Jay Simons is a General Partner @ Bond Capital, with their $1.25Bn debut growth fund in 2019 they made their mark on the venture landscape and have since made investments in the likes of Revolut, Canva, NextDoor, IronClad and my favourite, On Running. As for Jay, prior to entering venture, he spent an incredible 12 years at Atlassian including 9 years as President, playing an instrumental role in their hyper-growth journey. Jay is also a board member with both Zapier and HubSpot, two of my favourite SaaS companies.
1.) How Jay made his way into the world of startups following a stint as a pianist in Asia and how that startup journey led to his joining Bond on the venture side?
2.) Why does Jay believe the best companies build economies around themselves? What does this look like in reality? When is the right time for the company to start building these economies? As an investor, what are the signs that a founder is proactively thinking about this? What are some of the biggest mistakes people make when building economies?
3.) Why does Jay believe Partner/Channel networks can be so powerful? When is the right time to build out channel partners? What is the training framework for these partners before they can represent your products in market? How do channel partners change the internal structure and resource allocation for a company? What mistakes do people make with these partners?
4.) How does Jay think about when is the right time to build a second product? What were the biggest takeaways from his time at Atlassian on building product suites? How does Jay determine when is the right time to move upmarket into enterprise? How does this change in a world of product-led growth?
5.) Why did Jay decide now was the right time to move into venture with Bond? For what reasons did Jay choose Bond, over all the other firms? What have been the biggest surprises for Jay from his first 100 days in venture? What have been the most challenging elements? How did Jay embrace the common challenge of building the conviction to write the first check?
Jay’s Favourite Book: The River Why
Jay’s Most Recent Investment: Sentry
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Tony Xu is the CEO and Co-founder of DoorDash, the company empowering merchants to grow their businesses by offering on-demand delivery, data-driven insights, and better in-store efficiency. Prior to their IPO in December 2020, Tony raised over $2.5Bn for DoorDash from some of the best including Sequoia, Coatue, Softbank, Kleiner Perkins and DST, to name a few. Before co-founding the business in 2013, Tony worked in Product at Square, led special projects for the CEO and CFO at eBay, and began his career at McKinsey and Company.
1.) How did Tony make his way into the world of startups and what was that founding a-ha moment for Tony with the founding of DoorDash? What were Tony's biggest takeaways from seeing his parents work ethic at such a young age? How did it impact his operating mentality?
2.) Leadership Style: What does great leadership mean to Tony today? In what ways has Tony's leadership style changed over the DoorDash journey? How does Tony assess his own persistence and grit? Through what framework does Tony decide what to delegate vs what to control?
3.) Decision-Making & Risk: How does Tony evaluate his decision-making process today? What does Tony mean when he says, "you have to reduce the scope"? How does Tony think about understanding the interplay of different variants in a decision? Through what framework does Tony assess risk today? How has Tony's approach to risk and decision-making changed over time?
4.) Talent Acquisition: What have been Tony's biggest lessons in acquiring the best talent? What has worked well in the past? In what ways have they not acquired talent they should have acquired? What type of talent worked in the early days? How has that changed? Through what framework does Tony decide between a stretch VP and a stretch too far?
5.) Culture & Diversity: How does Tony think through the breakpoints in the scaling of culture? At what points did Tony feel the DoorDash culture was not what he wanted it to be? How did he react to change it? Through what process has Tony measured the success of DoorDash's diversity efforts? Which initiatives have worked? Are there any that have not?
Tony’s Favourite Book: Score Takes Care Of Itself: My Philosophy of Leadership
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Eric Glyman is the Founder and CEO @ Ramp, the only corporate card and spend management platform designed to help you spend less. To date, Eric has raised over $390M for the company from some of the best including Thrive, Stripe, Founders Fund, Coatue and Box Group to name a few. Prior to changing the game of spend management, Eric founded Paribus, the price-tracking app that raised seed funding from General Catalyst and Greylock, which was acquired by Capital One in 2016.
