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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, 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.

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.

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

SCROLL BELOW FOR LINKS AND SHOW NOTES…

SELECTED LINKS FROM THE EPISODE

  • Connect with Roelof Botha:

Sequoia | Twitter | Facebook | Instagram | LinkedIn

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.

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8 Replies to “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)”

    1. Hi, Tony –

      Happy to help. Are you trying to find them, or is there something else we can help with?

      Best,

      Team Tim Ferriss

      Reply

  2. Tim, just finished reading Tools of Titans and I’ve been listening to the podcasts the last 4+ years. Thank you for your vulnerability in that book and some of the podcast episodes, and for bringing out the human-ness of your podcast guests. The 4-Hour Workweek changed my life and that of my 2 children. You’re having a significant and positive on the lives of many people, thank you for everything you’re doing! (posting here since I don’t have twitter)

    Reply

  3. Hi Tim,
    Thank you for this amazing podcast. Really enjoyed the content.
    I’m working on a series of blogs that highlights the prevalence of the power law in the tech investing ecosystem. I’m keen to use nuggets of wisdom from this podcast and others that you have been doing in my blogs. I hope you don’t have an issue with this.

    I’m not sure if this is the best medium to reach out to you. I’ve also dropped you a line on LinkedIn. Looking forward to many more of such amazing podcasts!

    Reply

    1. Hi, Abhishek –

      Thank you for your inquiry. As a general rule, Tim does not grant permission for any of his copyrighted content, including his podcasts, to be republished in any form, and we regularly submit takedown requests to various platforms where Tim’s copyright has been infringed. With regard to what is permissible by law, we recommend you consult with an intellectual property attorney.

      Best,

      Team Tim Ferriss

      Reply

      1. I would not be infringing any content.

        I will reference Tim, Roelof and the podcast wherever I use information from the podcast. Would you advice against referencing them also?

        If required, you can take a look at my first blog (https://abhim30.medium.com/) wherein I have used certain snippets from various individuals and referenced them accordingly.

        Please do clarify.

        Best,
        Abhishek Mehta

      2. Hi Tim, Team Tim Ferris,

        I would request you to clarify my previous comment. Would you advise against referencing the Tim, Roelof and the podcast also? I don’t intend to republish any information or infringe any copyright rights.

        I would really appreciate clarity on the same.

        Best,
        Abhishek

  4. Dear Tim,

    I have been meaning to thank you for a long time. I discovered your podcast during the pandemic. My job as a teacher had made me into a traveling teacher and I found myself in the car more often and wishing for some good conversation. Between raising small children and then spending more time with children all day at my job, your guests and their compelling ideas gave me much food for thought during a very dark time. I continue to listen, learn and come home with fascinating ideas to discuss with my husband because of your show. You have helped me reclaim my adult mind. I can now say I’m a huge fan! Thank you for what you do.

    Paula
    Kansas girl turned Missourian/ World traveler

    Reply