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

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20VC: Figma Founder, Dylan Field on How Leadership Needs To Evolve with Scale, The Transition from Application to Platform & The Future of Remote Work, Education and Digital Spaces

Dylan Field is the Founder & CEO @ Figma, the company that helps teams create, test, and ship better designs from start to finish and is one of 2020’s fastest-growing companies. To date, Dylan has raised over $132M with Figma from some of the best including Sequoia, a16z, Index, Greylock, Founders Fund and Kleiner Perkins. Figma’s latest round valued them at a reported $2Bn. Prior to founding Figma, Dylan enjoyed internships at Flipboard, LinkedIn and O’Reilly Media.

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In Today’s Episode You Will Learn:

1.) How Dylan made his way from an internship at O’Reilly Media and a Thiel Fellowship to founding Figma, one of the fastest-growing unicorns?

2.) How does Dylan feel about the future of education? What core questions do students need to ask before entering? How does Dylan assess the impact of the Thiel Fellowship today? Why does Dylan believe that everyone should be an intern? What did he take from that experience?

3.) How would Dylan describe his leadership style today? How has it changed over time? How did he get past micro-managing in the early days and learn to delegate? How does Dylan think about insecurity and vulnerability as a young leader today?

4.) What does Dylan forsee as the biggest challenges in Figma’s transition from application to platform? How does Dylan evaluate the success of the Figma plugin ecosystem? How does Dylan think about the right cadence to roll out new products? How does Dylan think about catering to power users vs catering to the standard everyday user?

5.) What have been the most significant impacts of COVID for Figma? Why did Dylan choose to adopt a hybrid model for Figma in terms of working styles moving forward? What have been Dylan’s biggest lessons of what it takes to attract the very best talent? What works? What does not?

Item’s Mentioned In Today’s Episode

Dylan’s Favourite Book: Snow Crash

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20VC: Hopin, The Breakout Startup of 2020 on Scaling from 10 to 230 People and $174M in Funding in just 13 Months, The 3 Phases of Startup Scaling, How To Lead Remote Teams Effectively, The Future of Events Post-COVID and more

Johnny Boufarhat is the Founder & CEO @ Hopin, one of the fastest-growing companies on the planet, providing an online events platform where you can create engaging virtual events that connect people around the globe. In the last 13 months, Johnny has raised over $174M for Hopin from the likes of Accel, IVP, Slack, Northzone, Coatue, Salesforce and of course, 20VC Fund. With the funding, again in just 13 months, Johnny has grown the team from 10 people to over 210 people in 37 countries. In October of this year, Semil Shah awarded Hopin the label, “The Breakout Tech Startup Of 2020”.

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In Today’s Episode You Will Learn:

1.) How Johnny made his way into the world of startups and how severe health challenges led to his realisation and founding of Hopin?

2.) What have been Johnny’s biggest lessons scaling the team from 10 to 235 in just 12 months? What start to break and when? What does Johnny believe are the 3 stages of startup growth? What have been Johnny’s learnings on what it take to acquire the very best talent?

3.) Why does Johnny believe that remote has so fundamentally changed the game? How does remote culture differ to physical culture? What advice does Johnny have for those shifting from physical to remote? Where does Johnny see so many make mistakes with the remote model?

4.) Why does Johnny believe fundraising is a game of leverage? How does Johnny advise founders to structure their raise? Should they shop their term sheets around? Should founders always be raising? How should they think through pre-emptive round? How does COVID change the world of fundraising?

5.) What does the world of virtual events look like in a post COVID world? What events will remain virtual? What will not? How does Hopin expand beyond purely events into the much wider “connection” space? How does that look both from M&A and product expansion?

Item’s Mentioned In Today’s Episode

Johnny’s Favourite Book: Nineteen Eighty-Four

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20VC: Reid Hoffman on Investing in Airbnb and Passing on Stripe, The Different Styles of Truly Great Leaders, How To Think Through Ownership and Price in Venture & How To Ensure Venture Partnerships Always Have Trust and a Learning Mindset

Reid Hoffman is a Silicon Valley stalwart in the modern technology world. On the investing side, he is a Partner @ Greylock, one of the leading venture firms of the last 2 decades with a portfolio including Facebook, Airbnb, Dropbox, Figma, Appdynamics and Okta to name a few. Reid has led investments in Airbnb, Convoy, Coda and Aurora to name a few. As an operator, Reid co-founded LinkedIn, the world’s largest professional network and before LinkedIn, Reid served as executive vice president at PayPal, where he was a founding board member. If that was not enough, Reid is the co-author of Blitzscaling and two New York Times best-selling books: The Start-up of You and The Alliance

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In Today’s Episode You Will Learn:

1.) How Reid made his way into the world of startups, came to found Linkedin and how that led to his joining Greylock?

2.) Does Reid consider himself an innate and natural leader today? How has his leadership style changed over time? What elements does Reid struggle with? How has he scaled to these leadership challenges? What does Reid believe are the different strands of leadership?

3.) How does Reid think about what separates the good from the great board members? What is the biggest danger for board members today? How do the very best founders manage their boards? How does Reid think about the weight of his words today?

4.) How does Reid think about the importance of ownership? How does Reid analyse price today? What was the story behind Greylock investing in Airbnb? What did Reid see so clearly and before anyone else saw it? What is the story with Stripe? Why did Reid turn Stripe down?

5.) How does Reid think about ensuring venture partnerships always have a learning mindset? What can be done deliberately to ensure this? Where do many people struggle here? How can partners develop trust within venture partnerships? Where does trust most often break down?

Item’s Mentioned In Today’s Episode

Reid’s Favourite Book: Thinking, Fast and Slow, Amusing Ourselves to Death: Public Discourse in the Age of Show Business

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20VC: Stitch Fix Founder Katrina Lake on Growth vs Profitability, Her Biggest Lessons From Working with Bill Gurley at Benchmark and The Importance of Mental Flexibility as a Leader

Katrina Lake is the Founder & CEO @ Stitch Fix, a multi-billion dollar public company, which has brought an entirely new model to retail apparel by combining data science, technology, and personal stylists, to create a unique
shopping experience tailored to the individual consumer. Prior to their IPO in 2017, Katrina raised just $42M in venture funding from some of the best in venture including Bill Gurley @ Benchmark and Steve Anderson @ Baseline. In just 6 years Katrina took the company from founding moment to $2BN IPO and was even cash flow positive after just 3 years. If that was not enough, Katrina is also on the board of both Grubhub and Glossier.

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In Today’s Episode You Will Learn:

1.) How Katrina made her way from being an associate at a venture firm to reshaping the world of fashion with Stitch Fix?

2.) On reflection, is Katrina happy that the business was forced to be so capital efficient so early? What did Katrina do to structure the business and their inventory management to presever cash? How does Katrina think about the balance between growth vs profitability?

3.) What have been some of Katrina’s biggest lessons from working with Bill Gurley? How does Katrina ensure not to overweight his opinion on the board? What have been Katrina’s biggest lessons on effective board management? How has being on the Grubhub and Glossier board changed the way she operates the Stitch Fix board?

4.) How does Katrina think about imposter syndrome and self-doubt today? How does she remedy it? How does Katrina ensure she remains on the front lines with customers despite being a public company CEO? What benefits are there for founders to stay in the trenches even when a large company?

5.) How does Katrina think on the importance for founders to have a vision today? Where do they need to be flexible? What are some dangers or pitfalls associated with “the vision”? How far are Stitch Fix along in cementing their vision?

Item’s Mentioned In Today’s Episode

Katrina’s Favourite Book: Between The World And Me

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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