Sequoia's Doug Leone: Trauma, Hardship, Purpose, and Silicon Valley's Top Firm

Making mistakes and learning from them, I think that's what keeps you alive. I think the moment you have the answers and you've made it, that to me is equivalent to being dead.

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Since its founding in 1972, Sequoia has provided funding for some of the very best startups and entrepreneurs, from Apple to Oracle, Google to Atari, WhatsApp to Nvidia. Before joining Sequoia in 1988, Doug held sales positions at Sun Microsystems. He holds a degree from Cornell, Columbia, and MIT. Doug Leone is seen as one of the great venture investors of the industry. For nearly 30 years, he helped lead Sequoia while investing in companies like ServiceNow, Wiz, Nubank, and Aruba Networks. I hope you enjoy it.

Genoa? Am I saying that right? Genoa. Genoa. Genoa.

Okay.

There's no salami in Genoa. Okay? Just to be clear. Yeah.

There must be.

No. I mean, there is, but it's like saying there's pumpkins in California. It's seasonal? No, it's just not known. It's not known for salami. Only in America. It's a marketing thing. Some company decided to call it Genoa salami and it hit.

Did they lean into that or is it offensive? They don't even know about it. What part of you do you think is still Italian? How much?

The telling it like it is is a very Italian thing.

Yeah.

Very Italian thing. My mother and I used to talk, and my wife was convinced we were having an argument, where we were just talking. "You and your mom?" Yeah, my mother was just talking normally. My mother goes, "Why are you guys fighting?" "We're not fighting, we're talking."

You moved to Mount Vernon, New York, when you were 11. You came by boat. You had a good, great family, but you didn't come from—you came from a pretty humble circumstance. Can you tell us a little bit about what you remember from that?

Yeah, so I'm not sure I had a great family. My father left when I was 11 to come and work in America. We went on line for two years. I was raised by a loving mom and three aunts, none of whom, for different sets of reasons, had children. So I had a strong female upbringing influence. And so I was what you would call a very sensitive, sweet kid with a strong maternal influence when I came to America. And so even that, in and of itself, wasn't a balanced upbringing because I was missing the male figure—the strong male figure, such as, "Let them make mistakes, keep them independent," versus the nurturing, the loving nurturing of a mother. And I came to America at the age of 11. And I would say, from 11 to 17, I would clearly state that I experienced trauma.

There's no other way about it. "What do you mean?" The things I was put through during those tender, formative years as a sweet, tender, innocent kid were extremely painful. Let me give you a couple of examples. Maybe in Italy you don't take a shower every day. You don't learn to do that, and to be accused of smelling—that is devastating. America tends to be a very physical society. The sports are physical. I knew how to kick a ball. I didn't know how to throw a ball or catch a ball. I couldn't imagine being punched in the face as a little boy in Italy. It was just not part of the culture. I got punched in the face multiple times and simply didn't know what to do about it. I was frozen. And the list goes on and on.

I wrote a letter about a year ago of young Doug to old Doug. Asking old Doug for help and writing it wasn't easy writing it. Sorry was easy Reading it was devastating and because it brought back all the things I have forgotten about and What that caused was a lack of development emotional type of development for a number of years The manifested itself in going to Cornell and getting thrown out after the first year, being extremely mature, getting back in, and having to make a subconscious decision as to whether I was going to die or survive. And I was reading the Elon book a few weeks back. I'm no Elon Musk. I want to make sure everybody understands that. But boy, the parallels are there. You make a decision, not consciously,

And so I can trace back everything I've done, whether it's weightlifting, whether it's taking boxing lessons, whether it's not letting another man dominate me, whether it's wanting to be the best. I can trace everything I've done since, including the mistakes I've made—horrific mistakes, personal mistakes—to that period of my life.

As I think about your experience with Elon or with others, it seems like some of the great people, they really go through some of the hardest and worst things at the beginning. This is a—it's not everyone, but a lot of people. Why is that? Why are some of the strongest people the ones that have been through the worst things? Yeah, first of all, I'd like to say there are many roads to heaven, as my former partner Shailendra Singh said. I have a son-in-law who had a great upbringing. He's ultra-competitive; he does very well in the business world.

And he does that having been blessed with a great upbringing, simply because he has an ultra-competitive nature with his older brother. Not unlike my partner, Andrew Reed, who competes intensely with his twin brother. So there's many ways you can decide to fight and be someone. But there are also many cases of people that have undergone extreme pain. And when you live through that stress and you decide to overcome, you have a chip on your shoulder that just doesn't go away. It doesn't go away forever. I still have it. What was an insufferable Doug has become a bit of a more charming Doug. But nevertheless, I completely recognize that the chip on the shoulder is still there. And it's not a chip for selfish reasons.

