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Sequoia’s Roelof Botha: Why Venture Capital is Broken & How Great Companies Are Built

October 09, 2025 / 27:57

This episode features Roloff Botha from Sequoia Capital discussing venture capital, the Sequoia Scouts program, and the current state of the venture industry.

Roloff Botha shares insights on the Sequoia Scouts program, which he helped launch in 2010 to enable contemporary founders to invest in startups. He mentions notable scouts like Jason Calacanis and Sam Altman, who contributed to investments in companies like Uber and Stripe.

The conversation also covers the challenges facing the venture capital industry, including an oversaturation of capital and the need for transparency in returns. Roloff emphasizes that only a small number of companies achieve significant exits, highlighting the risks involved.

Roloff discusses Sequoia's approach to investment, focusing on maintaining a smaller organization and fostering a culture of teamwork and individualism. He reflects on the importance of curiosity and collaboration in making investment decisions.

Lastly, Roloff touches on the transition of leadership at Sequoia, the firm's success in life sciences investments, and the impact of regulations on entrepreneurship in China.

TL;DR

Roloff Botha discusses Sequoia Capital's investment strategies, the Sequoia Scouts program, and challenges in the venture capital industry.

Video

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[Music]
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Sequoia is the most soughta name in the
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venture capital business.
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The firm has made over a thousand
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investments now worth in the trillions
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in public market value.
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There's a list of five VCs who I think
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can really transform a company and
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you're one of those five.
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When I joined Sequoia, it was clear that
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if I wanted to make it as a partner, you
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needed to produce meaningful games.
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YouTube, Instagram, Square. This is a
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list of amazing amazing startups. Our
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ambition is to build a partnership that
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endures and that means we need to leave
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it in a better place than we found it.
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Ladies and gentlemen, please welcome
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Seoia Capitals Rolloff Botha.
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See you. See you. What's up, bro? How
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are you? Good to see you.
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Welcome,
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Ralph. There's a question.
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What's that? Where did Saxs go?
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Get to pee pee. He had to make a weiw
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wee.
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Come on.
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You Yeah, exactly. You guys did work
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together
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for 25 years ago and he just abandons us
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right now.
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He's had enough of you. Um, everybody
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wants to know who's your favorite
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Sequoia scout of all time.
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Let's go through it.
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Jason Calakanas.
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It is hilarious. Um, when you think
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about it, you came to me, gosh, 15 years
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ago, and you said, "I have an idea for a
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program. It's called Sequoia Scouts.
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We'd like to, um, have you go around and
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invest in some companies."
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And, uh,
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no good deed shall go unpunished.
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Absolutely. Created a monster. Um, but
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that program
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Sorry, before you ask your question, how
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far are you going to insert your head up
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Roloff's ass?
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[Applause]
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We sat him that far away for a reason. I
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mean, um, sorry, bro. Jesus Christ. Go
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on with your question.
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That's
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Let me land the question.
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What's your question, D?
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That program, um, had some that first
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cohort of individuals
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um, wound up being a pretty interesting
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group of folks. Maybe you could tell
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everybody just a little bit about that
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program you conceived of and then who
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were some of the first folks in it and
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the first investments. We conceived of
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this program as you mentioned in 2010
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when we launched it and the idea was
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that there were a bunch of contemporary
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founders who had very interesting access
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to upand cominging founders who are
