The Twenty Minute VC

Judith Elsea is a Co-Founder @ Weathergage Capital, one of the world’s leading fund of funds with over $950m AUM. Prior to Wealthergage, Judith was Chief Investment Officer of the Ewing Marion Kauffman Foundation from 1993 to 2001. As CIO, she directed a $2 billion globally diversified investment portfolio, committing over $600 million to US early stage venture funds and other private equity partnerships. She was also instrumental in the creation and implementation of the Kauffman Fellows Program, a global apprenticeship program designed to train the next generation of venture capitalists.

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In Today’s Episode You Will Learn:

1.) How Judith made her way into the world of LPs and what makes her think venture is such an attractive asset class?

2.) What gets Judith really excited when viewing prospective fund managers for potential investments? What differentiators does Judith look for?

3.) What are the most common reasons Judith finds for her rejecting fund managers for investment? What are they not doing and how can they optimise this?

4.) To what extent do LPs have a commitment to invest in further funds having invested in one fund? Are there any situations where this changes?

5.) What are the similarities and differences between fundraising for LPs vs fundraising for startups? How should the different elements be approached?

Items Mentioned In Today’s Show:

Judith’s Fave Book: Patrick O’Brian

Judith’s Fave Blog: The Twenty Minute VC, a16z, Founder Collective

Judith’s Most Recent Investment: Felicis Ventures

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

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

Eve make 1 perfect mattress – made with 3 layer technology and next generation memory foam. It comes packaged in a beautiful box and arrives the day after you order. You get 100 nights to try it with free return pick-up – it really is the perfect mattress for everyone. Just go online to evemattress.co.ukand enter the code 20VC for £50 off. Everybody deserves the perfect start with Eve.

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 atcooleygo.com.

Michael Skok is a Founding Partner @ Underscore VC. Michael started his first software business as a teenager, spent 21 years as an entrepreneur where he founded and recruited teams that attracted over $100m in private equity for investments in multiple software companies. Over the last 13 years Michael has been a venture investor. Along the way, he also mentored and taught for 4 years at Harvard as an EIR at Harvard Business School, and spent a year interviewing entrepreneurs on a “listening tour” before founding _Underscore.VC. Michael also started the most incredible education series, ‘Startup Secrets’, in collaboration with Harvard iLab, check it out here.

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In Today’s Episode You Will Learn:

1.) How Michael made his way into the wonderful world of VC with Underscore?

2.) From Michael’s listening tour, what did he discover that entrepreneurs wanted in an investor?

3.) How did Michael present the innovative model of Underscore to prospective LPs? What was their response? What did Michael look for in the LPs he selected?

4.) What does Michael mean when he says you have to create minimum viable segments?

5.) How does Michael view market creation? What his framework for this?

Items Mentioned In Today’s Show:

Michael’s Fave Book: Daemon

Michael’s Fave Blog: Mattermark

Michael’s Most Recent Investment: Mautic

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

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

Eve make 1 perfect mattress – made with 3 layer technology and next generation memory foam. It comes packaged in a beautiful box and arrives the day after you order. You get 100 nights to try it with free return pick-up – it really is the perfect mattress for everyone. Just go online to evemattress.co.ukand enter the code 20VC for £50 off. Everybody deserves the perfect start with Eve.

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 atcooleygo.com.

Ilya Fushman is a Partner at Index Ventures where he has made investments in the likes of Slack, Intercom, Dropbox and Optimizely. Prior to joining Index, Ilya was the head of product at Dropbox. As one of Dropbox’s first 75 employees, he helped build and run the company’s business and corporate development functions, before taking on a product leadership role and building out Dropbox, Dropbox for Business and the developer platform. Before Dropbox, he was a principal at Khosla Ventures and the Director of Technology at the solar cell startup Solar Junction.

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In Today’s Episode You Will Learn:

1.) How Ilya made his transition from Dropbox to return to the world of VC with Index?

2.) Does Ilya agree that to scale successfully you have to reinvent yourself every 6 months? Why does Ilya believe you must infuse an element of delight into the people side of the business? How can this be done effectively?

3.) How did Ilya and the Dropbox team look to effectively manage and scale the employee on boarding process with the growth of the company?

4.) Question from Lars @ Balderton: Does Ilya believe his extensive operational background allows him to get into deals he would otherwise not have been able to win?

5.) Question from Lars: Does Ilya believe an excess of capital is driving prices in the valley excessively high? Will we continue to see this in the coming years?

Items Mentioned In Today’s Show:

Ilya’s Fave Book: Mikhail Bulgakov: The Master & Margarita

Ilya’s Most Recent Investment: Slack, Culture Amp

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

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

Eve make 1 perfect mattress – made with 3 layer technology and next generation memory foam. It comes packaged in a beautiful box and arrives the day after you order. You get 100 nights to try it with free return pick-up – it really is the perfect mattress for everyone. Just go online to evemattress.co.ukand enter the code 20VC for £50 off. Everybody deserves the perfect start with Eve.

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 atcooleygo.com.

Nick Weaver is the Founder & CEO @ Eero. The company that makes your wifi hyper fast, super simple and brilliantly efficient. Prior to founding Eero, Nick was himself a VC at Menlo Ventures where he worked with companies like Uber, Betterment, Periscope and Dropcam. Before becoming a VC, Nick co-founded StartX, the community for the best Stanford entrepreneurs providing them with the required resources to build the next generation of leading companies.

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In Today’s Episode You Will Learn:

1.) How Nick made the move from VC with Menlo to Founder and CEO @ Eero?

2.) How can founders identify nascent and attractive markets that are ripe for disruption?

3.) How did Nick approach the pricing mechanism with Eero? Why do hardware startups need to have a greater margin than software startups?

4.) Why did Nick raise 2 rounds of funding before the product launched? Why did Nick decide he wanted to own all the parts of the production chain with Eero?

5.) How does Nick view the competitive landscape for such products? How does he view large incumbents like Netgear, compared to smaller startups like Luma?

Items Mentioned In Today’s Show:

Nick’s Fave Blog and Newsletter: Term Sheet: Dan Primack

Nick’s Fave Book: Man’s Search For Meaning by Viktor Frankl

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

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

Ryan Sarver is a Partner @ Redpoint where he focuses on early stage consumer startups. He sits on the board at Luxe, where he led the seed and A rounds, and was an early investor in Memoir. Prior to joining Redpoint, Ryan was a director at Twitter, where he oversaw the Twitter Platform and its developer ecosystem. Before Twitter, Ryan was director of consumer products at Skyhook Wireless, which pioneered the Wi-Fi and cellular tower triangulation technology incorporated in the Apple iPhone, iPod Touch, and MacBook.

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In Today’s Episode You Will Learn:

1.) How Ryan made his move into the world of VC?

2.) What were Ryan’s biggest takeaways from seeing Twitter scale from 30 to 2,500? How does he apply those to his formative days learning the investing game?

3.) Coming from the hustle of operation, do VCs have enough hustle and grit in Ryan’s opinion?

4.) What really is an EIR program? Why does Redpoint have it? What are the fundamental benefits? How do investors collaborate and work with EIR’s?

5.) Ryan has said before that AI is the next transformational platform. What does AI as a platform look like to Ryan? How does hardware and sensors integrate with this thesis? Why is it easier than ever to build these smart devices?

Items Mentioned In Today’s Show:

Ryan’s Fave Book: Sapiens

Ryan’s Most Recent Investment: Luxe

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.

Eve make 1 perfect mattress – made with 3 layer technology and next generation memory foam. It comes packaged in a beautiful box and arrives the day after you order. You get 100 nights to try it with free return pick-up – it really is the perfect mattress for everyone. Just go online to evemattress.co.ukand enter the code 20VC for £50 off. Everybody deserves the perfect start with Eve.

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.

Tom Tunguz is a Partner @ Redpoint Ventures, where he has invested in the likes of Axial, Dremio, Expensify, Electric Imp, Looker, and ThredUP. Tomasz is also the co-author of Winning with Data: Transform Your Culture, Empower Your People, and Shape the Future, which explores the cultural changes big data brings to business, and shows you how to adapt your organization to leverage data to maximum effect. Before joining Redpoint, Tomasz was the product manager for Google’s AdSense social-media products and AdSense internationalization.

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In Today’s Episode You Will Learn:

1.) When did Tom perceive the true power of data for the first time?

2.) What is the biggest difference between a company that is data driven and one that is not? What are the inherent benefits and how can non data driven businesses become data driven?

3.) What are the best data driven teams doing to operationalise their data today?

4.) Adam Grant: 8% of job interviews are productive. So what structure can management use to ensure higher efficiency in the hiring process?

5.) What are the complexities and skills required for strong data analysis in today’s environment?