1.) Entry to Startups: How Eric made his way into the world of startups with Paribus and how that journey and exit led to his founding the recently minted unicorn, Ramp?
2.) Decision-Making: How does Eric deal with moments of intense pressure as a leader? How does pressure impact Eric's decision-making quality? Through what framework does Eric evaluate his decision-making process today? Why does Eric believe operational velocity is so key to company success? How does Eric determine between being fast vs spending real time on something?
3.) Funding Rounds: Why does Eric believe that "funding rounds are science experiments"? What should founders look to prove or disprove with each round? Why does Eric believe "you should never take the highest price"? What are the downsides? How does it impact employee stock options? Does it change investor sentiment? How does it change customer acquisition through referrals?
4.) The Rise of Crossover Funds: What does Eric make of the rise of crossover funds? In what way does their value differ to the value provided by traditional VCs? How does their communication style differ compared to traditional VCs? Does Eric worry about the signalling risk of having crossover funds invested early? Does Eric believe they will change the landscape of venture?
5.) Board Management: How does Eric analyse his style of board management today? How has it changed over time? Where does Eric believe many founders go wrong when it comes to board management? How can boards be used to bring together the wider team and company? What documents does Eric always prepare for the board?
Eric’s Favourite Book: John Wooden: The Legendary UCLA Coach's Top 20 Quotes
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Byron Deeter is a Partner @ Bessemer Venture Partners and one of the world's leading investors in SaaS and cloud. To date, nineteen of Byron’s investments are valued above $1 billion, including ten IPOs and counting. Some of the incredible companies within Byron's portfolio include Twilio, ServiceTitan, Hashicorp, Canva, Intercom, DocuSign, SendGrid, the list goes on. Prior to joining the world of venture, Byron was an entrepreneur, raising a Series A from Bessemer and scaling the company to be one of the first global SaaS companies, reaching profitability and successfully selling to IBM.
1.) How Deven made his way into the world of venture and how that led to his becoming a Managing Director @ Insight, way back in 2000?
2.) The Market: Many people passed on Twilio, what did Byron see that others did not? Did Byron have concerns around the TAM? What made Byron feel comfortable they were not too early? How did Byron assess whether customers would churn off Twilio when they scaled to a size they could build their own infrastructure? How does Byron advise founders on this challenge today?
3.) The Team: What did Byron find some compelling about Jeff so early on? Jeff has been an incredible CEO from pre-seed to post-IPO, what has enabled Jeff specifically to scale with the company so successfully? What does Byron do to build the trust and rapport with founders that he does? What works? What does not work? How does that look today with Zoom?
4.) The Incumbents & Competition: Why does Byron believe the incumbent advantage is actually an incumbent disadvantage? What specifically has Byron found underwhelming about how the incumbents have tried to respond? In what tangible and specific way are startups better placed to win than incumbents? How does Byron advise founders to assess other startup competitors?
5.) The Funding: Twilio is Bessemer's single largest position ever, how does Byron know when is the right time to double down on an investment? What signals does he look for? Has this changed with the massive price inflation we have seen over the last year? How does Byron analyse the influx of new capital? Where is it good? What are the challenges to it?
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Nigel Morris is the Co-Founder and Managing Partner of QED Investors, one of the leading fintech-focused venture firms of the last decade with numerous unicorn investments, including Credit Karma, NuBank, Avant, SoFi, Klarna, GreenSky, and AvidXchange. Prior to QED, Nigel co-founded Capital One Financial Services in 1994. During his 10-year tenure, Nigel transitioned Capital One from an emerging start-up to an established public company valued at over $20 billion with over 15,000 employees. Finally, Nigel also sits on or has sat on the board of Nubank, Prosper, Zopa, Klarna, The Economist and London Business School to name a few.
1.) How Nigel made his way into the world of startups with Capital One back in 1994 and how that journey led to his founding one of the leading fintech investment firms in QED? What made Nigel want to develop QED from a family office into a large scaling venture firm?