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turning to them for advice but these
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founders didn't yet have money at the
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point that you became a scout. You
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didn't have the net worth you have now
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where you could write a check on your
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own. And so we thought it'd be a great
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program for us to provide the capital
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for founders like yourself to be able to
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invest in those companies and hopefully
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we would get an introduction to those
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companies for us to be able to make an
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investment too. So uh you were in that
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program you helped us with the
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investment in Uber. Sam Alman was in
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that group as well. He helped with an
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investment in a little company called
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Stripe.
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They did. Okay.
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So at this point that that fund is a 26x
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fund at this point.
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Wow. That's up there in the
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It's pretty good. What's the best fund
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in the history of Sequoia? Was it the
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Google fund, the WhatsApp fund? Which
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one has the highest multiple in history?
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Uh the highest multiple in history is uh
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I think Venture 12, which has Airbnb,
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Dropbox,
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Nera,
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ADM Mob and a couple of other companies.
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And then venture 13 which is the fund
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right after that has stripe and square
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now called block and a bunch of
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other companies. So those were both
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north of 20x funds. Tell us about the
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venture industry actually. So we're at a
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point in the cycle where there's been a
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lot of specialization both maybe at the
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stage level at the sector level. There's
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been all kinds of experimentation and
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approaches in strategy. Can you just
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level set on
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what you've learned and what the
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industry's learned and where we are?
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I'm glad you called it an industry, not
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an asset class. Um, I listened to one of
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the shows you guys had recently and I
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think there's a huge problem with the
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venture industry that there's too much
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money and you guys have talked about
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this before. Uh, venture industry as a
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whole invests right now between 150 to
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$200 billion a year was the last numbers
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I saw. If you think about reasonable
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assumptions for returns, let's just say
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12% peranom net, which isn't great.
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Might as well invest in an index fund,
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the math basically implies that you need
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three and a half to 4x funds to make
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that math work over a reasonable time
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frame. So if you're investing, let's
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just say $200 billion a year. The
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industry needs to give back 7800 billion
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a year. VCs don't own 100% of the
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company last time I checked. So that
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means that the aggregate exit value is
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north of a trillion a year.
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So Figma went public recently. They're
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worth 25$26 billion. You need 40 Figmas
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a year for the industry to make the
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returns work, which means that they
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don't. So in my opinion, investing in
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venture is a returnfree risk. You
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shouldn't. They're basically only about
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20 companies.
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You said return
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return free risk.
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risk.
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Exactly. If you look at every single
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decade, there are only about 20
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companies that end up getting exit
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values north of a billion dollars.
