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)

“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, 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!

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

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The transcript of this episode can be found here. Transcripts of all episodes can be found here.

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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. 

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

SCROLL BELOW FOR LINKS AND SHOW NOTES…

SELECTED LINKS FROM THE EPISODE

• Connect with Roelof Botha:

Sequoia | Twitter | Facebook | Instagram | LinkedIn

• Singing Afrikaans Around the Campfire | Gene Braaksma
• Sequoia’s Roelof Botha Has a Plan to Remake the VC Industry | Protocol
• Austin Powers in Goldmember | Prime Video
• How to Master Your Goals with the Ulysses Pact | Trello Blog
• The Odyssey by Homer | Amazon
• Tame Your Work, Organize Your Life | Evernote
• Actuarial Science | Investopedia
• University of Cape Town
• The End of South African Apartheid | ThoughtCo.
• The Confidential YouTube Investment Memo by Sequoia | 50Folds
• History of PayPal: Timeline and Facts | TheStreet
• Global Management Consulting | McKinsey & Company
• Roelof Botha: The Lessons Learned from Nearly 20 Years at Sequoia | 20VC
• Cisco Systems | History of Computer Communications
• Squaring The Circle That Is Square | PYMNTS
• Problem-Founder Fit: How Having a Felony Makes Me a Better Founder by Harley Blakeman | Denver Startup Week
• A Global Leader in cfDNA Testing | Natera
• The Death of a Venture Fund | Blakeir
• NASDAQ | Investopedia
• Man’s Search for Meaning by Viktor Frankl | Amazon
• The Best American Science And Nature Writing 2022 | Amazon
• Christmas Is, Above All, about Hope | Post Crescent
• Patient Capital for Building Enduring Companies | The Sequoia Capital Fund
• How Venture Capital Works | Harvard Business Review
• The Ford Foundation in Apartheid South Africa — Soft Solutions to Hard Problems | Alliance Magazine
• Esther Perel — Tactics for Relationships in Quarantine | The Tim Ferriss Show #418
• Afrikaners in South Africa: Overview and History | ThoughtCo.
• Afrikaans-English Geometry Flashcards | Quizlet
• Silkworms Spin Cocoons That Spell Their Own Doom | Deep Look
• Walter Isaacson on CRISPR, Jennifer Doudna, Gene Editing, and the Future of the Human Race | The Tim Ferriss Show #503
• The 4-Hour Body: An Uncommon Guide to Rapid Fat Loss, Incredible Sex, and Becoming Superhuman by Timothy Ferriss | Amazon
• Springbok Sevens | SA Rugby
• Shaun White and the Magic of “Who Cares?” | The Tim Ferriss Show #140
• What Is the Monte Carlo Simulation? | Investopedia
• Zip2 | Wikipedia
• Billpoint | Wikipedia
• PayPal Solves Fraud Challenges | Intel
• Ventures of the PayPal Mafia | Fleximize
• The Sunk Cost Fallacy | The Decision Lab
• The Power Law: Venture Capital and the Making of the New Future by Sebastian Mallaby | Amazon
• Simple, Secure, Reliable Messaging | WhatsApp

SHOW NOTES

• [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.

MORE ROELOF BOTHA QUOTES FROM THE INTERVIEW

“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

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

PEOPLE MENTIONED

• Pik Botha
• Ronald Reagan
• Margaret Thatcher
• Henry Kissinger
• Nelson Mandela
• Robert Dorrington
• Peter Attia
• Don Valentine
• Steve Jobs
• Leonard Bosack
• Sandy Lerner
• Jim McKelvey
• Jack Dorsey
• Lawrence Summers
• Michael Moritz
• Doug Leone
• Viktor Frankl
• Kevin Systrom
• Mike Krieger
• Tim Noakes
• Jim Goetz
• Elon Musk
• Peter Baird
• Peter Thiel
• Meg Whitman
• Evan Williams
• Max Levchin
• Jeremy Stoppelman
• Michael Jordan
• Sebastian Mallaby

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