As you get older, you mature. You do it for greater reasons—help young people. And the real decision you have to make as a human being is, are you going to do unto others what was done to you? Or are you going to do the opposite? And that includes your children. That includes your friends. That includes your work colleagues. And I know the decisions I made. And quite frankly, I'm proud of them. I made the decisions, for example, that with my children, I was going to try to figure out how to instill some drive without destroying them, without having to go through the darkness and the pain and the trauma that I felt, that I underwent.

How do you do that?

Give them jobs. Give them responsibilities early on. Don't join too many country clubs. You can play golf and horseback riding, nothing against that. But I wanted my kids to feel the dirt of the infield in their teeth more than the grass of the divot from the horse jump.

I've heard a story about you when you were a kid where you were working and you kind of saw like some kids at a country club or... Yeah.

Do you remember that story? Yeah. Let me give you some texture. We had a car called a Mercury Monterey that had a big dent on the side. That was the family car. How embarrassing. And we had no money. And the money that I that I generated was working the summers and when I mean working the summers I would work sometimes through the night because if you work through the night you get paid double time and you got time off for any hour you worked after midnight so it was not unusual for me to work until 8 o'clock the next day show up at work at 4.30 and start my day again and sometimes work 24 hours because I wanted some money I wanted some money to have some game So when I went to school, God forbid, I couldn't go out on a date with a girl.

Girls were new. Girls ran away from me in high school for all the reasons that you might imagine. And part of the work was working on sailboats. And in these yacht clubs, there'd be the sailboats and the water. And you could see the pool. And you could see the lifeguard, the 17-year-old who got the lifeguard job, with the 15-year-old, and the girls, and the girls are on the lifeguard and going to the snack shack. Well, I wasn't allowed there. What I was allowed to do is snake wires through the hulls of the boats so we can install electronic equipment, climbing up a mast, being hoisted up a mast, and do that, and do that for many hours a day where you sweat, you know, very hot weather in New York, 90, 100 degrees.

People jumping in the pool and getting cool and me being up in a mast and seeing everything. And, you know, you just get a look like this of—nothing against those kids. They might have been great kids. But all I thought is, 'I'm going to get you, you son of a gun.' That's all I could think about. And that's more of the developmental shit or chip on your shoulders that just stays with you.

Yeah, it's interesting to kind of hear you talk about that. And as I think about my own kids—you have four kids, is that right? I have four children. I have four children as well. And, you know, we live in this such a blessed world, you know, overabundant life. We live in California, the United States in 2025. And I think about my journey was not nearly as hard as yours, but some of the hard things that I went through, and how do you, you know, my kids aren't going to have that. And, you know, you wouldn't probably want to put your kids—wouldn't be right to put your kids in, you know, to move them to some place around the world just to make them suffer, right? So it's trying to figure out how do you create that fight in somebody?

And it's almost like a lot of people, the pain and the suffering, it can be debilitating and it can send people down a path that they never come back from. But it can also just absolutely make you incredible. And you're still, you're still thinking about—you're not dwelling on it, but it's still in the back of your mind. And the chip that you, you talk about on your shoulder, to me, it's one of the most—the things that's most inspiring about you, because you succeeded so many times, but, you know, you, you kept going. It's like you were great, but then you pushed beyond that to somewhere that, that hadn't been. I just, like, where do you find that next gear? Like, you, you made it, but then you made it 30 years ago, and yet you kept going to this other, you found this other gear.

Let me go back and then I'll answer the question. I think you have to give your children responsibilities early on. There are studies that say children who have household chores are more likely to be happy and successful. And household chores is not doing your homework. That is not for everybody; that's for you. And I've gone as far as to say to some of my children, 'You've got to inject some misery.' I don't know how to inject misery, but it just can't be all happy and fun and games. Then there is—we live in Silicon Valley—then there's the issue of how much you want to pre-program your children, you manage them to... you actually program them. You enroll them in all these sports, you get them a trainer, you do that, you actually are trying to do something.

Or the other side of that, similar though, you schedule them to death. And even though we're in Silicon Valley and it's a beautiful spot, I think that's detrimental to the children. I love reading what Wayne Gretzky says, how he got good not because he had coaches or lower because he loved the sport so much he spent hours in his backyard just shooting. And I think that's what you want in a kid. I refuse to pre-program my kids consciously. Now, to get further in what you asked me, I don't think I've made it. I don't think I've come close to having made it. And having made it means... Your question, I think, was a financial question. To me, having made it, is a holistic question. And I would say I'm a work in progress.

And may I be a work in progress until the day I die. I jokingly told my wife that in my epitaph, I wanted to say, 'He died a young man.' Why? Because he died a young man in spirit. Being a young man means being open to new ideas, learning from everybody, including your kids, staying fresh, making mistakes and learning from them. I think that's what keeps you alive. I think the moment you have the answers and you've made it, that to me is equivalent to being dead.

I'm not quite there yet. Do you feel like you missed things with your kids? Do you feel like that was okay? Do you feel like today we have to be at everything, everywhere, like you're saying, kind of like pre-programmed, but that's not how we were raised and we turned out okay?

