Doug Leone on Sequoia, Fear, Great Founders & Starting Over at 69

Doug Leone spent 26 years helping lead Sequoia Capital through successive eras of technological change. Born in Italy, he came to the United States without speaking English and carried the insecurity of an outsider into his career. That fear became fuel: whenever he felt himself falling behind, he forced himself to start over. After stepping down from Sequoia at 65 to make room for the next generation, he returned four years later. Now he considers himself a low-level analyst again, racing to understand an AI revolution that he believes is rewriting business more radically than anything he has seen before. Leone explains the three questions he asks before making an investment: Would he put his children's money into it? If he could make only 20 investments in his life, would this be one of them? Could it return the entire fund? He is interested only in extreme outliers—companies capable of returning 100 times the original investment—and says the biggest mistake venture investors make is selling their winners too early. Sequoia once owned enormous stakes in Apple, Cisco, Google and NVIDIA, but even the greatest investors failed to anticipate how long exceptional companies could continue compounding. His role as an investor is not to shape a founder's technology. It is to help turn a product into a business: recruiting the first team, building sales and marketing, navigating crucible moments and preserving the founder as the soul of the company. He describes backing David Vélez before Nubank existed, what Fred Luddy's unusual ServiceNow pitch revealed about him and why Sequoia looks for the same qualities in founders and its own partners: a hypercompetitive person with a heart of gold. Leone also discusses trust as the accelerant that makes business move quickly. Trust requires both competence and good intentions, and it is earned by helping founders when they are most vulnerable. He explains why founders should architect their boards as carefully as their products, why productive disagreement is different from argument and how to deliver difficult feedback so it can actually be heard. He closes with lessons from his longtime partner Michael Moritz: listen to the exact words people choose, put the other person first and always ask what a company could become if everything goes right. Show notes: https://www.davidsenra.com/episode/doug-leone Made possible by Ramp: https://ramp.com AppLovin: https://applovin.com/senra Deel: https://deel.com/senra Chapters (00:00:00) How to Dominate for Decades (00:03:17) Turning Fear Into a Tailwind (00:05:40) Immigrant Drive, Hard Work & the Beach Club (00:12:19) Simplifying Life & Choosing Discomfort (00:14:37) The Homeless Sequoia Partner With No Plan B (00:16:49) Stepping Down, Coming Back & Starting Over (00:20:04) Why AI Is Different From Every Previous Technology Shift (00:22:13) Doug's Three Investment Heuristics (00:23:52) The Cost of Selling Great Companies Too Early (00:25:39) Helping Founders Turn Products Into Businesses (00:28:28) David Vélez, Nubank & the Psychology of Founder Support (00:32:25) Why Founders Must Remain the Soul of the Company (00:36:13) Torturing Yourself Into Greatness (00:39:57) Don Valentine, Succession & the Sequoia School of Hard Knocks (00:44:28) Staying Grounded & Developing a Sniffer for People (00:47:46) Hypercompetitive With a Heart of Gold (00:50:13) Fred Luddy, Israeli Founders & Radical Directness (00:52:28) Trust Is the Accelerant of Business (00:59:57) Starting From Zero & Hunting for the Next Great Founder (01:05:59) Architect Your Board Like Your Product (01:10:24) Truth, Disagreement & the Art of Difficult Feedback (01:13:43) Humanity, Introversion & the Value of Relationships (01:18:18) What Doug Learned From Michael Moritz Learn more about your ad choices. Visit megaphone.fm/adchoices

Speaker names marked ? are inferred from speaking time and the show’s known hosts — they are not voice-verified.

• 0:02David Senra?

  All right, we were just talking before recording and you just said something that's very interesting. We're talking about people that dominate for decades. You're one of them that's done so. And you said, "An interesting question is to ask how and why somebody would dominate for decades." What's your answer to that?

• 0:15Speaker 01

  My partner in India said, "There are many roads to heaven." And so there are many ways to dominate. Take Steve Jobs. He had really one job. And he dominated in that domain for a lot of years. Or Jensen Huang. Those are more linear. Those are gifts where you find yourself in the middle of the hurricane. You just want to keep on going because as the world changes, your job changes. What's more interesting is how do you dominate when you have to remake yourself over and over again? And why do you dominate? Starting with the why, I think it's a deep and secure need to remain relevant

• 0:59Speaker 01

  and prove to yourself that you're not getting old and you're not going to be out of date. I mean, if I look back on my career, each time I remade myself, it wasn't really done out of vision of greatness. It was done out of fear of just being gone. Even a few minutes ago, I asked you, "Let's not make the interview be about yesterday. Let's make it about all tomorrow." And I still have that fear at the age of 69. And the how, I think you have to be willing to let go of your ego. I think you have to assume you know nothing each time and you're willing to start at the bottom.

• 1:40Speaker 01

  So when I came back to Sequoia, they gave me this fancy title of chairman. We were in front of our LPs, our investors, the first time about six months ago. And someone asked me about chairman. I told them, "It's a bunch of bullshit." What I really am is an analyst. I'm a low-level analyst and I have to prove myself. I just got back from vacation just this morning. I've had 90 days of getting all calibrated. And my partner's asked me, "How do you feel after 90 days?" I said, "I feel like I'm good for nothing." I feel like I've entered and AI has gotten further away from me than when I first started 90 days ago.

• 2:25Speaker 01

  And so I'm terrified. I told one of my partners just an hour ago that if nine months from now, which is the one year since I returned, I feel just as irrelevant, I'm going to take myself out. And so I don't know if I can do it yet another time. And therein lies the fun and therein lies the answer to your question.

• 2:46David Senra?

  Do you know who Jimmy Iovine is?

• 2:48Speaker 01

  No.

• 2:49David Senra?

  Okay, Jimmy Iovine, he, another guy dominated for decades. He was in the music industry for 50 years. But a lot of people know him because he's had the insight to start building businesses with his artists. So he co-founded Beats with Dr. Dre. They wound up doing Beats Music and the headphones. They sell to Apple.

• 3:04Speaker 01

  I think he's the guy that was involved with the Beatles at the very end.

• 3:08David Senra?

  John Lennon.

• 3:09Speaker 01

  Yeah, John Lennon.

• 3:10David Senra?

  He was an engineer and a producer for John Lennon.

• 3:13Speaker 01

  He just showed up on a Saturday and next thing you know, yes.

• 3:15David Senra?

  You'd love him. He's fucking Italian from New York.

• 3:17Speaker 01

  Yes, I know who he is. I forgot his name.

• 3:19David Senra?

  He's awesome. I did an episode with him, but now we've become friends. We talk all the time. He's a very extra character. But there's two things that where you were talking that he said the same thing. He's like, "I don't have a rearview mirror." He said the same thing when we said that. I was like, "I don't want to fucking talk about the past. I want to talk about what I'm doing now."

• 3:31Speaker 01

  Yes.

• 3:31David Senra?

  He's like, "There's no trophy room in my house."

• 3:33Speaker 01

  Yes.

• 3:33David Senra?

  "I can't even tell you what I did five years ago because I forgot. I'm worried about tomorrow." That was very interesting. But then my question, you brought up being terrified and then you said fear before that. What's your relationship like to fear? Because he gave me some of the best advice. He's like, "Most people, when they feel fear, they let it be a headwind." He's like, "I trained myself to make it a tailwind. As soon as I feel it, that means I have to fucking go forward right now."

• 3:55Speaker 01

  Yes.

• 3:55David Senra?

  Right now. Do not think, step forward.

• 3:57Speaker 01

  Yeah.

• 3:57David Senra?

  What's your relationship with fear? How do you deal with it?

• 3:59Speaker 01

  Throughout my life, I felt an awful lots of fear. And it's always been the challenge in front of me. I was afraid of public speaking. I made sure I became the very best. I was afraid of heights. I worked on sailboats. I made sure I was up 96-foot masts. That whenever I feel it, I face it head-on. It's almost a challenge. Look, there's a story that my partners know. I had to get a tooth removed. I actually drilled a two-drill for a Ford canal. And I had to go to a meeting right after that. And I told the dentist, "Drill without any Novocain." And he says, "You're out of your mind."

• 4:40Speaker 01

  And my whole life, I wanted to see if I was a badass or not. In other words, am I fake badass that has this envelope nobody could tell? Or am I really a badass on the inside? And I told the dentist, "Take it out with no Novocain." And he drilled and I jumped. And I told the dentist, "I'm will move again." And I didn't move again. And I used the trick of thinking what it must be like to go to war and lose an arm or two legs. That's pain with consequences. Mine was pain with no consequences. And so I just said, "It's just nerve endings from there to my spine, to my brain. Fuck it, I'm not moving."

• 5:23Speaker 01

  Now, I had to go home and change my shirt because I was a puddle of sweat. But I didn't move. And so I love fear. It does wonders for me. It gives me the challenge to overcome that gives me then a sense of security.

• 5:40David Senra?

  You mentioned working on sailboats. I read something about you. You were doing this when you were a young kid, right? We were in high school. We started working on boats.

• 5:46Speaker 01

  Yeah, high school and college.

• 5:48David Senra?

  And it was across the street from, or across the river from a country club?

• 5:51Speaker 01

  No, it was in a country club. The country club has the yachts, in the water, in the pool on the side.

• 5:56David Senra?

  Do you remember what you said about this?

• 5:58Speaker 01

  Yeah, I know exactly what I said.

