoom’s their partnership with Sequoia in their latest 100m funding round says it all. Zoom is a must for your business.

ViewedIt is a free video-recording tool that makes it easy for organizations to embrace the power of video for personalized communications. ViewedIt enables sales professionals, executive leaders and customer support teams to easily record personalized videos and add them to their email conversations. Plus, with built-in tracking powered by the Vidyard platform, video creators will know who is watching what, and which video messages resonate with viewers. They’ll receive immediate playback notifications that will eliminate the wondering of whether the recipient received or watched their content. Find out more and download ViewedIt for free at vidyard.com/viewedit.

Kevin Rose is a Venture Partner @ True Ventures, one of the leading early stage funds on the West Coast with portfolio companies including the likes of Automattic, Blue Bottle Coffee, About.me and recent unicorn, Peloton. As for Kevin, he is a serial entrepreneur best known for founding Digg and Revision3. Following such success in the field of operations, Kevin made the move into VC becoming a General Partner and advisor @ Google Ventures. Kevin has also been a prolific angel investor with a portfolio including the likes of Twitter, Square, Facebook, Foursquare, and Zynga just to name a few incredible companies.

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In Today’s Episode You Will Learn:

1.) How Kevin made his way from founding Digg to moving into VC with Google Ventures?

2.) How did Kevin alter his investment mindset when making the transition from angel to General Partner @ Google Ventures? How does the decision making process change? How does asset allocation change? How does portfolio theory change?

3.) Why is Kevin so bullish on the future of mobile? Why does Kevin believe that distribution channels are actually becoming more equal, allowing for greater startup access? Why does Kevin not believe in the future of VR?

4.) How does Kevin view the optimal relationship between VC and founder? Can a VC be a friend as well as an advisor and board member? What can the VC do to ensure their positioning alongside not above the founder?

5.) How does Kevin view the age old debate of work like balance? How does Kevin approach it? What does Kevin recommend to anyone looking to improve their worl life balance?

Items Mentioned In Today’s Show:

Kevin’s Fave Book: Essentialism 

Kevin’s Most Recent Investment: Lead.rs

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.

Zoom is the No 1 Video and WebConferencing Service, providing one consistent enterprise experience that allows you to engage in an array of activities including online meetings, video webinars, collaboration-enabled conference rooms and business instant messaging. Plus, it is the easiest solution to use, buy and scale with the most straightforward pricing. Do not take our word for it, Zoom’s their partnership with Sequoia in their latest 100m funding round says it all. Zoom is a must for your business.

ViewedIt is a free video-recording tool that makes it easy for organizations to embrace the power of video for personalized communications. ViewedIt enables sales professionals, executive leaders and customer support teams to easily record personalized videos and add them to their email conversations. Plus, with built-in tracking powered by the Vidyard platform, video creators will know who is watching what, and which video messages resonate with viewers. They’ll receive immediate playback notifications that will eliminate the wondering of whether the recipient received or watched their content. Find out more and download ViewedIt for free at vidyard.com/viewedit.

Brian Singerman is a Partner @ Founders Fund, one of the world’s most prestigious and successful VC funds with prior investments in the likes of Facebook, Airbnb, SpaceX, Spotify and many more incredible companies. Prior to Founders Fund, Brian spent 4 years at Google where, among other projects, Brian founded iGoogle. Whilst at Google, Brian also started his career as an investor, founding his own angel fund, XGYC Fund. Brian also currently sits on the board of Affirm, Oscar, AltSchool and Emerald Therapeutics. Due to Brian’s immense success he was named No 5 on Forbes Midas List for America’s Top VCs.

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In Today’s Episode You Will Learn:

1.) How Brian made the way from Google, to his own angel fund to being General Partner @ Founders Fund?

2.) How has Brian seen his investment mindset shift over the years from angel investing to his angel fund, XGYC to now being a partner at Founders Fund?

3.) Why does Brian believe that success in VC is purely about upside maximization? What does Brian think downside minimisation is unimportant?

4.) What does the investment decision-making process look like at Founders Fund? How does this change with the scaling cheque size? What are Brian’s views on conviction driven vs unanimous team voting structures?

5.) Why is Brian a staunch generalist when it comes to investing? For Brian, why does he believe that being a generalist will deliver outsized returns over being a specialist?

Items Mentioned In Today’s Show:

Brian’s Fave Book: Snow Crash

Brian’s Fave Blog: Dan Primack

Brian’s Most Recent Investment: Affirm

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.

Zoom is the No 1 Video and WebConferencing Service, providing one consistent enterprise experience that allows you to engage in an array of activities including online meetings, video webinars, collaboration-enabled conference rooms and business instant messaging. Plus, it is the easiest solution to use, buy and scale with the most straightforward pricing. Do not take our word for it, Zoom’s their partnership with Sequoia in their latest 100m funding round says it all. Zoom is a must for your business.

ViewedIt is a free video-recording tool that makes it easy for organizations to embrace the power of video for personalized communications. ViewedIt enables sales professionals, executive leaders and customer support teams to easily record personalized videos and add them to their email conversations. Plus, with built-in tracking powered by the Vidyard platform, video creators will know who is watching what, and which video messages resonate with viewers. They’ll receive immediate playback notifications that will eliminate the wondering of whether the recipient received or watched their content. Find out more and download ViewedIt for free at vidyard.com/viewedit.

Rolf Schrömgens is the Co-Founder and Managing Director @ Trivago, the world’s top hotel price comparison site. In 2012, Expedia acquired 62% of Trivago for $531m and in Dec 2016, Trivago raised $287m through their IPO on the NASDAQ. As for Rolf, he has been a serial entrepreneur since 1999 when he founded Amiro.de, later merged with Ciao.com. At Ciao, Rolf successfully led the product launch of the company in his role as Director of Strategy and Product Development.

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In Today’s Episode You Will Learn:

1.) How Rolf made his way into the world of startups and came to found Trivago?

2.) Having had one of Europe’s best-funded startups with Ciao, what is Rolf’s take on the number of startups taking large amounts of VC money today? What advice would Rolf give to those contemplating a more lean approach vs attaining large amounts of VC money?

3.) Why does Rolf believe transparency is so key for the flow of capital within a market? What can founders do to engender this basis of trust between the capital sources and them?

4.) Why does Rolf think it is unthinkable that the incumbents of today will survive the wave of disruption? Why does Rolf question their ability to a consolidator market environment?

5.) Why does Rolf think it is so important to destroy everything that is ego related? What are the dangers of ego in the company building process? How does Rolf look to stamp this out without damaging culture and internal morale?

Items Mentioned In Today’s Show:

Rolf’s Fave Book: How To Create A Mind by Ray Kurzweil

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

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

Zoom is the No 1 Video and WebConferencing Service, providing one consistent enterprise experience that allows you to engage in an array of activities including online meetings, video webinars, collaboration-enabled conference rooms and business instant messaging. Plus, it is the easiest solution to use, buy and scale with the most straightforward pricing. Do not take our word for it, Zoom’s their partnership with Sequoia in their latest 100m funding round says it all. Zoom is a must for your business.

ViewedIt is a free video-recording tool that makes it easy for organizations to embrace the power of video for personalized communications. ViewedIt enables sales professionals, executive leaders and customer support teams to easily record personalized videos and add them to their email conversations. Plus, with built-in tracking powered by the Vidyard platform, video creators will know who is watching what, and which video messages resonate with viewers. They’ll receive immediate playback notifications that will eliminate the wondering of whether the recipient received or watched their content. Find out more and download ViewedIt for free at vidyard.com/viewedit.

Brian Ascher is a Partner @ Venrock, a leading fund with prior investments including Nest, Dollar Shave Club, AppNexus and many more. At Venrock, Brian invests broadly across enterprise and consumer markets and has enjoyed no less than 10 of his investments exit successfully. Due to this exit rate,Brian has been named to the Forbes Midas List multiple times, for the VCs who have backed the most profitable winners in the last four years. Prior to Venrock, Brian was a Senior Product Manager at Intuit responsible for Quicken and Quicken.com.

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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 be a partner at Venrock?

2.) Does Brian believe that in today’s world of ‘ask for advice and get money’, that slide decks are necessary anymore?

3.) How does Brian like pitches to be structured? How should the deck start? Why should the deck not start with the team or the origin story? Should the deck include the amount being raised?

4.) What are the most common mistakes that entrepreneurs make in pitches? How can they turn these into an advantage and show the VC their unparalleled insight?

5.) How does Brian view the post-investment relationship with founders? What makes for the optimal relationship? Is it possible for VC to be both friend and board member? How does Brian look to scale the relationship curve when getting to know a founder?

Items Mentioned In Today’s Show:

Brian’s Fave Book: Extreme Ownership

Brian’s Most Recent Investment: Socrates

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.

Zoom is the No 1 Video and WebConferencing Service, providing one consistent enterprise experience that allows you to engage in an array of activities including online meetings, video webinars, collaboration-enabled conference rooms and business instant messaging. Plus, it is the easiest solution to use, buy and scale with the most straightforward pricing. Do not take our word for it, Zoom’s their partnership with Sequoia in their latest 100m funding round says it all. Zoom is a must for your business.

ViewedIt is a free video-recording tool that makes it easy for organizations to embrace the power of video for personalized communications. ViewedIt enables sales professionals, executive leaders and customer support teams to easily record personalized videos and add them to their email conversations. Plus, with built-in tracking powered by the Vidyard platform, video creators will know who is watching what, and which video messages resonate with viewers. They’ll receive immediate playback notifications that will eliminate the wondering of whether the recipient received or watched their content. Find out more and download ViewedIt for free at vidyard.com/viewedit.

MZ Zaveri is a Partner @ 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. Prior to KPCB, MZ was with Tencent, where he was part of the investment team in Palo Alto, working on investments in companies such as Vurb, Tile, Satellogic, and Weebly to name a few. Prior to Tencent, Muzzammil co-founded Proxino, a Y Combinator (S11) backed startup in the JavaScript error detection space.

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In Today’s Episode You Will Learn:

1.) How MZ made his way into the world of VC and came to be a partner at Kleiner Perkins?

2.) What were MZ’s biggest takeaways from his time with Tencent? How does that inform how he evaluates and analyses startups today with KPCB?

3.) MZ has said before, ‘success in venture is all about the 3 F’s’. What does he mean by this? Question from Niko Bonatsos @ General Catalyst: How does MZ look ensure the best opportunities are in the pipeline? How does MZ then look to manage and optimise that pipeline?

4.) What are MZ’s thoughts on deal heat? How does MZ look to avoid being sucked into echo chambers of Silicon Valley of what is “hot or not”? What does MZ mean when he says “deal heat can be a false positive when there are more seed funds than ever”?

5.) How does MZ evaluate the seed market today? Does he believe it is over financed with the 10x increase in funds we have seen over the last 10 years? What fund model innovations is MZ most excited by and why?

Items Mentioned In Today’s Show:

MZ’s Fave Book: Neverwhere by Neil Gaimon

MZ’s Fave Blog/Podcast: The Twenty Minute VC

MZ’s Most Recent Investment: UJet

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

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

Zoom is the No 1 Video and WebConferencing Service, providing one consistent enterprise experience that allows you to engage in an array of activities including online meetings, video webinars, collaboration-enabled conference rooms and business instant messaging. Plus, it is the easiest solution to use, buy and scale with the most straightforward pricing. Do not take our word for it, Zoom’s their partnership with Sequoia in their latest 100m funding round says it all. Zoom is a must for your business.

ViewedIt is a free video-recording tool that makes it easy for organizations to embrace the power of video for personalized communications. ViewedIt enables sales professionals, executive leaders and customer support teams to easily record personalized videos and add them to their email conversations. Plus, with built-in tracking powered by the Vidyard platform, video creators will know who is watching what, and which video messages resonate with viewers. They’ll receive immediate playback notifications that will eliminate the wondering of whether the recipient received or watched their content. Find out more and download ViewedIt for free at vidyard.com/viewedit.

Sean Rad is the Founder & Chairman @ Tinder, the world’s most popular app for connecting with new and interesting people around you. Every single day there are 26m matches made on Tinder. Alongside his role with Tinder, Sean is the Chairman of Swipe Ventures, the investment vehicle that will continue to grow Tinder’s reach through acquisitions, investment opportunities and development of new business. Prior to Tinder, Sean was the Founder and President of both Adly and Orgoo.

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In Today’s Episode You Will Learn:

1.) How Sean made his way into the world of startups and changed the way people connect with Tinder?

2.) How has Sean seen his startup evaluation process evolve since his time angel investing to now, investing institutionally with Swipe Ventures?

3.) What are the character traits that Sean most looks for when evaluating startup founders? Why is humility key to success as a founder? How can this be balanced with passion and vision?

4.) How has Sean seen his leadership and mentality evolve with the growth of Tinder?What have been the major inflection points in his learning as CEO?

5.) Why does Sean believe that today’s incumbents are different than any we have seen before? How does their mentality to startup competition differ from incumbents before them?

Items Mentioned In Today’s Show:

Sean’s Fave Book: The Nurture Assumption

Sean’s Fave Blog: TechCrunch

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

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

Zoom is the No 1 Video and WebConferencing Service, providing one consistent enterprise experience that allows you to engage in an array of activities including online meetings, video webinars, collaboration-enabled conference rooms and business instant messaging. Plus, it is the easiest solution to use, buy and scale with the most straightforward pricing. Do not take our word for it, Zoom’s their partnership with Sequoia in their latest 100m funding round says it all. Zoom is a must for your business. 

ViewedIt is a free video-recording tool that makes it easy for organizations to embrace the power of video for personalized communications. ViewedIt enables sales professionals, executive leaders and customer support teams to easily record personalized videos and add them to their email conversations. Plus, with built-in tracking powered by the Vidyard platform, video creators will know who is watching what, and which video messages resonate with viewers. They’ll receive immediate playback notifications that will eliminate the wondering of whether the recipient received or watched their content. Find out more and download ViewedIt for free at vidyard.com/viewedit.

Mar Hershenson is a Founding Managing Partner @ Pear.vc alongside Pejman Nozad. After earning a PhD in Electrical Engineering from Stanford University in 1999, Mar had developed a ground-breaking technique for optimizing the design of analog semiconductors. Having combined a hardware/software focus during her studies, she spent the next 13 years co-founding three startups in the mobile/e-commerce, enterprise software, and semiconductor industries, work that led eventually to her registering 14 separate patents. Mar has been recognized by MIT Technology Review as a Top Innovator Under 35 and named a Champion of Innovation by Fast Company.

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In Today’s Episode You Will Learn:

1.) How did Mar make her way from professor @ Stanford to startup founder to founding Pear.vc?

2.) Question from Matin @ Heap: How does Mar decide which founders have the highest potential? What are the seeds that suggest huge potential growth on initial screening?

3.) Question from Nicky @ Nova Credit: How does one look to balance the inherent challenge of vision and operations? What do the best founders do?

4.) How important is it for there to be role segmentation in a VC partnership? Why does it not matter at certain stages of the funding lifecycle?

5.) Why does Mar believe venture is an intensely service based industry? How does Mar look to maintain her scaling board roles with a scaling portfolio?

Items Mentioned In Today’s Show:

Mar’s Fave Book: The Four Steps To The Epiphany

Mar’s Fave Blog: Elad Gil, Dan Primack

Mar’s Most Recent Investment: Nova Credit

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

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

Zoom is the No 1 Video and WebConferencing Service, providing one consistent enterprise experience that allows you to engage in an array of activities including online meetings, video webinars, collaboration-enabled conference rooms and business instant messaging. Plus, it is the easiest solution to use, buy and scale with the most straightforward pricing. Do not take our word for it, Zoom’s their partnership with Sequoia in their latest 100m funding round says it all. Zoom is a must for your business. 

ViewedIt is a free video-recording tool that makes it easy for organizations to embrace the power of video for personalized communications. ViewedIt enables sales professionals, executive leaders and customer support teams to easily record personalized videos and add them to their email conversations. Plus, with built-in tracking powered by the Vidyard platform, video creators will know who is watching what, and which video messages resonate with viewers. They’ll receive immediate playback notifications that will eliminate the wondering of whether the recipient received or watched their content. Find out more and download ViewedIt for free at vidyard.com/viewedit.