So I was very lucky because when my kids were growing up until my last child, pressed the send button in the last application on December 15, I never traveled. I was a venture capitalist, local venture capitalist. And in the old days, Don Valentine didn't think that if you couldn't get to him by bicycle, you wouldn't make the investment. And so I used to coach my kids' teams at 4, maybe come back to work at 5.30. I was home for dinner, I would say, three out of five nights a week. We had family dinners. And my traveling... the growth fund business that took us nationally in the US, the international business that took us to India, China, Southeast Asia, South America, that came a lot later. So I was very fortunate.

I was there with my children. I was able to show up. Not everybody had the luxury due to the demand of the job. And if you don't have that luxury, you have to make sure you make time. Because the number one thing for children—and if you do this, you can make a lot of mistakes—is to show up. If you show up, you're halfway home. I've made so many mistakes with my kids. My son once growled at me. There was a tray here, and I took the tray and threw it. I didn't want to hit him in the head, just make the point. Now, you're not supposed to do that as a parent.

They teach you, right? I mean, they— Oh, yeah, yeah.

Child Services is going to come and get you if you do that. You know, you went through all that stage. And it's funny, after all this, my son said to me, "You weren't tough enough." Wow. Why would he say that? Because I think he believed it. At least in my case, I expected a lot. I loved intensely. I forgave easily. And we laughed a lot. So that was my... inadvertent formula. I can't say—I can't say that was part of the plan, but that's just the way I was, and certainly not to repeat the darkness that I had to go through in my upbringing. You ever had a founder say that? Say what? "You weren't tough enough"? Uh, they're all—I have a deep voice, I have a big, round, bald head. They all freak out when they meet me.

And later on, they figure out that all I do is care deeply about them and the cause, and I'll do anything they ask. And that usually happens after the first four or five months. They figure out I don't bite and I'm there to help in any possible way. But that's not where they start. Where they start first: "I want Doug Leone on my board," whatever that means. They think I have magical powers, and I don't. But then after that, we build a strong relationship. And in 90% of the cases, it leads to strong friendships after the fact. Usually, it's after the fact. You don't want to be that close friends while business is in the way, just in case you have to make a tough decision both ways.

We're in that house that Don Valentine built. Do you remember vividly your first meeting at Sequoia with him?

Yeah, I remember my first meeting. Don was transformational for me, and Don had a transformation himself. Don took what he understood to be an unguided missile—not a misguided, unguided, a missile that if you launch it, you had no idea which way it was going to go—and put the right flaps in the back and the right force in the engine, so it went where it was supposed to go. I think his attraction to me was the incredible drive and need that I had. And when I was about to be fired by Sequoia—and I may say, rightfully so, for just being insufferable—it was Don who said, "Give the young man some more time." And that turned out to be a good decision, clearly. I don't know why, when I think about Don, and when I went to some NVCA thing, I started crying.

Even right now, thinking about it, I think the effect he had on me was... probably more than any other person.

Into the person you became?

For sure.

Yeah.

And seeing his transformation from a son of a gun—because your son may be seeing this—to a man that decided it was time for him to step back, let the young people run the business, speak only when asked, not controlling things. That was a pivotal transformation for him, and I learned a lot just watching.

It's interesting how people... We all hopefully, hopefully everyone that sees this has these people that they can think of, but sometimes it's family and sometimes it's random people that cross us on the path. And sometimes, I mean, to think of somebody that you work with that could have in some ways, like, be that, you know, to have such an impact on you, and not just you, but also your family and their family. I mean, it's a really special thing. Yeah. Yeah.

He believed in me when nobody else did. Everybody had given up.

Can't be everybody.

All the other partners had given up. All the other general partners, which shall remain nameless, had given up.

So venture capital has somewhat... I'm going to put Sequoia over here to the side and maybe a few other people. But it has this general feeling of like, it kind of looks like a very cushy job for a lot of venture capitalists. It sort of feels like it's sort of top of the food chain, everything's coming at you. And one of the things about Sequoia and the partners, if you work here, is Sequoia partners working essentially as hard as founders work. It's a different kind of work than a founder. But I wonder if you could just talk about what are the expectations? How do you think about work ethic? And I think, I don't know, was it like that before you got here? I kind of assume you had a huge influence in how it is today.

Yeah.

So think of the economics of venture capital. They should be illegal. They work like this: you give me money. I charge you a fee for you giving me money. Thank you. I invest your money. If I lose it, too bad. And if I make it, I keep 30% or 20% or 25%. You keep the balance. If you wanted to have a fair economics, it would say, 'You give me money. I match it exactly with my own dollars. And if we lose it, we lose it together. And if we make it, we make it together. And I only get some of your money after I've generated 5x return for you.' That should be the fair deal. I think that's the root of all ills. Because now that we have the other deal, it affords people to take it easy. It affords people to have quality of life, work-life balance, whatever all those words are.