• 5:59David Senra?

  Can you repeat it?

• 6:00Speaker 01

  I said, "I'm going to get those fuckers later." You know, it was all the rich kids.

• 6:04David Senra?

  What does that mean?

• 6:05Speaker 01

  Well, it was all the rich kids, you know, being the lifeguards, talking to all the girls. At the age of 16, 17, by the pool, having the times of their lives. Kind of having the life that some of my kids have now. And I was crawling in sailboats, running wires through sweating like a pig, working overtime. And just looking over at kids my age having the times of their life. And I said, "I'm going to get you all fuckers later." And I did.

• 6:35David Senra?

  That is such a reoccurring theme throughout the history of entrepreneurship. I felt it that way. Like my, people are like, "Oh, I'm the first person to go to college." Like no one in my family even graduated fucking high school.

• 6:45Speaker 01

  Yeah.

• 6:45David Senra?

  And I remember going to public school and there was this kid that would drive. He had like $130,000 worth of cars, like 20 years ago. And he was in one of my classes. And his dad owned like a shit ton of Domino's franchises. I had no idea we were phenomenal businesses. The insight that he had phenomenal business, he's like, "Yeah, me and my dad just went to lunch." It took a helicopter, like 200 miles to lunch. I was like, "What are you, I'm working full-time at 15. What are you talking about?" And that's exactly how I felt. I'm working on this, this other, for my other podcast founders. I'm starting to read about Mike Tyson a lot. And Mike Tyson has a video where he talks about the difference where you just mentioned. The way he grew up compared to the way his kids. And he says his kids would be like, they're like 15 years old and they're like, "Look at the star athlete at school. It's like, wow, look, it's Tracy. He's so amazing." And he goes, "I wasn't like that."

• 7:28David Senra?

  He goes, "What I thought when I saw these people is, wait till I get my shot. Wait till I got my chance. I will show you."

• 7:33Speaker 01

  Exactly.

• 7:34David Senra?

  "When I come around, what that actually means."

• 7:36Speaker 01

  Now, what the trick is though, is to use that as a motivator by not being asshole when you're later in life. Don't do unto others as it was done unto you. So how do you take this incredibly negative experience, make it a positive experience? And then as you mature, use it in a positive way for the benefit of, not only for yourself, but everybody else around you. Point one.

• 7:59David Senra?

  Before you get to point two, how have you done that?

• 8:02Speaker 01

  My need to get them back, them, kind of ended by the time I got 50 or so on.

• 8:08David Senra?

  50?

• 8:09Speaker 01

  Yeah. Well, yeah. It seems like a long time, but it's not. It took, it took a good 30 years. It took a good 30 years to overcome that weakness. Because in some ways it is a weakness. Because it's a false narrative. Those were not bad kids. And I don't want to live in a false narrative. I finally outgrew it. But the other point, which is more important for me anyway, is what you do with your kids. To give your kids that level of life is not necessarily a good thing. Because what they're going to be missing is the drive that Mike Tyson, or you, or I, or many people that we know had. And that's not the best thing ever.

• 8:51Speaker 01

  I think you have to inject some misery in your kids' lives so they have that hunger. It can be fake because they know it, but you can't give them everything. Because otherwise they won't be hungry.

• 9:02David Senra?

  How many people that grew up wealthy have that drive that you know?

• 9:06Speaker 01

  A good amount of kids that grew up wealthy have drive. Drive can be caused by many things. We have a partner who I'm sure grew up with means that his drive came from competition with his twin brother. They were, they both attended the same college. They both were wide receivers on opposite side of the fields. They adore one another and they love nothing more than beating the shit out of one another. So drive comes in many ways. I have a son-in-law who is driven like crazy. Older brother, I'm sure they fought. He cannot stand cheese because his older brother loves eating cheese. I mean, it shows you, it shows you these little things. You know, we had a session at Sequoia where we checked in.

• 9:51Speaker 01

  And one of my partners suggested for the check-in to say, "What is the vignette in life that made you who you are?"

• 10:01Speaker 01

  And one partner said, and he cried when he said that. A lot of us cried. He got on a bus when he was 11 or 12. And a girl that he thought was cute looked at him and said, boy, you're fat. Now, to you and I, that sounds like a minor thing. To him, it changed his life. Forty years later, 30 years later, he still wakes up at four o'clock to work out. I mean, the stories were, in some ways, ridiculous. But in some ways, it's really amazing to see how a little kid is affected and how long that vignette carries someone through life.

• 10:45David Senra?

  What was your vignette?

• 10:46Speaker 01

  It was the beach club. It was the being ridiculed in high school because I couldn't speak English. It was the being made fun of in a classroom. It was being called pasta in high school. All the things that, you know, because I was an immigrant. All the things that, when you're not strong enough, you survive, you endure, and then you try to overcome. And doing it while remaining a good human being.

• 11:14David Senra?

  I want to tell you about the presenting sponsor of this podcast, Ramp. I have been reading a lot about SpaceX lately. SpaceX is one of the most valuable businesses in the world. And one of the main themes in the history of SpaceX is constantly attacking and questioning your costs. Ramp helps many of the most innovative businesses in the world do exactly that. The median company running on Ramp cuts their expenses by 5%. And one thing SpaceX has demonstrated is that a religious dedication to controlling costs can help actually increase revenue because you can pursue opportunities you couldn't otherwise. And we see that in the Ramp data, too. The median company running on Ramp also grows their revenue by 16%. So when you're running your business on Ramp and your competitors are not,

• 11:56David Senra?

  you have a massive competitive advantage that compounds over time. Ramp is the only platform designed to make your finance team faster and happier. Many of the top founders and CEOs I know run their business on Ramp. I run my business on Ramp, and you should, too. Go to ramp.com to learn how they can help your business save time, save money, and grow revenue. That is ramp.com. You mentioned inducing, the importance of inducing misery into your kids' lives. Do you still induce misery into your own?

• 12:24Speaker 01

  No, I've gone full cycle and have spoiled myself with material things, realized they don't make me happy at all. Got rid of a whole bunch of material things. I sold my fancy cars at a great discount. I just want them gone. It was one day I woke up, I just didn't want to have cars with vowels at the end of the name. I just got rid of them. I just wanted a more simple life. I wanted to, to start to enjoy the little things in life. Now, having said that, I do have toys. I don't want to make sound like I'm leaving the life, I'm leading the life of a monk. But I've shedded assets on purpose, just to simplify my life. And if you will, get down to the really important things in life,

• 13:09Speaker 01

  which really, at the end of the day, is your family and friends. That's really the most important thing.

• 13:15David Senra?

  Not just shedding material, like inducing pain or misery into your life at this time, at this point in your life?

• 13:21Speaker 01

  Well, I think going back to work, definitely, that was not the easiest move I've ever done. And I'm in the middle of that right now. I'm quite miserable at Sequoia right now. Not because of what anybody else does, because I feel that three months into it, I'm really good for nothing.

• 13:37David Senra?

  Let's say when you were building, right? Your first few decades there. Did work always feel like work? Or is it something like you just like, you were addicted to doing it? You're obsessed with doing it?

• 13:45Speaker 01

  No, it felt, it felt like an overwhelming challenge that I didn't know how to conquer. And I felt that until the day I stopped working at 65.

• 13:57David Senra?

  You got to spend time with Jimmy Iovine, dude. I'm telling you, I think you'd love him. He's been around some of the greatest, you know, people, or most famous people in history. You know, worked with John Lennon and Bruce Springsteen, Dr. Dre, Eminem, just like crazy people. And he's like, everybody great has a bend in the pipe. There's just something wrong with them that just makes them different. And also, like, the same side of their genius is also their dysfunction. And he's like, for himself, it's the same thing. He's like, he's like, it was never fun to me. It was, work always felt like work. And he goes, my bend in the pipe was that it has to be. And what he meant by that is like, if I'm taking on this business, if I'm taking on this project, if I'm telling you I'm going to do something, I will do it to the point where I almost kill myself before I give up. I have to succeed at it. Very similar to like, the vibe I'm getting off of you.

• 14:40Speaker 01

  Yeah, look, failure was never an option in my life. I had no Plan B. I remember when I was made a partner at Sequoia, I was down to zero money. I actually, I have never said that to anybody. But there was a time in my first month where I became a partner that I was homeless. I slept in my car for a week. I showered at 3000 Sand Hill Road. I was down to no money. I was down to zero, zero money. Sequoia, back then, would buy you a car when you made partner. I bought a car. I didn't have a home. I slept in my car for a week. And then, and then I had some money and I started getting a rental and so on.

• 15:25David Senra?

  What was going on in your life that you were homeless?

• 15:27Speaker 01

  I went through a divorce when I was 30 years of age and I gave my ex-wife everything. And I was living on my car allowance, so $400 a month. So I didn't have a home for a month. And so, for a week or so, I slept in my car. And then, one of the other associates let me live with him for about three weeks. And then I had enough money to go buy, to go rent a, to go rent an apartment. So I chuckled for a week that I was a partner at Sequoia and I was homeless. I was the only homeless partner at Sequoia I've ever had. I don't think I've ever told that in a public setting.

• 16:04David Senra?

  I mean, at this point, you can't go any lower than you already are.

• 16:07Speaker 01

  Oh, no, you could go a lot lower. First of all, I was healthy. So you can get a lot lower than that. You can be sick with a disease.

• 16:14David Senra?

  Good point.

