Roelof Botha — Investing with the Best, Ulysses Pacts, The Magic of Founder-Problem Fit, How to Use Pre-Mortems and Pre-Parades, Learning from Crucible Moments, and Daring to Dream | Brought to you by Wealthfront's high-yield savings account, Eight Sleep’s Pod Cover sleeping solution for dynamic cooling and heating, and Shopify global commerce platform providing tools to start, grow, market, and manage a retail business. More on all three below.Roelof Botha (@roelofbotha) has spent over 20 years building companies in Silicon Valley. He began within the walls of nascent PayPal, which he joined in March of 2000 while completing his MBA at Stanford. He became CFO in 2001 and led the company through both its IPO in early 2002 and subsequent acquisition by eBay. Roelof joined Sequoia Capital in 2003 to help founders build enduring businesses. He leads the US/Europe business as Managing Partner and serves as Senior Steward of the global Sequoia Partnership. Roelof is a director of 23andMe, Bird, Ethos, Evernote, Inside.com, Landis, mmhmm, MongoDB, Natera, Pendulum Therapeutics, Square, and Unity Technologies. Previously, he was a director of companies that include YouTube, Tumblr, Xoom, Assurex, and Eventbrite. He also led Sequoia’s investment in Instagram.Please enjoy!This episode is brought to you by Wealthfront! Wealthfront is an app that helps you save and invest your money. Right now, you can earn two percent APY—that’s the Annual Percentage Yield—with the Wealthfront Cash Account. That’s twenty times more interest than if you left your money in a savings account at the average bank, according to FDIC.gov. It takes just a few minutes to sign up, and then you’ll immediately start earning two-percent interest on your savings. And when you open an account today, you'll get an extra fifty dollar bonus with a deposit of five hundred dollars or more. Visit Wealthfront.com/Tim to get started.*This episode is also brought to you by Shopify! Shopify is one of my favorite platforms and one of my favorite companies. Shopify is a platform designed for anyone to sell anywhere, giving entrepreneurs the resources once reserved for big business. In no time flat, you can have a great looking online store that brings your ideas to life, and you can have the tools to manage your day-to-day and drive sales. No coding or design experience required.More than a store, Shopify grows with you, and they never stop innovating, providing more and more tools to make your business better and your life easier. Go to Shopify.com/tim for a FREE 14-day trial and get full access to Shopify’s entire suite of features.*This episode is also brought to you by Eight Sleep! Eight Sleep’s Pod Cover is the easiest and fastest way to sleep at the perfect temperature. It pairs dynamic cooling and heating with biometric tracking to offer the most advanced (and user-friendly) solution on the market. Simply add the Pod Cover to your current mattress and start sleeping as cool as 55°F or as hot as 110°F. It also splits your bed in half, so your partner can choose a totally different temperature.And now, my dear listeners—that’s you—can get $250 off the Pod Cover. Simply go to EightSleep.com/Tim or use code TIM at checkout. *[07:25] What’s the right way to say Roelof Botha?[08:14] 10 to the ninth: motivation in the margins of a Monday meeting notebook.[11:16] The Ulysses Pact.[13:38] Who was Roelof’s grandfather?[15:47] What is actuarial science, and why did Roelof choose it as his major?[20:05] Advice for young, aspiring entrepreneurs.[21:44] Don Valentine and his 2×2 matrix.[24:59] The founder-problem fit.[27:33] Don Valentine’s succinctness writ green.[29:46] Pre-mortems and pre-parades.[32:40] Why Sequoia is aptly named.[36:38] Keeping the team small can be such a big deal.[41:34] Book recommendations.[44:07] Finding balance in the relentless pursuit.[46:37] What it was like for Roelof to finally achieve his “10 to the ninth.”[47:40] The Sequoia Capital Fund.[49:40] How Sequoia’s fee structure maximizes value for clients and keeps the company strong.[58:15] Failure? It all depends on the scale of your ambition.[1:01:37] How Roelof guides founders who wants to sell too soon and for too little.[1:06:48] Founders Roelof considers influential.[1:09:39] Growing up Afrikaner.[1:12:43] How Roelof set his sights on graduating school in first place.[1:14:24] Silkworms.[1:16:40] What Roelof’s TED Talk about a secondary interest would entail.[1:18:05] Rugby.[1:21:26] Roelof’s physical routines for staying in shape.