20VC: Why Valley Investors Are Really Gamblers, Why The Business Model of Selling To The Biggest Sucker Is Wrong & Why The Best Potential Hires Don’t Care Who Your VC is with David Barrett, Founder & CEO @ Expensify

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

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In Today’s Episode You Will Learn:

1.) How David went from founding Red Swoosh with Travis Kalanick to changing the sexy world of expense reporting with Expensify?

2.) Why does David want to change the cult of the second time entrepreneur? Why does David believe that Silicon Valley fundamentally changes exits in the wrong way? How does David define true operational success?

3.) Why does David believe that Silicon Valley investors are not investors but gamblers? Why does David believe that the business model VCs have created is not only not optimal for founders but poor business practice with “profit” being a dirty word?

4.) What does David believe are the fundamental benefits of capital constraints? How does having financial independence influence your stance when speaking with investors? When does the decision of financially lean or VC backed need to be taken?

5.) Why does David believe the more hiring you do, the more problems you have? What are the core issues of revenue being tied to headcount growth? Why does David believe Silicon Valley is poor for hiring and you must look further afield?

Items Mentioned In Today’s Show:

David’s Fave Book: Guns, Germs, and Steel, Enders Game

As always you can follow HarryThe Twenty Minute VC and David on Twitter here!

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

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

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

20VC: Why VCs Fundamentally Assess Founders The Wrong Way, Why VC Needs To Innovate On The Scouting Model & Why SAFE’s and Convertible Notes Are The Future Of Investing with Elizabeth Yin, Founder & General Partner @ Hustle Fund

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

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In Today’s Episode You Will Learn:

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

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

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

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

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

Items Mentioned In Today’s Show: 

Elizabeth’s Most Recent Investment: The Pill Club

As always you can follow HarryThe Twenty Minute VC and Elizabeth on Twitter here!

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

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

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

20VC: a16z’s Alex Rampell on The Struggle Between Innovation vs Distribution, When How To Determine Whether An Application is Optimised Through Centralised or Decentralised Networks & Why Most ICOs Today Are Ridiculous

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

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In Today’s Episode You Will Learn:

1.) How did Alex make the move from serial entrepreneur with numerous successful exits to General Partner @ a16z?

2.) Question from Chris Dixon: What were the key takeaways for Alex from his time in operations? Having been both entrepreneur and VC, how does Alex view the continuous struggle between innovation and distribution? Can you succeed with only one?

3.) How does Alex believe the new generation of large incumbents are acting in the market? Why does he believe that a counter-revolutionary strike from them would not be atypical?

4.) How does Alex really define “data network effects”? How does Alex look to analyse them effectively? How does Alex believe that startups can use inflection points in the sales process to enter an incumbent heavy market?

5.)How does Alex view the rise of ICOs? Does Alex share Charlie Lee’s concerns that they are the most concerning element of the crypto world? What framework does Alex use to determine whether an applications is optimised through centralised or decentralised databases? Why does Alex believe that most ICOs are ridiculous?

Items Mentioned In Today’s Show:

Alex’s Fave Book: The Metamorphosis by Franz Kafka

Alex’s Fave Blog: Chris Dixon

Alex’s Most Recent Investment: Propel

As always you can follow HarryThe Twenty Minute VC and Alex on Twitter here!

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

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

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

20VC: Why Self-Awareness Is The Most Important Characteristic For Founders, When Is The Right Time For A CEO To Hand Over The Reigns & What CEO’s Can Learn About Company Culture From Teaching Middle School with Lloyd Tabb, Founder & Chairman @ Looker

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

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In Today’s Episode You Will Learn:

1.) How did Lloyd make his way into the world of startups and come to sell his first to Netscape at such a young age?

2.) Why did Lloyd decide to hand over the reigns of CEO to Frank at such an early stage? What was the thought process? What advice does Lloyd have for founders contemplating the same? What is the most important skill for the original founder to have?

3.) How did Lloyd learn about creating and scaling company culture from teaching middle school kids? What are the inflection points in scaling company culture? What are the foundations that must always be core? Why does Lloyd dislike the “burnout culture so much”?

4.) What is the hardest element for Lloyd in scaling Looker to this day? How does Lloyd believe automation must be used within business processes to create a streamlined and efficient organisation? What should the ultimate goal of all CEOs be?

5.) Why does Lloyd believe that the conventional wisdom, “the common path is the safe path”, is fundamentally not true? How does Lloyd view the role of mentors, in terms of career progression? What can people do to attain the mentor they would like?

Items Mentioned In Today’s Show:

Lloyd’s Fave Book: Seth Godin

Lloyd’s Fave Blog: What The F*** Just Happened Today

As always you can follow HarryThe Twenty Minute VC and Lloyd on Twitter here!

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

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

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

20VC: The Lean Startup’s Eric Ries on The Missing Function of Entrepreneurship in Most Companies, Creating A New Accountability Paradigm & How To Structure Promotions and Compensation In The New Structure

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

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In Today’s Episode You Will Learn:

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

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

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

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

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

Items Mentioned In Today’s Show:

Eric’s Fave Book: Ancillary Justice

Eric’s Fave Blog: Kickstarter Blog

As always you can follow HarryThe Twenty Minute VC and Eric on Twitter here!

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

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

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

20VC: Oren Zeev on Why Diversification Does Not Work, Thesis Based Investing Is Sceptical & Partners Mostly Stay Together For LPs

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

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In Today’s Episode You Will Learn:

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

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

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

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

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

Items Mentioned In Today’s Show:

Oren’s Fave Book: The Innovator’s Dilemma

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

Oren’s Most Recent Investment: Next Insurance

As always you can follow HarryThe Twenty Minute VC and Oren on Twitter here!

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

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

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

20VC: What Is Core To The Best Investor – Founder Relationships, The Biggest Risk For Founders In The Early Days & Why EQ Is The Most Important Trait For Managers with Jack Altman, Founder & CEO @ Lattice

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

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In Today’s Episode You Will Learn:

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

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

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

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

Items Mentioned In Today’s Show:

Jack’s Fave Book: Meditations

Jack’s Fave Blog: SaaStr

As always you can follow HarryThe Twenty Minute VC and Jack on Twitter here!

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

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

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

20VC: Y Combinator’s Paul Buchheit on Creating Gmail Version 1.0 & Leadership Lessons from Working With Zuckerberg and Larry Paige

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

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In Today’s Episode You Will Learn:

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

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

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

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

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

Items Mentioned In Today’s Show:

Paul’s Fave Book: Eckhart Tolle

Paul’s Most Recent Investment: Greo

As always you can follow HarryThe Twenty Minute VC and Paul on Twitter here!

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

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

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