2.) Where does Nigel's passion for mental health stem from? Why does Nigel believe VC and entrepreneurship is riddled with mental health problems? How does Nigel deal with his own self-doubt and insecurity? In what way does Nigel analyse his own relationship to money today? How has it changed over time? How has that relationship to money changed how he thinks about investing?
3.) What does Nigel believe it takes to be a great listener? How does Nigel think about asking the risk questions to move the founder to the right insight? How does Nigel create the conditions where the entrepreneur can be much more open? What questions would Nigel never ask? How does Nigel describe his style of board membership? How has it changed?
4.) How does Nigel think about the centrality of unit economics? What does Nigel look for in the way that the entrepreneur thinks through and analyses unit economics? When does Nigel believe you have tangible data to rely on to justify unit economics? What is the biggest challenge with unit economics? What should companies do when their competitors raise massive funding rounds?
5.) Why does Nigel believe that "bundling" is a canard? What does not work regarding how traditional "bundling" works? Why might it be different for the next generation of fintech providers to bundle different products? Why does Nigel believe lending is a much harder insertion point to start than current accounts? How does Nigel think about the right insertion point?
Nigel’s Favourite Book: Leadership and the New Science: Discovering Order in a Chaotic World
Nigel’s Most Recent Investment: Bitso
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José Neves is the Founder, CEO & Chairman @ Farfetch, the #1 destination for high-end fashion offering the world's Greatest Selection of Luxury. Now a public company, José has raised over $1.7Bn with Farfetch from some of the biggest names including Alibaba, Richemont, JD.com, Index Ventures and DST to name a few. Prior to Farfetch, José has been involved in the fashion start-up world since the mid-1990s when he launched footwear business SWEAR. José later founded SIX London, a fashion licensing and wholesale company selling to 600 retailers worldwide. Finally, in 2001 José opened the renowned boutique bstore, which won the British Fashion Award for Retailer of the Year in 2006.
1.) How José made his way from creating footwear brands in the days of the Spice Girls and cyberpunk to changing the fashion industry itself with Farfetch?
2.) Why does Zen Buddhism resonate with José in such a profound way? How does his adoption of it impact his style of leadership today? How does José deal with the loneliness of being a CEO? What does José mean when he says the most successful leaders, "know how to fall and how to get up"? How has José responded to his greatest failures?
3.) How does José think about decision-making today? What are the biggest misconceptions people have with regards to effective decision-making? Why is head vs heart the wrong way to think about decision-making? How does José adopt a sense of emotional detachment when making decisions? What works? What does not work?
4.) How does José evaluate his relationship to money today? In what ways has it changed over time? What does José believe that others do not believe when it comes to risk and risk management? How does José balance the demands of Wall St and investors with the knowledge that everything is inherently uncertain?
5.) Does José ever feel self-doubt? How does he manage it? In what ways does he advise earlier stage founders to grapple with their own self-doubt? How does José think about tying one's own identity to their company? Why is this so dangerous?
José’s Favourite Book: The Master and His Emissary: The Divided Brain and the Making of the Western World
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Deven Parekh is a Managing Director at Insight Partners, one of the leading investing franchises of the last 25 years with $30Bn+ in capital commitments, 400+ primary investments and over 200 portfolio acquisitions. Deven himself has made more than 90 investments since joining in 2000 including in the likes of Twitter, Alibaba, JD.com, Chargebee and Automattic (WordPress) to name a few. Deven also sits on the boards of Checkout.com, Calm, Saks.com, Optimizely and 1stDibs, again naming a few. If that was not enough, Deven also serves on the Board of the Carnegie Endowment for International Peace and the Board of the Tisch New York MS Research Center. As a result of his investing success, Deven has been named on Forbes Midas List 5 time and has been selected as a Top 100 Venture Capitalist by CB Insights 4 times.
1.) How Deven made his way into the world of venture and how that led to his becoming a Managing Director @ Insight, way back in 2000?
2.) How does Deven analyse the current fundraising mania? Does portfolio discipline and temporal diversification matter anymore? How has Deven and Insight seen the velocity of fundraises change over the years? What can Deven and Insight do to get compress their decision-making timeliness with the compression of fundraising timelines?