6.) Data often leads to over confidence in decision making, how do you prevent illusion bias once data has been obtained?

Items Mentioned In Today’s Show:

Tom’s Most Recent Investment: Dremio

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

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

Adam Leibsohn is the Founder and COO @ Giphy, the company that brings you joy and laughter through gifs. Earlier this year, Giphy raised a phenomenal $55m Series C financing from the likes of General Catalyst, Lerer Hippeau, Lightspeed and Betaworks. As for Adam he is one of the coolest and most genuine founders I have ever interviewed and is so committed to the startup cause that at one point he went without a home to pay for the startup dream!

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In Today’s Episode You Will Learn:

1.) How Adam went from being homeless to the Founder of Giphy?

2.) What were the biggest lessons Adam learnt from his failed startup? When should founders know when is the right time to stop?

3.) Why gifs and why now? What has allowed for the spectacular rise of gifs?

4.) How has Adam created such a unique culture at Giphy? What have been his key learnings? What has worked, what has not worked?

5.) Giphy is now a cultural icon but how does Adam look to turn that into a massive globally profit making business?

Items Mentioned In Today’s Show:

Adam’s Fave Blog and Newsletter: The Information, Dealbook

Adam’s Fave Book: East of Eden

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

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

Brett DeMarrais is a Partner @ Ludlow Ventures, who have investments in the likes of ProductHunt, Sprig, AngelList and uBeam. Prior to joining Ludlow, Brett founded Wedit, a crowd sourced wedding video platform that reduced the cost of wedding videos and made them social. Within the first year of launching the company Wedit had won the top industry awards for customer satisfaction (Brides Choice 2012 and Best of The Knot 2012). Previously, Brett worked at Out of the Blue Entertainment.

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In Today’s Episode You Will Learn:

1.) How Brett made his move into VC and came to be a partner @ Ludlow?

2.) What do most VCs mean they say ‘founder friendly’? How does Brett and Ludlow approach the popularised saying?

3.) How does Brett balance between being an investor and advisor to a founder and then being their friend and confidante?

4.) How does Brett look to balance the fiduciary responsibilities to his LPs when appreciating that the needs of the founder come before the needs of the company?

5.) Brett has previously said, ‘car ownership will be a thing of the past’. Why does Brett think this and what does this mean for the car industry as a whole?

Items Mentioned In Today’s Show:

Brett’s Fave Blog and Newsletter: Both Sides Of The Table, Dan Primack: Term Sheet

Brett’s Fave Book: Ready Player One

Brett’s Most Recent Investment: Gather

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

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

Eve make 1 perfect mattress – made with 3 layer technology and next generation memory foam. It comes packaged in a beautiful box and arrives the day after you order. You get 100 nights to try it with free return pick-up – it really is the perfect mattress for everyone. Just go online to evemattress.co.uk and enter the code 20VC for £50 off. Everybody deserves the perfect start with Eve.

Ben Lerer is a Managing Partner at Lerer Hippeau Ventures and co-founder & CEO of Thrillist Media Group. Ben was among Ernst & Young’s 2013 Entrepreneur of the Year Award Winners, Forbes list of “Most Powerful CEOs Under 40”, ” Entrepreneur Magazine’s “Top 5 Entrepreneurs of the Year,” and Silicon Alley Insider’s “100 Coolest People in Tech”. Ben is also an active mentor for NYC Venture Fellows, TechStars and E[nstitute].

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In Today’s Episode You Will Learn:

1.) How Ben came to found Thrillist and then join the founding team at Lerer Hippeau?

2.) How did Ben’s mentality shift from investing angel money to the fiduciary responsibility of a fund?

3.) How does Ben view FOMO? How does he look to negate and control his emotions when investing?

4.) How has Ben seen his personal pattern recognition change over time? How does Ben use data to further improve his ability of pattern recognition?

5.) Why have we seen the rise of direct to consumer businesses? Is it easier to build a brand today than in previous years? Will we see continued M&A in the retail world with the likes of Jet.co and Dollar Shave Club?

Items Mentioned In Today’s Show:

Ben’s Fave Book: The Goldfinch

Ben’s Most Recent Investment: Everytable

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.

Eve make 1 perfect mattress – made with 3 layer technology and next generation memory foam. It comes packaged in a beautiful box and arrives the day after you order. You get 100 nights to try it with free return pick-up – it really is the perfect mattress for everyone. Just go online to evemattress.co.ukand enter the code 20VC for £50 off. Everybody deserves the perfect start with Eve.

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.

Kathryn Minshew is the Founder & CEO @ The Muse, named to Forbes’ 30 Under 30 in Media and Inc.’s 15 Women to Watch in Tech. Before founding The Muse, Kathryn worked on vaccines in Rwanda and Malawi with the Clinton Health Access Initiative and was previously at McKinsey. Kathryn has spoken at MIT and Harvard, appeared on The TODAY Show and CNN, and contributes on career and entrepreneurship to the Wall Street Journal and Harvard Business Review.

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In Today’s Episode You Will Learn:

1.) How Kathryn came to be Founder of The Muse following charity work in Rwanda?

2.) Question from Adam Quinton (investor): What is it about Kathryn and Alex’s relationship that works so well? How do they deal with founder disputes?

3.)  Prior to The Muse, Alex and Kathryn founded another business with 2 other founders. What did they learn from the breakup and how have they applied to The Muse?

4.) How has Kathryn managed to maintain startup ownership culture as the team has grown to over 100 people ?

5.) The Muse has now raised large Series A & B rounds. What were the lessons Kathryn learnt along the way and what would she do differently for the C round?

Items Mentioned In Today’s Show:

Kathryn’s Fave Blog and Newsletter: The Atlantic, The New York Times

Kathryn’s Fave Book: Arcadia by Tom Stoppard 

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

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

Jesse Middleton is a General Partner @ Flybridge Capital Partners. Prior to joining Flybridge, Jesse was an early executive at WeWork, one of the fastest growing and most valuable startups in history. He co-founded WeWork Labs in 2011, and ran WeWork X, M&A, startup investments, business and digital product development as well as inside sales during his five-year tenure at the company. Prior to WeWork, Jesse was the co-founder and CEO of Backstory, a venture backed startup. Jesse also has experience as a prolific angel investor having invested in the like of Fitmob (acq by ClassPass) YourTrove acq by LiveNation and inDinero, who you might remember we had Jessica Mah, Founder @ inDinero on the show.

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In Today’s Episode You Will Learn:

1.) How Jesse made the transition from operator with WeWork to General Partner @ Flybridge?

2.) At what stage does founder vision transition to become stubbornness? How does Jesse approach the situation of telling a founder when it is not working?

3.) How does Jesse’s investment mindset shift from making the move from angel to VC with fiduciary responsibility?

4.) How does Jesse look to develop pattern recognition as a new entrant to VC? How important a role does mentorship play for Jesse?

5.) What are the characteristics Jesse looks for in a founder that suggest an innate problem solver? How does Jesse deal with problems when the ‘shit hits the fan?’

Items Mentioned In Today’s Show:

Jesse’s Fave Blog and Newsletter: Purple, The Skimm

Jesse’s Fave Book: Leadership & The Challenge of Self Deception

Jesse’s Most Recent Investment: Squire

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

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

Eve make 1 perfect mattress – made with 3 layer technology and next generation memory foam. It comes packaged in a beautiful box and arrives the day after you order. You get 100 nights to try it with free return pick-up – it really is the perfect mattress for everyone. Just go online to evemattress.co.ukand enter the code 20VC for £50 off. Everybody deserves the perfect start with Eve.

Peter Pham is a Co-Founder at Science, the startup studio that helps incubate companies co-building them alongside CEO’s, with recent companies like Dollar Shave Club (acquired by Unilever for $1B) and leading marketplace, DogVacay. More recently Science created created one of the top 100 iOS Apps called Wishbone. Peter has also helped his portfolio raise over $350M in that time. Previously as an operator, he led Photobucket to its $300M acquisition by Fox Interactive Media as well as CEO of BillShrink (acquired by MasterCard.)

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In Today’s Episode You Will Learn:

1.) How Peter made the transition from operator to company builder with Science?

2.) How does Peter approach the fundraising process itself? How does he instruct founders about the right ways to approach and enter the fundraising game?

3.) How can entrepreneurs determine whether a VC is saying not to them? What are the signs that an investor is genuinely interested?

4.) With 3,000 no’s from investors, how does that affect Peter’s mentality? How does he avoid the negativity surrounding a VC saying no?

5.) What are Peter’s major learnings on how companies scale effectively today? How important are network effects to this scaling?