Kevin Hartz is a Partner @ Founders Fund, one of the world’s most prestigious and successful VC funds with prior investments in the likes of Facebook, Airbnb, SpaceX, Spotify and many more incredible companies. Prior to Founders Fund, Kevin was Founder & CEO @ Eventbrite, the company that powers thousands of millions of events around the world with backing from the likes of Sequoia and SV Angel. Before that Kevin was the Founder of Xoom Corporation, the international money transfer company that went public in 2012 and was acquired by Paypal in 2015. Kevin has also been a prolific angel with a personal portfolio including Airbnb, Uber, Paypal, Pinterest and Yammer.

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In Today’s Episode You Will Learn:

1.) Question from Brian Singerman: How did Kevin come to be the world famou Kevin Hartz? What was Kevin’s entry into the world of VC?

2.) How has Kevin seen his investment decision making and evaluation process change when comparing his angel deals in Uber, Paypal and Airbnb to today, investing institutionally with Founders Fund?

3.) How does Kevin see believe his time in operations lends to him being a better investor today? Does Kevin agree with Pat Grady @ Sequoia in stating, ‘the rate of decay on operating experience has never been greater’?

4.) With no Monday morning Partner meetings, if a Partner wants to push a deal through, how do you do it at Founders Fund? How do you structure those conversations internally?

5.) What have been Kevin’s biggest learnings since joining Founders Fund? How did Kevin look to scale the VC learning curve as fast as possible? What elements did Kevin find most challenging?

Items Mentioned In Today’s Show:

Kevin’s Fave Book: Peter Thiel: Zero To One

Kevin’s Most Recent Investment: HyperTrack 

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.

Zoom is the No 1 Video and WebConferencing Service, providing one consistent enterprise experience that allows you to engage in an array of activities including online meetings, video webinars, collaboration-enabled conference rooms and business instant messaging. Plus, it is the easiest solution to use, buy and scale with the most straightforward pricing. Do not take our word for it, Zoom’s their partnership with Sequoia in their latest 100m funding round says it all. Zoom is a must for your business. 

Vidyard is the video platform for business that helps marketing and sales teams drive more revenue through the use of online video. Going beyond video hosting and management, Vidyard helps businesses drive greater engagement in their video content, track the viewing activities of each individual viewer, and turn those views into action. Global leaders such as Microsoft, McKesson, Lenovo, and LinkedIn rely on Vidyard to power their video content strategies and turn viewer into customers. Check them out at vidyard.com.

Jonathan Downey is the Founder & CEO @ Airware, the startup that allows you to make better-informed decisions with aerial date, captured by drones. They have raised over $65m in VC funding from some of the very best in the industry including a16z, Kleiner Perkins and Google Ventures just to name a few. Jonathan is also the General Partner @ Commerical Drone Fund, making $250K-$1m investments in early stage companies in the commercial drone space. Prior to Airware, Jonathan was a commercial pilot and a flight controls engineer @ Boeing.

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In Today’s Episode You Will Learn:

1.) How Jonathan made the move from commercial pilot to startup founder with one of the hottest drone startups, Airware?

2.) What has been the catalyst for the rising belief in the potential for drones? What has changed about the landscape to make them now not only a commercially viable opportunity but also consumer viable?

3.) How does Jonathan view the commercial landscape today? Where does Jonathan see the highest potential for the commercial application of drones? How does one approach go to market strategy and business model in a completely undefined landscape?

4.) What are the current barriers to adoption for corporations with drones? What does it mean and entail for an organization to adopt drones in terms of new workflows and training? What are the key transformative technologies that will enable new applications and market expansion?

5.) With incumbents now heavily investing in the space, does Jonathan believe this will be a market of disruption or consolidation and acquisition by the exisiting incumbents?

Items Mentioned In Today’s Show:

Jonathan’s Fave Book: Elon Musk by Ashley Vance

Jonathan’s Fave Blog: Chris Dixon

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

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

Eight is a sleep innovation company. With their latest product, the Eight Smart Mattress, being a bed that literally tells you how well you slept last night, paired with an intelligent sensor cover that measures the quality of your sleep and delivers a daily sleep report. In order to bring you the best product, Eight used anonymized sleep data and feedback from over 10,000 people, to understand which materials and types of mattresses give customers the best sleep resulting in their unique blend of four responsive and high-density foam layers plus one layer of proprietary technology that helps people track and improve their sleep. You can check it out on Eightsleep.com – and if you use the code 20VC you will get a whopping 20% discount!

FullContact provides the ability to organize your contacts, gain rich insights into them and therefore build deep relationships. With features like automatically identifying and merging duplicate contacts to the ability to snap a photo of a business card and FullContact will transcribe them for you, so no more lost and loose business cards at events. It is with these features just being the tip of the iceberg, FullContact really is the best all in one solution for contact management and you can check them out on fullcontact.com.

Keith Rabois is an investment partner at Khosla Ventures where he has led investments in Stripe, Thoughtspot, HealthTap and Teespring among many others. He also started OpenDoor, which aims to transform the process of selling a home through technology. Keith’s unparalleled operational track record does not stop there as he has forged several of the most important new social and commerce platforms over the last decade holding key roles at LinkedIn, Paypal and being COO at Square. As a board member, Keith guided Yelp [NYSE: YELP] and Xoom [NASDAQ: XOOM] from inception to successful IPOs. Simultaneously, he also invested in other like-minded entrepreneurs with early stakes in YouTube [acquired by GOOG], Yammer [acquired by MSFT], Palantir, Lyft, AirBnB, Eventbrite and Quora.

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In Today’s Episode You Will Learn:

1.) How Keith made the move from key executive at LinkedIn, Paypal and Square to being a VC with Khosla?

2.) Question from Lee Hower: What were the biggest learnings from playing a key role at LinkedIn, Paypal and Square? How do they compare to learning from Slide, a not so successful project? Does one learn more from success or failure?

3.) Question from Jason Lemkin: How can founders assess the potential of their teams? How long is it possible to allow individuals to stretch to their roles? What are the signs that people are either exceeding or falling below expectations?

4.) Eric Yuan @ Zoom has previously illustrated the importance to me of sustainable growth. What is Keith’s view of this? Why does he not like this term? What are his thoughts on the key constraints on growth for most startups?

Items Mentioned In Today’s Show:

Keith’s Fave Book: The Upside of Stress

Keith’s Fave Blog: Stratechery

Keith’s Most Recent Investment: Forward 

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

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

Eight is a sleep innovation company. With their latest product, the Eight Smart Mattress, being a bed that literally tells you how well you slept last night, paired with an intelligent sensor cover that measures the quality of your sleep and delivers a daily sleep report. In order to bring you the best product, Eight used anonymized sleep data and feedback from over 10,000 people, to understand which materials and types of mattresses give customers the best sleep resulting in their unique blend of four responsive and high-density foam layers plus one layer of proprietary technology that helps people track and improve their sleep. You can check it out on Eightsleep.com – and if you use the code 20VC you will get a whopping 20% discount!

FullContact provides the ability to organize your contacts, gain rich insights into them and therefore build deep relationships. With features like automatically identifying and merging duplicate contacts to the ability to snap a photo of a business card and FullContact will transcribe them for you, so no more lost and loose business cards at events. It is with these features just being the tip of the iceberg, FullContact really is the best all in one solution for contact management and you can check them out on fullcontact.com.

Harley Finkelstein is the COO @ Shopify, the e-commerce platform that has allowed a generation of people to become entrepreneurs and business owners. Harley joined the business with revenues of $5m, today the company has targeted this year for over $600m with over 400,000 merchants on the platform. They have raised over $120m in VC funding from very good friends of the show including Aydin @ Felicis, Jeremy @ Bessemer and Amish @ Firstmark. In May 2015, Shopify went public with a valuation north of $1bn.

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In Today’s Episode You Will Learn:

1.) How did Harley make the move from laywer to COO @ Shopify?

2.) Question from Aydin @ Felicis: What have been some strategic inflection points that at the time did not seem like a big deal? How have Harley and Shopify produced and maintained such consistent revenue growth? What is the secret?

3.) Why does Harley believe that the future of retail is not online vs offline? How does Harley react to the suggestion that retail stores need to transition from transaction based, to experience based?

4.) How does Harley view the rise of personal brand in today’s technological world? How has this allowed previously non-monetized channels to be monetized? What are some good examples of this?

5.) Why did Harley and Shopify choose to IPO in 2015? How was the roadshow? What was the key learnings for Harley both pre and post-IPO? What does Harley believe it means to be a trusted public company?

Items Mentioned In Today’s Show:

Harley’s Fave Book: High Output Management

Harley’s Fave Blog: Wait But Why

Harley’s Fave Shopify Store: Boosted Boards

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

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

Eight is a sleep innovation company. With their latest product, the Eight Smart Mattress, being a bed that literally tells you how well you slept last night, paired with an intelligent sensor cover that measures the quality of your sleep and delivers a daily sleep report. In order to bring you the best product, Eight used anonymized sleep data and feedback from over 10,000 people, to understand which materials and types of mattresses give customers the best sleep resulting in their unique blend of four responsive and high-density foam layers plus one layer of proprietary technology that helps people track and improve their sleep. You can check it out on Eightsleep.com – and if you use the code 20VC you will get a whopping 20% discount!

FullContact provides the ability to organize your contacts, gain rich insights into them and therefore build deep relationships. With features like automatically identifying and merging duplicate contacts to the ability to snap a photo of a business card and FullContact will transcribe them for you, so no more lost and loose business cards at events. It is with these features just being the tip of the iceberg, FullContact really is the best all in one solution for contact management and you can check them out on fullcontact.com.

Josh Wolfe is the Co-Founder and Managing Partner @ 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. Josh is a founding investor and board member with Bill Gates in Kymeta, making cutting-edge antennas for high-speed global satellite and space communications. In 2008 Josh co-founded and funded Kurion, the company was among the first responders to the Fukushima disaster. In February 2016, Veolia acquired Kurion for nearly $400 million—more than 40 times Lux’s total investment.

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In Today’s Episode You Will Learn:

1.) How did Josh make his way into VC from the science lab? What was it about venture that got Josh hooked?

2.) How does Josh view the rise of thematic investing? Why does Josh believe there are a lot of tourist VCs who are going to lose a lot of money?

3.) Investing in such frontier technologies, how does Josh view market creation? How does Josh look to build a thesis and a methodology when investing in a company without an existing market?

4.) What is the inflection point for Josh for when heavy science and R&D becomes investable? What is that tipping point where science becomes commercialized?

5.) Does Josh get concerned that with such heavy IP and corporations not investing in R&D that this is a market for acquihires? What are the pros and cons of this shortened liquidity cycles?

Items Mentioned In Today’s Show:

Josh’s Fave Book: Sapiens

Josh’s Fave Blog: Media Redefined

Josh’s Most Recent Investment: Recursion Pharmaceuticals

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

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

Eight is a sleep innovation company. With their latest product, the Eight Smart Mattress, being a bed that literally tells you how well you slept last night, paired with an intelligent sensor cover that measures the quality of your sleep and delivers a daily sleep report. In order to bring you the best product, Eight used anonymized sleep data and feedback from over 10,000 people, to understand which materials and types of mattresses give customers the best sleep resulting in their unique blend of four responsive and high-density foam layers plus one layer of proprietary technology that helps people track and improve their sleep. You can check it out on Eightsleep.com – and if you use the code 20VC you will get a whopping 20% discount!

FullContact provides the ability to organize your contacts, gain rich insights into them and therefore build deep relationships. With features like automatically identifying and merging duplicate contacts to the ability to snap a photo of a business card and FullContact will transcribe them for you, so no more lost and loose business cards at events. It is with these features just being the tip of the iceberg, FullContact really is the best all in one solution for contact management and you can check them out on fullcontact.com.

Bill Clerico is the Co-Founder & CEO @ WePay, the most complete payments solution for platforms. To date, they have raised close to $75m in VC funding from some of the best in the business including Max Levchin, Dave McClure and August Capital just to name a few. As for Bill, alongside his role with WePay, Bill is a part-time partner @ Y Combinator and an angel investor. Prior to startups, Bill cut his teeth in the industry at Jefferies in investment banking.

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In Today’s Episode You Will Learn:

1.) How Bill made his way into the world of startups from investment banking?

2.) How does Bill assess the pivot? What is required to pivot successfully? How can this be communicated to both your board and your team?

3.) How does Bill look to relationship build with investors? What are the fundamentals to a healthy and sustainable investor relationship?

4.) Why should founders ensure they are not the only company representative with the board? What are the benefits of the board having many touchpoints within the family? How can this be done effectively?

5.) What does Bill mean he says you must have an ‘opinionated culture’? How can this be conveyed to the team and across the organisation?

Items Mentioned In Today’s Show:

Bill’s Fave Book: Failure Is Not An Option

Bill’s Fave Blog: The Information

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

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

Eight is a sleep innovation company. With their latest product, the Eight Smart Mattress, being a bed that literally tells you how well you slept last night, paired with an intelligent sensor cover that measures the quality of your sleep and delivers a daily sleep report. In order to bring you the best product, Eight used anonymized sleep data and feedback from over 10,000 people, to understand which materials and types of mattresses give customers the best sleep resulting in their unique blend of four responsive and high-density foam layers plus one layer of proprietary technology that helps people track and improve their sleep. You can check it out on Eightsleep.com – and if you use the code 20VC you will get a whopping 20% discount!

FullContact provides the ability to organize your contacts, gain rich insights into them and therefore build deep relationships. With features like automatically identifying and merging duplicate contacts to the ability to snap a photo of a business card and FullContact will transcribe them for you, so no more lost and loose business cards at events. It is with these features just being the tip of the iceberg, FullContact really is the best all in one solution for contact management and you can check them out on fullcontact.com.

Brendan Wallace is a Co-Founder of Fifth Wall, the fund that specializes in technology for the built world and real estate tech. Prior to Fifth Wall, Brendan was Co-founder & CEO of Identified, a data & analytics company that raised $33 million of venture capital and was acquired by Workday (WDAY) in 2014. Brendan also co-founded Cabify, the largest ridesharing service in Latin America, which has raised $143 million and operates in 14 countries and 50 cities. If that was not enough, Brendan has been an active angel investor and manages one of the largest syndicates on Angellist, having led over 50 angel investments including Bonobos, Dollar Shave Club, Earnest, Philz Coffee and Zenefits.

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In Today’s Episode You Will Learn:

1.) How Brendan made the transition from the world of startup founding to investing with Fifth Wall?

2.) How does Brendan feel fund managers can approach LP composition in order to provide strategic value add to portfolio companies? How did he approach this?

3.) How do the differing sources of LP money differ when comparing corporate LPs to more traditional fund of funds and endowment funds? Why did Brendan decide it was optimal to have both in Fifth Wall?

4.) Brendan has previously said ‘autonomous cars are the next meteor to hit the real estate industry’. What are the 3 differing types of risk that could prevent this rise? What timeline does Brendan believe we are looking at for self-driving?

5.) How does Brendan see the urban landscape evolving and developing over time? Will we see a renewed period of urbanisation or urban spread? How do the macro levers affect this?

Items Mentioned In Today’s Show:

Brendan’s Fave Book: The Accidental Superpower

Brendan’s Fave Blog: CB Insights

Brendan’s Most Recent Investment: VTS: The Leading Asset and Asset Management Platform

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

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

Eight is a sleep innovation company. With their latest product, the Eight Smart Mattress, being a bed that literally tells you how well you slept last night, paired with an intelligent sensor cover that measures the quality of your sleep and delivers a daily sleep report. In order to bring you the best product, Eight used anonymized sleep data and feedback from over 10,000 people, to understand which materials and types of mattresses give customers the best sleep resulting in their unique blend of four responsive and high-density foam layers plus one layer of proprietary technology that helps people track and improve their sleep. You can check it out on Eightsleep.com – and if you use the code 20VC you will get a whopping 20% discount!