3.) How does Deven assess his relationship to price and price sensitivity? What have been some core lessons for Deven when comparing deals that they did which were "cheap" vs "expensive"? How do Insight think about required levels of ownership today? Does Deven believe it is possible to build ownership over time? What is required to do so? What are the challenges?
4.) How would Deven describe his style of board membership today? How has it changed over time? What advice does Deven have for younger board members scaling into the role? How does Deven think about his time allocation across the portfolio? What is the optimal? How does this differ from reality? Why do your winners never need you?
5.) How does Deven evaluate his own insecurities and self-doubt today? In what way have these changed over time? How does Deven analyse the "weight of his words" within Insight? How does Insight structure the internal decision-making process to ensure that everyone's voice is heard? In what ways can firms foster that security for young partners to feel they can bring anything to the table?
Deven's Favourite Book: What We Know About Climate Change (The MIT Press), Draft No. 4: On the Writing Process
Deven’s Most Recent Investment: TetraScience
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Ryan Smith is the Founder and Executive Chairman @ Qualtrics, the leader in customer experience and creator of the experience management (XM) category. Ryan has grown the company from a basement startup to one of the fastest-growing technology companies in the world, with 25 offices globally and more than 13,000 customers. Qualtrics raised $400M in funding from Accel, Sequoia, and Insight Venture Partners. Three days before the company was initially scheduled to go public, SAP announced its intent to acquire Qualtrics for $8B, which was the largest private enterprise software acquisition ever. In 2020, Qualtrics and SAP announced plans to take Qualtrics public as an independently operated company.
1.) How Ryan made his way into the world of startups having travelled the world and came to found Qualtrics in his basement over 21 years ago?
2.) How does Ryan think about his relationship to happiness and what it means to "be happy"? How does Ryan think about identity and founders aligning their identities to their company? How does Ryan think, if not careful, tech can eat you up? What does Ryan mean when he says he would rather be "opportunistic than an entrepreneur"?
3.) How does Ryan approach decision-making today? In what situations does Ryan think with his head vs his heart? How does Ryan approach risk today? How has his relationship to risk changed over time? What did the sale process to SAP look like? What was that decision-making process to sell to SAP for $8BN in cash vs IPO? What advice did his wife give him?
4.) How does Ryan evaluate his relationship to money today? How did it feel when Ryan sold Qualtrics to SAP for $8BN in cash? How does Ryan think about giving his children the right mentality and upbringing while being brought up in extreme wealth? What are the challenges of doing so?
5.) How does Ryan think about the weight of responsibility? Ryan and his brother Jared, did a lot very young, did Ryan feel the pressure of having to grow up faster than one usually would? How did that impact his mentality? How did Ryan's travels to Mexico and Japan change the person he is today?
Ryan’s Favourite Book: Alchemist: A Fable about Following Your Dream
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Marcos Galperin is the Founder and CEO @ MercadoLibre, one of LATAM's most successful companies of the last 2 decades. Today MercadoLibre's market cap exceeds $78Bn and the business includes everything from commerce to payments to logistics. Marcos is widely considered one of the great entrepreneurs of the last 2 decades scaling the business from its founding in 1999 while in business school at Stanford to today, a leader in LATAM operating across 18 countries and plans to end 2021 with over 32,000 employees.
1.) How Marcos made his way into the world of startups and came up with the idea for MercadoLibre while at Stanford Business School?
2.) Talent Acquisition and Retention: What have been some of Marcos' biggest lessons on what it takes to acquire A* talent? Does Marcos believe individuals can scale across company stages? When is a stretch hire a stretch too far? What has been the secret to Marcos having such a retained leadership team? What works? What does not?
3.) Risk and Decision-Making: How does Marcos evaluate his relationship to risk today? What frameworks does Marcos use to make effective decisions today? How does Marcos think about short term vs long term when it comes to resource allocation? How does Marcos prioritise where he makes decisions vs where he is willing to delegate?