Items Mentioned In Today’s Show:

Peter’s Fave Blog and Newsletter: Recode

Peter’s Fave Book: How To Win Friends & Influence People

Peter’s Most Recent Investment: Handstand App

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.

Sean Brecker is the CEO @ Headspace where he is the driving force behind all financial and commercial matters including overseeing the company’s growth of it’s product line which now has over 8m downloads. Sean was also instrumental in attaining the first  institutional round of financing which included investment from the likes of LinkedIn’s Jeff Weiner, Jim Breyer, Jessica Alba and Jared Leto, just to name a few. Prior to Headspace, Sean spent 15 years in banking with the likes of JP Morgan, Lehmann Brothers and Citigroup.

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In Today’s Episode You Will Learn:

1.) How Sean made the move from banking to CEO of meditation service, Headspace?

2.) Meditation can be viewed with some hippy stereotypes, how does Sean look to optimise the onboarding for new users and incorporate elements of education?

3.) How does Sean implement a strategy of habit forming within the users? In the words of Nir Eyal, how do we get them ‘hooked’? How long on average does it take for an action to be completed before it becomes a habit?

4.) How does Sean try and optimise the transition from free to paid user with Headspace? How does Sean try and remove as much friction as possible in the process?

5.) How has Sean seen the growth of the health and wellness space over the last few years? We obviously have the likes of Calm, is this market a winner takes all and how does Sean approach market competition at Headspace?

6.) How was the fundraising process for Sean? How did he come to meet investors like Jeff Weiner, Jim Breyer, Jessica Alba and Jared Leto?

Items Mentioned In Today’s Show:

Sean’s Fave Blog and Newsletter: The Information, Recode

Sean’s Fave Book: The Hard Thing About Hard Things, A Man In Full

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.

Eve make 1 perfect mattress – made with 3 layer technology and next generation memory foam. It comes packaged in a beautiful box and arrives the day after you order. You get 100 nights to try it with free return pick-up – it really is the perfect mattress for everyone. Just go online to evemattress.co.uk and enter the code 20VC for £50 off. Everybody deserves the perfect start with Eve.

Chad Byers is a General Partner @ Susa Ventures and very exciting news, Susa last week announced the raise of Susa II, a new $50m fund, testament to the quality of fund 1 which included the likes of former guests Lyst, RobinHood, LendUp and many more incredible companies. As for Chad, he focuses on investments in enterprise software, fintech, and healthcare. Prior to Susa, Chad spent time in various marketing and product management roles. As well as being a prolific angel investor in over 30+ companies.

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In Today’s Episode You Will Learn:

1.) How Chad made the transition from angel investor to General Partner @ Susa?

2.) How was the fundraise with Susa 1? How was the fundraise for Susa II? How did the funding rounds change for each fund?

3.) How does Chad assess LP fit? Is all LP money not equal? What does Chad look for in his LPs?

4.) Question from Michael Kim @ Cendana: How does Chad look to establish the mindshare with entrepreneurs and other VCs for Susa in today’s competitive environment?

5.) How does Chad approach the reserve structure of Susa fund II? How did Chad come tot hat conclusion as the optimal amount for follow on?

Items Mentioned In Today’s Show:

Chad’s Fave Blog and Newsletter: Coding VC, Bill Gurley: Above The Crowd

Chad’s Fave Book: When Breathe Becomes Air

Chad’s Most Recent Investment: Modsy

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

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

Eve make 1 perfect mattress – made with 3 layer technology and next generation memory foam. It comes packaged in a beautiful box and arrives the day after you order. You get 100 nights to try it with free return pick-up – it really is the perfect mattress for everyone. Just go online to evemattress.co.ukand enter the code 20VC for £50 off. Everybody deserves the perfect start with Eve.

Paul Berberian is the CEO of Sphero, the robotic ball controlled from your smartphone. They have investment from our friends in Boulder, Brad Feld and David Cohen. Prior to Sphero, Paul was the co-founder of Raindance Communications (NASDAQ: RNDC). Paul also founded Market Force Information, an emerging information company with a vision to provide retailers. As well as, LINK-VTC, a video teleconferencing company, which was sold in 1995 to Frontier Communications.

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In Today’s Episode with Paul You Will Learn:

1.) How Paul came to be CEO @ Sphero?

2.) Paul has founded and run 7 businesses, How has Paul seen his style of leadership change over the past decade or so?

3.) Question from Brad Feld: When Paul disagrees with his board, how does he resolve it? What have been Paul’s learnings in maintaining a happy board environment?

4.) Sphero have raised, at last count, $80m? How has Paul seen investor sentiment to hardware alter over the 5-6 years? How did he meet his investors? What did Paul do well and what would Paul like to improve upon for next time?

5.) Question from Brad Feld: ‘Sphero looks like a massive success but every startup has had failures, so what have Paul’s failures been and what did he learn from them?’

Items Mentioned In Today’s Show:

Paul’s Fave Blog and Newsletter: Quora

Paul’s Fave Book: The Black Box

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

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

Eve make 1 perfect mattress – made with 3 layer technology and next generation memory foam. It comes packaged in a beautiful box and arrives the day after you order. You get 100 nights to try it with free return pick-up – it really is the perfect mattress for everyone. Just go online to evemattress.co.uk and enter the code 20VC for £50 off. Everybody deserves the perfect start with Eve.

Ben Einstein is Founder and General Partner @ Bolt, Bolt is a fund designed to address the unique needs of early-stage startups at the intersection of hardware and software, investing up to $500K in pre-seed, pre-product companies. They have created and backed some world class businesses that have received later funding from Khosla, Kleiner Perkins, NEA, and Softtech just to name a few.

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In Today’s Episode with Ben You Will Learn:

• How Ben made his way into VC from such a product centric background?
• Why have we seen a rise in hardware investing over the last 5 years? How has this affected the hardware ecosystem?
• To what extent do hardware and software integrate today? Why have we seen the rise of software determining the hardware winners?
• Why is brand the most important thing in consumer hardware? Who has done it best? Who has not done it well?
• What is Ben’s biggest advice to hardware founders today? Why is raising too much money extremely dangerous for hardware founders?

Items Mentioned In Today’s Show:

Ben’s Fave Blog and Newsletter: Ben Evans

Ben’s Fave Book: The Box

Ben’s Most Recent Investment: Grow: Redesigning Gardening

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.

Eve make 1 perfect mattress – made with 3 layer technology and next generation memory foam. It comes packaged in a beautiful box and arrives the day after you order. You get 100 nights to try it with free return pick-up – it really is the perfect mattress for everyone. Just go online to evemattress.co.uk and enter the code 20VC for £50 off. Everybody deserves the perfect start with Eve.

Dave McClure is the founding partner of 500 Startups, who have made over 1500 investments in the likes of Twilio, SendGrid, Intercom and Makerbot just to name a few. Prior to 500 Dave was on the investment team at Founders Fund, he also led the Facebook Fund Incubator and was Head of Marketing @ Paypal pre IPO.

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In Today’s Episode with Dave You Will Learn:

• How Dave made his way into VC and came to found 500 Startups?
• Do you need unicorn exits to have significant venture returns? What is the 500 view with regards to the hit ratio of finding unicorns?
• How much ownership does 500 typically take? Does this allow Dave enough of a right to follow on in further rounds with such a small initial slice?
• How does Dave and 500 avoid the inherent signalling risk involved with their fund and accelerator? How prominent is signalling in today’s market?
• What did Dave think of Sam Altman’s statement on YC not accepting companies from other accelerators? How does Dave view YC companies?

Items Mentioned In Today’s Show:

Dave’s Fave Blog and Newsletter: Brad Feld, AVC, Mark Suster

Dave’s Fave Book: Guns Germs and Steel, The Mystery of Capital

Dave’s Most Recent Investment: Markhor

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

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

Eve make 1 perfect mattress – made with 3 layer technology and next generation memory foam. It comes packaged in a beautiful box and arrives the day after you order. You get 100 nights to try it with free return pick-up – it really is the perfect mattress for everyone. Just go online to evemattress.co.uk and enter the code 20VC for £50 off. Everybody deserves the perfect start with Eve.

Adam Nash is the President and CEO of Wealthfront, where he is on a mission to put the client first and change the bad practices of the financial services industry. Adam joined Wealthfront from Greylock Partners, where he was an Executive-in-Residence. Prior to Greylock, he was VP of Product Management at LinkedIn, where he built the teams responsible for core product, user experience, platform and mobile. Adam also held a number of roles at Ebay, Atlas Venture Preview Systems and Apple.

4.) How was the transition for Andy in making the move from PM to COO to CEO? What were the biggest challenges and surprises?

5.) Why does Andy believe that building software through hierarchy does not work? How can leaders empower their team with a sense of ownership?

