Navigating Investment Failures and Emotional Resilience

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.

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[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.

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