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Actual IPOs or M&As north of a billion.
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Not the paper writeups, only 20
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companies. More money doesn't create
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more great ideas or more great founders.
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So, I think there is way too much money
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in the industry. The industry does
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provide a lot of value. It provides some
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of the knowhow for entrepreneurs to
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succeed and obviously leads to job
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creation and all the attendant benefits
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for America. But there is too much money
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and too many people who want to be
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investors.
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How does the money get level set then
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and right sized for what is needed?
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I've been wondering that for 20 years.
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Uh this problem is a problem 20 years
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ago. It is only
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it's an incredibly sexy asset class. I
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mean look, Jason writes a bestselling
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book. It doesn't, you know, dissuade
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people. It incentivizes more people to
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say, "Oh, I can try this. I'll be like
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it." I mean, it's just a self-fulfilling
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prophecy. The more successes there are,
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there's just um
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Yeah. Everybody wants to go to Vegas
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and, you know, strike it rich. It
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doesn't happen.
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Yeah.
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That's part of the dynamic is that you
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get a firm that has one success in their
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fund and then they attract more capital
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because people think it's repeatable and
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it's not.
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And you don't know you don't know that
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till fund three or four. Like often they
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raise fund three before they've even
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oh they've raised fund two, three, four,
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and five before even fund one is really
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fully distributed a lot of times. So
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what could change for one one of the
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things that I thought was transparency
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but nobody wants to publish their
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returns. You could publish your returns.
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I publish my returns but you know I'm
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not taking outside capital but would
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that help? Like is it working with
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people like Cambridge so that these
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things become more public and more
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understood? It seems like there's an
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education element here that's missing on
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behalf of the industry to the potential
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LPS. I think people will still hide
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behind the J curve effect and they'll
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say yeah my fund is only at 1.5x right
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now but it's only four years in and you
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know the winners are going to emerge and
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so I think this this hope springs
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eternal dynamic and such a long time
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period of gestation before the companies
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get realized that I don't think that uh
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will change that dynamic unfortunately
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there's also been this really
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interesting effect where it's been this
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industrialization of venture capital I
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will call it so if you look at the
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organization that has built the
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organization that General Catalyst has
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built. It's about this girthiness,
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right, across many different things.
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How has Sequoia reacted when they've
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seen those movements? And I'm sure
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you've had to sit down as a partnership
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and say, are we matching this? Are we
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copying this? Are we going to do the
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same thing? Are we doing something
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different?
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That is a great question. The industry
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has changed a lot since I got into
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venture just over 20 years ago. If you
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go back to the proverbial 1990s venture