6.) Why do humans suck at investing? Will we see the domination of full scale financial robo advisors in the next 10 years?

David Pakman is a Partner at Venrock and the man behind Venrock’s leading of the Series A and B rounds for Dollar Shave Club. Prior to Venrock David spent 12 years as an internet entrepreneur. Including being CEO of eMusic, the world’s leading digital retailer of independent music, second only to iTunes. Prior to eMusic, David co-founded Myplay in 1999, which he later sold, in 2001, to Bertelsmann’s ecommerce Group. If that wasn’t enough David is also the co-creator of Apple Computer’s Music Group.

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In Today’s Episode You Will Learn:

• How did David make his way into the world of VC with Venrock?

• David invested in Dollar Shave when subscription ecommerce funding was largely out of favour. What was it that excited Dave about Dollar Shave and why did he choose to invest?

• To what extent do we see the existence of party rounds in today’s funding environment?

• Venrock took the rather unusual position to lead both the A and B rounds for Dollar Shave. What was the internal conversations like within Venrock towards this decision?

• Dollar Shave was growing at phenomenal rates with impressive growth, what was behind the decision to sell at this time? What were the incentives behind selling to Unilever?

• Will we see other large e-commerce exits in the future? What does the future M&A environment look like for consumer businesses?

Items Mentioned In Today’s Show:

David’s Fave Book: Mindset by Carole Dweck

David’s Most Recent Investment: Pearl

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

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

Eve make 1 perfect mattress – made with 3 layer technology and next generation memory foam. It comes packaged in a beautiful box and arrives the day after you order. You get 100 nights to try it with free return pick-up – it really is the perfect mattress for everyone. Just go online to evemattress.co.uk and enter the code 20VC for £50 off. Everybody deserves the perfect start with Eve.

Matt Ocko is the Co-Managing Partner and Co-Founder @ Data Collective and has over 3 decades of experience as a tech entrepreneur and VC and has made investments in the likes of Facebook, Zynga, Uber and AngelList just to name a few. If that was not enough he is also an inventor on over 40 granted or in process patents. A truly deep thinker and one of my fave ever shows to record.

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In Today’s Episode with Matt You Will Learn:

• How Matt made his way into VC and came to co-found Data Collective?
• Why does Matt believe “All Fund Size Models are Wrong”. Does the current bifurcation of VC into angels/micro-VCs, small seed/A funds, big bruisers, and post-C/pre-IPO make for sub-optimal returns both on a societal and monetary perspective?
• What does the opportunity fund allow Data Collective? How do they use the initial fund to invest for insight in into companies at the earliest stages? How do they avoid the negative signalling risk that is normally ensued with an opportunity fund?
• How important is thesis driven venture firms? Does specialisation aid or hinder venture returns and why?
• How does Matt view the lifecycle of current venture? Matt has previously said it is inherently inefficient, why?

Items Mentioned In Today’s Show:

Matt’s Fave Blog and Newsletter: MIT Technology Review

Matt’s Fave Book: The Way Things Work

Matt’s Most Recent Investment: Tradeshift

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

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

Eve make 1 perfect mattress – made with 3 layer technology and next generation memory foam. It comes packaged in a beautiful box and arrives the day after you order. You get 100 nights to try it with free return pick-up – it really is the perfect mattress for everyone. Just go online to evemattress.co.uk and enter the code 20VC for £50 off. Everybody deserves the perfect start with Eve.

4.) How does the investment decision making process differ when comparing the Seed to Series A round?

5.) Why does Steve think there needs to be greater mentoring in the ecosystem? What can individuals do to build relationships and gain mentors?

Sean Flynn is a Managing Partner @ Shasta Ventures where he invests in mobile-enabled consumer Internet and enterprise software companies. Sean has led Shasta’s investments in Dollar Shave Club, Whisper and serves on the board of directors for the likes of TimeHop, Zefr, Swipely, Bloc and TigerText. Before joining Shasta, Sean worked at Yahoo, where he focused on growing the company’s communication and messaging products such as Yahoo! Mail, Messenger, Groups and Flickr.

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In Today’s Episode You Will Learn:

1.) How Sean made his way into VC from the titan that is Yahoo?

Now today I want to do something slightly different and do a myth busting episode, take a couple of sectors and discuss whether they are truths and complexities to the core statement.

2.) Starting with the most common assumption in VC that it is all about team, to what extent does Sean place team ahead of product and is this a slight misconception?

3.) Many are saying mobile is a dying space. Sean previously said, ‘it is not dead yet’. Why is there promise for mobile? What will be the catalyst of it’s death? How does this affect Sean’s investment decision making?

4.) Another much hyped topic is AR/VR, is the excitement surround AR and VR justified? Where does Sean stand on investing in the installation phase of cycles?

5.) Similar to AR/VR is the hype surround bots justified? What will be the sustainable business model for bots?

Items Mentioned In Today’s Show:

Sean’s Fave Book: What Do You Do With An Idea 

Sean’s Fave Blog or Newsletter: Nuzzel, 538 Blog

Sean’s Most Recent Investment: Tally

Semil Shah is the founder of Haystack, an early stage investment firm now investing out of it’s third fund, with previous investments being Instacart, DoorDash, Managed by Q. In the past he has also been a consultant to some of the leading funds in the valley including the likes of Kleiner Perkins, DFJ, General Catalyst and more. If that was not enough, Shah also has an extensive career in media having been a contributor for both TechCrunch and the Harvard Business Review in the past. Due to all of this Shah was listed by Marc Andreesen as one of his ’55 Unknown Rockstars in Tech’.

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In Today’s Episode You Will Learn:

1.) How Semil made his way into VC? How did he come to create Haystack?

2.) What were the challenges and concerns for Semil in raising and establishing his own fund?

3.) Question from Michelle Tandler: How does Semil send deals through to Series A? What is his ‘cool’ process? What are the commonalities of those that make it to Series A and those that do not?

4.) How has Semil approached the aspect of personal VC branding? How does he evaluate the rise of the personal VC brand in the last few years?

5.) Why does Semil believe he is not ‘founder friendly’ in the conventional sense?

Items Mentioned In Today’s Show:

Semil’s Fave Book: Burmese Days by George Orwell

Semil’s Most Recent Investment: AquaCloud

4.) What are David’s thoughts on the emerging platforms like AR and VR? How does he incorporate them into Unity’s future product roadmap?

5.) How was the fundraising process for David with Unity? How did the Sequoia investment happen and what has it been like to work with them and Roelof Botha?

Alex Bangash is the founder of Trusted Insight, the largest online asset management platform for institutional investors. He is also the managing director of TI Platform Fund, an online venture capital fund-of-fund. Prior to founding Trusted Insight, Alex was also the founder of Rumson Group, an advisor to institutional investors. Alex has helped invest over $1 billion in over 50 funds.

4.) Why does Alex believe true early stage is getting smaller and smaller? How does his return expectations differ according to the size of the fund?

5.) What happens when funds do not go to plan or do not have notable exits to raise fund II? What happens then?

Jeff Bussgang is a Co-Founder and General partner @ Flybridge Capital, where has made investments in numerous incredible companies including 2 former guests of the show, Jeff Seibert @ Crashlytics (sold to Twitter) and Josh Udashkin @ Raden. Jeff is also a Senior Lecturer @ Harvard Business School where he has co-authored no less than 15 cases. He is also an author having written the renowned, Mastering The VC Game to the acclaim of The Financial Times, TechCrunch, BusinessWeek and more. Jeff also has an incredible blog, Seeing Both Sides, which you can find here.

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In Today’s Episode You Will Learn:

1.) How Jeff made his way into VC? How did he come to co-found Flybridge?

2.) To what extent does Jeff believe there is a glass ceiling for people without operations experience to progress up the VC ladder?

3.) How can companies establish cultures and processes when they have to change and reinvent every 6-12 months?

4.) What are venture returns? What metrics does Jeff use to determine his success?

5.) Is a focus on unit economics now one of the only ways to achieve equity value creation? How can consumer adoption drive equity value creation?

Items Mentioned In Today’s Show:

Jeff’s Fave Book: Man’s Search For Meaning by Viktor Frankl

Jeff’s Fave Blog or Newsletter: Mattermark Daily

Jeff’s Most Recent Investment: Sentenai

Kyle Hill is the Co-Founder & CEO @ HomeHero, one of the largest providers of non-medical home care in California. HomeHero has provided over 1 million hours of care to thousands of families and won “Best Employment Website of 2014”. Due to this immense success Kyle has been on CNN, Forbes, Wall Street Journal and many more. HomeHero has raised funds from some of the world’s best investors including Chamath & Mamoon @ Social Capital, Jason Calacanis @ TWIST and Peter & Michael @ Science Inc.

