Chris Fralic is a Board Partner @ First Round Capital, one of the leading seed-stage venture firms of the last decade with investments in the likes of Uber, Square, Notion, Warby Parker and more. As for Chris, he has led deals in Roblox, Ring.com, HotelTonight, Rec Room and many more incredible companies. Prior to the world of venture, Chris was VP of Business Development at social bookmarking and tagging company del.icio.us through the Yahoo! acquisition. He was also one of the early employees at Half.com and after the eBay, acquisition spent six years with eBay in a variety of business development, media and entertainment roles.
1.) How did Chris come to first meet Dave and the team at Roblox? Where was the first meeting? Who was in attendance? How did Chris feel post that first meeting with the team?
2.) Turning the company down: Why did First Round turn down Roblox on first look? How does Chris assess his own relationship to price? Through what mechanism does he determine whether to pay up or not? How does Chris retain relationships with founders when saying no? Does Chris believe you can buy up ownership post first check today, with the capital proliferate we have?
3.) What does Chris mean when he discusses the lessons from First Round's portfolio when it comes to "slow bake vs fast bake"? How did the First Round partnership analyse the Uber, Square, Roblox portfolio at the time? Through what framework does Chris think about reserves management given the challenge of "slow bake companies"? How does he address it today?
4.) What does Chris mean when he discusses the hype to substance ratio? Why is it more important than ever today? What does this mean for startups? How can startups with a low hype to substance ratio raise funds at good prices? What advice does Chris have for them? How does Chris think about the importance of firm and individual brand in venture today?
5.) How has Chris seen Dave evolve as a leader and CEO over time? What caused the changes in his leadership style? What moments stand out as the most challenging moments to Chris in the scaling of Roblox? Who does Chris believe are the behind the scenes rockstars that made Roblox possible?
Parker Conrad is the Founder and CEO @ Rippling, the employee management platform allowing you to manage your employees' payroll, benefits, devices and more—in one place. To date, Parker has raised over $197M for Rippling from the likes of Founders Fund, Kleiner Perkins, Initialized, Bedrock, Greenoaks and Coatue. Prior to founding Rippling, Parker was the Co-Founder and CEO @ Zenefits and if that was not enough, Parker is also a prominent angel having invested in the likes of Census, Pulley and then also AgentSync and TrueNorth, alongside 20VC Fund.
1.) How did Parker make his way into the world of technology and startups? What was the founding a-ha moment for Parker with Rippling? How did his journey with Zenefits change or alter his leadership style today with Rippling?
2.) Why does Parker believe that the conventional advice of focus, focus, focus is BS? What does Parker mean when he states, "The Compound Startup"? How does the approach of the compound startup differ from traditional approaches of product and company building? What are the core benefits of using the compound startup approach?
3.) How does Parker think about providing sufficient product quality with an increasing breadth of product offering, entailed within a compound startup? In what way does pricing differ when comparing compound startups to traditional startups? How can compound startups optimise their pricing on a bundle basis? What has Slack and Microsoft taught us about this?
4.) Why does Parker disagree with the conventional analogy of the VC <> founder relationship being a marriage? Why does Parker refer to it more as a "General Contractor" relationship for a house? What can founders do to sufficiently protect themselves from overarching VCs? What can VCs do to be the very best partners to the founders they work with?
5.) How does Parker evaluate his relationship to money today? How has it changed over time? What does Parker know now that he wishes he had known at the start of his founding of Rippling? What have been Parker's biggest lessons on talent acquisition? Why did Parker decide to bring on a COO when he did? How has it changed his role?
Parker’s Favourite Book: Matilda by Roald Dahl
Peter Reinhardt is the Founder and CEO @ Segment, the leading customer data platform with over 20,000 companies using Segment to collect, clean, and control their customer data. Prior to their $3.2BN acquisition by Twilio in 2020, Peter raised over $283M for Segment from Accel, Thrive, Meritech, GV, General Catalyst and Kleiner Perkins to name a few. Peter is also an active angel investor having made investments in the likes of Retool, Newfront, Pilot and more.
1.) How Peter made his way into the world of startups and how he came to found a company, Segment, by actively trying to prove to his co-founder that it would not work? Why does Peter believe the Airbnb story is the most destructive myth for founders to follow?
2.) Learning: How does Peter think about learning frameworks for new topics? How does he construct his? How does Peter use data within this learning process to increase his rate of learning? Where do the majority of people go wrong in constructing their framework for learning?
3.) Listening and Debate: What does Peter believe is required to be "a good listener"? What questions do the best listeners ask? What tone do they use to ask these questions? How does Peter create an environment of safety internally where people feel they can debate? How does one balance between debate and thinking vs putting those thoughts into action?
4.) Problem-solving: How does Peter breakdown problems into their component parts? Through what mechanism does he determine what to prioritise first? How would Peter describe his decision-making process? How does he determine between head vs heart in decisions? In what way does Peter use data to further inform the decisions he makes?