[1:24:17] Crucible moments.[1:27:18] How Roelof wound up in the world of Silicon Valley startups.[1:34:01] Early days (and challenges) at PayPal.[1:38:05] Memorable failures and the lessons they imparted.[1:44:32] Coping with VC’s high rate of failure as someone who hates to lose.[1:48:01] In case of doldrums, please present homemade pesto.[1:49:15] What Peter Thiel taught Roelof about changing his mind.[1:56:01] How professionalization in VC has developed over time.[2:02:25] Roelof’s billboard.[2:04:58] Parting thoughts.*For show notes and past guests on The Tim Ferriss Show, please visit tim.blog/podcast.For deals from sponsors of The Tim Ferriss Show, please visit tim.blog/podcast-sponsorsSign up for Tim’s email newsletter (5-Bullet Friday) at tim.blog/friday.For transcripts of episodes, go to tim.blog/transcripts.Discover Tim’s books: tim.blog/books.Follow Tim:Twitter: twitter.com/tferriss Instagram: instagram.com/timferrissYouTube: youtube.com/timferrissFacebook: facebook.com/timferriss LinkedIn: linkedin.com/in/timferrissPast guests on The Tim Ferriss Show include Jerry Seinfeld, Hugh Jackman, Dr. Jane Goodall, LeBron James, Kevin Hart, Doris Kearns Goodwin, Jamie Foxx, Matthew McConaughey, Esther Perel, Elizabeth Gilbert, Terry Crews, Sia, Yuval Noah Harari, Malcolm Gladwell, Madeleine Albright, Cheryl Strayed, Jim Collins, Mary Karr, Maria Popova, Sam Harris, Michael Phelps, Bob Iger, Edward Norton, Arnold Schwarzenegger, Neil Strauss, Ken Burns, Maria Sharapova, Marc Andreessen, Neil Gaiman, Neil de Grasse Tyson, Jocko Willink, Daniel Ek, Kelly Slater, Dr. Peter Attia, Seth Godin, Howard Marks, Dr. Brené Brown, Eric Schmidt, Michael Lewis, Joe Gebbia, Michael Pollan, Dr. Jordan Peterson, Vince Vaughn, Brian Koppelman, Ramit Sethi, Dax Shepard, Tony Robbins, Jim Dethmer, Dan Harris, Ray Dalio, Naval Ravikant, Vitalik Buterin, Elizabeth Lesser, Amanda Palmer, Katie Haun, Sir Richard Branson, Chuck Palahniuk, Arianna Huffington, Reid Hoffman, Bill Burr, Whitney Cummings, Rick Rubin, Dr. Vivek Murthy, Darren Aronofsky, and many more.See Privacy Policy at https://art19.com/privacy and California Privacy Notice at https://art19.com/privacy#do-not-sell-my-info.

Roelof Botha, one of Silicon Valley's most highly respected investors and a former CFO at PayPal, shares insights on his journey from South Africa to Sequoia Capital. He discusses the firm's unique culture, emphasizing risk-taking and learning from failures. Botha reveals how team dynamics and overcoming imposter syndrome shape success in venture capital. He also explores the game-changing role of AI in investment strategies and highlights the importance of founder vision in navigating today's startup landscape.

My guest today is Roelof Botha, a partner at one of the world’s oldest and most successful venture firms, Sequoia Capital. A few days ago before I sat down with Roelof, he announced Sequoia’s boldest innovation since the firm was founded by Don Valentine in the early 1970s. Going forward, the firm will break from the traditional VC mould of fund cycles and instead restructure around a single, open-ended, permanent structure named The Sequoia Fund. In our conversation, we first discuss the details of this change from all different angles and then dive into Roelof’s career. We talk about what’s changed over the past twenty years, his days at PayPal, what legendary investors he’s worked with have had in common, and what he’s learned from being involved in businesses like Square, YouTube, and Unity. Please enjoy this great conversation with Roelof Botha. For the full show notes, transcript, and links to the best content to learn more, check out the episode page here. ------ Invest Like the Best is a property of Colossus, LLC. For more episodes of Invest Like the Best, visit joincolossus.com/episodes.  