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1In Today’s Episode You Will Learn:

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

2.) Question from Mamoon @ Social Capital: Considering that this is not your typical software business; being largely people centric, how does Kyle think about the profitability of such a business?

3.) How much of a role does unit economics lay in the mind of Kyle? How does Kyle look to balance growth with profitability?

4.) How was the fundraising process for Kyle with Chamath & Mamoon @ Social Capital? What did Kyle do to prepare for the pitch? What did Kyle do well? What would Kyle look to improve upon? How would Kyle like VCs to treat him as a Founder?

Items Mentioned In Today’s Show:

Kyle’s’s Fave Book: Black Swan

Kyle’s Fave Blog: The Best Designs.com

Brad Burnham is the Co-Founder & Managing Partner @ Union Square Ventures. I feel Brad is far better described by his partner Fred Wilson, than I ever could so this is Fred’s words on Brad. “Brad and I founded USV together in 2003. We had both been in the venture business for more than a decade, had made a fair bit of money, but were still hungry to prove ourselves. Brad is the strategist and the most principled investor in our firm. It was Brad’s idea to write a treatise on venture capital and the internet before we set off to raise our first fund and that exercise we did together continues to be our guding light. Brad is the person behind phrases like “the application layer of the technology stack” and “large networks of engaged users” that I use all the time. He gives me most of my good stuff which I often get credit for.”

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In Today’s Episode You Will Learn:

1.) How Brad made his way into VC? How did he come to co-found USV with Fred in 2003?

2.) How did Brad approach team building with USV? What does he look for in his partners?

3.) Brad has previously stated his belief that ‘history does not repeat itself but it does rhyme,. How does this affect Brad’s view toward market cycles, the way tech is adopted and ultimately replaced?

4.) What does Brad make of the extension of the private market? Are we entering a period of consolidation? What makes Brad believe this?

5.) Looking back at the history of USV, what have been the inflection points in both the stature of the firm and then Brad’s learnings as a VC?

Items Mentioned In Today’s Show:

Brad’s Fave Book: The Irrational Optimist

Brad’s Most Recent Investment: OB1

4.) Why does Albert want to limit network effects that are provided to winning companies? What does Albert think makes a contestable market? What are the characteristics?

5.) Why is Albert such a protagonist for the basic income guarantee? What are the challenges? How will this affect human’s relationship to automation? What will mankind do with this increased abundance of time?

6.) Why does Albert believe that every individual has the right to be presented by a personal bot? What are the prominent use cases? How does it invert the power relationships between networks and their participants?

Frank Mycroft is the Founder & CEO @ Booster Fuels, the on-demand fuel delivery service backed by the likes of our friends at Maveron and Version One. As for Frank himself, he is literally a former rocket scientist with Nasa and has more degrees that I have done podcast episodes, making him one of the smartest guests we have ever had on the show. Directly prior to Booster Fuels, Frank was the VP of Strategy @ Planetary Resources, the Redmond based, asteroid mining company.

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In Today’s Episode You Will Learn:

1.) How Frank came to Found Booster Fuels from his days with Nasa?

2.) How important a role does naivety play for founders starting building their company?

3.) With Fuel being such a  low margin business, how does Frank balance growth vs profitability with Booster Fuels? What are the tips for doing so in the on-demand economy?

4.) When is the transition point between growth at all costs to focusing on profitability and unit economics?

5.) To what extent is regulation a limiting factor for the growth of Booster fuels?

6.) Question from Dave Wu @ Maveron: What did Frank look for in his Series A investors? Question from Angela @ Version One: What is Frank’s wider vision for the future of on demand and Booster Fuels?

Items Mentioned In Today’s Show:

Frank’s Fave Book: Oh The Places You’ll Go

Michael Kim is the founder and Managing Partner of Cendana Capital, a fund of funds which invests in seed VC funds. Michael has many of our previous guests in his portfolio including the likes of SoftTech, Freestyle, Founder Collective, Collaborative Fund and many more, clearly great minds think alike! Prior to Cendana, Michael was one of the original partners of Rustic Canyon Partners a VC firm with $1bn AUM.

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In Today’s Episode You Will Learn:

1.) How Michael made his way into VC and then made the transition into the world of LP?

2.) Why have we seen the proliferation of seed funding? Is this a good thing for the economy? Is dumb money good or bad for the early stage environment?

3.) Chris Douvos states we will begin to see the hybridisation of LPs and GPs, does Michael agree? What are the inherent problems with this happening?

4.) What is Michael’s blackbox for assessing emerging fund managers? What does he look for? How can they present their edge?

4.) How does Michael respond to Dave McClure’s portfolio construction theory of allocating capital to many startups with the realisation that 0.5% become unicorns?

Items Mentioned In Today’s Show:

Michael’s Fave Book: Catcher & The Rye

Michael’s Fave Blog or Newsletter: Techcrunch, The Twenty Minute VC

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

Ann Miura-Ko has been called “the most powerful woman in startups” by Forbes and is the Co-Founder of Floodgate, one of the valley’s leading early stage funds with investments in the likes of Twitter, Twitch and TaskRabbit. Some of Ann’s investments at Floodgate include Lyft, Ayasdi, Xamarin, Refinery29, Chloe and Isabel, Maker Media, Wanelo, TaskRabbit, and Modcloth. Ann is also a lecturer in the School of Engineering at Stanford University, where she got her PhD focused on mathematical modeling of computer security.

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In Today’s Episode You Will Learn:

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

2.) Ann’s 2nd day in VC was 9/11, how does Ann view investing in times of crisis and downturn? How does this effect the macro-economy and her investing cadence?

Floodgate state that all venture bankable high growth companies share 4 very common characteristics with regards to power. Here we break them down:

• Proprietary Power: What is it? What are it’s characteristics?
• Product Power: What does this imply about product market fit? What are the nuances and complexities?
• Company Power: What does it take to be created and maintained? How have so many unicorns established themselves without credible and sustainable business models?
• Category Power: Why it is so important to create a new category? How can this be done and who has done it well in the past?

Items Mentioned In Today’s Show:

Ann’s Fave Book: The Poisonwood Bible

Ann’s Fave Blog or Newsletter: Benedict Evans

Ann’s Most Recent Investment: The Greatist

Wesley Chan is a Manging Director @ Felicis Ventures where he has led investments in the likes of Canva, Flexport and Luma, just to name a few. Prior to Felicis, Wesley was a General Partner @ Google Ventures. Before Google Ventures he was an early employee at Google, where he founded and launched Google Analytics and Google Voice, resulting in his being awarded Google’s Founders Award–the company’s most prestigious recognition–for leading the development of Google’s early client efforts, which led to the development of Google Chrome. Fun fact about Wesley he is a massive hacker and IOT enthusiast with over 100 connected devices in his home.

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In Today’s Episode You Will Learn:

1.) How Wesley made the transition from Foundering Google Voice and analytics to being a VC?

2.) What were Wesley’s biggest takeaways from leading investment at Google Ventures? When looking at Google’s investment in Nest, what makes Nest such a truly phenomenal connected device?

3.) Wesley previously said, ‘I look for patterns similar to Google Analytics in how if you build something great.’ What are those patterns and what does that thought process lead to in terms of thought outcome? What is a good example of this?

4.)  Where does Wesley think we are on the programmable interface element of consumer hardware? What would he like to see change or improve in the space?

5.) How has Wesley seen the investor sentiment to hardware change over the last decade? What have been the rivers in the rising positivity of investing in hardware?

Items Mentioned In Today’s Show:

Wesley’s Fave Book: The Big Short

Wesley’s Most Recent Investment: Luma

If you are looking to make your move into the world of VC or improve your investing skills,  Venture Capital Unlocked: Secrets of Silicon Valley Investing is a must! It is a 2 week crash course at Stanford run by Stanford Professional Development Centre and 500 Startups. You will learn the mechanics of all things Silicon Valley investing, check it out here.

The Twenty Minute VC is brought to you by Leesa. Leesa is like the TOMS Shoes or Warby Parker of the mattress industry. Here are 3 reasons why they are the best place to get your new mattress: Leesa has done away with the awkward mattress showroom experience by allowing a fully online experience, shipping to your doorstep for free. Their 10 inch mattresses come in all sizes and is crafted with 3 unique layers o foam including2 inches of memory foam and 2 inches of really cool latex like foam design to keep you cool. All Leesa mattresses are made 100% in the US or UK and they give you a 100 night trial, to make sure the mattress is perfect for you. Go to leesa.com/VC and enter promo code VC75 to get $75 off!