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firm, it was, you know, a dozen people
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sitting around a table making investment
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decisions with very lightweight staff.
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Uh, and it was much more of a cottage
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industry. I think the industry is
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professionalized and really the founders
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are the ones who benefited from it
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because all these firms have built
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larger operating teams to be able to
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help those founders with talent, with go
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to market and so I think it's really
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helping founders. That's probably the
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main takeaway I have from that. We've
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decided to not build as big an
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organization. Most of the operating
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teams we have at Sequoia help us. So we
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have about as many developers at Sequoia
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as we have investors and they're
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building products for us so that we are
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much more effective and productive than
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we might have been 20 years ago.
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What's an example of that that they're
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building for you?
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Uh so you know my phone I can pull up an
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app that I if you give me any company
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name I'll be able to tell you who my
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team last met, how we rated it. I'll
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give you uh data on what's happening
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with their hiring. Uh how many vouched
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employees they have, how good do we
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think their engineering team is based on
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their history, their academic profiles,
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etc. All this information is at my
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fingertips. Uh if we get business plan
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submissions, we have an AI system that
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will summarize it for me. So I get a
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very quick read on the company, a quick
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summarization of the quality of the team
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and a very quick analysis of the
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competitive dynamics and the other
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companies I should consider alongside
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them. So these are just small examples
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of the things we do. We just had Joe
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Saiion on. We're talking a bit about the
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relationship between America and China.
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You had a fabulous business in China for
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two decades, I believe,
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with Neil.
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Yeah.
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And it did absolutely fantastic. But
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then the government of the United States
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said, "Hey, we cannot as venture
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capitalists invest in China anymore."
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So, what are your what's your take on
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the the opportunity in China? Will that
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return? and and just the the experience
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you had with all those incredible hits
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at the time.
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When we first went into China, it was
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2007 I think. Uh the world was flat was
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the moniker at the time. China gained
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admission to the World Trade
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Organization in I think 2001
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and we all believed that it would
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integrate into the global economy. That
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premise proved wrong. And so we had a
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period where it was really interesting
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to be able to share knowledge and share
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ideas and sort of figure out how we can
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build a globally interconnected set of
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systems and companies. Uh and life just
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got too hard for that honestly and we
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saw just more division between the two
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countries. So we embarked on global
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separation just over 2 years ago and
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what used to be China is now an
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independent business called Hongchan and
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they're off to the races. I think
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there's a real challenge in China right
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now. Uh some stat I got recently in 2018
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there were 51,000 companies started in
