Dare to Dream: Embracing Risks and Opportunities

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-sponsors

Sign 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/timferriss

YouTube: youtube.com/timferriss

Facebook: facebook.com/timferriss 

LinkedIn: linkedin.com/in/timferriss

Past 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.