FullContact provides the ability to organize your contacts, gain rich insights into them and therefore build deep relationships. With features like automatically identifying and merging duplicate contacts to the ability to snap a photo of a business card and FullContact will transcribe them for you, so no more lost and loose business cards at events. It is with these features just being the tip of the iceberg, FullContact really is the best all in one solution for contact management and you can check them out on fullcontact.com.

The thoughts, comments and opinions in this podcast do not represent investment advice and do not necessarily reflect the views of Sapphire Ventures.

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

Eight is a sleep innovation company. With their latest product, the Eight Smart Mattress, being a bed that literally tells you how well you slept last night, paired with an intelligent sensor cover that measures the quality of your sleep and delivers a daily sleep report. In order to bring you the best product, Eight used anonymized sleep data and feedback from over 10,000 people, to understand which materials and types of mattresses give customers the best sleep resulting in their unique blend of four responsive and high-density foam layers plus one layer of proprietary technology that helps people track and improve their sleep. You can check it out on Eightsleep.com – and if you use the code 20VC you will get a whopping 20% discount!

FullContact provides the ability to organize your contacts, gain rich insights into them and therefore build deep relationships. With features like automatically identifying and merging duplicate contacts to the ability to snap a photo of a business card and FullContact will transcribe them for you, so no more lost and loose business cards at events. It is with these features just being the tip of the iceberg, FullContact really is the best all in one solution for contact management and you can check them out on fullcontact.com.

Jason Brown is the Founder & CEO @ Tally, the startup that is building a better credit card experience giving power to the consumer. They have investment from some of the leading names in early stage finance including Shasta Ventures, Cowboy Ventures, Ludlow Ventures and Blake Byers @ GV just to name a few. As for Jason, prior to Tally, he founded 3 further startups including most recently Gen110 where helped to bring a new consumer debt product market that finances residential solar installs.

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In Today’s Episode You Will Learn:

1.) How did Jason come to found Tally following his 3 prior startup founding experiences?

2.) Why does Jason think you should never settle with candidate hires? What shall startups do when they are growing fast and need someone now? Why does Jason believe you should never use external recruiters?

3.) As this is Jason’s 4th startup and he has raised from the likes of Kleiner Perkins in the past, what has Jason learned in terms of fundraising through his past entrepreneurial experiences? What does Jason believe founders should look for from their VCs?

4.) Why does Jason believe that in the majority of cases ‘move fast and break things is completely wrong’? What industries does Jason believe you have to lean into the regulators?

5.) How does Jason look to instill radical candor within Tally as a fast scaling startup? What does Jason think this is important for all startups to have engrained in them?

Items Mentioned In Today’s Show:

Jason’s Fave Book: Science of Interstellar

Jason’s Fave Blog: First Round Review

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

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

Eight is a sleep innovation company. With their latest product, the Eight Smart Mattress, being a bed that literally tells you how well you slept last night, paired with an intelligent sensor cover that measures the quality of your sleep and delivers a daily sleep report. In order to bring you the best product, Eight used anonymized sleep data and feedback from over 10,000 people, to understand which materials and types of mattresses give customers the best sleep resulting in their unique blend of four responsive and high-density foam layers plus one layer of proprietary technology that helps people track and improve their sleep. You can check it out on Eightsleep.com – and if you use the code 20VC you will get a whopping 20% discount!

FullContact provides the ability to organize your contacts, gain rich insights into them and therefore build deep relationships. With features like automatically identifying and merging duplicate contacts to the ability to snap a photo of a business card and FullContact will transcribe them for you, so no more lost and loose business cards at events. It is with these features just being the tip of the iceberg, FullContact really is the best all in one solution for contact management and you can check them out on fullcontact.com.

Gene Frantz is a Partner of CapitalG, Alphabet’s growth investment fund which has investments in the likes of Airbnb, Snap Inc and Stripe. As for Gene, before joining CapitalG, Gene was a partner at TPG Capital, a global private equity fund. During his 13 years at TPG, Gene was responsible for multiple technology and telecom investments and represented TPG on multiple public and private company boards of directors. Prior to TPG Capital, Gene worked at Oracle Corporation leading its venture capital effort and previous to that in corporate development.

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In Today’s Episode You Will Learn:

1.) How Gene made his way from the world of traditional private equity to investing with Google?

2.) Gene has seen many investment cycles, how has Gene experience of both the ups and the downs of the market affected how he invests today?

3.) What does a company need to show or provide today in order to get a large late-stage cheque or IPO? How has this changed over the years?

4.) Why does Gene think that late stage financing has been massively commoditized? How can late stage funds looks to differentiate themselves in today’s market?

5.) How does Gene view the extension of private markets and the delayed IPO? Why does he think management teams are less willing to IPO today? Does it concern him?

Items Mentioned In Today’s Show:

Gene’s Fave Book: The Righteous Mind: Why Good People Are Divided By Religion & Politics

Gene’s Fave Blog: The Information

Gene’s Most Recent Investment: Looker

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.

Eight is a sleep innovation company. With their latest product, the Eight Smart Mattress, being a bed that literally tells you how well you slept last night, paired with an intelligent sensor cover that measures the quality of your sleep and delivers a daily sleep report. In order to bring you the best product, Eight used anonymized sleep data and feedback from over 10,000 people, to understand which materials and types of mattresses give customers the best sleep resulting in their unique blend of four responsive and high-density foam layers plus one layer of proprietary technology that helps people track and improve their sleep. You can check it out on Eightsleep.com – and if you use the code 20VC you will get a whopping 20% discount!

FullContact provides the ability to organize your contacts, gain rich insights into them and therefore build deep relationships. With features like automatically identifying and merging duplicate contacts to the ability to snap a photo of a business card and FullContact will transcribe them for you, so no more lost and loose business cards at events. It is with these features just being the tip of the iceberg, FullContact really is the best all in one solution for contact management and you can check them out on fullcontact.com.

Laela Sturdy is a Partner @ CapitalG, Alphabet’s growth investment fund that have invested in the likes of Stripe, Snap Inc, Airbnb and many more incredible companies. As for Laela, she has made investment in category leaders such as language learning platform, Duolingo, payroll and benefits provider, Gusto and jobs site, Glassdoor. Prior to investing with CapitalG, Laela was a Director of Sales & Business Operations at Google where she helped start, scale, and lead teams in several emerging product areas including video and display advertising, local and SMB services, and mobile commerce.

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In Today’s Episode You Will Learn:

1.) How Laela made the transition from an operator at Google to one of the industry’s rising star investors with CapitalG?

2.) Market size is fundamental to CapitalG decision-making process so; what is a large enough market? How does Laela look to evaluate market size; bottoms up or top down?

3.) How does Laela look to assess product differentiation? Is brand significant enough IP to be classed as product differentiation?

4.) Why does ownership not play such a pivotal role in investment decision-making process? How crucial is unit economics to Laela at this stage of investment?

5.) With Google’s obvious operational value add, does Laela believe we will see the further rise of operational value add within VC? What does this mean for entrepreneurs?

Items Mentioned In Today’s Show:

Laela’s Fave Book: Americanah

Laela’s Fave Blog: Dan Primack: Axios

Laela’s Most Recent Investment: Care.com

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.

Eight is a sleep innovation company. With their latest product, the Eight Smart Mattress, being a bed that literally tells you how well you slept last night, paired with an intelligent sensor cover that measures the quality of your sleep and delivers a daily sleep report. In order to bring you the best product, Eight used anonymized sleep data and feedback from over 10,000 people, to understand which materials and types of mattresses give customers the best sleep resulting in their unique blend of four responsive and high-density foam layers plus one layer of proprietary technology that helps people track and improve their sleep. You can check it out on Eightsleep.com – and if you use the code 20VC you will get a whopping 20% discount!

FullContact provides the ability to organize your contacts, gain rich insights into them and therefore build deep relationships. With features like automatically identifying and merging duplicate contacts to the ability to snap a photo of a business card and FullContact will transcribe them for you, so no more lost and loose business cards at events. It is with these features just being the tip of the iceberg, FullContact really is the best all in one solution for contact management and you can check them out on fullcontact.com.

Leo Polovets is a Co-Founder and General Partner @ Susa Ventures, one of the west coast’s most exciting new seed funds. They have investments in the likes of previous guests RobinHood, Flexport, Andela, LendUp, and Qadium, just to name a few from their stellar portfolio. As for Leo, Prior to Susa, Leo was one of the first engineers at LinkedIn in 2003, then worked on payment fraud detection at Google, then designed and built the data cleaning and deduping engines at Factual. He is an angel investor in over a dozen companies, including DataFox, Boomtrain, Lumoid, and Momentum Machines.

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In Today’s Episode You Will Learn:

1.) How Leo made the transition from the world of operations with LinkedIn to co-founding Susa Ventures?

2.) How does Leo evaluate the supposed success that comes from investing with a contrarian mindset? This that the only way? Is investing merely a game of access without picking?

3.) If one is to follow the crowd, there is often a high price? What is Leo’s approach to valuation sensitivity? At what stage does price become unreasonable? How does Leo instill a sense of disciple and rigor in maintaining this mindset?

4.) How does Leo react to founders who raise large sums of capital on slowly increasing caps? How central should dilution be to the mindset of founders when raising?

5.) Why does Leo think there is very little valuable to be gained from engaging in technical due diligence at seed? What else does need to be examined pre-investment?

Items Mentioned In Today’s Show:

Leo’s Fave Book: Traction: A Startup Guide To Getting Customers

Leo’s Fave Blog: Mattermark Daily, 25IQ

Leo’s Most Recent Investment: TalentIQ

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

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

Foundersuite makes the leading CRM for raising startup capital. Since March of 2016, Foundersuite customers have raised over $130M in seed and venture capital. Foundersuite’s CRM sits on a database of over 50,000 investors, which will help you quickly populate your fundraising funnel including a beautiful and easy-to-use investor update tool, and the recently launched a new portal that helps investors and accelerators track their portfolio companies on a single dashboard. For a whopping 40% off a Monthly or Annual subscription use the code “20MinuteVC” at checkout.

Greenhouse Software designs tools that help companies hire great people and ultimately build better businesses. Greenhouse works with over 1,500 of the world’s most innovative companies such as Airbnb, Slack, Snap Inc. and Lyft. A wrong hire is not only costly for a company but can also turn an employee into an unhappy one. With Greenhouse’s Applicant Tracking System, companies can make well-informed decisions and hire qualified candidates who are empowered to do the best work of their careers. Anybody who has a company that’s scaling quickly but has trouble hiring and retaining the right people. Visit www.greenhouse.io today to discover how your company can grow.

Spencer Kimball is the Founder & CEO @ Cockroach Labs, the open-source database for building global, scalable cloud services that survive disasters. They have backing from some of the greats of the world of VC having raised from the likes of Sequoia, Benchmark, Google Ventures and Index. As for Spencer, prior to Cockroach he spent 10 years at Google where he oversaw their hyper growth transition from startup to global behemoth. He also spent two years at unicorn payments company, Square as well as co-founding 2 prior startups.

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In Today’s Episode You Will Learn:

1.) How Spencer made his move from a decade @ Google to starting Cockroach Labs?

2.) Why does Spencer enjoy speaking to VCs? What has Spencer taken away from the best of VC conversations? What are the best ways Spencer feels investors can make initial contact? What are the signs of bad investor interactions?

3.) How does Spencer want his VCs and board members to interact with him? How do the best board members provide constructive advice and feedback?

4.) How can investors get into the best deals? If they fail the first time, what can be done on their behalf to show continued interest?

5.) How does Spencer implement a 4 day work week at Cockroach and remain so highly productive? What are the benefits of this for the team and culture?

Items Mentioned In Today’s Show:

Spencer’s Fave Book: The History of The Decline & Fall of The Roman Empire

Spencer’s Fave Blog: Ben Bernanke, Paul Krugman

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.

Foundersuite makes the leading CRM for raising startup capital. Since March of 2016, Foundersuite customers have raised over $130M in seed and venture capital. Foundersuite’s CRM sits on a database of over 50,000 investors, which will help you quickly populate your fundraising funnel including a beautiful and easy-to-use investor update tool, and the recently launched a new portal that helps investors and accelerators track their portfolio companies on a single dashboard. For a whopping 40% off a Monthly or Annual subscription use the code “20MinuteVC” at checkout.

Greenhouse Software designs tools that help companies hire great people and ultimately build better businesses. Greenhouse works with over 1,500 of the world’s most innovative companies such as Airbnb, Slack, Snap Inc. and Lyft. A wrong hire is not only costly for a company but can also turn an employee into an unhappy one. With Greenhouse’s Applicant Tracking System, companies can make well-informed decisions and hire qualified candidates who are empowered to do the best work of their careers. Anybody who has a company that’s scaling quickly but has trouble hiring and retaining the right people. Visit www.greenhouse.io today to discover how your company can grow.

Anna Shedletsky is the Founder & CEO @ Instrumental, the startup that helps consumer electronics companies ship high-quality hardware, on time. They have funding from some of the best in the business including First Round Capital and a huge thanks to Phin Barnes @ First Round for the intro to Anna today. As for Anna, prior to Instrumental, Anna was a product design lead and manager for the Apple Watch and before that, a product design engineer for the Apple iPod.

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In Today’s Episode You Will Learn:

1.) How Anna made the move from working on the Apple Watch to starting her own startup Instrumental?

2.) How does Anna approach the learning of new things? What is the methodology? What elements in particular has Anna found most challenging to grasp?

3.) Anna has experienced 2 very strange and different fundraising processes? What was strange about them? How did they differ? What did she learn from this experience?

4.) How can founders create a feeling of FOMO within their investors? What is core to this? What should founders be careful of when doing this? How should this be structured?

5.) Coming from Apple, Anna did not have a network among VCs and Founders. How did Anna build her network of VCs and founders? How can others founders do this? What is required for this to be done in a non-transactional organic way?

Items Mentioned In Today’s Show:

Anna’s Fave Book: The Lord of The Rings

Anna’s Fave Blog: First Round Review

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

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

Foundersuite makes the leading CRM for raising startup capital. Since March of 2016, Foundersuite customers have raised over $130M in seed and venture capital. Foundersuite’s CRM sits on a database of over 50,000 investors, which will help you quickly populate your fundraising funnel including a beautiful and easy-to-use investor update tool, and the recently launched a new portal that helps investors and accelerators track their portfolio companies on a single dashboard. For a whopping 40% off a Monthly or Annual subscription use the code “20MinuteVC” at checkout.

Greenhouse Software designs tools that help companies hire great people and ultimately build better businesses. Greenhouse works with over 1,500 of the world’s most innovative companies such as Airbnb, Slack, Snap Inc. and Lyft. A wrong hire is not only costly for a company but can also turn an employee into an unhappy one. With Greenhouse’s Applicant Tracking System, companies can make well-informed decisions and hire qualified candidates who are empowered to do the best work of their careers. Anybody who has a company that’s scaling quickly but has trouble hiring and retaining the right people. Visit www.greenhouse.io today to discover how your company can grow.

Melody McCloskey is the Founder & CEO @ StyleSeat, the largest and fastest growing marketplace in the $78b beauty and wellness industry. They have raised over $40m in challenging funding conditions from some of the true greats of the business including Alfred Lin @ Sequoia, Chris Sacca, Jeff Clavier, Aileen Lee, Lightspeed, the list goes on. As for Melody, as well as running StyleSeat she is also a mentor for the Thiel Fellowship working with some of the brightest and best next generation entrepreneurs.

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In Today’s Episode You Will Learn:

1.) What was the origin story of StyleSeat for Melody and how did Travis Kalanick and Garrett Camp come to be angel investors?

2.) Melody has previously stated that ‘CEOs do not have all the answers’. What did Melody find most challenging that she struggled to answer? How has her approach to decision making and delegation changed over the last few years?

3.) Melody has been CEO for 6 years, a rarity in tech today, so what has been the core to her success long term as the leader of StyleSeat?