At Sequoia Capital, the culture has always been to take money only from endowments and foundations, so as we think of them as charities that make the world a better place. That is an aspirational goal that's far greater than building a great company. It's far greater than taking care of your family. It is we're managing somebody else's money that allow for scholarships like I got at Cornell, allows for funding, whether it's for Boston Children's or Sloan Kettering, for worthwhile causes. And that to me is the foundation of everything. We take this extremely seriously. That makes up about—I could be wrong, it may have changed—about 70% of our capital. For a while, it was 100% of our capital, but as the funds grew, there's just not enough of that money around.

Second, we have the culture started by Don Valentine, continued by Pierre Lamond—a name you may or may not know—certainly enhanced by Michael Moritz, and certainly enhanced by Doug Leone, of looking for these somewhat injured humans with a lot to prove. Injured humans that, if you peel the onion and look inside, they're all good souls. We've hired some not-good souls and we've excused them, even though they may have performed. These people are usually not used to the 'we' pronoun. Not because they're selfish, but because they were never allowed as part of a 'we.' They're always shunned in the corner as part of an 'I.' Take those people, put them in a circle of trust. You need to get compensation right.

Because if you talk about all this and you make 20 times what another partner makes, you're full of shit. And now it's all make-believe if you have what I call the hedge fund mindset. And at least in my case, I never preached the word family. I always said, 'I have family members I'm stuck with forever.' I preached high-performance team—not everybody plays sports. I preached a production, a movie production, if that's what you're into, where everybody has to do their job at the highest possible level. And if they don't, the whole team suffers. And if they don't, you shed a tear, you give them a hug. We have the money to take care of them on their way out, unless they're a fraud or they did something terrible, in which case we're not as nice.

And we take care of them on the way out and we help them find another role. And we want to stay at the tippy-tippy-top performance, recognizing that trust is the foundation, performance is the next level, and teamwork is the third. I call that the sacred triad of Sequoia. We got to get those three things right. And that's what we do. And so when you say work ethic, we never really think in terms of work ethic. Everybody just works. Roelof sent a note: 'We want to talk about something over the weekend.' The responses were, 'I'm free any...' You know, Roelof said, 'Between 9 and 12, Saturday, Sunday, Monday.' All responses were, 'Any time works, pick a time.' There wasn't, 'Oh, I have lunch, I've got brunch, I'm skiing.'

Maybe they are skiing.

Pick a time.

Pick a time and we're on.

Do you think you're bringing people in that are looking for that? You're bringing people in that have this chip on their shoulder that are, I think as you said, wounded in some way?

They're not looking for that. They don't even know what they're looking at. They come in here having heard Sequoia is a tough place. They quickly realize it's the opposite of a tough place. I can tell you that every single hire that we brought in said, 'My God, everybody told me tough, tough, tough. It could not be a more supportive environment.' Because we recognize when you come into this environment and you work as a team, you have to support one another. Now, we will do things if someone is struggling. We make the decision: Do we help them or we let them get through the abyss alone, knowing they'll be better off? That might be a conscious conversation among the senior partners to help the individual, to, in our judgment, what helps the person most.

But it's certainly not meant to squeeze. It's certainly not meant for 'I,' 'me,' none of that. And the last thing we want to do at Sequoia is take credit for anything we do. All the wins are theirs. And when there's a loss, you won't believe how many people raise their hands: 'My fault. That was my mistake.'

There's this sort of joy of work. There's a sort of feeling of satisfaction around work. And, you know, I don't know if it's an age thing. You know, I remember being an intern here at Electronic Arts, as my first job and Sequoia seed and Sequoia company with Trip Hawkins. And You know, we were there till one in the morning and we still talk about it like it was the greatest thing they ever did for us. And, you know, I don't know. I love work. I learned to love work. And, you know, I love being creative. And I think, you know, the schedule you talked about with yourself of going. doing your kids baseball or whatever, having dinner and continuing to build and to push this, this reflects what you see a lot of high achieving people do.

And Sequoia kind of feels like, you know, there's, there's this very unique thing in venture capital with the, with the people at Sequoia in that way around work.

Yeah. It doesn't feel like work. It doesn't feel like you're working too hard. You clearly need to have a home system that is supportive of that. Because clearly, if people complain at home, then that creates stress. But if you get that all right, it's a magical—it's the good old days. It's always the good old days. I mean, I think of Sequoia in the late '80s, when I joined, all throughout until now, as the good old days. I don't have a somber period of Sequoia where, oh no, maybe the first couple of years when I was suffering. But besides that, I only have the fondest of thoughts.

What about during the dot-com? I think you've talked about this being one of the hardest times. Your first three companies you IPO'd that you invested in, and then the sort of dot-com bubble hits.