4.) Funding and The Crash: How does Marcos reflect on his biggest lessons from going through 2 crashes with MercadoLibre? How did he change the way he ran the business post crash? How does Marcos advise founders today when big rounds are on offer, take the money or wait? What other components are important to consider in this decision?
Parker’s Favourite Book: Built To Last: Successful Habits of Visionary Companies
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David Tisch is the Founder and Managing Partner @ Box Group, one of the leading seed focused firms of the last decade with a portfolio including Airtable, Glossier, PillPack, Plaid and many more. Prior to founding Box, David was Managing Director of Techstars New York and was a prolific angel investor making early angel investments in the likes of Vine and Warby Parker to name a few.
1.) How David made his way into the world of tech and startups and came to change the state of seed funding in NYC with the founding of Box Group?
2.) Why does David believe that ownership requirements are "VCs projecting their problems on founders"? Why does David believe that ownership today fundamentally does not matter? How does David feel about his own relationship to price? Why is it important to be price aware across the portfolio, not on a per deal basis?
3.) What does David make of the rise of pre-emptive rounds? How does David advise portfolio founders who have them on the table? What other arguments does David use to founders contemplating taking seed rounds from multi-stage funds? How does David believe founders should assess their importance to the fund investing in them?
4.) How does David feel about his relationship to FOMO today? What have been some of his biggest misses in recent years? How have some of his biggest misses changed how he acts as an investor today? How have some of his biggest successes changed his investing lens? What changes did David and Box make to their decision-making process as a result?
5.) What does David believe are the biggest mistakes to turn down a company? Why is "too early" never a reason to turn down a company? How does David assess and think about market size today? Through what framework does David evaluate and assess competition today? What does David believe are some core concerns that are reasonable to turn down an opportunity?
David’s Most Recent Investment: Ramp
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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?
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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
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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?
Peter’s Favourite Book: The Chalice and the Blade, Crucial Conversations
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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?
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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
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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)
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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
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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
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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?
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Peter Fenton is a General Partner @ Benchmark, one of the great venture firms of the last 3 decades with a portfolio including the likes of SNAP, Twitter, eBay, New Relic, Stitchfix and many more. As for Peter, he has led deals, sits or has sat on the boards of Elastic, New Relic, Digits, Docker, Optimizely, Yelp and Zuora to name a few. Prior to Benchmark, Peter was a General Partner @ Accel Partners in San Francisco. As a result of his incredible track, Peter has been on the Forbes Midas List more times than I have done podcast episodes!
1.) How a round of golf led to Peter Fenton leading the New Relic Series A? What did the deal look like both in check size and valuation? What does Peter think that round would be in today's market?
2.) How does Peter create an environment of safety with entrepreneurs where they feel they can be vulnerable with him? How does Peter approach building relationships of trust in compressed fundraising timelines? In what way has Peter seen relationships go bad? What can been done to mitigate that and optimise the Founder <> VC relationship?
3.) How does Peter assess market timing when making investments today? What does Peter mean when he says, "you have to understand whether you are unlocking consumption"? What does unlocking consumption look like in reality? How does Peter think about positive or negative externalities that could impact the business?
4.) Does Peter agree with Bill Gurley that the biggest challenge today is the "oversupply of capital"? Where does the oversupply of capital become a real challenge? What does Peter advise growth-stage founders do to prevent this from damaging them? How does Peter think about capital efficiency in the companies where he is on the board?
5.) What were Peter's biggest lessons on what it takes to be a great board member from his 12 years at New Relic? How did he see his style of board membership change? On the founder side, how do the very best founders manage and navigate their board? What do most boards misunderstand or mismanage?
Peter's Favourite Book: Nonviolent Communication: A Language of Life
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David Velez is the Founder & CEO @ Nubank, one of the fastest growing digital banks in the world with operations in Brazil, Mexico, Argentina and Colombia. To fuel this growth, David has raised over $1.5BN for Nubank from some of the best in the business including Doug Leone @ Sequoia, Micky @ Ribbit, Thrive, Founders Fund, DST, Tiger and more. Before changing the world of LATAM finance, David was a Partner @ Sequoia where he was responsible for all LATAM investments. Prior to Sequoia, David was the co-founder of General Atlantic's South American investment programme.