Past guests include Tobi Lutke, Kevin Systrom, Mike Krieger, John Collison, Kat Cole, Marc Andreessen, Matthew Ball, Bill Gurley, Anu Hariharan, Ben Thompson, and many more. Stay up to date on all our podcasts by signing up to Colossus Weekly, our quick dive every Sunday highlighting the top business and investing concepts from our podcasts and the best of what we read that week. Sign up here. Follow us on Twitter: @patrick_oshag | @JoinColossus Show Notes[00:02:53] - [First question] - What led Sequoia to change their structure[00:05:53] - Parallels between their approach and the problem Square set out to solve[00:07:36] - The mechanics of the new fund and how it’ll affect their clients[00:13:11] - What the future looks like and how public securities could be a dominant force[00:15:02] - Benefits and value-unlocks that the new fund offers that weren’t available before[00:16:55] - Comparing their structure to the current crossover funds we see emerging[00:18:21] - What alignment looks like in this new structure for LPs[00:22:02] - Cost of capital, interest rates, and their impacts on rates of return[00:25:39] - Changes in the industry and founders that he’s noticed[00:28:56] - What matters to him when meeting with young companies for the first time[00:31:47] - The importance placed on value creation over value capture in the early days[00:33:09] - Things that would dissuade him from partnering with a company[00:34:18] - What the growth and leadership at Square has taught him over the years[00:35:44] - Things he’s most excited about for payments looking forward[00:37:34] - How often a company lowering friction with technology appeals to him [00:38:38] - Thoughts on Unity and its role in the growing trend of the metaverse[00:40:28] - Why the open and decentralized nature of the future is so beneficial[00:42:05] - Lessons learned about content and internet from working with YouTube[00:44:08] - The landscape of developers today and MongoDB's role in it [00:49:26] - Learning to identify and hunt for crucible moments[00:50:50] - Curiosity is the key ingredient of a great investor[00:52:05] - What makes for a fantastic investment memo[00:53:20] - The most memorable investment memo he’s ever read[00:54:07] - Honing his leadership as his role has changed at Sequoia these past years[00:55:51] - Thoughts on Sequoia’s brand and the scope of his ambition[00:58:05] - What he’s most curious about in the world today[00:58:46] - What technology wants most from people today[01:01:13] - The difference between an accountant and an actuary's mindset and when each one is appropriate to inhabit[01:02:38] - Differences between talent and genius [01:04:12] - Closing principals about business building he finds important to consider[01:06:17] - The kindest thing anyone has ever done for him

Roleof Botha is a Partner @ Sequoia Capital, one of the world’s leading venture firms with a portfolio including the likes of Airbnb, Instacart, Stripe, UiPath, Zoom, the list goes on. As for Roelof, at Sequoia he has led rounds into the likes of YouTube, Instagram, Eventbrite, Square, MongoDB, 23andMe and Unity Technologies to name a few. Before joining the world of venture, Roelof was the CFO @ Paypal playing a key role in their hyper-growth from 2000-2003. In Today’s Episode You Will Learn: 1.) How did Roelof go from actuary in South Africa to CFO @ Paypal? What were his biggest lessons from seeing Paypal burn $10M per month? How did Paypal lead to his joining Sequoia as a Partner? 2.) Market Evaluation: Does Roelof agree that the market is crazy today? How does today compare to prior vintages? How does Roelof assess the compression of fundraising timelines? With compressed timelines, how does he build relationships of trust with founders? 3.) Founder Evaluation: What were Roelof's lessons on founder assessment from Don Valentine? What matrix did Don teach Roelof to assess founders on? How does Roelof feel about the rise of competitive rounds? When should founders take them vs remain heads down on execution? 4.) Investment Mentality: How did Roelof prevent becoming too confident when early investments went well? How does Roelof prevent relying on past failures as a reason for turning down opportunities today? What can investors do to retain a very flexible mind? Why does Roelof believe you are only as good as your next investment? 5.) Sequoia's Edge: How does Roloef think about what it takes for Sequoia to retain it's edge at the top? How does Roloef measure the success of the Sequoia scout program? How did they structure it? How has the structure changed? What do they plan to do moving forward? 6.) Board Membership: How would Roloef evaluate his current style of board membership? How has that style changed over time? What elements did he find challenging? What advice would Roelof give to new board members adopting their first board seats? Items Mentioned In Today’s Show: Roelof’s Favourite Book: Man's Search For Meaning Roelof’s Most Recent Investment: mmhmm As always you can follow Harry and The Twenty Minute VC on Twitter here! Likewise, you can follow Harry on Instagram here for mojito madness and all things 20VC.