• 16:15Speaker 01

  And second, I was a partner at Sequoia. Are you kidding me? My, my present value, my future earnings are going to be terrific. So I was in panic. I just knew, it was only an inconvenience. And I saw the humor in that for about a week. I mean, clearly, it would not have been funny to be homeless for a lifetime if you're truly homeless. And that's not funny. But in my case, it was, I was a partner at Sequoia showering at the sund, at the shower on 3000 Sand Hill Road, parking my car a little bit further away from the office and sleeping in my car.

• 16:49David Senra?

  So go back to, you're saying that the level of discomfort that you felt when you came, right now, that you're, that you're currently experiencing. Why did you retire to begin with? And then, why did you?

• 16:58Speaker 01

  Well, I didn't retire. If you found a company, you have season seats. You can stay as long as you want. You can take it public. You can sell it. It's your gig. I didn't found Sequoia. I was a hired gun. So it seemed to me the right thing to do is to get out of the way and let the next generation have their turns at bat. Don Valentine, he founded it. He stepped away at around the age of 63. I figured 65 was the natural age. And on my 65th birthday, I stepped down. I chose a successor.

• 17:31David Senra?

  Did you want to step down, though?

• 17:33Speaker 01

  It wasn't a matter whether I wanted or not. It was the right thing to do for Sequoia. And so, I chose Rulov. I was the old king. He was the new king. It seemed to me that being on the old king with the new king around, you shouldn't be around, you should be removed. And so, I stepped out. I was on 10 boards. And I thought that would keep me busy. I founded a biotech company. I thought, 10 boards, biotech company, I'm going to be busy as heck. Not even close. Because I had the curse that all my companies were working. When a company's working, there is no, there's nothing to do.

• 18:17Speaker 01

  And so, I had a great backlog of companies, and I wasn't busy. So I started taking drum lessons and guitar lessons and piano lessons. And that took me for about a year. And after a year, I thought I was going to lose my mind. It turned out, Rulov stepped down, Pat and Alfred took over. They weren't the kings I chose. And 30 days into it, they came to my house and they said, would you like to come back? You're not on 10 boards anymore. You're on six boards. We sold four companies. There were companies like Wiz and so on. And I said, sure. And we cut a little deal in an afternoon and a, you know, on a single sheet of paper that we scrabbled.

• 18:58David Senra?

  Did you see that coming?

• 19:00Speaker 01

  They always wondered to me publicly for the two years before, why aren't you around more? And my answer was, it seemed to me that it's best to stay away and let the new king just do his thing. And when the old king, new king dynamic went away because Rulov was gone, it was much easier for me and for them. And so, they came over, surprise visit. I don't know why they wanted to see me. And I said, sure, right on the spot. It wasn't that long a conversation.

• 19:32David Senra?

  Yeah, that's why I asked if you saw it coming, because you.

• 19:34Speaker 01

  No, it was, it was, of course. And we agreed that I would attend partners' meeting. I would be in a cer, in the inner circle. I would help them spot crucible moments, as we say, to figure out how to navigate them and make a couple of investments. And I've done everything but make a couple of investments. I told them I wanted to do nothing for 90 days. I want to get calibrated. And here I am now, day 91, panicked.

• 20:04David Senra?

  Yeah, but I would, I mean, you, you obviously know this, like, we're going through this massive technological revolution, this technological shift. Somebody with decades of experience that has seen so many things and so many different companies and founders come and go, like, that's invaluable, invaluable wisdom to have inside the company.

• 20:20Speaker 01

  Yeah, except that the world changes and this change more dramatically to, through AI.

• 20:26David Senra?

  Yeah, but how many, how many different changes have you been through?

• 20:29Speaker 01

  I understand, but this is the most radical change. This is an industry revolution kind of change. And so, as I said, I'm 90 day into it, I feel further away now than when I got into it. I mean, look, we're looking at a company, I came back from vacation over the weekend. I saw a memo, I won't tell you the name, of a startup company that wants to raise money without anything, a 10 billion pre. You know, it gets my head spinning. I, I didn't know if it was a joke. I didn't know if their partners wanted to do that to make fun of me. No, because they would do that.

• 21:05David Senra?

  Yeah.

• 21:06Speaker 01

  And it wasn't a joke. And so I've never seen revenue growth at this pace. I've never seen prices like this. One could say, all you have to do is F3 zeros. It's the same type of business, but it's more complicated than that. And so I've seen a lot of changes. I have good instincts.

• 21:25Speaker 01

  But I don't want to rely too much on, on the past. I want to use the past as a little corner here that I check things against. And I have my heuristics, my three or four questions I ask myself with each investments, I can discuss those. But I'm focused on what the world's going to look like.

• 21:40David Senra?

  I would love to know these questions and these heuristics that you ask. I'm very skeptical because I read, I read history for a living, right? And every time throughout history, you hear, this time is different, this time is different. And it's never different, right? And, but this time actually might be different. So I was like, well, who could I talk to that could actually answer this question for me that's, they're seeing a lot more. And so I was talking to Michael Dell about this.

• 21:59Speaker 01

  Yeah.

• 22:00David Senra?

  And I asked, I was like, is this time actually different? And he's like, yes. And then he gave like this, we had like this 30 minute talk where he actually went through why he thinks that actually business is being rewritten and this time is actually different. What are the heuristics that you were mentioning earlier?

• 22:13Speaker 01

  I have two or three of them. One of them is, would I put my kids' money into it? Second, if I only make 20 investments in my life, is this one of the 20? Third, can I return the whole fund with this investment? And if I don't pass those three, I'm not going to make the investment. And the reason I put my kids, it gives me the judgment of quality, the reason for the 20, it raises the bar of, it could be investable, but is it really the home run, which is the same thing as the third? And those are questions that I've always asked myself.

• 22:56David Senra?

  Say more about the, the, the bounding of only having 20.

• 23:00Speaker 01

  There's probably 200 investments that you can make in your lifetime. And a lot of them are going to return two X of money, three X of money. I only want the ones where you can return 100 times your money. That's all I'm interested in. I want the outliers. I want the ones that really drive tremendous return. That in my lifetime were, first it was 100 million, then 500, then a billion, then 5 billion, then Alfred hit 10 billion, and now Sean hit 20 billion. I, I told Sean, you fucker, you kind of ruined it for me. I'm not going to show up now with a $4 billion gain.

• 23:35David Senra?

  Was that SpaceX? What was that?

• 23:36Speaker 01

  Yeah, it's SpaceX. Now, we haven't cashed out yet or whatever, but you know, there's a shot of a, of a $20 billion gain and more. And so he ruined it for all of us.

• 23:46David Senra?

  The ones that you're best performing investments, I'm always curious if like you can actually see it back then.

• 23:53Speaker 01

  They always surprise you on the upside.

• 23:55David Senra?

  Right?

• 23:56Speaker 01

  Always. They never surprise you when they fail because that was always one of the scenarios you had, you had thought about. Or mostly as, but when they run, they surprise you. And every venture investor has made the mistake of selling too early their winners, every single venture investors. Because if you look at the, at the great companies, they've compounded 20 years after the IPO. Nvidia or, or Google or Meta. If you had a little sniffer that this thing had essentially an unbounded market for many years, you should never sell a share. And you can make way more money holding those. Cause if you're compounding a $5 billion gain, that can turn into a 50 billion gain.

• 24:39Speaker 01

  If we held Google and had sold Google, that'd be worth, or Nvidia, that'd be half a trillion dollars. You know, and there's no investments that can give you that.

• 24:50Speaker 01

  And, you know, we own 20% of Nvidia. Think about that. I mean, you know, we own 10% of Google. And, and there's many others, you know? Apple, are you kidding me? We were the first investor of Apple, in Apple. Cisco, we own a quarter of Cisco Systems. You know, those are big ownership in very big companies. But we all made that mistake.

• 25:13David Senra?

  Yeah, sometimes the best financial decisions are not financial at all. So if you look at, like, if you think about the wealth created by Sam Walton, yeah, obviously he gave it away before it accumulated to his kids, but it, you know, if it was still in one person, it'd be worth, you know, half a trillion, whatever the number is now. And you realize like he wasn't making a financial decision. He just liked Walmart. It goes back to what Nick Sleep said. Nick Sleep has this great quote where he's like, the best investors aren't investors at all. They're entrepreneurs who never sold.

• 25:36Speaker 01

  Yeah, exactly. That's exactly right.

• 25:38David Senra?

  You've mentioned a few times, I've heard you in other places where you're like, hey, I'm on boards of cybersecurity companies. I don't know anything about cybersecurity. I'm on board a financial services company. I don't know anything about financial services. What does that mean?

• 25:50Speaker 01

  It means that I'm interested in the business and the building, the business of a company, not in shaping the technology of a company. Meaning that I'm not a product manager type. That's what founders know. In some cases, that's the only thing they know. The only thing, they're, they're getting younger and younger. They're, they're, they're 23 years old or 22. They're engineers and they know that domain. If they have to rely on me to help shape the product 10, 20%, we're in big trouble. Okay. But then you have the business, you have the selling of shares, not the selling of product. And in the selling of shares, you have to wrap everything into it, which is the analysis of market,

• 26:32Speaker 01

  the product marketing of the final 10% of the product, so it's saleable. I can help with that. The product marketing and messaging, the demand gen, the lead gen and the revenues. Then you've got support and counting and so on. Oftentimes, companies break, or they sub-optimize that. That's what they get involved in. And in order to do that, I don't have to be an expert in the technology. In fact, I'm only partially interested in technology. I'm much more interested in, in helping founders build a business.