4.) With $40m in funding over 3 rounds, how did Melody find the fundraising experience? How did she feel the rounds differed? What does Melody believe she did well and what would she improve for further rounds?

5.) How does Melody approach transparency internally with fundraising? Should founders tell the team about fundraise opportunities? When is the right and wrong time to do so?

Items Mentioned In Today’s Show:

Melody’s Fave Book: Hard Thing About Hard Things

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

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

Foundersuite makes the leading CRM for raising startup capital. Since March of 2016, Foundersuite customers have raised over $130M in seed and venture capital. Foundersuite’s CRM sits on a database of over 50,000 investors, which will help you quickly populate your fundraising funnel including a beautiful and easy-to-use investor update tool, and the recently launched a new portal that helps investors and accelerators track their portfolio companies on a single dashboard. For a whopping 40% off a Monthly or Annual subscription use the code “20MinuteVC” at checkout.

Greenhouse Software designs tools that help companies hire great people and ultimately build better businesses. Greenhouse works with over 1,500 of the world’s most innovative companies such as Airbnb, Slack, Snap Inc. and Lyft. A wrong hire is not only costly for a company but can also turn an employee into an unhappy one. With Greenhouse’s Applicant Tracking System, companies can make well-informed decisions and hire qualified candidates who are empowered to do the best work of their careers. Anybody who has a company that’s scaling quickly but has trouble hiring and retaining the right people. Visit www.greenhouse.io today to discover how your company can grow.

Jared Friedman 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. Prior to YC, Jared was Co-Founder & CTO @ Scribd, the digital library and document sharing platform, which has over 80 million users and attained funding from the likes of Marc Andreessen, Redpoint and CRV. As well as his time in operations, Jared is also a prolific angel investor with investments in the likes of Instacart, FundersClub and Cruise Automation just to name a few.

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In Today’s Episode You Will Learn:

1.) How Jared made his way from founding the immensely successful, Sribd, to being a YC partner?

2.) What is the process behind the invites for YC demo day? What does it take for one to get a hotly anticipated seat? Is there really a black list?

3.) A lot of investors suggest that if you are seeing the company at demo day it is too late, what is the thesis around letting friends and family in to view and invest in the companies before demo day?

4.) How can investors look to get into the best YC companies? What can the investors do to show their value to both the companies and the YC partnership? How do you look to advise companies with regards to selecting investors?

5.) Demo days have scaled massively so I have to ask, is there enough capital to go into the 120+ companies now being produced at YC demo days? What are the strategies for scaling YC effectively?

Items Mentioned In Today’s Show:

Jared’s Fave Book: Sapiens: A Brief History of Humankind

Jared’s Fave Blog: HackerNews

Jared Most Recent Angel Investment: Starcity

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

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

Foundersuite makes the leading CRM for raising startup capital. Since March of 2016, Foundersuite customers have raised over $130M in seed and venture capital. Foundersuite’s CRM sits on a database of over 50,000 investors, which will help you quickly populate your fundraising funnel including a beautiful and easy-to-use investor update tool, and the recently launched a new portal that helps investors and accelerators track their portfolio companies on a single dashboard. For a whopping 40% off a Monthly or Annual subscription use the code “20MinuteVC” at checkout. 

Greenhouse Software designs tools that help companies hire great people and ultimately build better businesses. Greenhouse works with over 1,500 of the world’s most innovative companies such as Airbnb, Slack, Snap Inc. and Lyft. A wrong hire is not only costly for a company but can also turn an employee into an unhappy one. With Greenhouse’s Applicant Tracking System, companies can make well-informed decisions and hire qualified candidates who are empowered to do the best work of their careers. Anybody who has a company that’s scaling quickly but has trouble hiring and retaining the right people. Visit www.greenhouse.io today to discover how your company can grow.

Saar Gur is a General Partner @ CRV, one of the nation’s oldest and most successful VC firms now on their 16th fund. At CRV, Saar has made investments in some incredible companies including DoorDash, Dropbox, Patreon and Ring to name a few. His brilliance in VC is not just acknowledged by us but Forbes and Venture Capital Journal who named Saar to the top 8 up and coming Venture Capitalists and a top 10 VC under the age of thirty-six. Prior to VC, Saar was the Founder of Brightroll, a leading video ad network that was acquired by Yahoo for a reported $640m.

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In Today’s Episode You Will Learn:

1.) How Saar made his way into the world of VC and came to be a GP at CRV?

2.) When can VCs know when to pull the plug on an investment? How does Saar balance financial prudence with vision and belief in the startup and founder?

3.) What does Saar’s relationship building process look like? How does Saar build relationships with founders in natural and organic ways?

4.) How can VCs handle founder disputes? How does Saar look to be as helpful and productive in this process as possible? What does Saar recommend to other VCs in this situation?

5.) How does Saar view the inflection points in the growth of startups? At what moments is their the potential for elements to break? How should this be mitigated?

Items Mentioned In Today’s Show:

Saar’s Fave Book: The Wright Brothers

Saar’s Fave Blog or Newsletter: TechCrunch

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

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

Foundersuite makes the leading CRM for raising startup capital. Since March of 2016, Foundersuite customers have raised over $130M in seed and venture capital. Foundersuite’s CRM sits on a database of over 50,000 investors, which will help you quickly populate your fundraising funnel including a beautiful and easy-to-use investor update tool, and the recently launched a new portal that helps investors and accelerators track their portfolio companies on a single dashboard. For a whopping 40% off a Monthly or Annual subscription use the code “20MinuteVC” at checkout. 

Greenhouse Software designs tools that help companies hire great people and ultimately build better businesses. Greenhouse works with over 1,500 of the world’s most innovative companies such as Airbnb, Slack, Snap Inc. and Lyft. A wrong hire is not only costly for a company but can also turn an employee into an unhappy one. With Greenhouse’s Applicant Tracking System, companies can make well-informed decisions and hire qualified candidates who are empowered to do the best work of their careers. Anybody who has a company that’s scaling quickly but has trouble hiring and retaining the right people. Visit www.greenhouse.io today to discover how your company can grow.

Christian Lanng is the Founder & CEO @ Tradeshift, the startup with the vision to transform the way businesses work together. With 250+ people, offices in 9 countries and over $200m in funding from some of the best including Data Collective, HSBC and Intuit, they are likely one of the biggest and best startups you might not have heard of. As for Christian, he is one of the most visionary European entrepreneurs of the last decade having grown from digitising invoices in Denmark when he was at Uni to working on digitizing the EU later.

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In Today’s Episode You Will Learn:

1.) How Christian made his way from Denmark to founding one of the hottest startups in Silicon Valley?

2.) What does Christian mean when saying, “we should be discussing the globalization of technology”? How will we see the evolution of manufacturing over time? What is the bottleneck for automation?

3.) Christian has previously stated that his competitors have ‘hostages not customers’. Why does he say this and how does that affect his view of competition and customer service?

4.) Christian has raised over $200m in varying fundraising climates, how did the rounds differ? What were Christian’s keys to fundraising success? What does he know now that he wishes he had known in the beginning?

5.) How does Christian approach networking in a very unconventional style? What are the benefits of doing so? What does Christian advise startup founders looking to expand either their founder network or their investor network?

Items Mentioned In Today’s Show:

Christian’s Fave Book: The Subtle Art Of Not Giving A Fuck

Christian’s Fave Blog: SaaStr

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

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

But before we dive into the show today, there are some products that you simply cannot remember what life was like before them—for me that is x.ai. They bring you Amy and Andrew, the AI-powered personal assistants who schedule meetings for you. The beauty of Amy or Andrew is that you interact with them just like you would any other person, in plain English. You hand over meeting scheduling, and they get the job is done. Which means that you can avoid the tedious hours of email ping pong usually required to schedule a single meeting. Even better though, there is no sign in, no password, nothing to download. All you do is cc amy@x.ai Beautiful! And you can check it out now on https://x.ai/20vc/ It really is a must!

Workable is the all-in-one recruiting software for ambitious companies. From posting a job to tracking and managing candidates, Workable provides everything you need to hire better. Transparent communication, organized candidate profiles, structured interviews and a full reporting suite gives hiring teams the information they need to make the best choice. Workable is available for desktop and mobile and you can find out more on workable.com where you can try it for free.

Jason Lemkin is the Founder @ SaaStr, now with the $70m SaaStr Fund, Jason has paved the way for the new wave of VC in what I describe the ‘platformification of VC’. Jason has led or sourced the first VC investment in some of the fastest growing SaaS companies of today with the likes of Algolia, TalkDesk, Rainforest QA and PipeDrive. Prior to being in VC, Jason was the Co-Founder @ Echosign, leading to the very successful acquisition by Adobe where he oversaw Jason oversaw the growth of Adobe Document Services ARR from $50m in 2012 to $100m in 2013.

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In Today’s Episode You Will Learn:

1.) How Jason made his way into the world of VC from being a $100m+ exit founder to founding SaaStr and SaaStr Fund?

2.) What is it like for Jason having his own fund vs being part of a bigger fund? What does the investment cheque size say to founders about the fund? Should they be concerned if the investment represents less than 1% of the fund?

3.) What was the fundraising process and environment like for Jason with SaaStr? Is all LP money the same? What differentiated value-add elements can LPs provide fund managers?

4.) Does Jason agree that most VCs do not add value? How does Jason look to add value with his 3 pronged approach? Where does Jason believe that most startups need help and advice?

5.) How does Jason evaluate the micro-VC stage at present? Where does Jason see opportunity? Where does he believe the space is over-heated?

Items Mentioned In Today’s Show:

Jason’s Most Recent Investment: Automile

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

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

But before we dive into the show today, there are some products that you simply cannot remember what life was like before them—for me that is x.ai. They bring you Amy and Andrew, the AI powered personal assistants who schedule meetings for you. The beauty of Amy or Andrew is that you interact with them just like you would any other person, in plain English. You hand over meeting scheduling, and they get the job is done. Which means that you can avoid the tedious hours of email ping pong usually required to schedule a single meeting. Even better though, there is no sign in, no password, nothing to download. All you do is cc amy@x.ai Beautiful! And you can check it out now on https://x.ai/20vc/ It really is a must!

Workable is the all-in-one recruiting software for ambitious companies. From posting a job to tracking and managing candidates, Workable provides everything you need to hire better. Transparent communication, organized candidate profiles, structured interviews and a full reporting suite gives hiring teams the information they need to make the best choice. Workable is available for desktop and mobile and you can find out more on workable.com where you can try it for free.

Kevin Chou is co-founder and CEO of Kabam, a world leader in mobile free-to-play games. At Kabam, Kevin catapulted revenue to $400 million and a valuation of more than $1 billion in 2014. Under Kevin’s leadership, Kabam has raised more than $240 million from venture and strategic investors, including some of the world’s largest entertainment and internet companies such as Alibaba, Google, Intel and Warner Brothers. Before Kabam, Kevin worked at Canaan Partners, Kabam’s initial investor and where he invested in 14 consumer technology and online media companies. In 2014 Kevin was named one Fortune magazine’s prestigious “40 Under 40” and, in 2012, was identified by Fortune as one of the “Smartest People in Tech.”

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In Today’s Episode You Will Learn:

1.) How Kevin came to found the wildly successful Kabam from a life in VC with Canaan Partners?

2.) How does Kevin respond to investors that say games is so challenging as it is so hits driven? What are the requirements to build an enduring and successful games company?

3.) What are the metrics that define success in gaming? Why does Kevin believe that gaming is unlike any other in terms of metrics?

4.) To what extent does Kevin believe it is right to monetise games from the beginning vs the free to play market? What are the features and challenges required for success in the premium end of the market?

5.) How does gaming alter both in terms of design and monetisation when comparing the East to the West? What feature sets are preferrable in both? Why doe the East want to pay for as much up front as possible?

Items Mentioned In Today’s Show:

Kevin’s Fave Book: Sapiens: A Brief History of Humankind

Kevin’s Fave Blog or Newsletter: Dean Takahashi: VentureBeat

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.

But before we dive into the show today, there are some products that you simply cannot remember what life was like before them—for me that is x.ai. They bring you Amy and Andrew, the AI powered personal assistants who schedule meetings for you. The beauty of Amy or Andrew is that you interact with them just like you would any other person, in plain English. You hand over meeting scheduling, and they get the job is done. Which means that you can avoid the tedious hours of email ping pong usually required to schedule a single meeting. Even better though, there is no sign in, no password, nothing to download. All you do is cc amy@x.ai Beautiful! And you can check it out now on https://x.ai/20vc/ It really is a must!

Workable is the all-in-one recruiting software for ambitious companies. From posting a job to tracking and managing candidates, Workable provides everything you need to hire better. Transparent communication, organized candidate profiles, structured interviews and a full reporting suite gives hiring teams the information they need to make the best choice. Workable is available for desktop and mobile and you can find out more on workable.com where you can try it for free.

Carl Eschenbach is a Partner @ Sequoia Capital, one of the world’s leading funds with investments in the likes of Google, Apple, Whatsapp, Paypal and Stripe just to name a few. As for Carl, prior to Sequoia, Carl was President and CEO @ VMWare where he grew the team from 200 to 20,000 people. If that was not enough Carl has also stepped in as CFO at a $5Bn company and transitioned 3 CEOs.

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In Today’s Episode You Will Learn:

1.) How Carl made the move from President and CEO @ 20,000 person company, VMWare to Partner @ Sequoia?

2.) Question from Alfred Lin, Partner @ Sequoia: How did Carl look to build a culture of performance at VMWare?

3.) Question from Pat Grady, Partner @ Sequoia: What were Carl’s biggest learnings with regards to high performance teams? What are the common mistakes in scaling a go to market strategy?

4.) How does Carl view the internal workings at Sequoia to the external perception? Was the move to Sequoia everything he expected? What was different or challenging?

5.) What does Carl believe are the core components that make a great board member? How has Carl’s time in operations affected his view of boards and their working?

Items Mentioned In Today’s Show:

Carl’s Fave Book: Half Time

Carl’s Most Recent Investment: Zoom

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

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

But before we dive into the show today, there are some products that you simply cannot remember what life was like before them—for me that is x.ai. They bring you Amy and Andrew, the AI powered personal assistants who schedule meetings for you. The beauty of Amy or Andrew is that you interact with them just like you would any other person, in plain English. You hand over meeting scheduling, and they get the job is done. Which means that you can avoid the tedious hours of email ping pong usually required to schedule a single meeting. Even better though, there is no sign in, no password, nothing to download. All you do is cc amy@x.ai Beautiful! And you can check it out now on https://x.ai/20vc/ It really is a must!

Workable is the all-in-one recruiting software for ambitious companies. From posting a job to tracking and managing candidates, Workable provides everything you need to hire better. Transparent communication, organized candidate profiles, structured interviews and a full reporting suite gives hiring teams the information they need to make the best choice. Workable is available for desktop and mobile and you can find out more on workable.com where you can try it for free.

Pat Grady is a Partner @ Sequoia Capital, one of the world’s leading funds with prior investments in the likes of Apple, Google, Whatsapp, Paypal, Stripe and many more. At Sequoia, Pat has made investments in many past guests of this show and the SaaStr podcast including Zoom, Namely and Qualtrics, just to name a few. Prior to Sequoia, Pat spent 3 years with the team at Summit Partners.

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In Today’s Episode You Will Learn:

1.) How Pat made his way into the world of VC and one of the most famous funds in the world, Sequoia?

2.) How does Pat view the apprenticeship model in VC? How can VCs attempt to develop and convey the founder empathy when they have not been a founder? Do ‘career VCs’ get the same respect from founders?

3.) What does Pat believe to be the defining characteristics of the next generation of great software? What are the commonalities?

4.) Pat has said before that ‘data is the new oil’, what makes Pat think this? How does this affect his investment thesis going forward? Are there elements of being ‘data long’ that make Pat nervous?

5.) How does Pat think the data incumbency advantage can be mitigated? What can startups do to build a moat?