1.) How David made his way into the world of startups through becoming a Partner @ Sequoia? How that led to his founding of Nubank? How his time at Sequoia impacted how he thought about building Nubank?
2.) How does David think about the relationship between growth and quality in company scaling? When scaling so fast, what are the first things to break? How does one know when is the right time to expand geographically? What is the right thought process to go through when determining how to know when is the right time to expand product lines?
3.) Looking at the market today, how does David for-see the future of digital banks? Will we seen increased consolidation over the coming years? How does David think through the verticalisation of neo-banks? What does the reduction in barriers to creating neo-banks really mean? How did Nubank scale to the scale it is today with $0 CACs?
4.) How has David seen his leadership style change with the growth of the company? Why does David feel it is wrong that the titles of Founder & CEO are so inextricably linked? What element of being a great founder are actually not good for CEOs to have? What elements of great CEOs are bad for founders to have? What has David found the hardest to scale in himself?
5.) How does David use "the responsibility framework" when making decisions today? What are David's thoughts on imposter syndrome within leaders today and how it can be harnessed for good? How does David approach head vs heart when it comes to decision-making today? Does David engage with regret minimisation as part of this?
David’s Favourite Book: One Hundred Years of Solitude
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Jeremy Levine is a Partner @ Bessemer Venture Partners, one of the leading venture firms of the last 2 decades with a portfolio including the likes of Pinterest, Shopify, LinkedIn, Yelp, Twilio and many more. As for Jeremy, five of his early-stage investments—LinkedIn, MindBody, Pinterest, Shopify and Yelp—grew into billion-dollar publicly traded companies. As a result of his incredible portfolio, he has featured on the Forbes Midas List for several years running.
1.) How Jeremy came to make one great decision and make one big mistake all in one rainy afternoon in Palo Alto? What was the story behind meeting the Pinterest team for the first time? Who was there? How did it go down?
2.) Market: How did Jeremy analyse the market at the time of the investment? What had been some core lessons Jeremy had learned on what made successful user-generated content plays? Where was Jeremy wrong in how he analysed the market? In what way is Jeremy surprised with how the market evolved? How does Jeremy analyse market timing today?
3.) Team: Jeremy has previously called Ben Silberman a "product visionary", what made Jeremy say this about Ben? How did Jeremy get over the concern of many VCs that Pinterest did not have a technical co-founder? Having seen Ben change over the last decade, what have been the biggest changes in Ben's leadership style over the last 10 years?
4.) Traction: When evaluating traction, where does Jeremy think so many investors make mistakes today? How should founders determine what is their core North Star metric? What gave Jeremy the confidence Pinterest could "cross the chasm"? How did the early Pinterest cohorts look both from usage and retention? What elements surprised and impressed?
5.) Pre + Post Mortem: What did Jeremy see as the likely reasons why Pinterest would not work? How did Jeremy think through what it took for UGC platforms to monetise at the time? Where was he wrong here? What did Jeremy see as the upside? What did he believe Pinterest could be if all the stars aligned?
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Jason Fried is the Founder & CEO @ Basecamp, the project management and team communication tool trusted by millions. Over an incredible 22 year journey, they have scaled to over 3.5M accounts and in 2020 they went back to being a multi-product company with the launch of their integrated email client & service, HEY. Jason is also the co-author of the widely acclaimed, ReWork and has also made several angel investments in the likes of Intercom, Gumroad and Hodinkee to name a few.
1.) How Jason Fried made his way into the world of startups and came to found one of the leading project management and team communications tools in the form of Basecamp?
2.) How does Jason analyse and evaluate his relationship to money? Why does Jason believe that he has this inherent downside protection when it comes to money? How does he structure his personal finances between stocks, cash, crypto etc etc? What have been some of Jason's biggest lessons when it comes to tying happiness to monetary levels?
