20VC: Twitter Co-Founder Biz Stone on The 3 Stages of Wealth, The Return To Twitter in 2017 and the Associated Missions and Challenges & Why Silicon Valley is not an “Insiders Only” Universe?

Biz Stone is best known as the Co-Founder of Twitter and Medium. Biz is also an investor in the likes of Slack, Square, Intercom, Beyond Meat and Blue Bottle Coffee. Biz also co-founded Jelly, a “human in the loop” AI search service, which was acquired by Pinterest. Due to his many successes, Biz has been recognized as INC Magazine Entrepreneur of the Decade and one of TIME’s 100 Most Influential People in the World.

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In Today’s Episode You Will Learn:

1.) How did Biz make his way into the world of startups and come to found Odeo/Twitter one day on a car trip with Ev Williams?

2.) How does Biz evaluate his relationship to money? How does Biz think about teaching his son the value of money? What does Biz mean when he says wealth ‘accentuates your current self”? How did Biz get off the treadmill of always wanting and chasing more?

3.) How does Biz think about insecurity and self-doubt? How does Biz approach saying no? How does he get comfortable with not always being Mr Popular? What is so challenging here? How does Biz feel about founding tieing their identities to their company?

4.) Why did Biz come back to Twitter in 2017? With hindsight, what would he have done differently if he were to return again? What were the biggest challenges when he arrived? Why was internal morale low? What did he and Jack do to increase it? What worked? What did not?

5.) Why does Biz not feel Silicon Valley is an “insider only” universe? Why does Biz feel Silicon Valley is a mindset? How does Biz think about the decentralisation of talent moving forward? How does Biz compare the UK to the US startup ecosystem? What is worse in the UK?

Item’s Mentioned In Today’s Episode

Biz’s Favourite Book: Emergence: The Connected Lives of Ants, Brains, Cities and Software

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

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

20VC: Bill Gurley and Howard Marks: What Happened In 2020? What Can We Expect Looking Forward to 2021?

Howard Marks is co-chairman and co-founder of Oaktree Capital Management, a leading investment firm with more than $120 billion in assets. Prior to founding Oaktree, Howard spent 10 years at The TCW Group, where he was responsible for investments in distressed debt, high yield bonds, and convertible securities. Howard has also written two books, most recently Mastering the Market Cycle: Getting the Odds on Your Side, and it was Warren Buffet who said, “When I see memos from Howard Marks in my mail, they’re the first thing I open and read. I always learn something.”

Bill Gurley is a General Partner @ Benchmark Capital, one of the most successful funds of the last decade with a portfolio including the likes of Uber, Twitter, Dropbox, WeWork, Snapchat, StitchFix, eBay and many many more. As for Bill, widely recognised as one of the greats of our time having worked with the likes of GrubHub, NextDoor, Uber, OpenTable, Stitch Fix and Zillow. Prior to Benchmark, Bill was a partner with Hummer Winblad Venture Partners. Before entering venture, Bill spent four years on Wall Street as a top-ranked research analyst, including three years at CS First Boston.

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In Today’s Episode You Will Learn:

1.) In March Ray Dalio stated we would be entering a “global recession”, how do Howard and Bill feel about this statement? How does today’s environment remind Howard and Bill of 2010/11? What is similar? What is different? How does Bill think about investing through cycles?

2.) How does Bill think about investing through cycles? What have Bill’s lessons been from seeing many venture vintages on LP performance across cycles? How does Howard think about investing through cycles from a distressed debt perspective? What have his lessons been from Oaktree’s performance over the years?

3.) Do Howard and Bill agree we will not see interest rates go anywhere for the next 3-5 years? What is the impact of this sustained low-interest rate environment? What could be done that would see interest rates increase in the future? How does Bill believe this will impact the supply of LP dollars in venture?

4.) How do Bill and Howard evaluate the state of the public markets today? Why does Howard believe that FOMO has really taken effect? How does Bill think about network effects and the laws of compounding with regards to public companies?

5.) Do Howard and Bill agree we are seeing a retreat from globalisation? What are the core impacts of this retreat? Why is Bill so concerned about “regulatory capture”? Why does Bill fear that today, “Washington is for sale”? What would he like to see change?

Item’s Mentioned In Today’s Episode

Howard’s Favourite Book: Across That Bridge: A Vision for Change and the Future of America

Bill’s Favourite Book: How Innovation Works

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

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

20VC: Lessons From Working with Bill Gates, How To Lead Without Authority and The Difference Between Leadership and Management & How Fundraising Changes In A COVID World with Quentin Clark, Managing Director @ General Catalyst

Quentin Clark is a Managing Director @ General Catalyst, one of the most prominent firms of the last decade with a portfolio including Stripe, Airbnb, Snap, Anduril, Deliveroo and Cazoo to name a few. As for Quentin, at GC he has led deals in the likes of Kernel, Coda, Commure just to name a few. Before entering the world of venture Quentin was the CTO @ Dropbox and before that he was the Chief Business Officer @ SAP. Finally, before SAP, Quentin spent an incredible 20 years at Microsoft in a variety of different roles play a key part in their hyper-growth.