Items Mentioned In Today’s Show:

Pat’s Fave Book: The Boys In The Boat

Pat’s Fave Blog: CB Insights

Pat’s Most Recent Investment: Namely 

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

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

But before we dive into the show today, there are some products that you simply cannot remember what life was like before them—for me that is x.ai. They bring you Amy and Andrew, the AI powered personal assistants who schedule meetings for you. The beauty of Amy or Andrew is that you interact with them just like you would any other person, in plain English. You hand over meeting scheduling, and they get the job is done. Which means that you can avoid the tedious hours of email ping pong usually required to schedule a single meeting. Even better though, there is no sign in, no password, nothing to download. All you do is cc amy@x.ai Beautiful! And you can check it out now on https://x.ai/20vc/ It really is a must!

Workable is the all-in-one recruiting software for ambitious companies. From posting a job to tracking and managing candidates, Workable provides everything you need to hire better. Transparent communication, organized candidate profiles, structured interviews and a full reporting suite gives hiring teams the information they need to make the best choice. Workable is available for desktop and mobile and you can find out more on workable.com where you can try it for free.

Lee Hower is a co-founder and Partner at NextView Ventures, one of the East coast’s leading early stage funds with investments in the likes of Dia & Co, Sunrise, TaskRabbit and GrabCad just to name a few. As for Lee, prior to being a VC with NextView, Lee started his career as an early employee of PayPal in product and business development roles, through the company’s 2002 IPO and sale to eBay. After PayPal, Lee was a co-founder of LinkedIn (NYSE: LNKD) and served as head of corporate development.

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In Today’s Episode You Will Learn:

1.) How Lee made his way from the early days of PayPal with Elon Musk to the founding team of LinkedIn with Reid Hoffman to founding NextView and being a VC?

2.) What were Lee’s biggest takeaways from his time working with Elon Musk, Peter Thiel, Reid Hoffman in the early days of PayPal? How has that experience affected how he invests today?

3.) Unlike other Paypal mafia members, Lee decided not to pursue the multi-stage investing strategy. Why was this? How does Lee evaluate the current seed environment?

4.) Why does Lee believe it is fundamental to study the history of VC and innovation? How does this affect his mindset when investing?

5.) What would Lee advice to a junior VC or someone looking to move into the industry in terms of differentiation and personal branding? What is key? How should this be approached?

Items Mentioned In Today’s Show:

Lee’s Fave Book: The Globalisation Paradox

Lee’s Most Recent Investment: Optimus Ride

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

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

But before we dive into the show today, there are some products that you simply cannot remember what life was like before them—for me that is x.ai. They bring you Amy and Andrew, the AI powered personal assistants who schedule meetings for you. The beauty of Amy or Andrew is that you interact with them just like you would any other person, in plain English. You hand over meeting scheduling, and they get the job is done. Which means that you can avoid the tedious hours of email ping pong usually required to schedule a single meeting. Even better though, there is no sign in, no password, nothing to download. All you do is cc amy@x.ai Beautiful! And you can check it out now on https://x.ai/20vc/ It really is a must!

Workable is the all-in-one recruiting software for ambitious companies. From posting a job to tracking and managing candidates, Workable provides everything you need to hire better. Transparent communication, organized candidate profiles, structured interviews and a full reporting suite gives hiring teams the information they need to make the best choice. Workable is available for desktop and mobile and you can find out more on workable.com where you can try it for free.

John Borthwick is the Founder & CEO @ Betaworks, the New York-based startup platform combining 3 areas of expertise. They have a studio where they have built products including Giphy, Dots, Bitly and more. They have a fund with prior investments including Tumblr, Medium and Kickstarter. Finally they have a camp, a thematic accelerator program for companies in frontier technology sectors. As for John, Prior to Betaworks, John was an SVP at Time Warner Inc following John’s previous company, WP-Studio, being acquired by AOLTW.

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In Today’s Episode You Will Learn:

1.) How John made his way from AOL and Time Warner to founder of Betaworks?

2.) Why is John skeptical of the traditional VC model? Why does John believe that the market has adapted but the VC model has not?

3.) Why does John believe fund cycles are simply too short, in the same school of thought as Matt Ocko @ Data Collective? What are the problems with this?

4.) How does John evaluate Fred Wilson’s post on the consumer downturn? Why does John think we are addicted to short term rapid fire hits?

5.) Why is John not surprised that AI, Bots, VR and AR are being ‘labeled a disappointment for the last year? What does he think will be the catalyst for their rise?

Items Mentioned In Today’s Show:

John’s Fave Book: King Lear

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

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

X.ai is AI-poweredered personal assistant for scheduling meetings bringing you Amy or Andrew. The assistant you interact with like you would to any other person and it allows you to avoid the tedious hours of email ping pong in order to schedule one meeting. Even better, there is no sign in, no password, no download, all you do is cc amy@x.ai beautiful! And you can check it out now on x.ai it really is a must!

Workable is the all-in-one recruiting software for ambitious companies. From posting a job to tracking and managing candidates, Workable provides everything you need to hire better. Transparent communication, organized candidate profiles, structured interviews and a full reporting suite gives hiring teams the information they need to make the best choice. Workable is available for desktop and mobile and you can find out more on workable.com where you can try it for free.

Dennis Mortensen is the CEO and Founder of X.ai, the artificial intelligence driven personal assistant that lets people schedule meetings using plain English and nothing more than a CC to amy@x.ai. Their female persona Amy is so lifelike that users have asked her on a date at a rate of one request per month! X.ai is now one of the best funded AI startups having raised over $30m from our friends at FirstMark and DCM and a big thanks to Matt Turck for making the intro and from DCM, who also helped us with some of the questions for Dennis!

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In Today’s Episode You Will Learn:

1.) How Dennis came to found one of the leading AI startups today with X.ai?

2.) Why is product market fit like porn? How does this analogy affect Dennis’ evaluation of product market fit?

3.) What are the fundamental features required to turn a single user consumer product into an enterprise product? How should that transition be managed?

4.) Is Dennis concerned by large incumbents making their entrance into the world of more traditional enterprise companies with the likes of GSuite and Facebook for Work?

5.) How did Dennis evaluate the right pricing method for X.ai? What pricing mechanisms did he consider? What does Dennis believe is the future of enterprise pricing?

Items Mentioned In Today’s Show:

Dennis’ Fave Book: Shoe Dog

Dennis’ Fave Blog or Newsletter: Azeem Azhar: The Exponential View

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

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

X.ai is AI-poweredered personal assistant for scheduling meetings bringing you Amy or Andrew. The assistant you interact with like you would to any other person and it allows you to avoid the tedious hours of email ping pong in order to schedule one meeting. Even better, there is no sign in, no password, no download, all you do is cc amy@x.ai beautiful! And you can check it out now on x.ai it really is a must!

Workable is the all-in-one recruiting software for ambitious companies. From posting a job to tracking and managing candidates, Workable provides everything you need to hire better. Transparent communication, organized candidate profiles, structured interviews and a full reporting suite gives hiring teams the information they need to make the best choice. Workable is available for desktop and mobile and you can find out more on workable.com where you can try it for free.

Roger Ehrenberg is the Founder and Managing Partner @ IA Ventures, one of New York’s leading early stage funds with investments in the likes of TransferWise and The Trade Desk. Prior to IA, Roger was a prolific angel investor making investments in over 40 companies including BuddyMedia and previous guest, Howard Lindzon’s StockTwits. Before that, Roger served as President and CEO @ DB Advisors, Deutsche Bank’s internal hedge fund trading platform which managed $6Bn in capital across multiple geographies.

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In Today’s Episode with Roger You Will Learn:

• How Roger made his way into VC from the world of Wall St?
• How does Roger view the diversification model of 50+ in a portfolio in micro VC? What levels of ownership does that require?
• With regards to small and honed portfolios Roger has previously said that ‘small is beautiful’. How does Roger approach this with IA and what capital pools does this allow his partners?
• Roger has also said that ‘VC platforms are not a panacea’. What does he mean by this? What do founders really want from an investment partner today?
• What is the effect of Roger and IA being outside the traditional echo chambers of Silicon Valley? How does this affect Roger’s dealflow? Hiring ability? Partnership opportunities?

Items Mentioned In Today’s Show:

Roger’s Fave Blog and Newsletter: Maria Popova: BrainPickings

Roger’s Fave Book: Out Of The Crisis

Roger’s Most Recent Investment: Octane Lending

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

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

X.ai is AI-powered personal assistant for scheduling meetings bringing you Amy or Andrew. The assistant you interact with like you would to any other person and it allows you to avoid the tedious hours of email ping pong in order to schedule one meeting. Even better, there is no sign in, no password, no download, all you do is cc amy@x.ai beautiful! And you can check it out now on x.ai it really is a must!

Workable is the all-in-one recruiting software for ambitious companies. From posting a job to tracking and managing candidates, Workable provides everything you need to hire better. Transparent communication, organized candidate profiles, structured interviews and a full reporting suite gives hiring teams the information they need to make the best choice. Workable is available for desktop and mobile and you can find out more on workable.com where you can try it for free.

Scott Belsky is a Venture Partner @ Benchmark, one of the world’s leading VC funds. As an early-stage investor himself he has made investments in the likes of Uber, Warby Parker, Pinterest and Flexport just to name a few. Prior to Benchmark, Scott co-founded Behance in 2006, and served as CEO until Adobe acquired Behance in 2012. After Behance’s acquisition, Scott served as Adobe’s Vice President of Products, rebooting Adobe’s mobile product strategy and leading Behance until 2016. If that was not enough Scott is also, the co-founder and Chairman of a new marketplace product under development.

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In Today’s Episode You Will Learn:

1.) How Scott made his move into VC with Benchmark having founded Behance and been a VP @ Adobe?

2.) How did Scott see his investment decision making process change when comparing being an angel to a VC? What was it about VC that made Scott realise that he would not be a traditional VC?

3.) Why does Scott believe that when momentum is growing too fast it is generally likely to fade out? At what point is the transition point between large momentum that is and is not sustainable?

4.) Why is Scott fascinated by ‘the journey in between’? What gives Scott hope when reviewing a company in this stage? What does he always look for?

5.) Why does Scott think that autonomous vehicles in cities will be a public utility? Will the data sets produced be publicly or privately owned? Who will operate mass transit systems?

Items Mentioned In Today’s Show:

Scott’s Fave Book: Tribe: On Homecoming & Belonging

Scott’s Fave Blog or Newsletter: The Information

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

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

X.ai is AI-poweredered personal assistant for scheduling meetings bringing you Amy or Andrew. The assistant you interact with like you would to any other person and it allows you to avoid the tedious hours of email ping pong in order to schedule one meeting. Even better, there is no sign in, no password, no download, all you do is cc amy@x.ai beautiful! And you can check it out now on x.ai it really is a must!

Workable is the all-in-one recruiting software for ambitious companies. From posting a job to tracking and managing candidates, Workable provides everything you need to hire better. Transparent communication, organized candidate profiles, structured interviews and a full reporting suite gives hiring teams the information they need to make the best choice. Workable is available for desktop and mobile and you can find out more on workable.com where you can try it for free.

Jeremy Johnson is the Founder & CEO @ Andela, the startup that aims to bring a scientific approach to building engineering teams. They have backing from some of the best investors in the world with the likes of the Zuckerberg-Chan Initiative, Spark Capital, Google Ventures and our friends at Susa Ventures just to name a few. As for Jeremy, prior to founding Andela, Jeremy co-founded 2U, one of the fastest-growing education technology startups in history. 2U went public in 2014 (NASDAQ:TWOU) and continues to transform higher education. Jeremy has spoken on education and entrepreneurship at meetings hosted by the White house and Congress and was named “30 Under 30” by Inc. Magazine in 2012 and Forbes in 2013 and 2014.

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In Today’s Episode You Will Learn:

1.) How Jeremy made his entry into startups and came to found Andela?

2.) Question from Paige Craig: How did the Zuckerberg-Chan Initiative deal come about? What has been the effect of taking that round for the company and for you as the founder?

3.) How does Jeremy view the contrast between being CEO and being founder? What does he believe makes a truly great CEO?

4.) Andela is an intensely operational and logistics based business, how did Jeremy learn to handle this? What were the fundamental challenges?

5.) How does Jeremy view the future wof work? Why does Jeremy believe the future can only be in decentralised work forces?

Items Mentioned In Today’s Show:

Jeremy’s Fave Book: The Power of One

Jeremy’s Fave Blog or Newsletter: Social Snippets, Charles Hudson @ Precursor

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.

Intercom is the first to bring messaging products for marketing and customer support together on one integrated platform. With Intercom, businesses can chat directly with prospective customers on their website, engage current users with targeted messages based on their behavior, and provide personal support at scale with an integrated help desk and knowledge base. This is perfect for Businesses that want to help people visiting their website become customers. Marketing and growth teams that want to onboard and retain users by sending the right messages at the right time and Support teams that want to move beyond email to provide personalized, scalable support so simply head over to Intercom.com/20MVC

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.

Ben Blumenfeld is the Co-Founder & General Partner @ Designer Fund, they invest in startups co-founded by designers and build and educate design teams through their program, Bridge. Designer Fund’s portfolio includes the likes of Gusto, Stripe, Shyp, Operator and many more incredible companies. As for Ben, previously Ben was a design lead at Facebook for over 5 years where he helped build products for nearly a billion people and grow Facebook’s world-class design team. He was also the design director at Varien which he helped build into one of the world’s leading e-commerce firms.

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In Today’s Episode You Will Learn:

1.) How Ben made the move from designer to General Partner @ Designer Fund?

2.) How does Ben’s design background inform how he invests in companies and then supports them post-investment? How does he evaluate design opportunities from the design perspective?

3.) Why now has design become such a competitive advantage in tech? What has changed? What are the fundamentals of beautifully designed products today?

4.) How does Ben believe the current crop of VCs view design? What do they not understand? What should they look to understand? Will we see a new class of design-centric VCs?

5.) From seeing the likes of Facebook, Medium and Asana scale deign teams, what have been the takeaways to effectively scaling design teams with the growth of an organisation? What is required for this to be successful?

Items Mentioned In Today’s Show:

Ben’s Fave Book: The Power of One

Ben’s Fave Blog or Newsletter: Social Snippets, Charles Hudson @ Precursor

Ben’s Most Recent Investment: Hustle

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.

Intercom is the first to bring messaging products for marketing and customer support together on one integrated platform. With Intercom, businesses can chat directly with prospective customers on their website, engage current users with targeted messages based on their behavior, and provide personal support at scale with an integrated help desk and knowledge base. This is perfect for Businesses that want to help people visiting their website become customers. Marketing and growth teams that want to onboard and retain users by sending the right messages at the right time and Support teams that want to move beyond email to provide personalized, scalable support so simply head over to Intercom.com/20MVC

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.

Pejman Nozad is the Founding Managing Partner @ Pear.vc, one of the leading seed stage funds in the valley. However, Pejman did not enter the tech industry like most venture capitalists. Having immigrated from Iran, he lived in an attic above a yogurt shop and took a job at a rug store in the Valley. But he immersed himself in what was happening in technology. Slowly, with a few small investments, he developed a reputation for identifying talent and helping take promising ideas to the next level. From next to nothing, he built a $20B portfolio, investing in over 100 startups and seeding several multi-billion dollar companies such as Dropbox, Lending Club, SoundHound and Gusto.

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In Today’s Episode You Will Learn:

1.) How Pejman made his way from football in Iran to rug dealer in Palo Alto to leading seed stage VC?

2.) Mike Moritz has previously said that ‘a call from Pejman is a call he will always take’. What led Mike to say this? What makes Pejman the brilliant networker and community builder that he is?

3.) How does Pejman assess early stage founders and teams? From seeing an early Andy Rubin, what did Pejman take from that as to what makes the best founders?

4.) Pejman invested $400K in Andy Rubin’s Danger which exited 8 years later for $500m yet Pejman only 2x his money. What did he take from this? What have been the other major learning inflection points for Pejman in the journey?

5.) From working alongside some of the best investors of our generation, what does Pejman perceive to be the commonalities of the best investors? How do they operate? How do they evaluate early stage opportunities?