David Cohen is the founder and managing partner at Techstars, so a few amazing stats on techstars first, they have a total of 762 companies of which 90% are active or have been acquired, having raised more than 2bn in funding. As for David he is a serial entrepreneur having founded Pinpoint Technologies which was acquired by ZOLL Medical Corporation in 1999. David was also the founder and CEO of earFeeder.com, a music service which was sold to SonicSwap.com in 2006.

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In Today’s Episode You Will Learn:

1.) How David made the transition from Founder to VC with Techstars and Fund I?

2.) Fund I is one of the most successful funds in history; what was the structure with Fund I? Why did David choose a $5m fund size? How did he decide initial to follow on ratio?

3.)  Why was David so valuation sensitive with Fund I? Why was David so rigid on a consistent cheque size on Fund I?

4.)  Why did David decide to expand from being a solo GP fund? What are the challenges and complexities of fund scaling and did David approach this?

5.) Question from Ari Newman: What does David think about uncapped notes? Why does David like big boring companies? Brett Jackson: How did you meet Ryan Graves @ Uber and how did the Uber deal come about? Jason Seats: Where does David still see inefficiencies in the current venture model?

Items Mentioned In Today’s Show:

David’s Fave Book: The Soul Of Money

David’s Fave Blog: Mattermark Daily

If you are looking to make your move into the world of VC or improve your investing skills,  Venture Capital Unlocked: Secrets of Silicon Valley Investing is a must! It is a 2 week crash course at Stanford run by Stanford Professional Development Centre and 500 Startups. You will learn the mechanics of all things Silicon Valley investing, check it out here.

The Twenty Minute VC is brought to you by Leesa. Leesa is like the TOMS Shoes or Warby Parker of the mattress industry. Here are 3 reasons why they are the best place to get your new mattress: Leesa has done away with the awkward mattress showroom experience by allowing a fully online experience, shipping to your doorstep for free. Their 10 inch mattresses come in all sizes and is crafted with 3 unique layers o foam including2 inches of memory foam and 2 inches of really cool latex like foam design to keep you cool. All Leesa mattresses are made 100% in the US or UK and they give you a 100 night trial, to make sure the mattress is perfect for you. Go to leesa.com/VC and enter promo code VC75 to get $75 off!

Annie Kadavy is a General Partner @ Charles River Ventures. The prestigious VC fund that is now on it’s 16th fund and has backed the likes of Twitter, Yammer and Mailbox just to name a few. At CRV, Annie focuses on all things consumer and has either led or sourced their investments in ClassPass, Cratejoy, Patreon, Laurel & Wolf and DoorDash. Prior to CRV, Annie spent time with SV Angel and Warby Parker.

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In Today’s Episode You Will Learn:

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

2.)Why have we seen the explosion of marketplaces in recent years? What are the inherent challenges of two sided marketplaces; typically consumers and micro-entrepreneurs? Does Annie agree with Jeff Jordan in stating that these marketplaces need to nurture and manage conditions of perfect competition?

3.) What are the core components to growing traditional producer consumer marketplaces? How do they broach the chicken and the egg problem of supply and demand?

4.) Why is Annie so excited for the potential of bots? 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:

Annie’s Fave Book: Mindset: How You Can Fulfill Your Potential by Carol Dweck

Annie’s Fave Blog: The Skimm

Annie’s Most Recent Investment: Roam

If you are looking to make your move into the world of VC or improve your investing skills,  Venture Capital Unlocked: Secrets of Silicon Valley Investing is a must! It is a 2 week crash course at Stanford run by Stanford Professional Development Centre and 500 Startups. You will learn the mechanics of all things Silicon Valley investing, check it out here.
The Twenty Minute VC is brought to you by Leesa. Lees is like the TOMS Shoes or Warby Parker of the mattress industry. Here are 3 reasons why they are the best place to get your new mattress: Leesa has done away with the awkward mattress showroom experience by allowing a fully online experience, shipping to your doorstep for free. Their 10 inch mattresses come in all sizes and is crafted with 3 unique layers o foam including2 inches of memory foam and 2 inches of really cool latex like foam design to keep you cool. All Leesa mattresses are made 100% in the US or UK and they give you a 100 night trial, to make sure the mattress is perfect for you. Go to leesa.com/VC and enter promo code VC75 to get $75 off!

Jessica Mah is Founder and CEO of inDinero, which she started back in 2010 to help entrepreneurs with all their accounting and tax needs after going through the same challenges with her own businesses. Jessica has grown inDinero from zero to multi-million dollar revenues with over 100 full-time employees and has been featured in the Forbes and Inc 30 Under 30 Lists.  The company has raised over $10M to date and is growing rapidly. Her goal is grow inDinero into being the leading accounting provider for businesses.

Sam Lessin is a Partner at Slow Ventures who have made investments in the likes of Facebook, Twitter, Mattermark, AngelList,Dropbox and many more. On top of this, Sam is also the Founder and Co-CEO at Fin, which is basically like Siri Echo or Google now except it actually works, truly a phenomenal product. Prior to Fin and Slow, Sam was VP of Product Management at Facebook following the acquisition of his company, Drop.io by Facebook in 2010. Sam is also an intern at The Information where he reports directly to the boss Jessica Lessin!

Rob Go is a co-founder and Partner at NextView Ventures, Next View are hands on, high conviction true seed stage investors. Prior to founding NextView, Rob was at Spark Capital and focused on early stage investments in consumer web and mobile. Before joining Spark Capital, Rob worked at Ebay as the Business Product Lead for “Finding”. In this role, he oversaw the launch of major products that enhanced the search, browse, and product discovery experience for tens of millions of users.

Aaron Hirschhorn is the founder, CEO and “Top Dog” of DogVacay, the leading online and mobile pet sitting company. DogVacay connects pet parents in need of services with more than 25,000 vetted and insured pet caregivers in 10,000 cities across the country. Founded in March 2012 and based in Santa Monica, CA, the company has over 80 employees and has raised $47M from investors including Omers, Benchmark Capital and Andreessen Horowitz. Prior to DogVacay, Aaron spent several years in venture capital and technology, working at Monitor Group, Upfront Ventures, and Monitor Ventures. Previously, Aaron was an analyst at Kayne Anderson Capital Advisors.

Brian O’Malley is a Partner @ Accel Partners, where he spearheads Accel’s work with next-generation marketplaces and consumer-focused companies. He led the firm’s investments in Amino, Gametime, HotelTonight and Luma, as well as disruptive software-as-a-services businesses Duetto and Narvar. Brian joined Accel from Battery Ventures, where as a general partner he led investments in companies like Dollar Shave Club, BazaarVoice (public), Coupa, Skullcandy (public) and TradeKing (acquired by Ally). Prior to Battery, Brian led sales efforts and built some of the first web service-based API integrations for Bowstreet, Inc. (acquired by IBM).

Byron Deeter is a Partner at Bessemer Venture Partners. Prior to being a VC, Byron himself was a veteran cloud CEO & Founder returning to venture capital in 2005 to lead Bessemer’s global cloud practice where he has been actively involved with over 100 cloud investments representing a third of the market cap of all public cloud companies. Byron has lead investments in the likes of Box, Twilio, Intercom, Cornerstone On Demand and many many more. Byron’s pedigree is recognised globally as he is consistently ranked one of the top global investors across all industries.

Roy Bahat is the head of Bloomberg Beta, a new venture fund backed by Bloomberg L.P. Prior to Bloomberg, Roy was chairman of OUYA, a new kind of game console, where he was the first investor. Before that Roy spent five years leading News Corporation’s IGN Entertainment, an online media company with a monthly audience of 70 million people, a top 10 YouTube channel, and the leading website in its category in almost every market globally. Roy served on the board of Revision3 (acquired by Discovery) and was a board observer at Flixster (acquired by Warner Bros). Before joining News Corp., Roy was in the public sector in the office of New York City mayor Michael Bloomberg and at New York’s 2012 Olympic bid.

 

Josh’s Most Recent Investment:

• Discord: Free Voice and Text Chat For Gamers

Baiju Bhatt is the Co-Founder and CEO at RobinHood, the wildly successful stock market trading app with absolutely no commission fees. Since launching RobinHood there have been many amazing milestones including being awarded an Apple Design Award (first Finch company ever to achieve this), funding from the likes of Index, Google Ventures, Andreessen Horowitz and even movie star Jared Leto. They were also nominated for best mobile app at The Crunchies by TechCrunch this year.

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In Today’s Episode You Will Learn:

1.) How Baiju made his way into the world of tech and came to be Founder @ RobinHood?

2.) How did Baiju deal with the regulatory hurdles heading into the fintech and trading world?

3.) How did Baiju go about building the waitlist for RobinHood to 1m people? What were the defining strategies and channels that made the difference?

4.) What is the thesis behind the decision of RobinHood? Will this design enable previously untouched markets to tap into the growing trading market?