• 27:04David Senra?

  Say more about that.

• 27:05Speaker 01

  So how do you take a 22 year old that when he comes to us is an outlier in something in life, probably IQ 150 or above,

• 27:17Speaker 01

  all the adjectives that venture guys use in the negative sense, I use in a positive sense. Irreverent, shithead, they don't listen. Love it. Give me those founders all day long.

• 27:27David Senra?

  Yeah, say more about that. Why do you like?

• 27:29Speaker 01

  Oh, because who wants a founder that changes his or her mind depending on who they last spoke to? I want a founder who for the last five months has gone to sleep and has woken up three hours into his sleep, just can, just thinking about the problem, thinking about the solution, crystal clear in what they want to build. No one can detract them, driven like crazy and so on. That's what I want. But now we got to build a business. And so who do you recruit as the first 10 engineers? What does your first salesperson look like? Do you want people that are up and comers? No one that's established and great is going to join you as a startup.

• 28:10Speaker 01

  That means you have to have an eye for these up and comer people in sales and marketing because the main people are, are going to play it a little safer. And so to help navigate all those sets of issues, that is what we at Sequoia, I think are the very best in the world at.

• 28:28David Senra?

  Can you give me some examples of the founders that you partnered with that you feel you had the best partnership with? That responded to this, that you helped build and shape and build their business with them?

• 28:37Speaker 01

  With David Velez of New Bank. And the reason I choose him for this example is that he was an associate at Sequoia, so I knew him well. I hired him out of Stanford Business School. And I had to give him the bad news that we were not going to open a Brazil office. After he moved to Brazil, he, he committed to Sequoia, he moved to Brazil, we made two investments. And we finally figured out there are no engineers, a few engineers come out of Brazil. And everything coming out of Brazil was, we are the Uber of Brazil. We are the DoorDash of Brazil. No real novelty. And one, we had to make the call, hey, David, we're not going to open the Brazil office. We offered him a job in California.

• 29:20Speaker 01

  And he had a notion of a financial services business, a credit card business in Brazil.

• 29:27Speaker 01

  Minor problem. He wasn't from Brazil. He knew nothing about financial services. But he had a heart of gold. He had a heart and a heart of a lion. So he was a good man with driven like crazy and no one could stop him. And so we seated him. And I remember the call one night I was epic roast house. I still remember I get a call at dinner. It's him. We committed to a million dollars. He says to me, what do I do next? And I was in the men's room. I took the call from the men's room. And, you know, we talked it through. He knew what to do next. He was just all alone.

• 30:09Speaker 01

  What do I do now? It was more a I viewed it more as a as a psychological assistance call than a call on what to do next. He wanted some support and we made a plan of the first two or three things and he didn't miss a beat. He didn't miss a single beat for the first two or three or four years. And we built a company now worth, I mean, it was big numbers a few years ago. It's $60 billion now. Like I said, I just saw a startup that wants to raise money at $10 billion pre with no code. So I don't know what things are worth anymore.

• 30:44David Senra?

  Well, Devi has a fantastic reputation. There's a ton of people that have come on the show or people that want to come on the show. And I always ask them like, what other founders should I talk to? It's like, this guy is incredible. This is surprising. So an associate at a venture firm then becomes a world-class founder. Is there other examples that you can think of that that follow his pattern?

• 31:01Speaker 01

  I've seen it the other way. I haven't seen too many associates becoming founders.

• 31:06David Senra?

  Yeah. You're actually one of the few. I think most VCs are full of shit when they say, oh, the founder is the star and the founder is the most important. You use this thing where like the zero to one is the black magic. And like, that's the founder's job. I can't help with that. If you need me to help with that, then we're all fucked.

• 31:21Speaker 01

  We're all fucked.

• 31:21David Senra?

  And he's like, if the VC could do that, they'd be founders then. And I'm like, you know, Devash from Iconic?

• 31:26Speaker 01

  Yes.

• 31:26David Senra?

  So I just

• 31:27Speaker 01

  He's a killer.

• 31:28David Senra?

  I just had a fucking crazy lunch with him.

• 31:30Speaker 01

  He is a

• 31:31David Senra?

  Dude, you should sit in our conversations.

• 31:32Speaker 01

  He's a killer.

• 31:33David Senra?

  I wish we just recorded that. But I literally just came from there. And I was talking to him about you. And because I'm like, I actually think Doug believes this. I think when other VCs say this shit, like, they're full of shit. They actually want to be the guy. And they're very uncomfortable, you know, not saying, no, I'm actually assisting them. I'm in the service business.

• 31:50Speaker 01

  We are the service

• 31:51David Senra?

  I think you actually fucking believe it.

• 31:52Speaker 01

  No, we are. And what the trick is, is to retain that founder in the company forever if you can, and for as long as possible. Because once you lose that founder, you do lose the soul of the company. A company has many refounding type moments. And we saw with Meta. Think of what Meta would be without Instagram. That company might be gone. And who pulled that off? Who bought that company on the weekend? We closed the investment in Instagram on a Thursday. And he sold it on a Sunday. Great IR, but we didn't make any money, really. And so you want that founder in the in the building for as long as possible. Think of the refounding of Apple.

• 32:37David Senra?

  Your partner, I quote this on my other podcast all the time. Moritz has that great so he wrote, obviously, The Little Kingdom in whatever the 80s or 70s, whatever it was. And then he updated it in, I think, 2009 to the Return of Little Kingdom. That updated forward. Again, Moritz is a crazy writer. Like, his writing is

• 32:52Speaker 01

  He's incredible. You should have seen his memos internally, his reports to the limited partners were funny as heck.

• 32:59David Senra?

  It kills me because I read biographies for a living. And that 60 page, you know, all these obscure ones that are not, and people are not supposed to have, they all come to me anyways because I do this for a living. And I sat down and read the Don Valentine one that he wrote in one sitting. And then somebody that's mentored by Moritz that I'm friends with, I backchaled like, dude, I gotta fucking do a founders episode on this. And it came back absolutely not. I'm like, god damn it.

• 33:20Speaker 01

  I remember that when I was, there's Mike and I, you know, we both ran Sequoia. A cold-blooded strategic Brit and a tactical Italian, gregarious Italian. We had no business being partners. But we made it work for 25 years. But I remember I had a dictionary in my desk, a little black dictionary, because Mike, in a partners meeting, he would use a word that you had to know the meaning of because it was the key to the sentence. I remember faking like I'm going to the bathroom, going and look it up. Like, what does that mean?

• 33:56David Senra?

  Well, the writing that he put in there, I think he said, you know, turnarounds are difficult no matter what. In technology business, they're doubly difficult. They're almost unheard of. He's like, when has there ever been essentially a refounding of a technology company in the middle of a turnaround? And then he has a great line. He was like, and the first time, you know, he had a partner, he had a co-founder, the second refounding was by himself.

• 34:19Speaker 01

  By himself, yes.

• 34:20David Senra?

  That even if people don't read the entire book, which I'd highly recommend reading, just buy the Return of Little Kingdom and read the foreword that Michael Moritz wrote.

• 34:27Speaker 01

  Yeah.

• 34:27David Senra?

  It gives you an insight into the psychology and just how rare the talent that Steve Jobs was.

• 34:32Speaker 01

  One could argue that Nvidia had a refounding moment. That was a graphics chip company. No, and no company up to then had made it through two cycles in graphics chip. And already it achieved the two-cycle thing, which shocked all of us. And then we all fell asleep. They came up with a GPU for many years. Okay, it's a faster CPU. And one day, we all woke up and Nvidia was an AI company. That was a complete refounding by the same founder.

• 35:02David Senra?

  I found one of my all time favorite quotes when I was reading the book Zero to One. The quote says, "The single most powerful pattern I have noticed is that successful people find value in unexpected places. And they do this by thinking about business from first principles instead of formulas." That is exactly what AppLovin has done with their advertising platform. AppLovin connects you with over a billion potential new customers inside mobile games. AppLovin allows you to capture undivided attention. AppLovin ads are full screen video ads that are watched for an average of 35 seconds. That is retention that blows other ad platforms out of the water. And you can launch on AppLovin in minutes. You set the goal and AppLovin achieves it. There's no complex setup, no expertise

• 35:46David Senra?

  needed, and AppLovin scales quickly. They can put your ads in front of over a billion potential customers. Other businesses have seen immediate results, have scaled to hundreds of thousands of dollars of spend per day, and increased their revenue by millions. So you want to get started quickly before all of your competitors are on AppLovin. And you can do that by going to applovin.com. That's applovin.com. When I asked you if you induce any misery into your life, like you were saying you should induce it to your kids, I was thinking about Jensen because there's this book by Taekim called Nvidia Way, which is kind of a company history of Nvidia, but it gives you enough biographical background. You can you can function as a biography of Jensen. And he

• 36:29David Senra?

  says something in there where he's like, you know, I don't like giving up on people. I'd rather torture them into greatness. You get to the end of the book, it's like, oh, he does that to himself.

• 36:37Speaker 01

  Of course he does.

• 36:37David Senra?

  He tortures himself into greatness. He wakes up in the morning, looks in the mirror and asks why he sucks so much.