Items Mentioned In Today’s Show:

Pejman’s Fave Book: Power of Now

Pejman’s Most Recent Investment: Senti Biosciences

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

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

Intercom is the first to bring messaging products for marketing and customer support together on one integrated platform. With Intercom, businesses can chat directly with prospective customers on their website, engage current users with targeted messages based on their behavior, and provide personal support at scale with an integrated help desk and knowledge base. This is perfect for Businesses that want to help people visiting their website become customers. Marketing and growth teams that want to onboard and retain users by sending the right messages at the right time and Support teams that want to move beyond email to provide personalized, scalable support so simply head over to Intercom.com/20MVC

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.

Micah Rosenbloom is Managing Partner @ Founder Collective, one of the leading seed funds in the world with investments in Uber, Buzzfeed, Makerbot, PillPack, Coupang and Cruise, just to name a few. As for Micah, prior to VC with Founder Collective, his career was varied starting as a Hollywood agent before becoming a serial entrepreneur founding 3 companies with the last, a successful exit alongside his now Partner Eric Paley with Brontes Technology. Micah also is a Board Member with Sequoia Funded Dia and Co and board observer with both MoveWith and Sense360.

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In Today’s Episode You Will Learn:

1.) How Micah made the move from Hollywood agent to leading seed stage VC?

2.) Why does Micah believe it is wrong to have themes to invest against? Why does he believe that the most interesting businesses can be found in weird and wonderful places?

3.) Why does Micah believe it is a problem for founders to focus exclusively on top line valuation? Why does Micah disagree with the common notion that a $100m exit is not exciting for VC?

4.) Why does Micah believe it is wrong for founders to build their company for the next round? Why does Micah disagree with Jason Lemkin in stating, ‘the best investors know the benchmarks clearly for the next round’.

5.) How does Micah deal with the fire hose of activities inherent within venture? How does he prioritise those activities? What thesis does he base all his decisions around?

Items Mentioned In Today’s Show:

Micah’s Fave Book: Thinking Fast and Slow

Micah’s Most Recent Investment: Skysafe

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

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

Intercom is the first to bring messaging products for marketing and customer support together on one integrated platform. With Intercom, businesses can chat directly with prospective customers on their website, engage current users with targeted messages based on their behavior, and provide personal support at scale with an integrated help desk and knowledge base. This is perfect for Businesses that want to help people visiting their website become customers. Marketing and growth teams that want to onboard and retain users by sending the right messages at the right time and Support teams that want to move beyond email to provide personalized, scalable support so simply head over to Intercom.com/20MVC

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.

Topher Conway is a Co-Managing Partner of SV Angel, one of Silicon Valley’s leading seed funds with investments in the likes of Facebook, AirBnB, Twitter, Dropbox and many more. At SV Angel, Topher works particularly close with Gusto, Github, Lookout and many more incredible companies. He was included in Forbes Magazine’s 30 Under 30 in 2015. Prior to SV Angel, he worked at EQAL, Inc. At EQAL, he worked with the Business Development and Sales teams and lead efforts in creating new business opportunities. Prior to EQAL, he held positions at eCost and a 2004 summer internship in Google’s Direct Sales Organization. He is also a member of the UCLA VC Fund, helping foster entrepreneurship at the University.

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In Today’s Episode You Will Learn:

1.) How Topher made his way into the wonderful world of VC and came to be Managing Partner @ SV Angel?

2.) How has the rise of the pre-seed market affected Topher’s access to deals? How has Topher reacted to the creation of this new market segment with their new fund size?

3.) How does Topher evaluate grit within founders? Do Topher and SV prefer serial or first-time founders? How does Topher and SV approach startup pivots? Where is the line between stubbornness and vision?

4.) To what extent does Topher focus on valuation and ownership? Why does he believe that it is not important at this stage? What is his determinant to see whether it will be a problem?

5.) To what extent has Topher witnessed the Series A Crunch? Where does he see gaps in the investment landscape? Why does Topher not have a problem with bridge rounds?

Items Mentioned In Today’s Show:

Topher’s Fave Book: The Score Takes Care Of Itself

Topher’s Most Recent Investment: BetterUp

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

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

Intercom is the first to bring messaging products for marketing and customer support together on one integrated platform. With Intercom, businesses can chat directly with prospective customers on their website, engage current users with targeted messages based on their behavior, and provide personal support at scale with an integrated help desk and knowledge base. This is perfect for Businesses that want to help people visiting their website become customers. Marketing and growth teams that want to onboard and retain users by sending the right messages at the right time and Support teams that want to move beyond email to provide personalized, scalable support so simply head over to Intercom.com/20MVC

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.

Gautam Gupta is the Co-Founder and CEO of NatureBox, the startup allows consumers to discover new & healthy foods through a monthly subscription service. They have raised over $50m in VC funding from the likes of General Catalyst, Redpoint, SoftBank and many more. Prior to launching NatureBox, Gautam was a Principal at General Catalyst Partners. While at General Catalyst, he sourced and was actively involved with the firm’s investments in GoodData, Bigcommerce, Honest Company and many more. Gautam joined General Catalyst from Procter and Gamble, where he analyzed brand strategy and consumer preferences in the Consumer Market Knowledge group.

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In Today’s Episode You Will Learn:

1.) How Gautam made the way from VC with General Catalyst to Founder of NatureBox?

2.) How does Gautam view the career VC we see often today? Does Gautam believe you need operating experience to be a good investor? How can investors without operating experience, build empathy for their founders?

3.) Why did Gautam choose to pursue both a B2B and B2C go to market strategy? How do the 2 models differ? What are the challenges and benefits to running both simultaneously?

4.) How does Gautam evaluate the rise of consumer subscription models? Following Jet and Dollar Shave, will we see further acquisitions from large CPG’s?

5.) Why have we seen such a rise in investor appetite for food startups? What is it about the market that is so attractive? What elements will see the most disruption? Does it concern Gautam to see traditional tech investors moving into waters they are unfamiliar with?

Items Mentioned In Today’s Show:

Gautam’s Fave Book: Shoe Dog

Gautam’s Fave Blog: Recode, TechCrunch

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

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

Intercom is the first to bring messaging products for marketing and customer support together on one integrated platform. With Intercom, businesses can chat directly with prospective customers on their website, engage current users with targeted messages based on their behavior, and provide personal support at scale with an integrated help desk and knowledge base. This is perfect for Businesses that want to help people visiting their website become customers. Marketing and growth teams that want to onboard and retain users by sending the right messages at the right time and Support teams that want to move beyond email to provide personalized, scalable support so simply head over to Intercom.com/20MVC

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.

Jules Maltz is a General Partner @ IVP where he has made investments in the likes of Slack, Zendesk, Twitter, Zenefits and many more incredible companies. Prior to IVP, Jules held roles at the likes of 3i, Admob and Bank of America. Jules has also been named to The Top 40 Under 40 Growth Investors and been featured in the likes of Inc and Fast Company.

Tim Junio is the Co-Founder and CEO @ Qadium, the startup that creates and organizes knowledge about the world’s devices. They are backed by some of the best in the business including the likes of Founders Fund (Peter Thiel), NEA (Scott Sandell) and our good friends at Susa Ventures. Prior to Qadium, Tim started his career at the Central Intelligence Agency, and also worked in the Office of the Secretary of Defense, the RAND Corporation, and DARPA. Tim remains a research affiliate at Stanford, where he lectures and advises students on cybersecurity research topics.

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In Today’s Episode You Will Learn:

1.) How Tim made his way from the world of the CIA to founding venture backed, Qadium?

2.) How does Tim view his role as CEO? Why does he view leadership and management as 2 different things?

3.) How does Tim view transparency as a leader? What are the conversations that must only be for the founding team? How are those decisions managed and discussed?

4.) Considering Peter Thiel’s recent press coverage how does Tim feel about taking ‘Thiel Money’? Why does he think Thiel is one of the most interesting and brilliant minds? What are the challenges for Silicon Valley in eschewing the world of politics for the next 4 years?

5.) What does Tim see as the worst of Silicon Valley? What are the benefits to many ‘shallow apps’ not getting funded? How does this affect startup economics and hiring programmes?

Items Mentioned In Today’s Show:

Tim’s Fave Book: Snowcrash

Tim’s Fave Blog or Newsletter: Bruce Schneier  

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

Ryan McIntyre is a Co-Founder @ Foundry Group, one of the leading VC funds of the last decade with investments in the likes of Fitbit, SendGrid and Makerbot. Prior to Foundry, Ryan started his career in VC at Mobius Venture Capital in January 2000.  While at Mobius Venture Capital, Ryan led the firm’s investments in Postini (acq. GOOG) and Sling Media (acq. DISH). Prior to Mobius, Ryan co-founded Excite in 1993, which went public in 1996 and later became Excite@Home following the $6.7 billion merger of Excite and @Home in 1999. At the time this acquisition was the largest internet transaction to date and created a company that achieved peak revenues of $616 million in 2000.

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In Today’s Episode You Will Learn:

1.) How Ryan made his way into the wonderful world of VC and came to co-found Foundry?

2.) At what moment did Ryan realise that he wanted to be a VC rather than his previous life of an entrepreneur? What was the catalyst moment for Ryan?

3.) What does the investment decision making process look like @ Foundry Group? What are the benefits and challenges of implementing such a model?

4.) What are the fundamentals to creating a successful venture partnership? How important is differing skill sets and contrarian thinking?

5.) What makes the great board members to Ryan? How has Ryan seen his style of being a board member alter over the time he has been on boards?

Items Mentioned In Today’s Show:

Ryan’s Fave Book: Dune by Frank Herbert

Investment Ryan Is Most Excited By: Sendgrid

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

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

Intercom is the first to bring messaging products for marketing and customer support together on one integrated platform. With Intercom, businesses can chat directly with prospective customers on their website, engage current users with targeted messages based on their behavior, and provide personal support at scale with an integrated help desk and knowledge base. This is perfect for Businesses that want to help people visiting their website become customers. Marketing and growth teams that want to onboard and retain users by sending the right messages at the right time and Support teams that want to move beyond email to provide personalized, scalable support so simply head over to Intercom.com/20MVC

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.

Jason Mendelson is Co-Founder @ Foundry Group, one of the leading VC funds of the past decade with investments in the likes of Fitbit, SendGrid and Makerbot just to name a few. Prior to Foundry Jason co-founded SRS Acquiom, the largest merger and acquisition closing platform that completed over $200Bn in merger transactions. Prior to co-founding SRS, Jason was a Managing Director and General Counsel for Mobius Venture Capital, where he also acted as its chief administrative partner overseeing all operations of the firm. If this was not enough Jason is also the Co-Author, alongside Brad Feld, of the best-selling book, Venture Deals: How To Be Smarter Than Your Lawyer, a must read for all.

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In Today’s Episode You Will Learn:

1.) How Jason made his way into the wonderful world of VC having been a lawyer?

2.) Why does Jason believe there is too much BS in VC? What does Jason think causes this opaqueness? How does he look to build a relationship of trust and clarity with his entrepreneurs?

3.) How has the rise of social media affected the transparency and BS element in VC and startups? How can entrepreneurs know when a VC is lying to them? What are the tells?

4.) Jason has previously said that some VC behaviour is ‘rather narcissistic’. What does he mean by this? How would he like to see this change in the future?

5.) How does Jason look to optimise board meetings? What are the expectations of both founders and VCs prior to board meetings when it comes to preparation?

Items Mentioned In Today’s Show:

Jason’s Fave Book: Atlas Shrugged

Jason’s Most Recent Investment: Borrowed and Blue

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

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

Intercom is the first to bring messaging products for marketing and customer support together on one integrated platform. With Intercom, businesses can chat directly with prospective customers on their website, engage current users with targeted messages based on their behavior, and provide personal support at scale with an integrated help desk and knowledge base. This is perfect for Businesses that want to help people visiting their website become customers. Marketing and growth teams that want to onboard and retain users by sending the right messages at the right time and Support teams that want to move beyond email to provide personalized, scalable support so simply head over to Intercom.com/20MVC

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.

Sarah Guo is an investor @ Greylock Partners, which she joined in 2013. Prior to Greylock, Sarah was at Goldman Sachs, where she invested in Dropbox and helped take Workday public. She advised pre-IPO private technology companies (as well as public clients including Zynga, Netflix and Nvidia) on strategic and financial issues. Previously, Sarah worked with Casa Systems, a venture-funded startup that enables cable operators to meet growing demand for broadband services. She is an advocate for STEM education for women and the underserved, as well as education more generally.

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In Today’s Episode You Will Learn:

1.) How Sarah made her way into VC with Greylock Partners?

2.) Question from Josh Elman: What were Sarah’s biggest learnings from taking key companies public with GS in 2011? Why is narrative so important? Who has done it well?

3.) How does Sarah view market size and market creation? What is a big enough market size to be attractive? How does this change with time and product?

4.) How does Sarah view the next fundamental platform shift? Where does conversational fit into this thesis? Will we see ‘machine learning as a service’?

5.) What does the future of VC look like? What does the next generation of VC need to do to stay on top and ensure pattern matching algorithms do not outperform them?

Items Mentioned In Today’s Show:

Sarah’s Fave Book: The Most Human Human

Sarah’s Most Recent Investment: Rhumbix

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

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

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Cirrus Insight is a plugin for sales pros who use Gmail and Outlook.  It automatically updates activities in Salesforce so you don’t have to.  It was named #41 on the Inc. 500 list of fastest-growing companies, and it has more than 1,700 customer reviews on the Salesforce AppExchange. Today, it serves over 150,000 sales people across 5,000 organizations using Gmail, Outlook, iPhone, iPad, and Android. Cirrus Insight is perfect for sales, support, and success teams who want to save time, schedule 3x more appointments, track email opens and much more with Salesforce information at their fingertips in the inbox. www.cirrusinsight.com/20VC

John Lilly is a Partner at Greylock Partners, one of the world’s leading venture funds of the past decade. At Greylock John has led investments in the likes of Instagram (acq by Facebook), Tumblr (acq by Yahoo) and Dropbox. John also sits on the board for Quip, Figma and ClearSlide just to name a few. Prior to Greylock, John was CEO of Mozilla, the organization behind Firefox, used by more than 450 million people. John also co-founded Reactivity, an enterprise security infrastructure company acquired by Cisco in 2007, where he served as founding CEO and later CTO.

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In Today’s Episode You Will Learn:

1.) How John made his way into the wonderful world of VC following his time as CEO @ Mozilla?

2.) John has invested in the likes of Quip, Figma and Dropbox, so why are we seeing such a rise in productivity tools beyond Office and Google Apps? Will it always be a market of consolidation like we have seen with the likes of Quip?

3.) Does John believe the first boom of mobile is over? What about sensors makes John excited for the future of the phone? Does John agree with Ben Evans in viewing the phone as the sun of the solar system?

4.) Question from Sarah Guo: How does Greylock to continue to invest in the next big markets, rather than in what has made them successful before? What does the brainstorming sessions and meta-thinking look like internally?

5.) Question from Josh Elman: How does John view growing one’s tribe and then growing together through all of your careers? What are the challenges and what is required in order to be successful?

Items Mentioned In Today’s Show:

John’s Fave Book: Thinking Fast and Slow by Daniel Kahneman

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

Tim Chang is a Managing Director @ Mayfield Fund and Tim was referred to me by many other VCs as ‘the fittest man in silicon Valley’, notable tech publications even write it. His eclecticness does not stop there as he is also a musician in 3 bands and a serious body hacker. As for his investments, he has had AdChina (acquired by Alibaba), Playdom (acquired by Disney) and Basis (acquired by Intel) just to name a few. Prior to Mayfield, he spent time at notable institutions including General Motors and Norwest Venture Partners. It is not only us that appreciate Tim’s skills though as he has also been named to ‘Top 100 Innovators’ on Forbes Midas List for 2 years running.

Maran Nelson is the Co-Founder & CEO @ Clara Labs, the truly human interface that uses conversational intelligence trained on high-quality data to schedule your meetings. They have secured funding from some of the best in the business including previous guest Kent Goldman @ Upside Partnership and Greg Brockman, Founder of the prestigious OpenAI. As for Maran, she is also the Founder of Interact, a community of 100 young makers and technologists coming together for an annual retreat in Tahoe.