5.) How would Peter describe his management style today? Has it changed over time? In what way has working with a coach changed the way Peter thinks about leadership? What elements do they focus on? How often does he see his coach? What have been some of his biggest takeaways?
David Sze is a General Partner @ Greylock where he has led some of the firms most notable investments including Facebook, LinkedIn and Pandora. David has consistently been at the forefront of innovation in the consumer landscape leading to his investments in Discord, Roblox, Medium and more. Prior to Greylock, David was SVP of Product Strategy at one of the first search pioneers, Excite and then Excite@Home. Before Excite, he was in interactive entertainment — in product marketing at Electronic Arts and development at Crystal Dynamics. As a result of his incredible investing track record, David has been frequently named to the Forbes Midas List.
1.) How David made his way into the world of venture and came to lead consumer investing at Greylock with investments in Facebook, Linkedin, Roblox and Discord?
2.) How did David's investments in Facebook and Linkedin challenge Greylock's investment strategy at the time? Paying $500M for Facebook, how does David reflect on his own relationship to price and price sensitivity? How does David evaluate the rise of pre-emptive rounds today? Is David concerned by the excess supply of capital in the market today?
3.) Having worked with Mark @ Facebook, Reid @ Linkedin, David @ Roblox, what are the commonalities of these incredible founders? What does David do to build relationships of trust and vulnerability with founders? How does David do this in the compressed fundraising timelines we have today?
4.) The Partnership: What does David believe Greylock have done well in terms of creating an environment of safety within the partnership where people can really challenge each other? What works? What does not? For younger VCs, what is the difference between those that succeed and those that do not? What is David's biggest advice to those in the earlier years of their VC career?
5.) The Board: How does David evaluate his own style of board membership today? How has it changed over the years? What does David believe are his biggest strengths and his biggest weaknesses as a board member? What advice does David give to younger VCs assuming their first board roles?
Wade Foster is the Co-Founder & CEO @ Zapier, the company that moves info between your web apps automatically, so you can focus on your most important work. Post YC in 2012, Wade raised $1.4M for the company from Bessemer and Threshold but since that round, he scaled the company to $140M in ARR and a $5Bn valuation with Sequoia and Steadfast buying out some early investors earlier this year.
1.) How Wade made his way from email marketing manager to founding one of YC's most successful alum in the form of Zapier? Does Wade agree with the "fake it till you make it theory"? How does Wade advise grads on starting a company vs joining a startup vs joining an incumbent?
2.) Remote Work: Zapier has been remote since 2012, what do Zapier do very specifically that Waade believes has enabled them to be so successful remote? What did not work? What were some of the biggest challenges of scaling the team remotely? In terms of tooling, what specific tools do Wade and Zapier use to make the org as transparent as possible?
3.) In the scaling journey, what have been the most significant breakpoints in the org scaling? How has Eade scaled his style of leadership? What has been the most challenging element to scale? How does Wade structure internal meetings? Who is invited to what? What materials are shared? How are the meetings structured?
4.) Why did Wade decide not to take the venture path and scale the company from revenues? What does Wade believe so many founders misunderstand when it comes to fundraising? What does Wade believe they gained from the bootstrapped approach? Why did Wade still maintain relationships with VCs? How did he choose those he wanted to stay in touch with?
5.) How does Wade feel about his relationship to money? What does Wade think about the rise of secondaries? In what framework does Wade advise founders who have the chance to take secondaries? What is the right amount to take off the table? How does one communicate this?
Wade’s Favourite Book: Harry Potter
Nikolay Storonsky is the Founder & CEO @ Revolut, one of the world's largest and fastest-growing fintechs offering everything from personal to business banking, providing a better way to manage your money. To date, Nikolay has raised over $905M with Revolut from Ribbit, Index, DST, Balderton and Bond Capital to name a few. Nikolay has scaled Revolut to over 2,000 employees across 4 continents. Before changing the world of neo-banking, Nikolay spent 8 years as a derivatives trader at both Lehman Brothers and Credit Suisse in London.
1.) How Nikolay made his way into the world of startups from derivatives trading and how that led to his changing the world of fintech with Revolut?
2.) How would Nikolay describe his style of leadership today? How did his time in banking impact his operating style? What elements has Nikolay found the hardest to scale into as a leader? How does Nikolay assess his relationship to ambition? What drives him today? How does Nikolay deal with self-doubt and vulnerability in leadership?
3.) Why does Nikolay feel the most important thing in a company is the speed of product shipment? From a product perspective, how does Nikolay determine what to do next vs what to do later? What does that prioritisation process look like? Has it changed over time?
4.) How does Nikolay think about gepgraphic expansion today? Given Monzo's challenges in the US, why did Revolut decide the US remained a good strategy? What does it take to launch and scale a new country? How does Nikolay think about the relationship between growth and profitability? What companies does Nikolay admire most for their international scaling?