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In Today’s Episode You Will Learn:

1.) How Quentin made his way from CTO @ Dropbox and 20 years at Microsoft to being an MD with General Catalyst today?

2.) What were Quentin’s biggest management takeaways from his 20 years at Microsoft? What is his favourite story about working with Bill Gates? How does Quentin think about the art of delegation? How does Quentin differentiate between leadership and management?

3.) How does Quentin believe the world of fundraising has changed with COVID? How does Quentin build relationships of trust in these compressed fundraising timelines? What works? What does not work? How can you really build that relationship off Zoom? How does this change the fundraising landscape moving forward?

4.) What does Quentin mean when he says he likes to “lead without authority”? How does that translate into his management style? How does Quentin evaluate his style of board membership? How does Quentin know whether to wear the investor vs the operator hat on the board?

5.) Does Quentin believe we are really moving the needle in terms of the projects that venture is funding today? What would Quentin like to see more of? What would Quentin like to change about the world of venture? How does Quentin evaluate market timing risk when investing?

Item’s Mentioned In Today’s Episode

Quentin’s Favourite Book: Stranger in a Strange Land

Quentin’s Most Recent Investment: Sprout Therapy

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

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

20VC: Why The Theory of Pro-Rata Can Often Be False, How Rolling Funds Impact Both Pricing and Competition and The Biggest Takeaways from Jack Dorsey with Avlok Kholi, CEO @ AngelList Venture

Avlok Kohli is the CEO of AngelList Venture which has facilitated the funding of over 5,000 startups including 47 unicorns and is home to 4,300 funds and syndicates with $2.2B in assets under management. This year, AngelList Venture launched the much-discussed, Rolling Funds and Avlok recently launched his own rolling fund, Avlok Capital. Prior to AngelList, Avlok built and sold two companies; FastBite, acquired by Square in 2015 and Fairy, also acquired. If that was not enough, Avlok is also an angel in 25 companies.

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In Today’s Episode You Will Learn:

1.) How Avlok made his way into the world of facilitating over $2Bn in AUM having sold 2 prior companies on the other side of the table as a founder? What is Avlok’s favourite Jack Dorsey story?

2.) Why does Avlok believe Rollings Funds are the “printing presses of innovation” for capital markets? Does Avlok believe that everyone should be a fund manager and managing capital? What are the benefits of rollings funds vs traditional micro funds?

3.) How does the rise of rolling funds impact the early stage pricing of companies? How does it impact the competitive landscape for seed and pre-seed allocations? Is Avlok concerned about a wave of undisciplined capital entering the market?

4.) How does Avlok evaluate reserve allocations for early stage and micro fund managers today? What does the data show for funds that do reserve for pro-rata vs those that do not? How has this impacted Avlok’s own approach to pro-rata and reserve deployment?

Item’s Mentioned In Today’s Episode

Avlok’s Favourite Book: Meditations

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

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

20VC: Retool Founder, David Hsu on Why YC Is Helpful Pre Product-Market Fit but Not Post and Why VCs Are Not Helpful Pre-Product Market-Fit but are Post, Why it is Difficult to Become Unprofitable if You Set Yourself Up For Profitability Early & Why VC Theory Around Ownership Is Not True

David Hsu is the Founder & CEO @ Retool, the company that allows you to build internal tools, remarkably fast. David has raised over $69M with Retool from the very best in startups including Sequoia, YC, Patrick and John @ Stripe, Henrique & Pedro @ Brex, Paul Graham, Nat @ Github, Peter @ Segment, Tomer @ Gusto and Elad Gil to name a few incredible names. Today Retool works with some of the biggest companies in the world from Amazon to Volvo to Mercedes Benz.

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In Today’s Episode You Will Learn:

1.) How David made his way from studying philosophy at Oxford to creating one of the valley’s hottest companies in the form of Retool?

2.) How does David analyse pivots today? How does one balance between vision and persistence vs realism and knowing when is the right time to pivot? How did a conversation with John Collison change the course of Retool? What advice does David have for founders on pivoting?

3.) Why does David believe that YC is useful pre-product-market fit but useless post-product-market fit? What elements are so helpful vs not about YC? Why did David raise his Series A as a split between Sequoia and prominent angels? Why was that transformational for the company?

4.) Why was David sceptical of VCs for a long time? Why does David believe VCs are useless pre-product-market fit and useful post-product-market fit? What have been David’s biggest takeaways from working with Bryan Schrier @ Sequoia?

5.) Why does David believe that once you are profitable and growing it is actually quite hard to become unprofitable? How does David advise founders considering raising VC vs bootstrapping? How does David know when to allocate resources more aggressively to a segment? What are the signs?

Item’s Mentioned In Today’s Episode

David’s Favourite Book: Godel, Escher, Bach: An Eternal Golden Braid

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

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

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