Yeah, and it rocks. Yeah, so, so Don Valentine turned the firm over to Mike Moritz and me in 1996. We'd never heard of the word clawback. Clawback is where one of your funds is in trouble and you've taken distributions and now you owe all the money back, and maybe those stocks went to zero and you held them and you owe money back. We didn't even know that existed. Mike Moritz and I didn't know how the back office of a venture capital firm worked. And one day we wake up in 1999, and I knew I owed three times my net worth back to the limited partners. I was insolvent. I could have declared bankruptcy. I know Mike was the same way. And it was war room time. What I mean by war room: meetings through the night.

What do we do? And we had two funds, both deeply underwater. And we gave up all our management fees so we could invest the management fees. And we turned two funds that at one point were about 0.3x. If the fund was 100 million, it was worth 30. And we turned one fund into—and I could be off a hair, but not much—one fund into a 1.4x fund and one fund into a 1.9x fund. And this was a time where every other venture firm, or most other venture firms, used the word Mulligan. For those people that don't play golf, a Mulligan is when you hit the first ball off the first tee and it goes over there instead of over there, and you say, 'It's a do-over.' They called it their do-over fund. And we just refused to have a do-over fund.

And we actually took it one step further, and that is we had individual investors in these things called the side funds. Because we recycled these fees—there were no fees to recycle in the side funds. Holy cow. We were able to bring the main funds up, but these side funds, we charged no fees, so there was no money to recycle. So we wrote personal checks to every one of our individual investors to bring them up to par so no one lost a dime. That was the decision we made in 1999 and 2000. So our nonprofit limited partners did acceptably well, especially compared to NASDAQ. It's nothing to brag about. 1.4x, 1.89x is nothing to brag about. But if you look at the NASDAQ over that time, it was devastating.

And our individual investors all broke even. They all got their money back. And I think that could be maybe our proudest moment at Sequoia Capital.

Because it's easy to thump your chest with a ServiceNow or a Google or an Airbnb, which are terrific wins. But to do the inconvenient, to do the painful, when it goes against your personal interest... I think very few human beings are willing to do that.

You talked about owing three times your net worth. It's a very relatable position for a lot of people. Could you sleep? Were you more difficult to work with? Were you more focused? What mindset did you go into in that role?

Sleep is a funny thing for me. When I go home at night, there's nothing left. I can sleep. I maybe can count on one hand all the times I didn't sleep. For Sequoia Capital, I wasn't more grumpy. I don't tend to get grumpy. I get quiet. But I was extremely focused. You take Mike Moritz and I. Mike is a strategic-thinking Brit with a dry sense of humor. I'm a fun, warm, loving, full-of-empathy Italian with an in-your-face sense of humor. No reason why we should get along. Mike and I are not friends. We're not enemies. We were colleagues. We made it up as we went along. And we were extremely complementary. And we just got very, very serious. I should say he took the lead during that time. When Mike and I ran Sequoia,

Mike was de facto chief executive officer. I was a de facto chief operating officer. We had equal economics, equal everything. But I looked to him as the lead. I basically became the lead at Sequoia when Mike stepped down in 2012. And then I had to do his role in mine. But I would say, if I'm brutally honest, under his leadership, in 1999, we got out of that jam. Why are startups so unbelievably hard? Because you're creating something from nothing. Something new that the world magically wakes up and realizes it needs. Not wants, it needs. And I call that black magic. Everything else is easy. I tell founders, I can get you product market fit. I can help you fine-tune it. But if you have the black magic, there's no one better than Sequoia Capital to help you build the business.

And I am 100% sure of that. Why is that? Because we have the operating experience, we have the know-how, we have made more mistakes than any venture—I almost want to say than all venture firms combined. We've been around for 52 years. We used to have in our marketing pitch a slide that says all the mistakes we've made. I can't tell you how many founders ripped that slide and used to put it in their own personal. They throw away the rest of the presentation, all the logos, the IPOs. They didn't care about that, but they cared about the mistakes that we made. And I often tell founders our job is to help you make one less mistake, to help you see around the corner. Because that's what building a business is.

Building a business is 90% execution, 10% strategy, and it really is just putting one foot in front of the other in the right direction.

What does that mean, 90% execution?

Go, go, go. What kind of VP of Sales do you hire when? How fast should you ramp? What can you expect from marketing? What percent of leads should come from marketing in the first two years? What kind of caliber engineer do you want in your first 10 employees? And on and on and on and on. What is the simplicity of the product versus the complexity? How should you position it? Should you position it as a point product or as a platform? How do you expand? Those are all the things that we know individually and as a partnership, just in the back of our hands. And you'd be surprised. A lot of venture folks do not. I tell founders, look, if there's 10 venture investors, two or three know what they're doing.

Two or three will be damaging to you, either because they have terrible judgment or because they're concerned about their trajectory in their own partnership. You don't count. You think you count. And six are just completely useless.

And that's just the reality. Yeah, in some ways it's like, if you can get at least—if you, hopefully, you get the best and the positive ones. Second, hopefully you get somebody that's neutral, just doesn't—

Yeah, I call them no-ops. No-ops. No-ops. The thing has no operation. It doesn't move.