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In Today’s Episode You Will Learn:

1.) How did Maran come to found one of the hottest AI startups of the day in Clara Labs?

2.) What is the right way to think about a digital assistant? How does Maran think consumer expectations and behaviours will change towards them in the coming years?

3.) Question from Shivon @ Bloomberg Beta: How does Maran think about building an AI company for the long term? How does Clara look to build scalable and transparent feedback loops?

4.) Why is Maran so bullish on the conversational interface? To what situation does this interface lend best? What other verticals and applications could this have in the future?

5.) Does Maran think that humans will always be needed in this process? At what stage will they become obsolete?

Items Mentioned In Today’s Show:

Maran’s Fave Book: East of Eden by John Steinbeck

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

Emily Melton is partner at DFJ, where she focuses on consumer and mobile technology, as well as healthcare technologies and marketplaces. Emily has made investments in the likes of BetterUp, Elation Health, Livongo, Redfin, Shift, and Wellframe. Early in Emily’s career, she sourced investments in Box (NYSE: BOX), Meebo (Google), Kudo (Google), RichRelevance, and Flux (MTV Networks). She was also an advisor to Pulse Network (LinkedIn), Healthtap, and Poshmark.

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In Today’s Episode You Will Learn:

1.) How Emily made her way into the wonderful world of VC following her meeting with Tim Draper?

2.) How does Emily view the importance of pattern recognition? Why does Emily believe that you should not invest from patterns? What is the difference between a pattern and an investing fad?

3.) Why does Emily hate analogies? Why does she believe it is simplistic thinking? How can this be mitigated for startup founders in describing their company?

4.) How does Emily view the portfolio approach to risk in venture? What questions need to be asked to determine the potential outcome of the business?

5.) Why does Emily get concerned by the rise of the ‘celebrity investor’? How can investors build their brand in the proliferated world of early stage startup investing?

Items Mentioned In Today’s Show:

Emily’s Fave Book: Mindset by Carol Dweck, A Theory of Justice by John Rawls

Emily’s Most Recent Investment: BetterUp

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

Josh Stein is Partner @ DFJ where his current board responsibilities include Box (NYSE: BOX), Chartbeat, LaunchDarkly, LendKey, SugarCRM, and previous guests with me on SaaStr in Periscope and Talkdesk. He is also actively involved with the firm’s investments in AngelList, Doximity and Twilio (NYSE: TWLO) just to name a few. Prior to joining DFJ, Josh was a VP at Telephia, where he managed a group providing strategic analysis and information to the nation’s largest wireless carrier. Previously, Josh was a co-founder for ViaFone (NYSE: SY), a DFJ portfolio company and a leading provider of wireless enterprise applications. Josh met the DFJ team when the firm co-led ViaFone’s Series A investment.

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In Today’s Episode You Will Learn:

1.) How Josh made his way from the world of operations to Partner @ DFJ?

2.) How does Josh analyze the VC/ Founder fit? How does Josh look to build trust and transparency in that relationship? What is an example of how Josh has changed his style to fit the character of an entrepreneur?

3.) Question from Greg Sands: What did Josh see in the early days of Box with a young Aaron Levie, what was it that made him so excited?

4.) Question from Mamoon Hamid @ Social Capital: Looking at Box today, what will it take for Box to 10x their value? What needs to happen in the market? What needs to happen to the product roadmap?

5.) Question from Jason Lemkin @ SaaStr: How is it that we are seeing companies like TalkDesk and Twilio grow at a rate never seen before in today’s SaaS environment?

Items Mentioned In Today’s Show:

Josh’s Fave Blog: TermSheet

Josh’s Fave Book: Insanely Simple: The Obsession That Drives Apple’s Success

Josh’s Most Recent Investment: LaunchDarkly

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

Henry Ward is the Founder & CEO @ eShares, the No 1 cap table management platform providing equity management, 409A valuations and liquidity all in one place. They are backed by leading investors and past guests including USV, SV Angel, Spark Capital, Semil Shah, Manu Kumar, Tim Draper and Kamal Ravikant, just to name a few. Prior to eShares, Henry was Founder @ SecondSight, the first registered investment advisor to go direct to your brokerage and improve your portfolio.

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In Today’s Episode You Will Learn:

1.) How Henry made his way into the world of startups and came to found eShares?

2.) How does Henry challenge the notion that investors should have such high fail rates? How does Henry believe investors can build a strong and sustainable portfolio without home runs?

3.) Why does Henry believe that investors will never accept market risk? How much of a role does Henry believe herd mentality plays in the VC ecosystem?

4.) How does Henry view the increasing exit horizons for startups? Is this a problem? How can we create liquidity options pre large exits?

5.) How does Henry view the role of regulation in private markets? How does this differ to public markets? What would Henry like to see change in the VC ecosystem?

Items Mentioned In Today’s Show:

Henry’s Fave Blog: Hacker News

Henry’s Fave Book: The Essays Of Warren Buffett

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

Phil Libin is Managing Director @ General Catalyst and Founder and Executive Chairman @ Evernote. At Evernote, Phil took the company from idea generation to productivity powerhouse allowing millions of users around the world to remember everything and in the meantime, providing Evernote with over $160m in VC funding from some of the very best including Sequoia Capital. Now in the world of VC, Phil has a particularly fondness towards all things bots, a theme we discuss heavily today. Phil has also made several angel investments in the likes of Gusto, TellApart and Binary Thumb just to name a few.

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In Today’s Episode You Will Learn:

1.) How Phil made his way from Founder @ Evernote to Managing Director @ General Catalyst?

2.) Niko Bonatsos, Managing Director @ General Catalyst asks: What were your biggest takeaways from your time with Evernote that lend to you being a better investor? What are the biggest surprises about the move into VC?

3.) Why have we seen an explosion of hype and excitement around the bot space over the past year? What was the catalyst for the rise of the bot?

4.) Why are we not there yet with bots? Should all be conversational? How does the infancy of messaging platforms affect the rise of bots? What unsolved technical challenges remain?

5.) Will the transition to bots and conversational interfaces represent a major point of disruption or more of an evolution in the interface paradigm?

Items Mentioned In Today’s Show:

Phil’s Fave Blog: The Economist

Phil’s Fave Book: The Three Body Problem

Phil’s Most Recent Investment: Sunflower Labs

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

Charlie O’Donnell is the Founder and Sole Partner @ Brooklyn Bridge Ventures, the first venture capital fund based in Brooklyn, who manage $23m across 2 funds. Prior to founding Brooklyn Bridge, Charlie worked at the prestigious First Round Capital, with the likes of Josh Koppelman and Union Square Ventures with Fred Wilson. If that wasn’t enough Charlie is one of only a dozen to be named to Business Insider’s 100 Most Influential People in NY Tech five or more times and has served on the founding board of the New York Tech Meetup and is one of the group’s first 100 members. His blog, This is Going to Be BIG!, is one of the ten most widely read VC blogs in the country with over 8,000 readers.

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In Today’s Episode You Will Learn:

1.) How Charlie made his move from college to venture and then struck out on his own from USV?

2.) Charlie has previously said that ‘venture capital is humbling’. How does Charlie look to construct his portfolio with Brooklyn Bridge? How does he come to terms with the fact he will be wrong most of the time?

3.) What are Charlie’s views towards follow-on funding and allocating reserves of the fund? How important is this from a return multiple perspective? How much of a difference does it make for founders to raise a next round with 100% of seed investors committed?

4.) Charlie has previously suggested the importance of being helpful and hard working. Is that really enough to build a brand in today’s competitive VC environment? Is brand a form of defensible IP?

5.) How does Charlie react to Ben Lerer’s suggestion that Jet.com and Dollar Shave Club are the first dominoes of an incoming wave of e-commerce M&A?

Items Mentioned In Today’s Show:

Charlie’s Fave Blog: Wait But Why

Charlie’s Most Recent Investment: Industrial Organic

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

Kent Goldman is the Founder of Upside Partnership, one of the leading seed-stage investment firms in SF with investments in the likes of Laurel and Wolf, Digit and Lily. In 2015, he was named to the Midas Brink List. Prior to forming Upside Partnership in 2014, Kent was a Partner at seed investment pioneer First Round Capital. While there he led investments in companies including Airware, Hotel Tonight, and MemSQL. He also served on the board of Mashery (acquired by Intel). Earlier in his career, Kent was a member of Yahoo!’s corporate development team and also led business strategy for Yahoo! products generating $1 billion in annual revenue.

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In Today’s Episode You Will Learn:

1.) How Kent made his way into the world of early stage investing and came to found Upside?

2.) What were the big takeaways from First Round for Kent? How has he applied those learnings to his formation of Upside?

3.) What does Kent look for in the LPs that invest in his fund? Why should founders look to learn which LPs are invested in the fund investing in them?

4.) How has Kent seen his investment decision-making process alter with time? What have been the big changes?

5.) Why does Kent believe valuation does not matter so much at the seed stage? What does really matter to him at the seed stage? How does this progress with rounds?

Items Mentioned In Today’s Show:

Kent’s Fave Blog: Howards Marks: Oaktree Capital

Kent’s Fave Book: A River Runs Through It And Other Stories

Kent’s Most Recent Investment: Live Neighborly

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

David Politis is the Founder & CEO @ Bettercloud, the first ever unified SaaS management platform. Bettercloud have raised over $40m in funding from some of today’s best investors including past guests from Accel, Greycroft Partners and Flybridge Partners, just to name a few. Before founding BetterCloud, David was an early employee of Cloud Sherpas (acquired by Accenture [NYSE: ACN]) where David led Cloud Sherpas to become the leading Google Apps services provider and reseller to SMBs worldwide. Prior to Cloud Sherpas, David was the founding employee and General Manager of Vocalocity (acquired by Vonage [NYSE: VG]), which he grew into one of the top providers of cloud PBX technology.

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In Today’s Episode You Will Learn:

1.) How Dave came to found Bettercloud? What was the a-ha moment for him?

2.) Why does David like to invest in everything but perks? What are the challenges of incentivising a team with Perks? What are the alternatives?

3.) What are the limits to transparency? Can there ever be too much transparency? How do you engender a culture of radical transparency within the workforce?

4.) How was the fundraising process for David? how did it alter and develop with every round? What did he do well and what would he improve upon?

5.) How can founders optimise the on boarding process for new hires? What is fundamental? What are the common mistakes and how can this be hacked for success?

Items Mentioned In Today’s Show:

David’s Fave Blog: Recode

David’s Fave Book: Banker To The Poor 

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

Parker Thompson is a Partner @ AngelList and creator of popular parody Twitter Account, Startup L Jackson. At AngelList Parker has made investments in the likes of former guests, Algolia, Realty Shares and Keen IO. Prior to joining AngelList, Parker was a Partner at 500 Startups in SF and his illustrious path prior to investing includes Pivotal Labs, co-founding PlaceSite, preserving the interwebs at the Internet Archive, and working on digital copyright at UC Berkeley’s iSchool.

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In Today’s Episode You Will Learn:

1.) How Parker made his way into the world of early stage investing from the world of operations?

2.) How does Parker look to evaluate startup founders? What questions does he like to ask? What traits does he like to see in the core exec?

3.) Why does Parker think “not enough traction” is a BS VC excuse? How should VC’s approach saying no to founders? What are the real reasons a VC is saying no in this case?

4.) Why does Parker believe the jump to Series A is bigger than ever? What has caused this? What metrics do startups have to achieve to make this move successfully?

5.) How should founders determine how much money to raise? If they can should they raise a ‘warchest’? Why should founders not be concerned with dilution in the early days?

Items Mentioned In Today’s Show:

Parker’s Fave Blog: Stratechery, Nuzzel

Parker’s Fave Book: The Modernist Cuisine 

Parker’s Most Recent Investment: Common Networks 

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

Rebecca Lynn is a Partner @ Canvas, where she focusses on Fintech, Digital Health, SaaS and mobile. Rebecca led an early stage investment in Lending Club, which was the largest US technology IPO of 2014 and the 4th largest Internet IPO since 2001. She has also led investments in the likes of Check (acquired by Intuit), RelateIQ (acquired by Salesforce), Proximity, Practice Fusion and more incredible companies. Prior to being in VC, Rebecca held operational roles at NextCard where she rose to become VP of Marketing and Head of Customer Acquisition and saw the company going public with a $1.3bn market cap.

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In Today’s Episode You Will Learn:

1.) How Rebecca made her way into the wonderful world of VC?

2.) How does Rebecca view the importance of brand and thematic focus in the world of VC today? How can a VC be focussed thematically without missing moonshots?

3.) What were Rebecca’s biggest lessons from sitting on boards with the likes of Mary Meeker and Larry Summers? How did that change how Rebecca viewed being a board member?

4.) “Fintech is all about distribution and acquisition”. What does Rebecca make of this statement? How have we seen evolution in both distribution and acquisition in the rising tide of new fintech startups?

5.) How does Rebecca analyse fund economics? What does she make of the mega $1Bn funds raised over the last year? What is the optimal size fund for Rebecca?

Items Mentioned In Today’s Show:

Rebecca’s Fave Blog: The Daily Shot

Rebecca’s Fave Book: Influence by Robert Cialdini

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

Ryan Smith is the Founder & CEO @ Qualtrics, an online survey company with 1,200 employees and a valuation of more than $1bn. They have backing from some of the world’s best investors including the likes of Sequoia, Accel and Insight Venture Partners having raised a $150m Series B in 2014. As for Ryan, there are many awesome things, first, he has built Qualtrics from Utah allowing him to gain perspective outside of the traditional tech bubbles, second, he held off on attain VC funding for many years despite the common belief that it is necessary for unicorn growth and finally he has the most incredible work life balance I have seen and if you have not already you must check out this piece on him in Forbes, it really is a must.

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In Today’s Episode You Will Learn:

1.) How Ryan made his way into startups and came to found Qualtrics?

2.) Sequoia’s Bryan Schreier states that Ryan’s success is due to running the company on ‘first business principles’. What does he mean by this? How does this affect the way Ryan runs Qualtrics?

3.) Why did Ryan decide to bootstrap the company for such a long time with the likes of Accel and Sequoia looking to invest? What are the benefits of retaining such control? What are the financial requirements to do so?

4.) What makes the best CEO’s? How do they view the internal structure of the company? How do they perceive their role? How do they manage their day and optimise their time?

5.) How does Ryan look to instill ‘radical transparency’ in the organisation? What are the benefits of doing so? Can an organisation ever be too transparent? What are the challenges of such transparency?

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

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

Pearl believes the latest automotive technology should be available to every driver – whether it’s time for you to buy a new car or not. RearVision is our first step in driving this commitment forward. Pearl RearVision is the only wireless backup camera and alert system that installs in minutes and updates throughout its lifetime. Pearl literally takes less than 10minutes to install and is completely wireless because it’s solar powered. Since RearVision is software based, we’re able to push updates and new features over the Pearl App in the exact same way you receive updates for other apps on your phone. Pearl RearVision is perfect for anyone who wants to upgrade their car in minutes. Pearl RearVision is $499.99 and available at PearlAuto.com. It’s also available on Amazon and through Crutchfield.

Xero is beautiful, easy-to- use online accounting software for small businesses. With Xero, you can easily manage your accounting anytime, anywhere from your computer or mobile device.When you add Xero to your small business you are able to: Send online invoices and get paid faster. Get an instant view of your cash flow. Track your payroll and keep tabs on your inventory. Partner with your accountant and bookkeeper in real time whenever you like. You can also customize your Xero experience with over five hundred business apps, including advanced solutions for point-of- sale, time tracking, ecommerce and more. Sign up for a free thirty-day trial at xero.com/20vc

Garry Tan is a Co-Founder and Managing Partner @ Initialized Capital, one of Silicon Valleys leading early stage seed funds. Prior to founding Initialized, Garry was a Partner at Y Combinator where he invested in and directly worked with over 700 companies in 5 years from the earliest possible stage, often just an idea. Garry’s portfolio includes the likes of previous guests Tilt, Eero, Flexport, LendUp and many more incredible companies.
Before being at YC, Garry Co-Founded Posterous and helped build it to a world-class website used by millions, ultimately acquired by Twitter. Garry also co-founded the engineering team for Palantir Technology’s quant finance analysis platform.

