Investing with the Best, Founder-Problem Fit, Pre-Mortems and Pre-Parades, and More — Roelof Botha

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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

Resources from the episode:

00:00 Start
01:06 Motivation in the margins of a Monday meeting notebook.
04:13 The Ulysses Pact.
06:39 Who was Roelof’s grandfather?
08:50 What is actuarial science, and why did Roelof choose it as his major?
13:16 Advice for young, aspiring entrepreneurs.
15:02 Don Valentine and his 2×2 matrix.
18:29 The founder-problem fit.
21:02 Succinctness in green.
23:17 Pre-mortems and pre-parades.
26:18 Why Sequoia is aptly named.
29:08 Keeping the team small can be such a big deal.
34:13 Book recommendations.
36:56 Finding balance in the relentless pursuit.
39:31 What it was like for Roelof to finally achieve his “ten to the ninth.”
40:37 The Sequoia Capital Fund.
42:38 How Sequoia’s fee structure maximizes value for clients and keeps the company strong.
51:19 Failure? It all depends on the scale of your ambition.
54:47 How Roelof guides founders who want to sell too soon and for too little.
01:00:01 Founders Roelof considers influential.
01:03:01 Growing up Afrikaner.
01:06:21 How Roelof set his sights on graduating school in first place.
01:08:06 Silkworms.
01:10:19 What Roelof’s TED Talk about a secondary interest would entail.
01:11:50 Rugby.
01:15:16 Roelof’s physical routines for staying in shape.
01:17:50 Crucible moments.
01:12:21 How Roelof wound up in the world of Silicon Valley startups.
01:28:16 Early days (and challenges) at PayPal.
01:32:18 Memorable failures and the lessons they imparted.
01:38:53 Coping with VC’s high rate of failure as someone who hates to lose.
01:43:44 What Peter Thiel taught Roelof about changing his mind.
01:50:51 How professionalization in VC has developed over time.
01:57:25 Roelof’s billboard.
01:59:57 Parting thoughts.

About Tim Ferriss:
Tim Ferriss is one of Fast Company’s “Most Innovative Business People” and an early-stage tech investor/advisor in Uber, Facebook, Twitter, Shopify, Duolingo, Alibaba, and 50+ other companies. He is also the author of five #1 New York Times and Wall Street Journal bestsellers: The 4-Hour Workweek, The 4-Hour Body, The 4-Hour Chef, Tools of Titans and Tribe of Mentors. The Observer and other media have named him “the Oprah of audio” due to the influence of his podcast, The Tim Ferriss Show, which has exceeded 700 million downloads and been selected for “Best of Apple Podcasts” three years running.

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