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.
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
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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.
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
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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.
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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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.
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 foresee 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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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".
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 starts to break and when? What does Johnny believe are the 3 stages of startup growth? What have been Johnny's learnings on what it takes to acquire the very best talent?
3.) Why does Johnny believe that remote has so fundamentally changed the game? How does remote culture differ from 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 a 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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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.
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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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.
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 its inventory management to preserve 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
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