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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