• 36:43Speaker 01

  And if you're willing to do that to yourself, people will follow you. And people will torture themselves all the way until the goal's met. But you have to be able to do, you have to be willing to do that to yourself. And people see that.

• 36:57David Senra?

  Did you torture yourself?

• 36:58Speaker 01

  Absolutely. My whole life. That's all I know.

• 37:02David Senra?

  So your inner monologue is negative?

• 37:04Speaker 01

  I'm kind of a miserable soul on the inside.

• 37:07David Senra?

  Say more about this.

• 37:09Speaker 01

  I'm always a little unhappy. My instincts are to be unhappy. And I carry a positive vibe and people see me as fun to be around. It's not an act, but when in my private moments, I'm pretty unhappy. Always. I'm pretty miserable.

• 37:28David Senra?

  And nothing changes that?

• 37:31Speaker 01

  My kids. I have had reprieve when I'm with my kids and my grandkids or some good friends on a golf course. I don't, I play golf. I suck at golf. It's the same three guys. So we can laugh for four hours.

• 37:45David Senra?

  I'm going to interrupt you real quick. Does this start when you come to this country? You go from the, you tell the story of being like this precious, like

• 37:53Speaker 01

  Precious? I don't know.

• 37:55David Senra?

  Well, positive boy at 10.

• 37:57Speaker 01

  Sweet, sweet, little boy.

• 37:59David Senra?

  And then at 15. So that divine, Dave Ogilvie has this great way to put this. And he says, all great people do great stuff are divinely discontent.

• 38:09Speaker 01

  Yes.

• 38:09David Senra?

  It's like, just never satisfied.

• 38:10Speaker 01

  A word I've always hated that I've learned to like is content. I hated that word until about two or three years ago. I hated the word content. It felt like settling for something.

• 38:23Speaker 01

  I hated it. Now, as I get older, it's okay to be content at this point. Maybe I'm over the hill because I've accepted that word.

• 38:31David Senra?

  Stop talking about yourself that way.

• 38:32Speaker 01

  No, I'm serious.

• 38:33David Senra?

  And you're not quitting either. I don't like this attitude I'm getting from you.

• 38:37Speaker 01

  No, I haven't.

• 38:37David Senra?

  You're 91 days in, you're not giving up nine months from now.

• 38:40Speaker 01

  I'm not giving up, but maybe it came through that I'm scared shitless.

• 38:44David Senra?

  Good.

• 38:45Speaker 01

  Yeah.

• 38:45David Senra?

  That means you're fucking doing something.

• 38:47Speaker 01

  I haven't done anything yet.

• 38:48David Senra?

  Dude, I've been okay. You're not looking to be out of the game.

• 38:50Speaker 01

  So I was never out of the game.

• 38:52David Senra?

  Exactly. It's my point.

• 38:52Speaker 01

  I was never out of the game. Well, one of them, I don't think of it as a game. I think of it as a business where people are employed. 70% of our capital comes from nonprofits, charities. So I never thought of it as a game. In fact, when I ran Sequoia, I made sure we use all the right words. It's not a game. It's not money in the ground, none of that bullshit. It's a business where we're trying to help founders build great companies so we can have great returns for our limited partners. That's the business we're in. But if I take myself out, it won't be down out of fear. It'd be out of good taste and kindness for my partners. It's not out of fear. I'll never give up out of fear. But if after a year, I'm not good for any, I'm going to be the one

• 39:32Speaker 01

  that's going to have a look in the mirror and say, you're done, that you couldn't do it this last time. Now, I've done a whole bunch of good things in the last couple of years that I want to get into, including starting a company and so on. I happen to think I'm a tip top of my game. But in this one, I have to show it. I haven't shown it yet. And it's all in performance. It doesn't matter what you do, it's the results at the end.

• 39:56David Senra?

  Have you seen anybody in your business stay too long?

• 39:59Speaker 01

  Stay too long? A million people.

• 40:02David Senra?

  Did Don?

• 40:03Speaker 01

  No. Don stepped down in 1993. I believe, I'm going to guess, he was probably 58 to 60 years of age. He didn't stick around for too long.

• 40:20David Senra?

  Why did he stop?

• 40:22Speaker 01

  I think he had enough. I think he had enough. He had two guys in Mike Moritz and me that he thought could take over. He had older people that wanted to take over. And it's interesting how Don told us we were the guys. There wasn't a big conversation. It was a yellow sheet of paper. Don always wrote in green pen and a yellow sheet of paper. One day, we get a little note that said, Mike, 1.1. Doug, 1.1. The other name, another young man, I don't want to embarrass anybody, 1.0. The older guys, 0.7, 0.6.

• 41:05Speaker 01

  That was the vision of the carry for the next fund. DTV, Don, question mark. You figure out what you want to give me. And that's how Mike and I knew we were the two guys that were chosen.

• 41:19David Senra?

  There's not even a conversation?

• 41:20Speaker 01

  No conversation.

• 41:21David Senra?

  So I'm a big fan of the way he thinks. He gave a few talks.

• 41:25Speaker 01

  Maybe talk to Mike Moritz. Didn't talk with me. I just saw the sheet of paper.

• 41:29David Senra?

  That's, to me, when I think about him, he's like a simple genius to the way he thought and operated. Would that be an accurate way to describe him?

• 41:38Speaker 01

  I think part of it was accidental. You know, look, I love Don Valentine. And there's not a bad things I could say about Don Valentine. But Don also made a ton of mistakes, as we all did. We sold our Cisco shares for cash for the total gain of 90 million. We owned a quarter of Cisco Systems.

• 41:57David Senra?

  How big is that mistake in dollar terms?

• 41:59Speaker 01

  What's Cisco's market capital's high might have been, half a billion? So like, what's a quarter or half a billion?

• 42:05David Senra?

  A lot more than.

• 42:05Speaker 01

  No, sorry. Not a half a trillion.

• 42:08David Senra?

  Yeah, I understand.

• 42:09Speaker 01

  Half a trillion. A lot of money.

• 42:11David Senra?

  A lot more than 90.

• 42:12Speaker 01

  But, but look, we all made mistakes. How many distributions I pushed for at ServiceNow? I left a 10xer on a table. 10x, you know? It's crazy. We'd left billions upon billions of dollars, as we all did in the venture industry. But you know the story. I'm sure that you've heard the story of my review from Don Valentine.

• 42:33David Senra?

  I don't know.

• 42:35Speaker 01

  So I came out of a presentation with a, it was Don, me and two other guys and a founder. And I guess I asked some questions, maybe too aggressively. There was a note on the table when I got up. Doug, dash, not fit to listen to founders. He left on a table for me to see. I love whenever I hear, young guys, I like some feedback and I get a three month review. That was my review, right then and there. And so, hey, that was a school of hard knocks. It was a semiconductor days. Of course, we evolved through time. Founders are the most important person in our business. Founder first, our client second, and us third. It's not that we're Boy Scouts. It's not we're third.

• 43:20Speaker 01

  But we know if we do right by founders, we'll have great returns of which we'll share. So Don was wonderful. Don was the one, when everybody wanted me out of Sequoia because I was insufferable, Don was the one that said, give the young guy a little more time. So he saved my ass.

• 43:37David Senra?

  Back to this mistake of selling early, I just finished reading this book. It's essentially a biography published in 1966 on all the merchant bank families. It's called The Merchant Bankers. And at that time, they're all family businesses. And there's, one of my favorite quotes in the book is this guy bitching because they own like, whatever, 20% of some company like DuPont or something back in the day. And they're like, do you understand if we didn't sell this? And he's saying this is like 1915. He's like, we'd be billionaires in 1915.

• 44:02Speaker 01

  Yes, yes, yes.

• 44:03David Senra?

  So that's a very, you know, common mistake.

• 44:07Speaker 01

  Yeah, but most companies, if you hold them too long, go away because technology changes. But if you have a sniffer for one of these that happens, maybe five or 10 a cycle, maybe it'll be a lot more in this cycle. If you can sniff one of those and hold on to it for 20, 25 years, there's really nothing else you have to do in life.

• 44:28David Senra?

  Are most of your friends investors or entrepreneurs?

• 44:31Speaker 01

  Most of my friends are neither. Most of my friends are people that I'd met in my early days of life who have blue collar jobs, who are nowhere near the techno world. I have maybe two friends in this world. Most of my friends are from high school and maybe college, completely, or maybe from Italy.

• 45:02David Senra?

  Even further back?

• 45:03Speaker 01

  Yeah, even further back. You know, I just came from Italy a couple of days ago. I spent a couple of days with a friend of mine who's a cop at the airport in Genoa, Italy. You know, he's one of my closest friends.

• 45:15David Senra?

  So you still able to relate to people even though?

• 45:19Speaker 01

  Still, just the notion relate to people, I find that kind of weird.

• 45:23David Senra?

  Okay.

• 45:24Speaker 01

  Well, let me relate to people. It's almost as a, ah, you're there, I can relate to you.

• 45:28David Senra?

  No, but you know how this goes. Like, yeah, people started with nothing, they were really successful. It's like they kind of isolate themselves.

• 45:33Speaker 01

  No, I have, thankfully, and that's maybe one of my few good traits, I'm still normal. I make sure that I lead my life with no handlers. Look, I have everything in life that somebody needs, but I have no handlers. I have no personal assistant. I don't have anybody who, you know, who cleans up after me. I still take my water glass down in the morning, put it in the dishwasher. I cooked yesterday afternoon. I wash all the pans and everything on my own. Those are the things that keep me grounded in this crazy world of ours in which we live here in Silicon Valley.