One thing I've heard one of your partners talk about you is you have this uncanny, unmatched way of figuring out if a company, through a series of questions and meeting the founders, if they're actually... one of these companies that can make it. What kinds of questions are you asking in those scenarios? It's not the things you'd expect. You're kind of coming in around the edges on certain things.

There's different stages of company. There is the one person, two founders, and an idea. There, you're looking to understand the source of the insight. My favorite question early on is, 'How did you get the insight?' And the answer that scares me the most is, 'Three of us wanted to start a company. We got in a conference room. We figured something out.' Now, having said that, many roads to heaven—eBay was started that way. But usually, you look for founders who have had first-hand experience, as shallow as they may be. Zappos couldn't find a pair of shoes. So it can't get any more shallow than that. But he couldn't find a pair of shoes. And you look for founder-market fit. What's that? Founder-market fit is, what right does the founder have to develop a product in that market?

And you look for second- or third-order understanding of the problem. I have to hear more. 'We talked to 10 CIOs. Their cloud security is weak.' I need to hear more than that. If that's where it ends, not good enough. And if the company gets bigger and now you've got product and sales and marketing and so on, you triangulate to see—first of all, you want to understand the vision of the founder, just see where they're going. But then you want to understand if the founder or the chief executive officer really understands the issues of the business. And, you know, those are operational questions. And by doing that, you do three things, two or three things. You understand the founders' appreciation.

You figure out what's right and wrong with the business. And the founder is blown away that you'd even go there because most venture investors don't even know. And you position yourself as the person they want to do business with when the time comes. And when people say, 'Oh, Doug, you win deals, you win deals. How do you do it?' Well, it's not because I have a charm gene. It's because the levels of questions I ask show the founder immediately, 'Holy cow, maybe this human being can help me.' You do win deals. I mean, you are known for that, though. One of the things I heard—I heard a story, uh, about you that

You were, you know, this person that you were going to do business with that said, 'Hey, we might not do it.' And you said—they were on the other side of the country—and you said, 'I'll be there for dinner. Like, get ready. Let's have dinner. I'll be there.' And it was, you know, I mean, and when you were at Sun Microsystems, too, you were like this kind of legendary salesperson. How do you think about getting deals done? Yeah.

The first thing may surprise you. I care deeply. That is... empathy. I care deeply about the founders. I care deeply about my role, in which I'm entrusted at Sequoia. I've actually flown to India for a two-hour meeting—never mind the other side of the country, when we had an India business—to help us there win a deal. And I don't go in with the notion of, 'I have to win the deal.' I go in with the notion of, 'Let me see what's going on here. Let me see if we even want to be investors.' It's not chasing at all costs. And when we go have dinner, I also like to pour a glass of wine, not only down my throat but down their throat, to get them relaxed a little. It's like the first 30 minutes of a job interview.

It's foreplay. The real stuff starts at minute 40, where we're going to really learn about you. So that's how I do it. And I am very proud of my winning rate at Sequoia Capital. But it's through deep caring, deep caring about the job at hand, which includes helping this founder try to achieve greatness. That is really the goal.

Yeah, how do you manage, how do you balance showing that care without being overbearing and kind of tipping the scales?

You don't always get it right. I mean, Frank Slootman a long time ago said to me, "You have a hell of a marketing problem." I guess he had heard that I was an overbearing pain in the ass. That started to disappear out of the water maybe 15 years ago. I was no longer overbearing. But remember, I do have a strong personality. I do speak unequivocally. Even during this meeting, you may have noticed that. I tell people, "Don't look for hidden meanings." The good and the bad, when you talk to me, there's not a second or third-order hidden meaning. You're going to get reality when I speak. And there's not another side to that. That is it.

What's the best position or leverage that you've seen founders get in, entrepreneurs, to negotiate with VCs? Where's the best place I can be coming into a negotiation?

So I think founders, unfortunately, make a mistake. First of all, I think the founders should have a right to maximize price. Let me not be a babe in the woods and say, "Keep price lower so we can own more." That is all bullshit. The founder needs to take care of maximizing price. But within that, they need to understand the following. And that is, we are business people too. We are on eight or nine of 10 boards. And if they're attempting maximizing price, they get one of us on a board and we own 3%, logic would only follow that it's probably not good. People have to understand that the very best deals are win-win deals. And a win-win deal is taking care of yourself because when you're in a negotiation, yourself comes first, but also taking care of the other side.

And when I find founders optimizing their own ownership or something like that at the cost of everything else, it shows me they just have no long-term perspective and they don't understand how business is carried out. Again, I love telling founders when they ask me, "How much do you want to own?" I usually tell them slightly above 100% just as a joke.

Or as a starting point?

Yeah, yeah. But at the end of the day, ownership has gone down and they need to understand that there's enough to go around so everybody can have some... I don't know what the word "fair" is, because I hear, "You've got to pay your fair share of taxes." That drives me crazy. But some reasonable amount of ownership so they can do extremely well and we can achieve our objectives as well.