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China. In 20123 it was 1,200.
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Wow.
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How many?
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1,200. You had a 98%
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reduction in the number of companies
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founded in China. Cuz if you're an
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entrepreneur in China, why would you
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want to start a company when the
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government regulations are so uncertain?
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Which by the way is an interesting
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warning sign for me for us in America as
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we think about AI policy and AI
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regulation. The more uncertainty we
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create for founders, the more difficult
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it is for them to actually take that
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risk, take that leap to start a
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business. So, but Chinese
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entrepreneurship is still strong. So,
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you see many Chinese entrepreneurs now
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operating in Latin America, they move to
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Singapore, they're in uh Japan, they're
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moving to Europe. I mean, you can't
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repress that spirit. Rolof, there's a
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interesting dynamic that I observed
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which is you have the early early stage
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venture companies who have had an
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incredible track record. you guys,
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Benchmark, Kosla,
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and then what happens is you have these
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latest stage firms, but many of the
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companies that they fund need so much
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money that the latestage firms can't
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service them. So, you have to go direct.
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You go right to Saudi, you go right to
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the Qataris, you go right to the
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Amiradis, you go right to Norway, you
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know, these sovereign wealth funds that
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are writing these big checks. And so, it
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creates this really weird dynamic where
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you almost become this kind of glorified
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placement agent almost. So there's this
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part of the curve and then there's all
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this money that goes over here. How do
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you adapt the business in the face of
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that dynamic?
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Well, we stick to our knitting. Uh the
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funds we operate today, our seed venture
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and growth funds today are no bigger
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than they were 5, six, seven years ago.
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We we realize that there's money to be
00:12:02
made for some people writing very large
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checks and very latest stage companies.
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But uh our aspiration is to be the
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number one investment manager for our
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limited partners. We literally want to
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be the best net IRRa and net multiple
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for our LPS and we're not interested in
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maximizing fees or maximizing share of
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industry value creation.
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That's the game we've chosen to play.
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And so there's no path where Sequoa for
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example tries to go public or take the
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you know that's like it's just not in
00:12:33
the strategy of the business. No,
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actually we've structured ourselves to
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be a private partnership in perpetuity
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to the extent possible under California
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law. We have the sense of stewardship.
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You have to leave the partnership in a
00:12:45
better place than you found it. Don
00:12:46
Valentine didn't call it Valentine
00:12:48
Ventures when he started it. He handed
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the partnership over to a next
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generation with Mike Meritz and Doug
00:12:53
Leone and Jim Gett. And you know, we're
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now part of a third generation, our team
00:12:57
currently running the partnership. We
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didn't have to pay to get the
00:13:01
partnership from the previous generation
00:13:02
and nor will we charge the next
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generation. That's that's our motto.
00:13:06
How would you describe the culture
00:13:08
that's driven the success rolloff? So
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when you select partners, what do you
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look for? How do you value those
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partners? How do you assess the
00:13:17