5.) What are the biggest challenges for Baiju and RobinHood going forward? What keeps Baiju up at night? What is Baiju’s biggest piece of advice to a founder scaling their startup?

Items Mentioned In Today’s Show:

Baiju’s Fave Blog or Newsletter: TechCrunch

Baiju’s Fave Productivity Tool: Slack

Baiju’s Fave Book: The Case For Mars

• Mattermark Daily

Satya Patel is a Partner @ Homebrew alongside Hunter Walk. Prior to Homebrew, Satya was VP Product at Twitter, building and leading the Product Management and User Services teams. Before Twitter, Satya was a Partner at Battery Ventures, where he co-led the seed and early stage investing practices. In 2003, Satya joined Google and was responsible for AdSense product management and partnerships. Before heading to Silicon Valley for Google, I worked for DoubleClick, in venture capital and as a strategy consultant.

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In Today’s Episode You Will Learn:

1.) How Satya made his way into the world of tech and came to Partner with Hunter @ Homebrew?

2.) Is hustle the key component of a great VC? What does Satya believes makes a great investor?

4.) How can startups present emotion and depict their narrative to the VC? What are the benefits of doing so? What founder is most

5.) From Satya’s experience, what are the most common reasons startups fail at the seed stage? What can they do to maximise their chances of survival?

6.) We always hear that products should focus on a niche but how then do you attract VC money that is looking for a broad opportunity that can return the fund?

Items Mentioned In Today’s Show:

Satya’s Fave Blog or Newsletter: CB Insights, Fred Wilson, Brad Feld

Satya’s Fave Book: A Fine Balance

Branko Cerny is the Founder and CEO at Immediately, the mobile platform for modern sales professionals whose mission is to elevate sales back to it’s core foundation, a relationship driven craft. Immediately has some of the US’s finest backing in terms of investment with the likes of Naval Ravikant @ AngelList, Ryan Holmes @ Hootsuite, Jonathan Abrams @ Friendster and Nuzzel and previous guest Kate Shillo @ Galvanize.

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In Today’s Episode You Will Learn:

1.) How Branko made his way into the world of tech and came to be CEO @ Immediately?

2.) How does Branko find being one of the youngest enterprise CEO in the business? What are the challenges and what are the benefits?

3.) What can enterprise companies learn from the likes of Tinder and Equinox? How important is brand building for emerging enterprise sales companies?

4.) To what extent will we see the bottoms up sales process continue in enterprise sales? How does this change Immediately approach to UX, UI and brand building? Why did Branko choose to focus on a mobile platform with Immediately?

5.) How did Branko come to meet his stellar lineup of investors? What value add was he looking for when assembling the lineup? Is he concerned by the large number of investors Immediately has at an early stage?

Items Mentioned In Today’s Show:

Branko’s Fave Blog or Newsletter: First Round Review, Nir Eyal

Branko’s Fave Productivity Tool: Intercom, Moleskin Notebook (Harry’s Productivity Tool too!)

Branko’s Fave Book: American Gods by Neil Gaiman

• Sarah Tavel, Brad Feld, Wait But Why

Rebecca’s Most Recent Investment:

• Booster Fuels

Rob Hayes is a partner at First Round Capital where he opened up the firm’s San Francisco office. Over the past ten years, he has led investments in companies such as Mint.com (acquired by Intuit), Gnip (acquired by Twitter), Square, Uber, eero, and Planet Labs. Prior to joining First Round, Rob became the first venture investor at Omidyar Network, the investment firm started by eBay founder Pierre Omidyar. While there, he led most of the initial venture capital deals and later built and ran the technology investing group.
Before that, Rob worked at Palm, where he product managed Palm OS and started the company’s corporate venture fund.

• Dan Primack: Term Sheet

Rob’s Most Recent Investment:

• eero: Blanket Your Home In Fast, Reliable Wifi

Puneet Mehta, Founder @ Msg.ai, an artificial intelligence startup for conversational commerce and for an AI founder you don’t get much better than starting your career at IBM’s TJ Watson Center, which is exactly what Puneet did. He then went on to build predictive platforms to power large-scale trading systems aka bots on Wall St. It is clearly not joust us who think he is awesome as Advertising Age named Puneet to the Creativity 50 list in 2014, honoring the most creative and innovative thinkers and doers.

• Paul Graham: Blog

Ciaran O’Leary is the General Partner at one of Europe’s newest funds, BlueYard. A $120m fund located at the early stage, centring around 3 key areas: The decentralisation of markets, the democratisation of capabilities, and the liberation of data. Prior to BlueYard, Ciaran was a Partner at Earlybird with investments in the likes of Peak Games (emerging markets social gaming), 6Wunderkinder (productivity apps), Moped (private messaging), B2X Care Solutions (outsourcing platform), madvertise (mobile targeting network) and simfy (digital music distribution company). Before Earlybird, Ciarán co-founded a startup and gathered operational experience at others.

We would like to say a special thank you to Mattermark for providing all the data used in the show today and you can check out Mattermark Search here!

Matt Mazzeo is Managing Director at Lowercase Capital, alongside legendary angel investor, Chris Sacca. At Lowercase Matt leads a seed and series A investment strategy managing a portfolio of over forty investments including Uber, Twitter, Stripe and Optimizely just to name a few. Prior to joining Lowercase Capital, Matt spearheaded many of the digital and venture efforts at Creative Artists Agency (CAA). Matt helped shape the agency’s seed stage investment strategy and played an integral role in the founding of CAA’s incubated start-up companies, including Funny or Die, WhoSay, and Moonshark. Matt has been recognized as an innovative force across technology, entertainment, and advertising for which Fast Company named Matt one of the Most Creative People in Business. In addition to making Forbes Midas Brink List in 2014, Matt has been recognized on both Ad Age’s 40 Under 40 List in 2013, and The Wrap’s Inaugural Innovators List.

• Jessica Lessin: The Information

Matt’s Most Recent Investment:

• Mobcrush

Niccolo De Masi is the CEO & Chairman @ Glu Mobile, one of the world’s hottest gaming companies with title including the current No 1 Game in the App Store with the Kendall and Kylie Game, Glu is also the maker of the Kim Kardashian game and the likes of Deer Hunter and many more. Prior to Glu, Niccolo was CEO at mobile entertainment company Hands On Mobile and before that Niccolo was the CEO at London listed mobile entertainment company, Monstermob Group Plc.

We would like to say a special thank you to Mattermark for providing all the data used in the show today and you can check out Mattermark Search here!

Christian Hernandez is the Co-Founder and Partner @ Whitestar Capital in London. Prior to co-founding White Star Capital, Christian worked at Facebook and led the international expansion of the company’s Business Development, Platform and Developer Network groups. He previously held leadership roles in the U.S. and Europe at Google and Microsoft and started his career in technology at MicroStrategy, a startup he joined prior to its 1999 IPO. Christian has worked closely with entrepreneurs and leading VCs and has been an active angel investor and advisor.  He represents White Star on the Boards of KeyMe, Glow Media, Bloglovin’ and Hole 19. Christian also serves as a Young Global Leader of the World Economic Forum.

We would like to say a special thank you to Mattermark for providing all the data used in the show today and you can check out Mattermark Search here!

Tom Tunguz is a Partner @ Redpoint Ventures, where he has invested in Axial, Dremio, Expensify, Electric Imp, Looker, and ThredUP. Before joining Redpoint, Tomasz was the product manager for Google’s AdSense social-media products and AdSense internationalization. Tom is also the author of the world famous blog and newsletter which can be found at http://tomtunguz.com

We would like to say a special thank you to Mattermark for providing all the data used in the show today and you can check out Mattermark Search here!

Hiten Shah is one of the most prominent players in the data marketing industry having co-Founded both KissMetrics (raised $10m+ VC Funding) and Crazy Egg (bootstrapped), both wildly successful businesses serving some of the world’s largest companies. Hiten is also an extremely successful angel investor with investments in the likes of Buffer, Mattermark and MessageMe (acquired by Yahoo.) In addition, Hiten is also a serial startup advisor having been an advisor with Linkedin, SlideShare and WordPress’ Automattic.

We would like to say a special thank you to Mattermark for providing all the data used in the show today and you can check out Mattermark Search here!

Jim Scheinman is the Founder and Managing Partner @ Maven Ventures, a leading seed stage consumer VC with investments in the likes of AngelList, WealthFront and Altspace. Prior to founding Maven, Jim was a pioneer in the early days of the social media revolution as Head of Business Development and Sales at the first social networking site, Friendster. However, in 2005, Jim left Friendster to join co-founders Michael and Xochi Birch to launch Bebo as the first employee and Board member. Bebo later went on to become a unicorn for Jim, however, that was not his only unicorn as he was also an investor in Tango ($bn valuation) and NBCi (IPOd for 6bn.)