You're—and have been for decades—one of the top investors in the United States. How are you feeling going in now to 2025, the current state of things, where we're headed as a country?

I feel as optimistic as I have felt since, I would say, Bill Clinton or Ronald Reagan. I think we lost our way. I would say starting the second Obama term—for the last, for 12, for in the second Obama term, uh, and the Biden term, which I thought was a disaster. And by the way, it's not a political comment. I, I did vote for Clinton. I voted for Dukakis, if you can believe that, uh, and so on. So I'm a centrist. You voted on both sides? I voted on both sides of the aisle over, over my life, yeah. But I feel wildly optimistic. When—when taxes go down, revenue goes up. That is in individual taxes, corporate taxes. We need to make America energy independent again. We have more energy than any other country in the world.

We need to make America productive again. We need to lower regulation again. We need to invite corporations to be in America again. We need to produce here again. We need to lower our reliance on China here again. I believe in immigration. I am a legal immigrant. And we should let scientists, farmers, we should let all kinds of people in. But you don't have a country unless you control your borders. So I'm very much for immigration. I'm very much for legal immigration.

You were one of the first people in Silicon Valley to support Trump in the spring and summer of last year. What made you shift that way? And what do you think has changed here with people sort of more openly speaking about supporting on both sides?

So I think in terms of having good reads, I think making investments is having good reads. All these impulses, you have all these set of data and which one's more relevant, how you weigh them and so on. And I started to notice the corruption of the Clinton Foundation and everything that was going on there, without getting into detail. And I was fairly unnerved by that, and I didn't trust Hillary one iota. I'm happy to have a female president—I don't care if you're black, white, green, four legs, I don't give a darn about that—but I did not trust Hillary. I recognize Trump for what he is: a son of a gun of a businessman. At the personal level, a very kind human being. I've had the pleasure—

Kind human being, son of a—you don't want to be on the other side of the table in business at all. I look at his family. If he was such a bad dude, he wouldn't have such a great family. Let me be very blunt about that. He didn't expect to win the election, didn't know what he was doing the first time. The first time, it was sabotaged 10 times over. I knew the spite of this campaign. I knew the Russian collusion was all, you know, you saw what went on in America. The impeachments were a joke. The lawfare this last time was a joke. And I voted for Trump, and then I voted for Trump, and then January 6th happened, and I renounced Trump. It's in my Wikipedia page. I renounced him the day after, not because he incited a riot, because I listened to his speech: 'Go protest in peace.'

He asked for the National Guard. We now find out there's 20-something agents that infiltrated January 6th. A lot more stuff is going to come out. But because I thought it was really dumb, a couple of days before we transferred power, to carry it to that extent. At that point, right or wrongly, the courts had spoken. And while they were sorting it out, we got to move on and to live another day. I thought that was just bad for America. And so I renounced him. And this time around, you know, the whole woke, open borders, Biden, I call it the upside-down world. You know, defund the police. I don't know what defund the police means. It means only partially defund the police. I know what's behind that. But I thought we had just lost our way as a country.

I mean, I could imagine China and Russia just laughing and wanting to see as much of that as possible. And so I was one of the first ones to speak up for Trump again in 2024. And I am super thrilled that he won the popular vote. He, I think, is going to follow through. I am pro-women's rights. I want to be very clear about that. I think he's going to follow through that it's at the state level, there'll be no national abortion ban. And I think his policies are going to—I mean, we're so lucky in America. We have the right geography. We have the natural resources. Can we stop getting in our own way and just build an incredible society here? I believe we need to take care of the environment. I believe all those things.

Yeah. I think as an entrepreneur, the thing that's exciting to me coming into this year is that it feels like in some ways the chains are coming off of regulation, of censoring, and letting people do business, letting big companies do business. That's right. And kind of just let the creativity of America flourish. Let it happen.

Lower the regulations, or lower the regulation. The higher the amount of laws and regulation, the greater the corruption.

Yeah. You've spent a lot of time in China and India, and Sequoia made expansions across the world. The entrepreneurs there are working at such a different pace than most people in the West. And in many ways, you know, we talked about your story, many stories of immigrants and others who are really hungry and who are really pushing. Just like, how do we compete with immigrants here in the United States, in this amazing place that we have, with these people that are really doing everything they can every hour of the day and night to build their ideas?

Well, it's even worse than that if you look at the number of engineering graduates from those countries that put our country to shame. So it starts there. Second, it's the first time those countries have given young people a chance to do something. I mean, think of our generations in 1950. This is what we are. Here we're extremely comfortable. But I think the way to unleash is to take the shackles off. To take the shackles off our youth, to take the shackles off our business, and to let them run. And I think if you do that, we have a good chance to compete. Because if you look at what's going on in China, President Xi has made some mistakes. I was reading that eight out of 10 people in China with over a million-dollar net worth would love to leave.