performance of those partners? And how
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do you guys operate that kind of defines
00:13:21
the culture?
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So I think the probably the most
00:13:23
important characteristic we look for is
00:13:25
an insatiable curiosity in the
00:13:28
individual. We look for people who are
00:13:29
extremely driven, but they need to have
00:13:31
a heart of gold. So one of the things we
00:13:33
talk about at Squay is um we cherish
00:13:35
individualism and teamwork. You need an
00:13:39
individual to be able to have a keen
00:13:40
insight and propose an investment but
00:13:43
you've got to work with a team and that
00:13:45
the whole teamwork aspect is really
00:13:46
important for us. So when you make
00:13:47
investment decisions at Sequoa it's a
00:13:49
consensus decision which blew my mind
00:13:52
when I first got there. I
00:13:53
meaning everybody has to agree.
00:13:54
Everybody has to agree.
00:13:56
So if one person says no it doesn't
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happen.
00:13:58
Correct.
00:13:59
So one person can veto an investment.
00:14:01
Correct. And that happens often or
00:14:03
it has. Sometimes it was a good decision
00:14:06
and sometimes not.
00:14:08
What do the statistics tell you?
00:14:09
What's the worst uh thing somebody
00:14:11
killed?
00:14:13
Oh jeez.
00:14:14
It's okay. We're all friends here.
00:14:16
What is that list called when you have
00:14:17
that?
00:14:17
Yeah, you would call it your anti
00:14:18
portfolio.
00:14:19
Anti portfolio.
00:14:20
But in this case, somebody
00:14:23
wasn't just an anti portfolio. It's like
00:14:24
everyone agreed we should do it except
00:14:26
the one.
00:14:27
Yeah. Yeah. And so you think about that
00:14:28
responsibility uh
00:14:31
and it weighs on people,
00:14:34
but it means that you need to show up
00:14:35
with your best game every single day.
00:14:37
And you know, part of what we've done is
00:14:38
we look at the vote distribution these
00:14:40
days and look, if somebody shows up and
00:14:41
everybody's really positive, there a
00:14:43
bunch of people that are eight nines out
00:14:44
of 10 and there's one person who clearly
00:14:46
woke up at the, you know, in a bad mood
00:14:47
and is a three, you know, at some point
00:14:50
that person will probably say, "Listen,
00:14:51
maybe I just don't get it."
00:14:53
This actually happened to me. We
00:14:54
listened to a company in late November.
00:14:56
This company is thriving right now.
00:14:57
They're in the it's pretty sax isn't
00:15:00
here because this company's benefiting
00:15:01
from stable coins with the genius act
00:15:03
that he helped put in place is really
00:15:04
benefiting from that and I didn't quite
00:15:07
get this company at the time and I was
00:15:08
the only person who was below the line
00:15:10
and I said listen there's something I'm
00:15:12
missing in this particular company. I
00:15:13
think we should proceed with the
00:15:14
investment even though my intuition
00:15:16
walking in was that we shouldn't
00:15:18
and I'm really glad that we proceeded.
00:15:20
So
00:15:20
can you tell us about the holding
00:15:22
company transition that you underwent
00:15:24
and the role of being a venture
00:15:25
capitalist in making an exit decision?
00:15:28
So we did this conversation on the show
00:15:30
a few weeks ago. Pulled up some
00:15:32
analysis. The biggest winners continue
00:15:34
to compound as public companies. 99% of
00:15:37
the returns are as a public company or
00:15:38
whatever it is. So it looks like an
00:15:40
amazing exit goes public.
00:15:42
But that's not the end of the value
00:15:43
creation. True compounders compound for
00:15:46
decades. Especially founders are still
00:15:47
in the seat. Amazon, Nvidia was a
00:15:50
Sequoia investment. I think Google, I
00:15:53
mean, these are multi-trillion dollar
00:15:55
companies that if you guys held your
00:15:56
position to today, I'm assuming things
00:15:59
would look a little bit different.
00:16:01
It would. Yes. So, so we backed a bunch
00:16:03
of very interesting companies over our
00:16:05
50 years. Uh, the companies in which we
00:16:07
were private investors when they were
00:16:09
little companies
00:16:11
today account for over 30% of the total
00:16:13
value of the NASDAQ.
00:16:15
Wow.
00:16:16
There's no other 30%
00:16:18
over 30% of the combined value of the
00:16:20
NASDAQ.
00:16:21
Apple, Nvidia,
00:16:22
Apple, Cisco, Nvidia, Google, Pala
00:16:25
Network, Service Now, uh I mean the list
00:16:28
goes on. So
00:16:28
pretty pretty good.
00:16:30
So So one of the things we realized,
00:16:32
what you're alluding to is in 2022, we
00:16:34
launched something called the Sequoa
00:16:35
Capital Fund. And so we realized that
00:16:37
the great companies continue to compound
00:16:39
as you talked about in that episode. It
00:16:41
was it was an excellent episode
00:16:42
obviously. Um, and by the way, even in
00:16:45
more recent memory, if you look at the
00:16:46
last 10-ish years, Palto, Service Now,
00:16:49
HubSpot, MongoDB, these companies have
00:16:52
all been 10 X's as public companies. And
00:16:55
so, we've realized that when we
00:16:56
distribute shares prematurely to LPs,
00:16:59
they don't know any better because, you
00:17:00
know, they run a big endowment. They
00:17:01
suddenly get $5 million worth of company
00:17:03
ABC. They don't know any better. They
00:17:05
sell the shares. So, what we've decided
00:17:06
to do is for the companies that we
00:17:08
believe have the ability to compound
00:17:09
longer term, we have a different fund
00:17:11
structure. And so 6 12 18 months after
00:17:14
the IPO, we can move those shares into
00:17:16
this fund called the Sequoa Capital
00:17:18
Fund. And this now becomes the vehicle
00:17:20
through which we fund all our next
00:17:22
underlying investment vehicles. Now to
00:17:24
give you a sense, since we launched this
00:17:26
3 and a half years ago, we've
00:17:28
accumulated another 6.7 billion in gains
00:17:32
by doing nothing except being patient.
00:17:35
$6.7 billion in gains that our LPs would
00:17:37
not have seen if we had just distributed
00:17:39
those shares outright.
00:17:40
Yeah, you're making him moan. He's
00:17:42
moaning.
00:17:42
I like it. I'm getting I'm getting
00:17:44
getting warm and he's getting emotional.
00:17:46
But what is but what is the So the
00:17:48
counterargument is as a public company,
00:17:51
you as venture capitalists who are
00:17:53
excellent at interrogating early stage
00:17:55
technology, early stage metrics, founder
00:17:58
personalities, all the things that might
00:18:00
make a good venture capital investor.
00:18:02
Maybe as a public company, quarter to
00:18:03
quarter, are they growing 12%, 14%.
00:18:06
There's a different analytical skill set
00:18:07
some might argue like you know that that
00:18:10
belongs in that investment domain and
00:18:12
frankly very hard to beat the indust
00:18:15
indices doing that. What's the argument
00:18:17
to be made to the counter and why would
00:18:21
you counter that argument?
00:18:22