• 46:11Speaker 01

  In a way, I think of myself, a fairly simple man who found himself in the right place at the right time, didn't screw it up, whose only true skill is a sniffer.

• 46:28David Senra?

  You keep saying sniffer. What is a sniffer?

• 46:30Speaker 01

  Sniffer on people, sniffer. I have an ability to walk in a room in a business meeting and kind of know what everybody's thinking, kind of know what everybody wants to hear. You know, I really haven't lost an investment in 30 years in Silicon Valley. People have beaten me because of price, but I haven't lost otherwise.

• 46:51David Senra?

  But relate, not losing an investment, a sniffer.

• 46:54Speaker 01

  I have a sniffer of what people want. And that same sniffer takes me through what businesses, like what's a real business? And what's a dream? And what's a pipe dream? Even though I do not know much about that technology, maybe a way to say that's EQ. That is really my, my main skill. And the other thing that I pride myself is I'm a very good soul. In fact, the Sequoia spec of people we want to hire has changed. We had this complicated spec. It's now down to a hyper competitive person with a heart of gold. That has become our spec in the people we hire. We want people not like me, but that are willing to do the right thing

• 47:38Speaker 01

  when it's highly inconvenient for the person doing it and is willing to walk through walls in order to win, in an ethical kind of way.

• 47:46David Senra?

  How does the people you want to hire differ from the founders you want to back?

• 47:51Speaker 01

  Same thing. Same. They need to be outliers. The founders we want to back have to be extreme outliers in something. IQ, drive. It's kind of the same thing in the people. We have all these adjectives when you walk in a Sequoia office, the reverence, the outliers. And I look at that, and to me, they're the same adjectives in people that we want to back and people we want to hire. I think we look a lot like our founders. We don't give up.

• 48:22David Senra?

  So when we go back to this idea that you said earlier, where it's like, hey, you know, some of these other traits that other venture people, you know, don't like in founders, I love. I'm very attracted to them. Going back to the founder of New Bank, did he have those founder traits?

• 48:36Speaker 01

  He had a combination of smarts, drive, clarity of thought, toughness, goodness, judgment.

• 48:49Speaker 01

  Mature way by way, way beyond his years, his years. Look.

• 48:56Speaker 01

  Here's what I have to tell you. We interview people. And Mike Moritz had a great line called them half pagers or full pagers. You interview someone. You write a half page. There's nothing else to write. You're there 30 minutes. You look in and you watch. God, I can't believe, you know, I'm done. And then you have people that you look at, you watch, and it's an hour's gone by and you can't believe it. And David was one of them. And I remember talking on the hour flew by. And it was clear to me that we love this person. And he tells the story to show you how Sequoia works. I said, yeah, there's somebody else that wants you to meet. He makes it to his car and his phone rang and it was Mike Moritz. He didn't make it out of the parking lot. That's how fast we move.

• 49:40Speaker 01

  We pulled him right back in and Mike met him. And within two minutes, Mike and I knew that we're going to hire this kid. And I had interviewed 10, 15 people from Brazil. They all looked the same. They were all these super smart, fine, wonderful guys and girls. They all went in consulting because that's how you self-select in these. In these new markets, that's I saw it in India and so on. But they all looked the same. I couldn't tell them apart. And then I met David Velez. And within one hour, I knew for sure that he was going to be the person we're going to hire.

• 50:13David Senra?

  Who were some other, other, the great founders besides him that you partnered with?

• 50:16Speaker 01

  Fred Luddy of ServiceNow. He was older. But he made everything simple. He came to Sequoia to present and he told us everything that was fucked up with his company. It was the wildest pitch. Yeah, everything that he screwed up. That, I mean, if you didn't want to sell shares. Of course, he knew what he was doing, but if you didn't want to sell shares, that would have been the type of pitch. Now, we all still saw through that and so on, but he was terrific. Complete clarity of product. He simplified this thing called workflow where, where I ask for something and you respond and you answer back and you ask for something. He simplified workflow to the most basic of ways that people can communicate.

• 51:00Speaker 01

  And that was the foundation to ServiceNow. That was incredible, incredible. And then you get into, into the Israeli founders, which I adore. They are tough, you know, keep in mind, they think incoming missiles are kind of everyday type of occurrences. And so they're naturally tough. They don't take any shit. They're smart as hell. Somehow they know what America needs way over there when they work at 8200, which is one of the units in a government, you know, in Israel. They're very trustworthy. They're terrific. I love, and they're tough as hell.

• 51:41Speaker 01

  And the conversation with one of these usually men, no, actually, there's a woman that I'm, she used to be a spy in Iran. She's tough as hell.

• 51:50David Senra?

  She's a founder?

• 51:51Speaker 01

  Yeah, she's a founder.

• 51:52David Senra?

  What's her company do?

• 51:52Speaker 01

  It's a cybersecurity company, but not with her, although a little with her. It's almost when you talk to these founders, have you seen those? I don't know what that sport is where you smack the shit out of when other guy smacks.

• 52:06David Senra?

  We had, we had the founder on the show, Dana, Dana White's company.

• 52:09Speaker 01

  And you take it and then the guy, now, it's not quite that bad with a Israeli founder, but there are no holds barred. They will tell it to you straight. You'll give it to them straight. It's productive. It's not personal. It leads to an outcome. It leads to an agreement and it takes 15 minutes. It's just terrific.

• 52:28David Senra?

  How do you build trust with the people that you want to invest in?

• 52:31Speaker 01

  It doesn't start with trust. It always starts with fear. We had the big bad venture guys who in their minds want to own their whole company. In fact, I love to tease founder when they ask me, how much do you want to own? I said, we usually start being happy at about 100%, but we can go from there. And I do that on purpose to almost take, take the nervousness out of the room. The way you build trust is first to go in and explain to them, we don't want to screw it up. It all starts with that. And then having the look or the conversation with them that begins to show them you might know something about their business.

• 53:08Speaker 01

  And then paving the way for them to ask you the first question, which may come in an email, the first little bind they find themselves in. And if you rush in and you help them and you take no prisoners and you don't make it painful. And when they're down, you help them. Don't turn the screws with them now. If you're going to turn the screws, do it when their ego's up here because they beat the quarter by 30% or something. When you help them out when they're in a jam, slowly by slowly, you build trust, which usually takes about a year. It's not done immediately. There's usually lots of fear at the very start. Oh no, I got Doug Leone in my board. It's almost they want Doug Leone, but they're scared to shit to have Doug Leone.

• 53:52David Senra?

  The reason I ask, because you have one of the greatest quotes I've heard, where he said, trust is the grease that makes all business run.

• 53:57Speaker 01

  It's accelerant. I created the tenants of Sequoia. One was performance, two was teamwork, and the other eight, I said, if you don't have the first two, the other eight don't matter. And after I wrote those and I published them, I said, shit, I forgot the zeroth one, which is trust.

• 54:15David Senra?

  Yeah.

• 54:16Speaker 01

  With trust, trust, if you have trust in an organization, you can fly. You can make decisions extremely quickly. Trust is interesting though, because it has both knowledge and intention. In other words, I can trust your intention, but I think you're a putz, in which case I'm not going to trust you. Or I can trust your skill, but I don't trust your intentions, which case I run the other way. And so I've taught my partners early on to make sure they understood trust as having those two components.

• 54:46David Senra?

  That's interesting. I've never heard it broken down like that. What came to mind when I read, when I heard that quote from you is like a quote from Charlie Munger, who said something very similar, where he said that trust is one of the greatest economic forces on earth.

• 54:57Speaker 01

  Yeah, it's necessary in order of a business. And you see these companies with broken culture where no one trusts one another. And you can't get shit done and you know, and by the time someone here that knows something makes a decision, which is the right decision, to the time it gets to the VP or the CEO, forget it. It's a whole different thing.

• 55:16David Senra?

  I'm glad you just said that because I had dinner with, at his house right before he died. And he told this story where he's like.

• 55:22Speaker 01

  Who's this?

• 55:22David Senra?

  Munger.

• 55:23Speaker 01

  Charlie.

• 55:23David Senra?

  And.

• 55:24Speaker 01

  The right page of 99 years of.

• 55:26David Senra?

  I know. And then I had another dinner scheduled after his 100th birthday and obviously he passed away in that November, this previous November, unfortunately. He said, he told us a story where it was during like the Enron blow up.

• 55:36Speaker 01

  Yes.

• 55:36David Senra?

  And him and Buffett would like, they knew all the assets they actually wanted and they had decade long relationship with a lot of people.

• 55:41Speaker 01

  Yes.

• 55:42David Senra?

  And they were wanting to, but they, they saw this, I think it was like a pipeline business that Enron owned. Guy Buffett trusted called on Friday and said, hey, this is happening, but you have to wire the money like now. Like, and it was like a couple hundred million dollars thing. I forgot what it was. Let's call it 400 million. And the first charge lawyer is like, you can't do this, like we have to check it. You're going to be liable if this thing blows up or whatever. And Munger goes, we wired the money without even an email. And then I think food was dripping down his mouth. If I remember correctly, he's like, we made a couple billion on that risk free.

• 56:12Speaker 01

  Yeah.

• 56:12David Senra?

  Cause like, why? Cause Buffett trusted the guy who was on the other end of the phone.