3.) What does Jason mean when he says, "I have a fantasy of getting fired"? How does Jason think about knowing when is the right time to step away from the business? What would he like to do with that time? How does Jason feel about the challenge of tying his identity to his company? What are the dangers of doing so?
4.) How does Jason approach decision-making frameworks? What does Jason believe is the right way to respond when a decision does not go as planned? Where do many make mistakes here? Does Jason feel regret with decisions? How does Jason try and minimise regret?
5.) How does Jason feel about his biggest insecurities as a leader and CEO today? What are Jason's views on a CEO's ability to have self-doubt and be vulnerable? How have his views on this changed over the years? In what way has having kids impacted Jason's operating mindset? How has it changed what he values and appreciates?
Jason’s Favourite Book: In Praise of Shadows
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Simón Borrero is the Founder & CEO @ Rappi, the startup that has become a cornerstone of the Latin American mobile ecosystem, coined as "the next Everything Store of Latin America". To date, Simon has raised over $1.7Bn for the company from the likes of Sequoia Capital, a16z, Softbank, DST Global, Y Combinator and more. Prior to Rappi, Simon was the founder of multiple former companies including Imaginamos, a software studio he grew to over 300 people.
1.) How Simon made his way into the world of startups and came to found "the next Everything Store of Latin America" in Rappi?
2.) How does Simon think about the importance of zone density for a business like Rappi? What are the number of deliveries required for Rappi to make for the business to be breakeven? What is the key metric that determines the success of the business for Rappi today?
3.) How does Simon approach the balance of capital efficiency vs growth? How does one know when to pour fuel on the fire and go for growth? When is the right time to really focus on unit economics? Why does Simon believe expanding Rappi can be analogised to scaling a coffee shop?
4.) Rappi has now raised $1.7Bn from some of the best investors in the world, what does Simon believe Rappi did to enable them to be so successful fundraising? Was it a difficult shift for Simon to make moving from lean to capital abundance with the successful fundraises? What changed? How did Simon change as a leader? What is the story of Sequoia coming in?
5.) Customer acquisition: What were some of the biggest challenges when it came to initial customer acquisition for Rappi? What does Simon mean when he says "donuts for downloads"? What is the story there?
6.) Driver acquisition: In the UK and the US, driver acquisition is a big challenge, what did Rappi to do enable them to scale their driver supply so efficiently? What works? What does not work?
7.) Restaurant acquisition: What were the hardest elements of onboarding the first restaurants? How did Uber Eats entering the market actually make Rappi so much more efficient as a business and service?
Simon’s Favourite Book: The Prosperity Paradox
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Tony Fadell, often referred to as “the father of the iPod,” is currently Principal @ Future Shape, a global investment and advisory firm coaching engineers and scientists working on foundational deep technology. Prior to Future Shape, Tony was the Founder & CEO @ Nest Labs, the company was ultimately acquired by Google for a reported $3.2Bn. Before Nest, Tony spent an incredible 9 years at Apple Inc, where, as SVP of Apple’s iPod division, he led the team that created the first 18 generations of the iPod and the first three generations of the iPhone. Fun facts, Tony has filed more than 300 patents for his work and is also a prolific angel investor having invested in the likes of mmhmm and Nothing to name a few.
What was the moment that Tony realised that he wanted to be an entrepreneur?
“I got my first money when I was in third grade, because I had an egg route. We'd go get eggs from the farmer, and I'd load them in my wagon. Then my younger brother and I would go door to door around the neighborhood, and we'd sell eggs. And that was an every week or every other week situation. And I got money in my hands. And I was like, Oh my God, I can do whatever I want with that money – I don't have to ask anybody, I can just do it. And so that was the level of freedom that, especially when you're young, feels really cool. And then as I got older, I started to buy Atari video game cartridges for my 2600 (yes, I'm that old!), and that was really, really fun too.”
What was the biggest lesson that Tony learned from his father on sales and building trusted relationships?