So see one of the things for us is that
00:18:24
the I mean most of these cases we're
00:18:26
involved with these companies literally
00:18:27
at inception. I mean Palo Alto Networks
00:18:30
was incubated inside our office with one
00:18:32
founder and my partner Jim Gates. So,
00:18:35
we've known these companies since the
00:18:36
earliest of days. Why should that
00:18:39
relationship end at the IPO?
00:18:41
And in most of these cases, as you
00:18:43
pointed out, the founders are still
00:18:44
there and there's so much more
00:18:45
innovation taking place. Um, Jack
00:18:48
Dorsey's one of Jack Dorsey's favorite
00:18:50
quotes to me was companies have multiple
00:18:52
founding moments. And so when you're in
00:18:55
a company where the the founder keeps
00:18:56
reinventing the business, you know, a
00:18:58
company like Square, half the revenue
00:19:00
today comes from a product called Cash
00:19:02
App that hadn't launched for the first 5
00:19:03
years in the company's life. And so if
00:19:06
you can find these companies, these
00:19:08
special companies where the founders
00:19:09
keep pushing the boundary on innovation
00:19:11
and they are relentless, then it works.
00:19:13
Google buying YouTube.
00:19:15
Don't remind me.
00:19:17
Do you think it would have been the
00:19:18
same? Would YouTube still have had the
00:19:20
same outcome if it wasn't acquired? To
00:19:23
be clear, RUF wrote in his first year or
00:19:26
two at the company, the deal memo to
00:19:27
invest in YouTube and it got bought for
00:19:31
1.6 billion. Standalone business today
00:19:34
would be worth 400500 billion.
00:19:37
And then Google then invested quite
00:19:39
significantly in infrastructure and
00:19:41
enabling scalability and building out a
00:19:43
team and building out an ad revenue
00:19:44
system, etc. We've got Neil here
00:19:47
tomorrow to talk about the current state
00:19:49
of YouTube, but do you think it could
00:19:52
have taken the same? It's hard to say.
00:19:53
Hard to say. Uh I think a lot of credit
00:19:56
should go to Google for the way that
00:19:57
they managed YouTube after the
00:19:58
acquisition, both in the resources they
00:20:00
provided, the leadership um and they've
00:20:03
enabled it to thrive. This is one of my
00:20:05
favorite things that Peter Thiel says is
00:20:07
uh you know when you make it when an
00:20:09
acquisition like this happens one side
00:20:12
was orders of magnitude off like it was
00:20:15
just a zero or it was 100 more than what
00:20:18
they paid. Something is always off.
00:20:19
Anyway,
00:20:20
Don Valentine um the founder of the firm
00:20:23
drew a four quadrant chart at one point
00:20:25
to explain the founders
00:20:28
that uh perform extremely well in terms
00:20:30
of returns. Maybe you could explain that
00:20:32
to the audience.
00:20:34
Yes. Uh Don pulled me aside in the early
00:20:36
days when I joined Sequoia and he said
00:20:38
2x2 matrix uh people are exceptional not
00:20:42
exceptional easy to get along with not
00:20:45
so easy to get along with. Ruof we
00:20:48
normally make money in one of those four
00:20:50
quadrants. Your job is to figure out
00:20:52
which one
00:20:54
and it's the exceptional people who are
00:20:56
not so easy to get along with.
00:20:59
Uh so then let's talk about the next
00:21:01
generation.
00:21:02
I'm sorry. Can we just double click on
00:21:03
that? Why do you think that is?
00:21:05
These people change the world. They
00:21:07
don't take no for an an for an answer,
00:21:08
right? They are
00:21:09
How does it Why does that make them hard
00:21:10
to get along with, per se?
00:21:12
Well, I think he was he was saying that
00:21:13
a little bit tongue and cheek, right?
00:21:14
But this is a guy who backed Steve Jobs
00:21:16
when Steve would walk around Sand Hill
00:21:18
Road without shoes. He'd come back from
00:21:20
a trip to India. Allegedly, he didn't
00:21:22
smell too great. Um, and he was unusual
00:21:25
and nobody wanted to back him. And you
00:21:27
know, Don wanted to find these
00:21:28
underdogs, these unknown
00:21:30
Atari.
00:21:31
Well, apparently some of the Atari board
00:21:34
meetings took place in hot tubs.
00:21:36
Yes.
00:21:36
Uh he told,
00:21:37
by the way, that's how he got to Steve
00:21:39
because Steve had worked at Atari.
00:21:42
That's how Don got the introduction to
00:21:43
Steve. So, so I think part of the point
00:21:45
he was trying to make is don't look for
00:21:47
the people that, you know, went to all
00:21:48
the right schools and wear the right
00:21:50
clothes, all the conventional stuff.
00:21:51
Founders are unconventional. These
00:21:53
people change the world. I mean, most of
00:21:55
us encounter challenges every single day
00:21:57
and we accommodate. you know, this thing
00:21:59
isn't quite to your liking, you adapt.
00:22:01
Founders don't. Founders see things and
00:22:03
go, hm, I think the world can look
00:22:04
different and then they go and try to
00:22:06
fix it. They just don't take no for an
00:22:08
answer.
00:22:08
So, let's fast forward to your two
00:22:10
mentors, Michael Moritz and Doug Leone.
00:22:12
Two very different characters when the
00:22:15
story gets told, maybe a rivalry there
00:22:18
um between the two of them. What did you
00:22:20
learn from each?
00:22:21
Sure. From Doug, I learned heart.
00:22:25
Unpack it. Doug has an incredible heart.
00:22:29
When did you see that most? What was the
00:22:31
moment that's coming to your mind right
00:22:32
now that you probably shouldn't talk
00:22:33
about?
00:22:36
Well, the I'll give you two examples.
00:22:38
One was in 2009 when I was in a funk. I
00:22:40
nearly quit the business. Um
00:22:41
I didn't know this really.
00:22:43
Well, we'd had the YouTube was a great
00:22:45
success. Uh and I felt very good about
00:22:47
that. And then you in venture after a
00:22:49
few years you val you walk through the
00:22:51
valley of despair and you start to
00:22:53
realize the things you should have
00:22:55
invested in that you didn't and the
00:22:57
lemons start to drop the things that you
00:22:59
did invest in that are not working out.
00:23:01
So yes there was the one great quick
00:23:02
exit but then a bunch of other things
00:23:04
and I was really having a lot of
00:23:06
self-doubt and Doug showed up at my
00:23:09
house with a homemade pesto jar
00:23:13
and he didn't need to. It was on a
00:23:14
Saturday afternoon. He knocks on my
00:23:16
door. Who's this person at my house? and
00:23:17
he just wanted to tell me that he was
00:23:18
there to support me through this dark
00:23:20
period. That was one example. Another
00:23:22
one was when uh my son was in hospital
00:23:25
and Doug showed up.
00:23:28
Didn't have to. Um that meant a lot to
00:23:30
me. So,
00:23:32
and Michael,
00:23:33
Michael's imagination.
00:23:36
Michael just has an unbelievable ability
00:23:37
to imagine how a company can succeed.
00:23:39
And when I thought about my mistakes as
00:23:41
an investor, by the way, every single
00:23:43
time it comes down to a failure of
00:23:44
imagination, that I didn't think big
00:23:46
enough. I didn't think about how this
00:23:47