Welcome to another episode of The Tim Ferriss Show, where it is my job to deconstruct world-class performers to tease out the routines, habits, et cetera that you can apply to your own life. This is a special inbetweenisode, which serves as a recap of the episodes from last month. It features a short clip from each conversation in one place so you can easily jump around to get a feel for the episode and guest.Based on your feedback, this format has been tweaked and improved since the first recap episode. For instance, @hypersundays on Twitter suggested that the bios for each guest can slow the momentum, so we moved all the bios to the end. See it as a teaser. Something to whet your appetite. If you like what you hear, you can of course find the full episodes at tim.blog/podcast. Please enjoy! ***This episode is brought to you by 5-Bullet Friday, my very own email newsletter that every Friday features five bullet points highlighting cool things I’ve found that week, including apps, books, documentaries, gadgets, albums, articles, TV shows, new hacks or tricks, and—of course—all sorts of weird stuff I’ve dug up from around the world.It’s free, it’s always going to be free, and you can subscribe now at tim.blog/friday.***Timestamps:Roelof Botha: 00:03:17Will MacAskill: 00:08:46Russ Roberts: 00:14:02Andrew Weil: 00:23:47Tim Q&A: 00:27:54Full episode titles:Roelof Botha — Investing with the Best, Ulysses Pacts, The Magic of Founder-Problem Fit, How to Use Pre-Mortems and Pre-Parades, Learning from Crucible Moments, and Daring to Dream (#618)Will MacAskill of Effective Altruism Fame — The Value of Longtermism, Tools for Beating Stress and Overwhelm, AI Scenarios, High-Impact Books, and How to Save the World and Be an Agent of Change (#612)Russ Roberts on Lessons from F.A. Hayek and Nassim Taleb, Decision-Making Insights from Charles Darwin, The Dangers of Scientism, Wild Problems in Life and the Decisions That Define Us, Learnings from the Talmud, The Role of Prayer, and The Journey to Transcendence (#613)Dr. Andrew Weil — The 4-7-8 Breath Method, Cannabis, The Uses of Coca Leaf, Rehabilitating Demonized Plants, Kava for Anxiety, Lessons from Wade Davis, The Psychedelic Renaissance, How to Emerge from Depression, Tales from 50+ Visits to Japan, Matcha Benefits, and More (#615)Q&A with Tim on Wealth and Money, Book Recommendations, Advice on Taking Advice, C.S. Lewis, Relationships, Behavior Change and Self-Awareness, Why We Are All (Mostly) Making It Up as We Go, and Much More (#614)*For show notes and past guests on The Tim Ferriss Show, please visit tim.blog/podcast.For deals from sponsors of The Tim Ferriss Show, please visit tim.blog/podcast-sponsorsSign up for Tim’s email newsletter (5-Bullet Friday) at tim.blog/friday.For transcripts of episodes, go to tim.blog/transcripts.Discover Tim’s books: tim.blog/books.Follow Tim:Twitter: twitter.com/tferriss Instagram: instagram.com/timferrissYouTube: youtube.com/timferrissFacebook: facebook.com/timferriss LinkedIn: linkedin.com/in/timferrissPast guests on The Tim Ferriss Show include Jerry Seinfeld, Hugh Jackman, Dr. Jane Goodall, LeBron James, Kevin Hart, Doris Kearns Goodwin, Jamie Foxx, Matthew McConaughey, Esther Perel, Elizabeth Gilbert, Terry Crews, Sia, Yuval Noah Harari, Malcolm Gladwell, Madeleine Albright, Cheryl Strayed, Jim Collins, Mary Karr, Maria Popova, Sam Harris, Michael Phelps, Bob Iger, Edward Norton, Arnold Schwarzenegger, Neil Strauss, Ken Burns, Maria Sharapova, Marc Andreessen, Neil Gaiman, Neil de Grasse Tyson, Jocko Willink, Daniel Ek, Kelly Slater, Dr. Peter Attia, Seth Godin, Howard Marks, Dr. Brené Brown, Eric Schmidt, Michael Lewis, Joe Gebbia, Michael Pollan, Dr. Jordan Peterson, Vince Vaughn, Brian Koppelman, Ramit Sethi, Dax Shepard, Tony Robbins, Jim Dethmer, Dan Harris, Ray Dalio, Naval Ravikant, Vitalik Buterin, Elizabeth Lesser, Amanda Palmer, Katie Haun, Sir Richard Branson, Chuck Palahniuk, Arianna Huffington, Reid Hoffman, Bill Burr, Whitney Cummings, Rick Rubin, Dr. Vivek Murthy, Darren Aronofsky, Margaret Atwood, Mark Zuckerberg, Peter Thiel, Dr. Gabor Maté, Anne Lamott, Sarah Silverman, Dr. Andrew Huberman, and many more.See Privacy Policy at https://art19.com/privacy and California Privacy Notice at https://art19.com/privacy#do-not-sell-my-info.