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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)

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“If you’re not a little discontent, I don’t think you’re alive.”

— Roelof Botha

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,, 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.

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Listen to the episode on Apple Podcasts, Spotify, Overcast, Podcast Addict, Pocket Casts, Castbox, Google Podcasts, Stitcher, Amazon Musicor on your favorite podcast platform. You can watch the interview on YouTube here.

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#618: 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

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You can also check out my interview with Mike Maples, Jr. from venture capital firm Floodgate, the man who taught me how to invest. 

#286: The Man Who Taught Me How to Invest — Mike Maples

What was your favorite quote or lesson from this episode? Please let me know in the comments.



  • Connect with Roelof Botha:

Sequoia | Twitter | Facebook | Instagram | LinkedIn


  • [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.


“If you’re not a little discontent, I don’t think you’re alive.”
— Roelof Botha

“There are so many problems to be solved. As long as there are problems, there are opportunities.”
— Roelof Botha

“At Sequoia, one of our cultural frameworks is maintaining tension between individualism and teamwork. It’s not either/or, it’s and. We want both. You need to stick your neck out, you need to do exceptional work, you need to be accountable for what you do. But you also need to be supportive as a team member, because that’s part of why we’ve been able to endure as a partnership.”
— Roelof Botha

“Dare to dream.”
— Roelof Botha

“Get over it. Go do it.”
— Roelof Botha


The Tim Ferriss Show is one of the most popular podcasts in the world with more than 800 million downloads. It has been selected for “Best of Apple Podcasts” three times, it is often the #1 interview podcast across all of Apple Podcasts, and it’s been ranked #1 out of 400,000+ podcasts on many occasions. To listen to any of the past episodes for free, check out this page.

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