company could uh progress from where
00:23:50
they were. You first introduced me to
00:23:52
Twitter 2007.
00:23:53
I have the emails
00:23:55
before smartphones launched and it was
00:23:57
an SMS app. I got tired of getting all
00:23:59
your I'm having cappuccino messages on
00:24:01
Twitter at the time. I remember
00:24:02
on your Blackberry. Yeah.
00:24:04
And I didn't quite imagine that it could
00:24:05
be what it is today. And so that to me
00:24:07
was an example. Uh, I remember an early
00:24:09
meeting with Yelp with Jeremy Stppleman
00:24:13
and Max Lechin in our offices and I mean
00:24:16
Yelp hadn't launched a web app that were
00:24:18
going to be an email newsletter thing
00:24:19
and Michael in this meeting said I
00:24:21
imagine that one day restaurants will
00:24:24
put a Yelp sticker in the window just
00:24:26
like a Zagat or a Michelin star. And he
00:24:29
saw that.
00:24:30
He saw that.
00:24:31
He saw that. I mean 10 years before that
00:24:32
became a reality he had the imagination
00:24:34
to think about that. That to me is
00:24:36
amazing. So now Doug is still there and
00:24:38
Mike has transitioned out. Is that the
00:24:40
what is
00:24:41
Yes, Michael has transitioned out
00:24:43
completely. Doug has stepped back from
00:24:44
day-to-day investing. So he's no longer
00:24:46
in partner meetings routinely, but he
00:24:47
continues to serve on several boards.
00:24:49
And you're in charge.
00:24:51
I'm the leader of a team and I think of
00:24:53
more like being captain of the team. You
00:24:55
play team sport. We play team sport at
00:24:57
Sequoia and you know we are equal
00:24:59
partners and you know it's
00:25:01
Was it hard to see those two guys go
00:25:03
just seeing how legendary they were?
00:25:06
to succeed them? No.
00:25:08
Well, both to succeed them, but also
00:25:09
just to see them walk out the door.
00:25:10
Like, is there a tendency to want to
00:25:11
keep them around as long as possible? I
00:25:13
understand the question. Um, well, well,
00:25:15
firstly, it is very hard to succeed
00:25:16
them. I think every single person in
00:25:18
Sequoia feels this enormous burden and
00:25:20
responsibility to try to match the
00:25:22
performance that we've been known for,
00:25:24
you know, but we have this great
00:25:26
generational transition at Sequoa. So,
00:25:28
Michael stepped back from day-to-day
00:25:29
activity in 2012
00:25:32
and he was
00:25:33
Morris did in 2012. of Michael stepped
00:25:35
back. He had personal health reasons and
00:25:36
he stepped back. He continued to serve
00:25:38
on the boards that he was on and we we
00:25:40
had him for another decade where I would
00:25:43
ask him for advice. You know, as we were
00:25:44
going through global separation that we
00:25:46
talked about earlier, I would ask Doug
00:25:48
and Michael, you know, what do you think
00:25:49
should we you know, what should we be
00:25:51
doing here? Do you have advice for me?
00:25:52
And so it's a we have this benefit of
00:25:54
intergenerational uh knowledge transfer.
00:25:57
Uh Doug was on a call earlier today.
00:25:59
Actually, we had a difficult
00:26:00
conversation. I wanted his input on an
00:26:02
important question and it's not because
00:26:04
he has the authority to tell me what to
00:26:06
do. It's because I seek out his advice.
00:26:08
You were investing in traditional
00:26:10
software, internet services for years
00:26:13
and then a couple of years ago you
00:26:14
started investing in some life sciences.
00:26:17
Does life sciences kind of work as a
00:26:19
venture investment today? And what's
00:26:21
been the challenge in biotech and life
00:26:23
sciences investing generally over the
00:26:24
last few years? There's a lot of
00:26:26
notoriety about the collapse of the
00:26:28
market and even Dave Ricks today was
00:26:29
saying most public biotech companies are
00:26:31
trading below cash. What's your
00:26:33
observations on the business model, what
00:26:35
you've seen, the types of businesses
00:26:37
you've invested in there? So,
00:26:38
so the business we invested in uh that
00:26:39
has done really well is a company called
00:26:41
Nater. Uh and we made a seed investment
00:26:44
of a million dollars in 2007 in this
00:26:46
company.
00:26:46
It's 20 billion now, right? Market cap.
00:26:48
$22 billion market cap. It was a million
00:26:50
dollars. two people uh with a a very raw
00:26:53
idea and today they're the leading
00:26:54
provider of prenatal testing, oncology,
00:26:56
recurrence monitoring, organ transplant
00:26:58
projection testing. And so that
00:27:00
company's been a huge success.
00:27:01
Diagnostics, genetic diagnostics, has
00:27:04
been a huge success. And you think about
00:27:05
the the dividend we're still collecting
00:27:08
from the human genome project 25 years
00:27:09
ago. It's incredible. And you've
00:27:11
obviously seen that in some of the
00:27:12
businesses that you've helped build as
00:27:14
well. uh we did make an investment in a
00:27:16
company called Bridge Bio which is
00:27:17
helping with rare genetic disease drug
00:27:19
development. Uh but other than that I
00:27:21
think we're we just don't have the
00:27:22
expertise for biotech. You know we don't
00:27:24
have any M
00:27:25
but there are still winners.
00:27:26
There are still winners but we have no
00:27:27
MD PhDs on our team at Sequoia. And I
00:27:29
think you know it's very dangerous when
00:27:31
people think that your success in one
00:27:32
domain just naturally makes you uh gives
00:27:34
you the right to compete in other
00:27:36
domains. I think I have tremendous
00:27:37
respect for the people who understand
00:27:39
that. I do not.
00:27:40
I learned that one the hard way.
00:27:44
Ladies and gentlemen, Roloff.
00:27:47
Thank you.
00:27:49
Thank you.
00:27:50
Thank you so much. Thank you, sir. I
00:27:53
appreciate you coming out. Thanks.

Badges

This episode stands out for the following:

  • 70
    Most heartwarming
  • 70
    Best concept / idea
  • 60
    Most inspiring
  • 60
    Best performance

Episode Highlights

  • The Importance of Founders
    Founders have a unique ability to reinvent their companies, leading to multiple founding moments.
    “Companies have multiple founding moments.”
    @ 18m 48s
    October 09, 2025
  • Heartfelt Support
    Doug's unexpected visit with homemade pesto showed true friendship during tough times.
    “Doug showed up with a homemade pesto jar.”
    @ 23m 13s
    October 09, 2025
  • Imagination in Investing
    Michael's visionary thinking helped shape successful companies long before they became reality.
    “Michael's imagination is unbelievable.”
    @ 23m 36s
    October 09, 2025
  • Lessons from Biotech Investing
    Navigating the complexities of biotech investing requires expertise that the team lacks.
    “I learned that one the hard way.”
    @ 27m 40s
    October 09, 2025

Episode Quotes

Key Moments

  • Emotional Growth17:44
  • Innovation Insights18:48
  • Supportive Friendship23:13
  • Visionary Mentorship23:36
  • Biotech Challenges27:40

Words per Minute Over Time

Vibes Breakdown

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