#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

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.


Please enjoy!


This episode is brought to you by
Wealthfront! Wealthfront is an
app that helps you save and invest your money. Right now,
you can earn two percent APY—that’s the Annual
Percentage Yield—with the Wealthfront Cash Account. That’s
twenty times more interest than if you left your
money in a savings account at the average bank, according to
FDIC.gov. 


It takes just a few minutes to sign up, and then you’ll
immediately start earning two-percent interest on your
savings. And when you open an account today, you'll get
an extra fifty dollar bonus with a deposit of
five hundred dollars or more. Visit
Wealthfront.com/Tim to get
started.


*


This episode is also brought to you
by Shopify! Shopify is
one of my favorite platforms and one of my favorite
companies. Shopify is a platform designed
for anyone to sell anywhere, giving entrepreneurs the
resources once reserved for big business. In no time flat, you
can have a great looking online store that brings your ideas to
life, and you can have the tools to manage your day-to-day and
drive sales. No coding or design experience required.


More than a store, Shopify grows with you, and they never stop
innovating, providing more and more tools to make your business
better and your life easier. Go to Shopify.com/tim
for a FREE 14-day trial and get full access to Shopify’s entire
suite of features.


*


This episode is also brought to you
by Eight
Sleep! Eight
Sleep’s Pod Cover is
the easiest and fastest way to sleep at the perfect
temperature. It pairs dynamic cooling and heating with
biometric tracking to offer the most advanced (and user-friendly)
solution on the market. Simply add the Pod Cover to
your current mattress and start sleeping as cool as 55°F or as
hot as 110°F. It also splits your bed in half, so your partner
can choose a totally different temperature.


And now, my dear listeners—that’s you—can get $250
off the Pod
Cover. Simply go
to EightSleep.com/Tim or
use code TIM at checkout. 


*


[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.


*


For show notes and past guests
on The Tim Ferriss Show,
please
visit tim.blog/podcast.


For deals from sponsors of The Tim
Ferriss Show, please
visit tim.blog/podcast-sponsors


Sign up for Tim’s email newsletter (5-Bullet Friday)
at tim.blog/friday.


For transcripts of episodes, go
to tim.blog/transcripts.


Discover Tim’s
books: tim.blog/books.


Follow Tim:


Twitter: twitter.com/tferriss 


Instagram: instagram.com/timferriss


YouTube: youtube.com/timferriss


Facebook: facebook.com/timferriss 


LinkedIn: linkedin.com/in/timferriss


Past guests on The Tim Ferriss
Show include Jerry Seinfeld, Hugh
Jackman, Dr. Jane Goodall, LeBron James, Kevin
Hart, Doris Kearns Goodwin, Jamie Foxx, Matthew
McConaughey, Esther Perel, Elizabeth
Gilbert, Terry Crews, Sia, Yuval Noah
Harari, Malcolm Gladwell, Madeleine
Albright, Cheryl Strayed, Jim Collins, Mary
Karr, Maria Popova, Sam Harris, Michael
Phelps, Bob Iger, Edward Norton, Arnold
Schwarzenegger, Neil Strauss, Ken Burns, Maria
Sharapova, Marc Andreessen, Neil Gaiman, Neil de
Grasse Tyson, Jocko Willink, Daniel Ek, Kelly
Slater, Dr. Peter Attia, Seth Godin, Howard
Marks, Dr. Brené Brown, Eric Schmidt, Michael
Lewis, Joe Gebbia, Michael Pollan, Dr. Jordan
Peterson, Vince Vaughn, Brian Koppelman, Ramit
Sethi, Dax Shepard, Tony Robbins, Jim
Dethmer, Dan Harris, Ray Dalio, Naval
Ravikant, Vitalik Buterin, Elizabeth
Lesser, Amanda Palmer, Katie Haun, Sir Richard
Branson, Chuck Palahniuk, Arianna Huffington, Reid
Hoffman, Bill Burr, Whitney Cummings, Rick
Rubin, Dr. Vivek Murthy, Darren Aronofsky, and many
more.


See Privacy Policy at https://art19.com/privacy and California
Privacy Notice at https://art19.com/privacy#do-not-sell-my-info.