"And he said, very clearly, Look, this is a relationship. If I make this person successful, he's gonna want to come back to me over, and over, and over. But if I sell him something and it doesn't sell, and he has to discount and he loses money, he's not going to come back. Even if I don't have the right product, I'll tell him where to go to get the right product they're looking for, or if they're picking the wrong one, I'll tell them, here's the right one, because my job is to make them successful. Because if they're successful, they'll come back to me year after year after year. And even when we have a down year, they're going to trust me, and they're going to come back."
How does Tony Fadell think about and assess his own relationship to money? How has it changed over the years?
"So my relationship to money now is that it's just a means to make change happen. And so literally, for me, I can just have a backpack, my computer, my phone, a couple of roller bags with my clothes. And that's enough to live life with my family. I don't need all this other stuff. COVID taught me that even further."
How does Tony determine true friendships vs transactional relationships?
“If it's not a reference – if it's not coming from somebody saying, Hey, you really need to meet this person – I take everything with a grain of salt. With anybody who comes to me cold, I think they probably want something. I try to find that out through the network, Do you know this person? What are they about?"
Why does Tony Fadell believe that founders have to be "coachable"?
“I think anybody who's trying to do something that the world has never seen before, or trying to work with people who are, they'd better be coachable. Because you're going to be so narrowly focused, you're going to be so heads down, you're going to be so on a mission, that sometimes you'll be blinded, and you'll need somebody to come from left field and go, Wait a second, dude, you're not thinking about this right."
What are the core signs that an individual is coachable?
2. Willingness to listen
What does Tony believe is the right way to deliver advice without fluff?
"First, it's about trust. You have to be able to have a trusted relationship with somebody. And second, there are different ways of delivering a message. You can deliver a message the first time in an iron-fist-in-a-velvet-glove kind of way. But sometimes the velvet glove is going to come off."
How do people make mistakes when giving advice?
“I'm in too many board meetings; we have over 200 investments. I've seen all kinds of different CEOs and different boards, where the investors don't want to feel like they're going to get a bad rep because the CEO is going to say something if they say something negative."
What does Tony Fadell advise founders when it comes to finding mentors?
“Usually, a really great mentor is going to be highly selective. They're going to be like, I don't want to work with you. They only have so much time for people who are actually coachable."
What are the characteristics of the best mentors?
"You're gonna have tough love with them, you're gonna say things that they don't want to hear, you're not going to be liked all the time. Hopefully, one day, you'll be respected if not liked. And that's what it means to be a mentor.”
How does Tony assess his own relationship to self-doubt?
“Everyone goes through imposter syndrome. Everyone does. We all have gone through it, I go through it. Because you know what, when you're doing stuff you've never done before, and you're changing the world, no one else has done it either. No one else has done it either. That means it's okay. And I always say, if you don't have butterflies in your stomach each day, you're either not paying attention, or you're not pushing hard enough and taking enough risk."
What are Tony's views on failure?
“Now, there's taking stupid risks versus risk mitigation and taking calculated risks. But you should always be living on the edge of pushing yourself because that's where the growth is, that's where the change is happening."
Does one learn more from success than from failure?
"How we do and change the world is through the same method. We go do, and then we fail, and then we learn from that, and then we do again.”
What does Tony mean when he says, "do, fail, learn."
“Look, it's do, fail, learn; do, fail, learn. There's no such thing as learn and then you're able to do. No, no, no. When you really learn in life is after you've tried to do it."
What is the right way for entrepreneurs to present their boldest of ambitions?
"Look at Elon now. If he was pitching what he's doing now 15 years ago, people would go, No way! A few people, like Jurvetson and others, said, Yeah, sure, okay, great. But very few people would get behind that huge boldness."
“So what they do is – and this is what I've had to do – they start and just pitch that simple ‘What's the next three to four years look like?’ and never tell anybody about the big picture. Because you scare most people off."
How do investors need to change how they think about ambition and upside?
5.) Why does Tony believe the first trillionaire will originate from the climate change space? Why is the majority of plastics recycling total BS today? Why does Tony believe we need to fundamentally transform our economies? How do funding markets need to change to fund this structural reshaping of society?