That is not good for a country. They have a birth rate issue, and they have a whole bunch of other issues. I think we just have to play to our strength, unleash the youth, and let them rock and roll.

In your 60s now, what motivates you at this point?

Spending time with young people. They view... I'm going to trade wisdom for sucking away some of their youthful energy that keeps me a little younger. So I think it's a fairly good trade for both sides, and helping build the next great business of tomorrow. I'm still on nine, 10 boards, and within those boards, there's some fairly meaningful companies. And going for that ride, going for that journey from being the first investor where we usually are, the first dime in the company, usually with one employee like in Nubank, or four founders in Wiz, or two founders in Sierra, or two founders in Island, that's just a thrill.

Yeah. You've talked about mentoring people. You spoke with one of your partners here. Somebody that I've heard mention you a lot who's currently ranked as the number one angel investor in the world is Pejman, who's somebody that you helped and mentored along the way and now has built his own little empire. And I think in a lot of places in the world, it's kind of like opportunity is like this finite resource with some people. How do you think about it? I see you sort of personifying the Silicon Valley ethos.

What a great story with Pejman. I don't know if you know the story. He was a rug salesman. Pejman sold me rugs for my house. 'He sold you rugs?' 'Rugs. He was a rug salesman. A rug AE.' Rug salesman from the Medallion Rug Gallery in Palo Alto. And he and the owner approached me, and they said, 'You know, we have contact with a lot of Iranian PhD students. Would you like to meet them?' 'You're like, you're buying a rug, and you kind of look up.' 'Let me tell you.'

I can get you PhDs.

Well, it shows you the extent. I could have been a snob and said, 'No, I'll take another 10% on a rug.' Instead, I said, 'Love to meet them.' And I went to the Medallion Rug Gallery at 6 p.m. And it was almost like a James Bond scene. The rugs came down. The flat screens came up. The PhD students came in. I was the only venture investor there. I went back to Sequoia. I said, 'Holy...' You know, and of course, at first you get teased for two seconds until they say, 'No, I'm serious about this.' And Pejman said, 'Why don't we do an Iranian, the three I's, Indian...' and I said, 'How about the Italians? Don't forget about the Italians.' The Three I event, and we had another event: Indians, Italians, Iranians.

Iranians, PhD students. We had an event three weeks later, except this time I showed up with five Sequoia partners. And, you know, and he never forgot. We never forgot. And then, and that's when the friendship started. And then he became a seed investor. Then he started Pear. He met with, he joined with Mar.

I think he introduced Sequoia to Dropbox.

He introduced me to Dropbox. Is that right? Yeah, and right away, because we don't hog deals, I said to a former partner, Samir Gandhi, and Mike Moritz, 'Please follow up on this. I have other meetings.' We, within that weekend, Mike went to somebody's house and we got the deal signed that same weekend. I'd say also maybe DoorDash, if I'm not mistaken. And as recently as two weeks ago, I got a call, 'Doug, we have an issue in a partnership. Can we do a Zoom call with you?' Help him out. We have a great friendship. And that to me is what work and life is all about.

How do I develop inner peace? How do I come to terms with who I am and the world around me?

Have a great family. Achieve a little something, which isn't to say you've got to be the best. Just some modicum of success so you have that look when you get 50 or 60 years old and you don't have to rely on watching six games of football and five beers, and that becomes the center of your life. Push yourself to do new things. Have great friends around you. Be vulnerable.

Stay healthy. Exercise. Yeah, tell me. I mean, you're—you look great. You've always—I feel like you've always—you're kind of ripped. I'm not ripped anymore. What's your—well, 'anymore,' okay. I'm not ripped anymore. Late 60s, I mean. Yeah. What do you do? What was your—I should say, what was your process on that?

Lifting for many years. A little stretching, because you've got to do stretching. Cardio. Eating well. And as you get older, you change it depending on your health. Now there's more walking, less cardio. I'm playing more golf. If I lift, my back hurts. Anything I push, my back hurts. So I have to almost make a choice whether I play golf or I lift. So I'm lifting a little less. I'm playing golf a little more. I suck at golf. Because there is no handicap. They're hitting the ball straight.

You're not a six handicap?

Yeah, exactly. Much closer to a 60 handicap.

And that's what you do.

Walk, just walk. Walk and eat well and do a little something.

In the words of Clay Christensen, how will you measure your life?

I love the line that someone told Warren Buffett. A Jewish woman told Warren Buffett that she measures her life by the number of people that would hide her if the Germans came looking. What is that? Who would risk their life to hide you? Yeah. That is how you measure your life. I think that's—I read that and it stuck with me like crazy. I'm happy to say that there's a fairly good number of people that would hide me. And likewise, me to them. Thank you, sir. Thank you. Thank you very much.

Divot on next week's episode.

We sold Twitch. I got everything I wanted and more than I ever thought I wanted, right? And then I found myself a month after we sold it thinking like, 'I'm just as unhappy as ever.'