We would like to say a special thank you to Mattermark for providing all the data used in the show today and you can check out Mattermark Search here!

• Medium Newsletter, Mark Suster: Both Sides Of The Table

Andy’s Most Recent Investment:

• Captain401

Gary Liu is the CEO @ Digg, the incredibly famous platform that allows users to find, read and share the most talked about stories on the internet. Prior to joining Digg, Gary was an early employee at Spotify holding numerous positions including, Head of Spotify Labs and Global Director of Ad Product Strategy. Gary joined Spotify from AOL, where he was the Director of Sales Strategy and Operations at Patch. Before joining AOL, Gary was a business and sales operations leader at Google and Clickable.

We would like to say a special thank you to Mattermark for providing all the data used in the show today and you can check out Mattermark Search here!

Adam Draper is a fourth generation venture capitalist and the Founder & CEO @ Boost VC, a specialised seed stage accelerator that invests in blockchain and virtual reality startups. Before starting Boost, Adam angel invested in 20 companies including Coinbase, Plangrid and Practice Fusion. During his angel investment period, Adam was also the Founder of Xpert Financial in his aim to revolutionise the financial markets for private companies.

We would like to say a special thank you to Mattermark for providing all the data used in the show today and you can check out Mattermark Search here!

Tim Draper is the founding partner of leading venture capital firms Draper Associates and DFJ. Some of his Venture successes include Skype, Baidu, Tesla, Hotmail, Twitch.tv, and hundreds of others. Fun fact about Tim, it was his original suggestion to use viral marketing in web-based email to geometrically spread an Internet product to its market was instrumental to the successes of Hotmail, YahooMail, and Gmail and has been adopted as a standard marketing technique by thousands of businesses. His prominence is evident through his being named 100 most influential Harvard Alumni, and seven on the Forbes Midas List. He was named Always-On #1 top venture capital deal maker.

We would like to say a special thank you to Mattermark for providing all the data used in the show today and you can check out Mattermark Search here!

Niccolo De Masi is the CEO & Chairman @ Glu Mobile, one of the world’s hottest gaming companies with title including the current No 1 Game in the App Store with the Kendall and Kylie Game, Glu is also the maker of the Kim Kardashian game and the likes of Deer Hunter and many more. Prior to Glu, Niccolo was CEO at mobile entertainment company Hands On Mobile and before that Niccolo was the CEO at London listed mobile entertainment company, Monstermob Group Plc.

We would like to say a special thank you to Mattermark for providing all the data used in the show today and you can check out Mattermark Search here!

Tyler Willis is probably one of the best angel investors around and has invested in seed stage companies that have gone on to raise from the likes of Index Ventures, Founders Fund, Khosla Ventures and others. Some of these investments include the likes of wildly popular ride sharing app Lyft, the incredible Patreon (now delivering 2m a month to creators) and Change.org which now has over 80m users.

We would like to say a special thank you to Mattermark for providing all the data used in the show today and you can check out Mattermark Search here!

Arielle Zuckerberg, Partner @ Kleiner Perkins Caufield and Byers. Arielle Zuckerberg joined KPCB in 2015 and focuses on early-stage investments in the firm’s digital practice as part of the venture team. Arielle joined Kleiner from Humin, where she led product for the company’s mobile apps. She started her career as a product manager by day and Hackathon host by night at Wildfire Interactive, Inc., which was acquired by Google in 2012. After the acquisition, Arielle worked as a product manager on social ads at Google. Outside of KPCB, Arielle has made several angel investments across the food tech and health sectors in the likes of Partender, Bitty Foods and The Ticket Fairy, just to name a few.

We would like to say a special thank you to Mattermark for providing all the data used in the show today and you can check out Mattermark Search here!

Ryan Caldbeck is the Founder & CEO @ CircleUp, the online investing platform that allows you to invest in innovative consumer companies. They have raised funding from some of the best including USV, Maveron and Canaan Partners (all past guests). Before Ryan founded CircleUp, he worked in consumer product and retail-focused private equity at TSG Consumer Partners and Encore Consumer Capital, where he was exposed to hundreds of great consumer and retail businesses that were too small to obtain funding through the customary private equity channels and did not fit the risk profiles many VCs demanded. As a result, Ryan decided to build the solution, a private equity marketplace with the economics and scale to make funding available to these promising companies.

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In Today’s Episode You Will Learn:

1.) How did Ryan make the move from the world of VC to founding his own tech startup?

2.) Why is CircleUp marketplace investing, not crowdfunding? What does Ryan believe are the misnomers around the term crowdfunding?

3.) Where does this sector make sense and where is it  inefficient? Why is it wrong for tech companies?

4.) One major aspect in the UK that this segment has struggled with is it’s ability to attract institutional investors to the sector. So with CircleUp, how are institutional investors getting into this market and is there anything more Ryan would like to see with this regard?

5.) To what extent does Ryan think this is disrupting private capital formation? Should VCs be concerned? What sector of the funding environment is most vulnerable to being disrupted by the rise of marketplace investing?

6.) How was the funding process for Ryan? CircleUp raised over $50m over several rounds with investors from our friends at USV and Maveron, how that came about and what Ryan would advise founders entering the process?

Items Mentioned In Todays Show:

Ryan’s Fave Blog: AVC, Jeff Jordan, Bill Gurley

Dustin’s Most Recent Investment:

• AtVenue (Tom Williams)

• Nuzzel

Gil’s Most Recent Investment:

• Happn

• Nuzzel

Hadley’s Most Recent Investment:

• Phhhoto: Instant Moving Pictures

• Ben Evans Newsletter

Jeff Seibert is an experienced serial-entrepreneur and currently Senior Director of Product at Twitter. Previously, Seibert was the CEO of Crashlytics, which he co-founded in 2011 with Wayne Chang. Crashlytics delivered crash analysis tools for iOS and Android apps via an SDK that reached 300 Million mobile devices worldwide. Crashlytics was acquired by Twitter in 2013 for $259m. In 2007, Seibert co-founded Increo and served as its COO and lead architect until its acquisition by Box in August of 2009. He subsequently oversaw the integration of Increo’s document preview and annotation technologies into the company’s cloud-based content platform.

• Ginkgo Bioworks

James Beshara is the Co-Founder @ Tilt the micro-crowdfunding platform that allows you to receive funding from friends—changing the way collaborative funding works. Tilt has raised $37 million from 3 rounds of funding from the likes of Andreesen, SV Angel, Alexis Ohanian, Naval Ravikant and Sean Parker just to name a few. As for James Before co-founding Tilt, he studied Development Economics as an undergrad and then went on to build dvelo.org, a site for crowdfunding loans and donations to poverty-alleviation organizations in developing countries. In order to vote for who you think will win James and Harry’s beer pong match, head over to @twentyminutevc on Twitter and vote using our poll.

Matt Lieber is cofounder and President of Gimlet Media. In a previous life, Matt produced radio shows (On Point, Fair Game) and podcasts (Slate Culture Gabfest). He also worked as a management consultant at The Boston Consulting Group, where he focused on media and digital business. Then he chucked it all for Gimlet. He holds an MBA from MIT Sloan. 

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In Today’s Show You Will Learn:

1.) Matt reveals the origins of Gimlet?

2.) What were the dilemmas for Matt in raising Gimlet’s round? What determinant made Matt realize raising was right? What advice would Matt give to founders who are unsure if they should raise or not?

3.) One of the main concerns with raising suggested by Alex Blumberg was that the company would feel like a totally different company, and by different ‘I mean worse’, to quote Alex. So how can a Founder maintain company culture as they grow excessively?

4.) Why did Matt decide to play it cool and not announce to VCs Gimlet were raising? Did Matt expect to get a term sheet as quickly and easily as he did? Were there any hiccups to the funding process? Were Gimlet tempted by any other offers? What value add about Tim O’Reilly made Gimlet most attracted to him?

5.) Question from Matt Hartman at Betaworks: How does Gimlet decide which new shows to create? Is it about creating new shows for an overlapping audience or to expanding audience demographics??

6.) Where does Matt see the future of podcasting going? Many do not believe in it’s potential to be a big business, what does Matt say? What are the challenges, what needs to happen to combat them?

Items Mentioned In Today’s Episode:

Matt’s Fave Book: Great Plains by Ian Frazier

Matt’s Fave Blog: Stratechery by Ben Thompson

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

Likewise, if you would like to see a more colourful side to Harry with many a mojito session, follow him on Instagram here!

matt hartman dyb, alex, surpisingly awesome adam mckay and adam davidson, chis sacca, matt mazzeo