• 56:15Speaker 01

  It's quite interesting because I'm a trusting soul by nature.

• 56:20Speaker 01

  And I've never been screwed in business. I've never pre-wired money, if you will, as a metaphor, and paid the price.

• 56:29David Senra?

  This is why I wanted to read about the merchant bankers, because there's just something very appealing to me, like they have an old school, like gentlemanly way of doing business. Where in many cases, there's no paper at all.

• 56:39Speaker 01

  Yeah.

• 56:39David Senra?

  It's just, you said you're going to do this. I said, I'm going to do this. There's not, we don't even write anything down and just do it.

• 56:45Speaker 01

  Yeah. Well, it's the value of a term sheet. A term sheet is not worth the paper it's written on. But once you sign it, both sides, I think you have to honor it. You know, many times.

• 56:57Speaker 01

  Where I'm on a board of a company and we signed a term sheet with an investor. And then three days later, someone's interested at a much higher price. There's no way. There's no way. No, no. We shook somebody's hand. And we both said, well, you have a fiduciary duty to take the higher price. No, I have a fiduciary duty to make sure the culture of the company is a clean culture and we do business the correct way.

• 57:21David Senra?

  Yeah. At the end of the day, you have to be comfortable with like your own self.

• 57:23Speaker 01

  Absolutely.

• 57:24David Senra?

  Yeah, 100%.

• 57:24Speaker 01

  Absolutely.

• 57:25David Senra?

  I'm actually surprised that you're trusting, like default trusting.

• 57:29Speaker 01

  Yes, I have a round head, a deep voice and people are scared shitless of me and, you know, and no, I'm serious. And then people find just the opposite. I will bust my ass to help you more, probably more than anybody else you've ever met. It makes me feel good. It's a very selfish thing on my part. I don't do it for you. I kind of do it for myself.

• 57:53David Senra?

  What, what do you mean?

• 57:54Speaker 01

  I really like helping others. It makes me really, really happy.

• 58:00David Senra?

  Yeah. One of my closest friends is kind of like an advisor and older brother. He says he finds it intoxicating to be dependable for his tribe. Is the way he puts it.

• 58:08Speaker 01

  Yeah, yeah. Look, I ran Sequoia for 26 years. I never viewed it as running Sequoia. I viewed it as working for all the other people. I used to tell them, we have a, you all have it backwards. I work for you guys or gals. Like it don't work for me. I mean, yes, I get to make a decision here and there, but the decision I make is that we could all win. But you tell me what you need and I'll do whatever I can just to get it done.

• 58:35David Senra?

  Deal is how the best founders turn the world into their talent pool. I've been studying how history's greatest founders operate for a decade. And one thing they all have in common is they understand that recruiting and hiring the very best talent is your most important priority. A players recognize other A players, which is why top companies like Ramp, Shopify, 11 Labs, Uber and DoorDash all use Deal. Many of the top founders I know have personally invested in Deal after using their product. And what they discovered is that Deal is the best company in the world at building infrastructure for global hiring. Deal will help your business hire, pay and manage any worker anywhere in the world. So you can retain the best talent anywhere and spend the rest of your time focusing on what you do best, delivering value to your customers.

• 59:16David Senra?

  The founder of 11 Labs has a great description of the value Deal can give your company. He said, we built 11 Labs to break down language and communication barriers. With Deal enabling us to hire and support exceptional talent anywhere. We can accelerate our innovation and bring more voices, stories and ideas to every corner of the world. Deal is trusted by over 40,000 businesses. Learn how they can help your business today by going to deal.com/cenra. That is deal.com/cenra. So looking forward. You're on day 91, like, what are you, what's gonna, you think, occupy most of your time in the next 30, 60, 90 days? Like, what is on your mind right now? If you're not looking backwards.

• 59:57Speaker 01

  Looking for investments. Because at the end of the day, it doesn't matter if it helps Sequoia during a crucible-type moment and so on. As I said, it's gonna matter what's on that sheet of paper, what I've done in the first year. So, we have a little thing we do on Mondays called MIT, the most important thing for the week. And everybody talks about, I've gotta do this, and I was, I have nothing going on, I just came back from vacation. I don't think, I don't think anybody ever said they had nothing going on. I mean, it takes guts to say in front of nine people, I have zero going on. My MIT is to go scrounge, I use that word, for deals.

• 1:00:39Speaker 01

  And that means getting in a phone, calling people I know, networking like crazy, and try to intercept some kind of very nice investments. It's one of the 20 or one of the 30 that I wanna make in my lifetime.

• 1:00:54David Senra?

  But is that process today different for you than it was when you were at Sequoia previously?

• 1:00:59Speaker 01

  It was because I was more in the deal flow of my generation. In fact, it's very different because the founders of the super interesting companies are 23 years of age. I don't have a network of 23-year-old age friends.

• 1:01:16David Senra?

  This is very interesting to me, I wanna hit on that before I forget, though. I really, I remember setting a friend of mine up with one of the smartest people I know. He had two businesses running, trying to figure out which business he should give his attention to. Then like 15 minutes, my smart friend just identified in the core of the issue. And so, the guy that I hooked him up with texted me, he's like, man, this guy was just fucking nailed it, he understood it. And I sent him a text back, I go, he's my favorite type of person. Very hard to get to, hard outer shell, but once you break through, he'll do anything for you. I think it was very similar to what you were saying, so like, don't be confused by the round head and the booming voice and the fucking everything.

• 1:01:51Speaker 01

  Balls round head.

• 1:01:52David Senra?

  Yeah, the balls round head. The, the other thing, it's very interesting to me, I've had a couple, like, I don't hang out with venture capitalists, like, I just hang out with founders, I have no friends that are not entrepreneurs. Like, I work on founders' podcasts during the day, hang out with founders at night, and...

• 1:02:08Speaker 01

  Well, I'm so proud that I'm a founder of a company, I actually, I actually love that.

• 1:02:14David Senra?

  Well, no, the reason I bring that up is because it, there's been, it happened on a few occasions, but this happened recently, where there's another venture capital firm that's like, hey, we have an issue with like our story and everything, can you just like meet with my partner and like talk to us about this, have lunch? I was like, I fucking like you, we'll just have lunch, I don't give a shit about you, really give a shit about your business, but let's talk. And then I would ask this guy who's been a venture his whole life, which is interesting to me, you know, like, who he thinks, like, if you're a young founder right now, like, who's the first person you're gonna call? You can pick anybody, and they're gonna be your first investor. And he starts naming off all these firms, so I go, how could you work in this business and not understand it? I go, you're hanging out with too many venture capitalists and not enough founders. There's nobody on that list, it's exactly what you're talking about.

• 1:02:53David Senra?

  It's these young kids are identifying a vastly different group of people than they, than the previous generation has done. So that is, is, is an interesting...

• 1:03:01Speaker 01

  I mean, in the ideal world, a 25-year-old says, let me get some experience, I mean, go call Doug Leone. It's not, it doesn't work that way.

• 1:03:11David Senra?

  So then, how's the solution?

• 1:03:12Speaker 01

  I have to find them.

• 1:03:13David Senra?

  Yeah, what's the solution to that?

• 1:03:14Speaker 01

  I think you have to hustle, just like everything else in life, it's what you're doing in your business. You know, like, you hustle like crazy, all the books you read, all the people you meet, all, all that you're doing for your business.

• 1:03:23David Senra?

  Yeah, but like, here's, I just talked to Devash about this, too, where it's like,

• 1:03:30David Senra?

  I have this fucking uncontrollable obsession. Like, I can't tell you why, since I was a little kid, all I wanna do is fucking sit in a room and read books, that's never stopped, right? And then once I found podcasting, I just can't stop fucking thinking about it, I get sad. This whole crew that you see here, all these fucking cameras and stuff,

• 1:03:46David Senra?

  they didn't tell me that somebody on the team was getting married, they went to Italy, they took two weeks off. I was like sad as fuck, I went to Italy for like, what, three days, Rob, how long was I gone? They're like, I'm like, I'm going back, I got shit to do, like, I wanna get to work. So, it doesn't even feel like hustle to me, it's just like this compulsion.

• 1:04:01Speaker 01

  I think it's the best kind.

• 1:04:03David Senra?

  Yeah.

• 1:04:04Speaker 01

  I mean, it can feel like a hustle because then you're exhausted, then you need, you know, Friday, Saturday, and Sunday off. No, it's your love.

• 1:04:11David Senra?

  Yeah, but one thing that did change, you know Brad Jacobs? Have you spent any time with him? I mean, it's in a beautiful way, weird cat. Unique, can just read his book, How to Make a Few Billion Dollars. Half of it's on his like, his mind, his, like, not hypnotism, his meditation practices, like, it's all about his mind and stuff. But he's an unbelievably joyful human.

• 1:04:32Speaker 01

  Yeah.

• 1:04:33David Senra?

  And he's the one that changed this for me because I was just like you, and like, all these other founders and anybody else, he's finally just getting to have people, it's like, my inner monologue, I just wake up every day and now focus on what I did, it's like, that wasn't good enough, you could've done it better, like, it's just super negative. And so, he sat me down one day and he's just like, this doesn't serve you anymore. It's like, that got you to where you started, to where you're now, but now your, your drive is generative. Your drive is that you fucking love what you do, so stop being mean to yourself. And it was weird, you know, he's 68 years old when I had this conversation with him, and overnight, overnight, you changed my inner monologue.