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In Today’s Episode You Will Learn:

1.) How Garry made the transition from Founder @ PostHaven to YC Partner to Initialized GP?

2.) What were Garry’s biggest takeaways from advising 700 startups at YC that he has taken with him to Initialized?

3.) Why does Garry believe now is the golden age for early stage investing? What opportunity does the mass of late stage capital provide the early stage?

4.) How does Garry approach desired ownership? What level of ownership provides incentive for a VC to work whilst also allowing collaboration with other VCs in a round?

5.) What are Garry’s thoughts on the rise of thematic investing? Why does he not believe it to be optimal at the seed stage?

Items Mentioned In Today’s Show:

Garry’s Fave Blog: SaaStr

Garry’s Fave Book: Chaos Monkeys

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

Alexis Ohanian is co-founder of Reddit & Initialized Capital. After graduating from UVA in 2005, Alexis and his co-founder Steve Huffman started Reddit, which they sold in 2006 to Conde Nast. In 2015, he returned to a full-time capacity with Steve Huffman as the two returned to the helm of a fully independent Reddit, which is now the 8th largest US website. In 2016, he joined Garry Tan in kicking off the third fund for Initialized Capital, an early stage venture capital firm. He’s invested in and advised over two hundred tech startups and was a partner at Y Combinator; Alexis has also written a national best-selling book, Without Their Permission and was named on Forbes 30 Under 30 list two years in a row.

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In Today’s Episode You Will Learn:

1.) How Alexis made his way into the world of VC from founding Reddit?

2.) What were the biggest surprises for Alexis about making the move into venture full time? What have been the biggest challenges?

3.) How do Alexis and Garry (Alexis’ partner) look to integrate process into their investing with Initialized? What is core to the success of this process? Why should more VCs be doing so?

4.) What does Alexis believe makes the best seed investors? What are the benefits of investors that have been in the trenches? How can they add to their companies in a way those without operating experience cannot?

5.) How does kindness integate into Alexis’ role as an investor? Can one win in investing while being kind? How does Alexis look to show his kindness to founders and investors?

Items Mentioned In Today’s Show:

Alexis’ Fave Blog: Reddit

Alexis’ Fave Book: Slaughterhouse 5 

Alexis’ Most Recent Investment: Workramp

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

Peter Weijmarshausen is the CEO and Co-Founder of Shapeways, the world’s leading 3D printing marketplace and community. Shapeways have raised funds from some of the world’s leading investors including the likes of USV, Andreesen Horowitz and Index Ventures just to name a few. Prior to Shapeways, Peter was the CTO of Sangine, where he and his team designed and developed satellite broadband modems. Peter was also Director of Engineering at Aramiska, where he was responsible for delivering a business broadband service via satellite.

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In Today’s Episode You Will Learn:

1.) How Peter made his way into startups and came to found Shapeways?

2.) Where are we in the 3D printing cycle today? Has it developed slower or quicker than Peter expected? How was it for Peter inhabiting a space with so much hype?

3.) When does 3D printing make the transition from early adopter market to mass market? What are the determinants that will allow for this to happen?

4.) Having started life in an incubator, why did Peter decide that for the origin of Shapeways? What are the benefits? What type of founder is this model right for?

5.) Shapeways have raised from Index, USV and a16z, so how was the fundraising journey for Peter? What would he like to improve upon for next time? What did he do well?

Items Mentioned In Today’s Show:

Peter’s Fave Blog: New York Times

Peter’s Fave Book: Leadership and Self-Deception

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

Kara Nortman is a Partner @ Upfront Ventures, one of LA’s leading venture funds. Kara is also co-founder of Seedling where she currently serves as Chairman. Prior to starting Seedling, Kara spent close to seven years at IAC where she acted as the Senior Vice President and General Manager of Urbanspoon and Citysearch. Prior to Urbanspoon/Citysearch, Kara co-headed the M&A group at IAC where she lead some of their most successful acquisitions, notably Urbanspoon, Dictionary.com and Aston Hotels. While at IAC, Kara also served as a board member to Hatch Labs, IAC’s mobile technology incubator, where she recruited and advised Tinder. Kara also spent time at Morgan Stanley, Microsoft, and Battery Ventures.

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In Today’s Episode You Will Learn:

1.) How Kara made her way into the wonderful world of VC?

2.) Question from Greg Betinelli and Jenny Lefcourt: What is the most surprising thing about moving from an operator to a VC? What does Kara prefer more about being a VC?

3.) Having been an entrepreneur with a board, what does a good board member look like to Kara? How does Kara allocate her time amongst her portfolio?

4.) How does Kara assess founder psychology? How does Kara look to get to know the founder both post and pre-investment? What are some signs and tells for Kara of the truly successful operators?

5.) How does Kara view diversity in the VC landscape? What are prime examples of where it is going wrong? What can be done to change this? What are Kara’s hopes and concerns for the future?

Items Mentioned In Today’s Show:

Kara’s Fave Blog: Both Sides of The Table

Kara’s Fave Book: Grit by Angela Duckworth

Kara’s Most Recent Investment: Stem

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

Scott Dorsey is the Managing Partner @ High Alpa, the startup studio that both builds and invests in some of the most exciting SaaS companies today. Prior to HighAlpha, Scott was a successful entrepreneur who co-founded ExactTarget and led the company from start-up to global marketing software leader. ExactTarget went public on the New York Stock Exchange in March 2012 and sold to Salesforce.com in July 2013 for $2.7 billion. At Salesforce, Scott worked directly with Marc Benioff to execute the ExactTarget vision within Salesforce.

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In Today’s Episode You Will Learn:

1.) How Scott made his way into the world of venture from founding ExactTarget?

2.) What was it like to work directly for Marc Benioff? What were the biggest learnings and takeaways? What were the biggest challenges?

3.) With a startup studio producing companies and a fund investing in them, how does Scott avoid the negative signalling that is inherent within these 2 structures?

4.) Having seen so many successful SaaS startups, what does product market fit look like to Scott? From the studio, what are the biggest challenges his startups face in hitting product market fit?

5.) What are the fundamentals that all startups should focus on in the quest for product market fit? What are the challenges? How should this be measured?

Items Mentioned In Today’s Show:

Scott’s Fave Blog: SaaStr

Scott’s Fave Book: Good To Great by Jim Collins

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

Ryan Petersen is the Founder and CEO of Flexport, the freight forwarder for the internet age. Flexport recently raised a phenomenal $65m Series B from the likes of Founders Fund, First Round, Felicis, Bloomberg Beta, Yuri Milner, Susa Ventures and more incredible investors. With none other than YC founder Paul Graham stating ‘Ryan has the rare ability to not just satisfy the market but grow it’. Prior to Flexport, Ryan was Founder and CEO of ImportGenius.com, the largest provider of business intelligence to the import-export industry.

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In Today’s Episode You Will Learn:

1.) How Ryan came to found Flexport? What was the a-ha moment for him?

2.) Why does Ryan believe it is crap that MBA’s do not make good entrepreneurs? How did Ryan design his life to be an entrepreneur without the opportunity to work for someone else?

3.) How has Ryan found the experience of being a single founder? What are the pros and cons? What was the investor reaction? What does Ryan advise other single founders?

4.) How did Ryan find the fundraising for the latest $65m raise? What did he do well? What would he like to improve upon for later rounds? How did he educate investors without being patronising?

5.) Why does Ryan want to see boards be rethought? What is so inefficient about boards? When did Ryan gain his board? What would Ryan advise fellow founders on building a board?

Items Mentioned In Today’s Show:

Ryan’s Fave Blog: SaaStr

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

Chris Farmer is a General Partner @ SignalFire, as he describes, ‘the most quantitative fund in the world.’ Chris has also assembled 50 other on-demand advisors to aid portfolio companies including Slack CEO, Stewart Butterfield, AltSchool Founder, Max Ventilla and Pinterest President, Tim Kendall. SignalFire’s portfolio includes the likes of Uber, ClassDojo and Rocksbox just to name a few. Prior to SignalFire, Chris was a Venture Partner @ General Catalyst where he aided the development of their seed program. Prior to General Catalyst, Chris spent 4 years as a VP @ Bessemer Venture Partners.

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In Today’s Episode You Will Learn:

1.) How Chris made his way into the world of venture and came to be Founding Partner @ Signal Fire?

2.) Why does Chris believe the VC industry has not changed in the last 40 years? Why are the old guard of VCs worried for the evolution?

3.) Why does Chris believe data and tech will be centre to the revolution that is happening in VC? How will data be used to enhance the VC value add to startups in the coming years?

4.) From interviewing over 500 Founders, what was the most common challenges and problems founders face today? How should VCs be positioning themselves to provide additional value?

5.) What does Chris believe boards are so inherently inefficient? What would Chris like to see change in the world of boards? How does Chris position himself in terms of, board to partner ratio?

Items Mentioned In Today’s Show:

Chris’ Fave Blog: Above The Crowd: Bill Gurley

Chris’ Fave Book: The Success Equation

Chris’ Most Recent Investment: Frame.io

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

Rory O’Driscoll is a founding member and Partner at Scale Venture Partners. An active investor for the past 20 years, Rory is focused on early-in-revenue software companies benefiting from the move to Software as a Service and the wider transition of enterprise computing to the cloud. Rory currently sits on the boards of Axcient, Bill.com, Box, Chef Software, DataSift, DocuSign, DroneDeploy, Forter, Katch, OneLogin, Pantheon, WalkMe and Wrike.  Prior investments include ExactTarget (ET; Acq: SFDC), Omniture (OMTR; Acq: ADBE), ScanSafe (Acq: Cisco), Frontbridge (Acq: MSFT), Placeware (Acq: MSFT) among others. Rory has been recognized by the Forbes Midas List and AlwaysOn Power Players in Venture Capital for his investments.

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In Today’s Episode You Will Learn:

1.) How Rory made his way into the world of venture and came to be a Partner @ Scale.

2.) How does Rory address market size? Does he utilise the bottom up or top dpwn approach? What is his strategy?

3.) Why are markets more important to Rory than management? What do each element have a different role in achieving?

4.) How does Rory look to navigate board conflict? When conflict does arise, how does Rory look to resolve a CEO who does not listen?

5.) What are the 4 fundamental roles of a board member? Why is competence underrated? What should founders and CEOs look for in prospective board members?

Items Mentioned In Today’s Show:

Rory’s Fave Blog: Term Sheet

Rory’s Fave Book: SuperForecasting: The Art & Science of Prediction

Rory’s Most Recent Investment: DroneDeploy

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

Balaji Srinivasan is the Founder & CEO @ 21.co, the company that believes for bitcoin to succeed we need to build the full stack infrastructure for bitcoin, from silicon to hardware. 21.co have backing from some of the best in the world including a16z, Peter Thiel, Scott & Cyan Banister, Naval Ravikant and previous guest Data Collective’s Matt Ocko. Balaji is also a Board Partner @ a16z, where he has served for the past 3 years. Prior to a16z and 21.co, Balaji was Co-Founder & CTO @ Counsyl, the genomics startup that now tests 4% of all US births and raised $65 in funding.

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In Today’s Episode You Will Learn:

1.) How Balaji made the move from operations to a16z and the back to startups? How did his time in operations affect his investing mentality and vice versa.

2.) Why does Balaji believe that the number 1 barrier for most startups is regulation? Why does Balaji look to the unseen?

3.) With such value being held back by regulation, what is the FDA, FAA, SEC etc holding back? How can that value be unlocked? How can you carve out jurisdictions where you can have early adopters?

4.) How can new products look to gain customer validation through micro testing market segments? What are the requirement to do this successfully? What are the common mistakes

5.) How does Balaji view the future of regulation? How can tech help make regulation faster and more efficient? What are the barriers to it’s widespread adoption and implementation?

Items Mentioned In Today’s Show:

Balaji’s Fave Book: The Sovereign Individual, The Princeton Companion To Mathematics

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

Eric Paley is the Managing Partner at Founder Collective, one of the world’s most successful seed funds with investments in the likes of Uber, Hunch, Makerbot and About.me. Prior to Founder Collective, Eric was the Co-Founder and CEO of Brontes Technologies, later acquired by 3M for $95m. Following it’s acquisition Eric began making angel investments and it was not long before Eric and David, ‘super angel’ at the time, saw the potential for a Founder First seed fund and Founder Collective was born.

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In Today’s Episode You Will Learn:

1.) How Eric made his move into the wonderful world of venture from founding Brontes Technologies?

2.) How does raising VC money affect the founders in both the long term and the short term? How does it alter exit expectations and time horizons?

3.) How does raising VC money affect startup management and burn rates? At what time is it too late to cut the burn? When should this moment of realisation be?

What are Eric’s rough expectations of valuation uptick based upon VC funding? How does Eric approach the bridge round? What metrics are required for Eric to think it is an acceptable round? Is it merely a case of failing to hit Series A metrics?

5.) Does Eric believe VCs really need $Bn exits to succeed? What is the math behind it? How should founders think of exits with the investors hat on? What does Eric make of the rise of mega funds?

Items Mentioned In Today’s Show:

Eric’s Most Recent Investment: Crayon

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

Paul Martino is a Co-Founder and General Partner @ Bullpen Capital, the fund that finds overlooked companies by understanding biases in venture capital. Paul has led several of Bullpen’s key investments including FanDuel, Namely, Ipsy, SpotHero, Classy, and Airmap. Prior to forming Bullpen, he was an active angel investor and personally invested in the first rounds of Zynga, TubeMogul, and uDemy. Before becoming an investor, Paul was the founder of four companies including Ahpah Software (a computer security firm acquired by InterTrust); Tribe (one of the world’s first social networks), and Aggregate Knowledge (a big data advertising attribution company acquired in 2014 by Nuestar).

Rick Marini is a serial entrepreneur and angel investor with over 45 investments in early stage startups. Some of Rick’s investments include the likes of Snapchat, AngelList, Luxe and Nuzzel, just to name a few. Prior to his prolific angel investing career, Rick was the Founder & CEO of BranchOut – the largest professional network leveraging the social graph with more than 800 million profiles. BranchOut raised $49 million in funding from Accel Partners, Redpoint Ventures, Mayfield Fund and more. BranchOut was acquired in 2014 by One-Page. Previously, Rick was also the Founder & CEO of Talk.co. Talk.co was acquired in 2014 by Hearst Corporation. Prior to BranchOut and Talk.co, Rick was the Co-Founder, of Tickle. Tickle operated as a profitable company with almost $40 million of revenue. Tickle was acquired in 2004 by Monster Worldwide for $100 million.

Jay Desai is Co-Founder and CEO of PatientPing, a company that connects health care providers across the country with real-time notifications to seamlessly coordinate patient care. They have raised funding from some of the best in the world including Google Ventures, First Round Capital and SV Angel. Prior to co-founding PatientPing, Jay worked at the Center for Medicare and Medicaid Innovation where he helped design and implement ACO, Bundled Payment, and other innovative payment models funded by the Affordable Care Act. Jay’s previous experience includes Triad Isotopes, Parthenon Capital, and Lehman Brothers.

Rudina Seseri is Founder and Managing Partner of Glasswing Ventures, Boston’s own AI focussed fund. Prior to Glasswing, Rudina was a Partner at Fairhaven Capital, sering as lead investor and Director on the Boards of Celtra, CrowdTwist, Jibo, SocialFlow and Statisfy. Before Fairhaven, she was a Senior Manager in the Corporate Development Group at Microsoft where she was responsible for sourcing, structuring, and negotiating Microsoft’s acquisitions and strategic investments. Rudina has served as Entrepreneur-In-Residence for Harvard Business School for 4 consecutive years and is an advisor for L’Oréal USA Women in Digital.