Nikolay’s Favourite Book: Principles by Ray Dalio (PDF)
Guillaume Pousaz is the Founder and CEO of Checkout.com, one of the world's leading global payments solutions providers and one of Europe's most valuable private companies. Guillaume founded Checkout.com in 2012 and bootstrapped the business until its record-breaking $230M Series A led by Insight and DST in 2019. Since, Guillaume has raised a further $600M for Checkout from the likes of Coatue, Tiger, Blossom, GIC and Greenoaks. As part of this process, Guillaume has scaled the team to over 900 people around the world and Checkout as one of the category leaders in payments with a reported $15Bn valuation.
1.) How Guillaume made his way into the world of payments following a travelling experience? How that experience led to his founding the now $12Bn, Checkout.com?
2.) Why did Guillaume wait 7 years into the running of the business before raising a massive $230M Series A? Why was then the right time? Was it a difficult mental transition to move from lean, capital efficiency to raising $230M? Why have Checkout never spent a single dollar on marketing? Is it true, Checkout has never spent a single dollar you have raised?
3.) What does Guillaume mean when he says he "has 3 roadmaps for life"? How does he structure his planning for the next 2,5 and 10 years? How does Guillaume think on his own identity and how it is tied to Checkout, the company? How does Guillaume advise founders in terms of tying their identity to their company?
4.) Why does Guillaume believe that becoming a father made him a better CEO? How did it impact his operating style? How does Guillaume analogise the role of the CEO to the profession of being a sailor? How does Guillaume think through his relationship to money today? How has it changed over time? How does he think about ensuring it does not impact his children?
5.) In what way does Guillaume structure his decision-making process today? What does Guillaume believe it is about the velocity of decisions that determine the quality of the leader? What topics does Guillaume struggle to make fast decisions on? What advice does Guillaume give to founders in situations when you just do not know what to do?
Guillaume’s Favourite Book: Dune by Frank Herbert
Olivier Pomel is the Founder & CEO @ Datadog, the company building the next generation of tools for DevOps teams. Prior to their incredibly successful IPO in 2019, Olivier raised over $147M for the company from Index, ICONIQ, Meritech, IA Ventures, Amplify and OpenView, to name a few. Prior to founding Datadog and changing the world of devops, Olivier was a VP with Wireless Generation for 8 years leading an engineering team of close to 100 of the best developers in NYC.
1.) How Olivier made his way into the world of startups and what was the a-ha founding moment for his creating of Datadog, changing the world of devops?
2.) Why does Olivier believe that "short term failure is a source of long term success?" Why did both seed and Series A investors not get Datadog? What would Olivier have done differently if fundraising again? What do investors misunderstand today when investing in big markets looking for the "entry wedge"?
3.) What has been Olivier's biggest learnings on how to run Datadog during a pandemic? What attributes does Olivier look for when hiring senior leaders? Why does Olivier believe the CEO has to be the "equaliser in chief"? What does that mean in practice? How can leaders creat eenvironments of safety where their team can approach them with anything?
4.) What have been the biggest challenges in moving from a single product to a multi-product company? How does one know when is the right time to add additional products? What is Olivier's decision-making process to determine which products to build next?
5.) How does Olivier assess his relationship to money today? How has it changed over time? In what ways has becoming a father impacted Olivier's operating mindset? What 3 traits would Olivier most like his children to adopt?
Olivier’s Favourite Book: Kurt Vonnegut
Linda Lian is the Co-Founder and CEO @ CommonRoom, the place where your organization and your community come together. To date, Linda has raised over $50M with CommonRoom from the likes of Danny Rimer @ Index Ventures, Sarah Guo @ Greylock, Dylan Field @ Figma, Dick Costolo and of course 20VC Fund. Prior to changing the world of community though, Linda spent close to 3 years at Amazon as a Senior Product Manager on AWS and Alexa. Before Amazon, Lida was on the other side of the table in venture as an associate at Madrona.
1.) How Linda made her way into the world of startups and came to start on the venture side with Madrona? How did Linda's time at Amazon shape her thinking around founding CommonRoom? What were Linda's biggest lessons from her time at Amazon and then also being mentored by Jeff Weiner
2.) How does Linda describe her leadership style today? What are the biggest lessons Linda has learned in terms of how to speak with compassion but also directness and clarity? Why is Linda not a fan of "the shit sandwich"? What is the most effective way to give feedback?
3.) What did Linda decide to only hire senior and experienced individuals with CommonRoom? What are the benefits of doing so? What are the downsides? How does Linda approach hiring such senior talent? What works? How is this also challenging? What does Linda mean by "the long poach"?
4.) How does Linda approach delegation today? What framework does Linda use to determine what to do vs what to delegate? How does Linda approach head vs heart when it comes to decision-making? What does it take for Linda to change her mind? What is required?
5.) What does Linda believe are the biggest misnomers around the search for product market fit? Why did Linda deliberately choose to stay in stealth despite raising over $50M from some of the world's best investors? How did that impact their ability on both product and customer discovery?