• 1:05:04Speaker 01

  No, the things I think about is not all the success I achieved, but all the opportunities I let slip. All the screw-ups I made as an investor. You know, I, I don't think too much about rebuilding my life, or redoing my life, I should say. But all I think about, oh my God, the community, the venture community, and I have screwed up so badly, we, I could've done so much better. Look, I've done fairly well.

• 1:05:31David Senra?

  Oh, that's an understatement.

• 1:05:32Speaker 01

  No, no, both, I'm not, I'm not saying just financially, but you know, in, in things I've done. But all I can think about is how much better I could've done it. As I think about my next board or two, I think about it the same way. I mean, all the other boards I've done, I've done a decent job, but I've got a lot of room to really go. I can't wait for my next one to exercise yet another time all my learnings for yet another next founder, for his benefit or her benefit.

• 1:05:59David Senra?

  We should actually talk about that because you have a ton of experience with that. So many of my founder friends just have completely fucked up their boards, don't know how to run one, don't like the one they have. Like, what advice do you have for them on this?

• 1:06:09Speaker 01

  Choose to architect your board the same way you architect your product. You know, a lot of people choose boards like they choose, like to find a girl or a guy kind of in a bar. You know, she talked to me, let's go out Friday night. He talked to me, let's go out, it's no more complicated than, and I'm not putting any thought into it. You know, a board is like a mate, a lifetime mate, only there you mate for the next five, seven years. I bet you most marriages last probably five, seven years these days. Be extremely careful, and it's not about the first term sheet, it's about who do you need? Who has the skill set and the temperament you need to complement what you have?

• 1:06:55Speaker 01

  And complement means a bit of discomfort, because if both of you have the same background, there's probably a little more comfort. And you wanna find a little bit of discomfort, you wanna find someone with a very different set of experiences. Which means that initially, you're gonna talk like this, initially, you're not gonna understand what he or she is telling you. But that's where the learning comes. And so, I find people, they don't do it at all. I got a term sheet, how many times I've heard, I got a term sheet, I got a lead term sheet. So what? Who cares? Of course you got a lead term sheet, everybody gets a lead term sheet.

• 1:07:27David Senra?

  So, talk about some of the mistakes you've seen in board construction, then. Is it just that, it's like, this person volunteered and I took him?

• 1:07:33Speaker 01

  So, there, there is domain skills, there's level of knowledge, and then there's personal traits. So, early on, when you're building a business, I don't think it helps you at all to find a board member who's an engineer. You're an engineer yourself, that's not the skill you need, that's what I mean by domain skill. And experience, you have no experience, to put a board member with no experience, I don't think it helps you at all. It doesn't mean you have to find someone who's 68 years old, but find someone who's been through the cycle. And then there's personal needs. Out of 10 venture folks, and I've said this, and I've taken a shift for it, maybe 30% are incompetent. They don't know what they're doing.

• 1:08:17Speaker 01

  Another 40%, I call them no ops, no damage, no anything, they nod, you know, they nod with the group. And maybe 30% or fewer, maybe 20% know what they're doing. And that's one overlay. The other overlay is, you know, managing their firms, their, their stature or their status in a firm. I need a win, I need an exit, what's my partner's gonna say? So you didn't really have the board member there, you have the shadow, you have the interpreter of what he thinks, he or she thinks the firm wants. If you take a combination of lack of experience, duplicative type domain, covers your ass with the partnership and incompetence,

• 1:09:02Speaker 01

  that's the worst of all kind. I see that all the time. I see that all the time. Just completely, let me put it in your terms, completely fucking clueless. Completely fucking clueless, to a damage, not a no-op stage, a damaging stage.

• 1:09:19David Senra?

  The best boards that you've been on are the board meetings contentious?

• 1:09:24Speaker 01

  No, but issues are put on the table, real conversations are put on the table.

• 1:09:29David Senra?

  But you're willing to argue, forcibly?

• 1:09:31Speaker 01

  You, you're willing to have the real conversation. The argument implies, implies a tonality, a combative stage. I don't view it as that, I view it as supportive stage to come up with the answer the founder needs. So, we're, we're willing to get the real job done. I won't concede the, the word argument.

• 1:09:53David Senra?

  Interesting.

• 1:09:53Speaker 01

  It's the same thing at a partner's meeting. We don't argue, but we have the real conversation. At times, at Sequoia, we have to take a five or 10-minute break. Five or 10 minute break. We walk around, we go back in a room. The temperature has cooled down by 10 degrees. We have the conversation. We come up to the answer. We're all in. We're all agree. No more conversations. When we go out, it's done. And it's the same thing about board meetings. And it's okay to disagree. It's okay to disagree.

• 1:10:24David Senra?

  I would say that one of the most interesting things I learned this year from doing the show, Ed Catmull was nice enough to let me come to his house and record a conversation with him. And he was like, hey, you know, a lot of people don't know that in the 10 years that Pixar was a public company before, you know, the acquisition of Disney, that Steve Jobs fired two of our board members. And they might know that he fired him, but they don't know why he fired him. And so I asked him one day, like, why he fired him? He's like, because they didn't disagree with me. He's like, they always agree with me. They serve no purpose. And he was saying that, you know, a lot of people say they want to get to the truth. And, and I think Ed on the episode said, most people that say that are actually full of shit.

• 1:10:58Speaker 01

  They are full of shit.

• 1:10:59David Senra?

  Steve actually wanted to get to the truth.

• 1:11:01Speaker 01

  They're full of shit. Here, here in California, more than the East Coast, people don't like the direct conversation. I had to learn that first coming, you know, I, I, I went from Italy to New York City, which was halfway to America and then to California, where, where, where everybody told me, yes, give me the, give me the feedback, the honest thing. Nobody wants to hear the honest feedback. Who, who, are you kidding?

• 1:11:25David Senra?

  Yeah.

• 1:11:26Speaker 01

  You know, are you, everybody's full of shit.

• 1:11:28David Senra?

  But the best founders have to.

• 1:11:30Speaker 01

  They have to, and you have to figure out a way to do it in a, in a fashion that it's understood, received, accepted, enacted upon. It's almost an art. It's not just giving it. It's giving it in the right way, at the right time, with the right tone, with the right words, with examples and so on. Look, it, it, it's like telling a founder, your VP of Sales sucks. You're not getting anywhere. What about if you said, there's a couple of VP of Sales I'd like you to meet? Just so you can gauge yourself. He'll meet or she'll meet two people that know what they're doing. Suddenly they'll say, holy shit.

• 1:12:12David Senra?

  Okay, this is like inception.

• 1:12:14Speaker 01

  Well, I don't know about inception.

• 1:12:15David Senra?

  Okay, so I just, I'm a big fan of Christopher Nolan. I just reread his biography for the second time. And one of my favorite lines in Inception is like, what is the most resilient parasite? You know, is it, you know, bacteria, is it worm? It's like, it's an idea. And the whole thing is like, but it can't be an idea that somebody else gave you. You can't say, Doug, you should believe this. You have to inception them with the idea so they believe that they came up with it.

• 1:12:36Speaker 01

  Yeah, it's like your kids. But you're gonna tell your kids all the things they shouldn't do. Good luck.

• 1:12:40David Senra?

  Yeah.

• 1:12:41Speaker 01

  Forget it.

• 1:12:41David Senra?

  Are you familiar with the shit sandwich?

• 1:12:43Speaker 01

  The shit sandwich.

• 1:12:44David Senra?

  On how to give feedback? I don't know if this is, this is the art you were talking about, but shit sandwich is like compliment, what you, the negative feedback, and then another compliment. That's why they call it the shit sandwich.

• 1:12:55Speaker 01

  I don't know how to do that. If anything, the mistake I make is I'm too direct. I remember there was a venture guy, Jim Breyer. I heard him turning down an investment once. And I said, oh my God, the, the founders are gonna walk away from this thinking he won the freaking lottery. And I don't know how to do that. And I was always admirers of how he could do that. And I'm more direct. I hear people talking on the phone for 20 minutes, 30 minutes. My conversations are three, four, three, four minutes at most. You know, hi, what do you need? This and that, done. Okay, yes, I got it. All right, I'll let you know.

• 1:13:38David Senra?

  30 seconds, not even three minutes.

• 1:13:39Speaker 01

  Yeah, most of my conversations are less than three minutes long.

• 1:13:43David Senra?

  Yeah. You know what you think is interesting? That you don't like hang around with other venture capitalists?

• 1:13:49Speaker 01

  Why?

• 1:13:50David Senra?

  I don't know. Founders hang out with other founders.

• 1:13:53Speaker 01

  I think it comes to the fact that I grew up from dirt and the inside of me, there's still mostly dirt. I really think that's it. You know, I really think that's it. I'm not an intellectual. I don't find, to me, technology is terrific. It's interesting. It changes every day, but it's not my lifeblood. I think humanity and, and one-on-one relationships are probably the most interesting thing for me.

• 1:14:26David Senra?

  Are you introverted?

• 1:14:27Speaker 01

  I'm right in line. According to Myers-Briggs, I'm right in the middle. I do not like meeting new people in general. In fact, every time I have to meet somebody new, the thought, and it's kind of nasty that goes through my mind is, shit, another asshole I gotta meet. Where I remember talking, where, where the extroverts, I'm told, find energy.

• 1:14:52David Senra?

  All they get energy is so gross.

• 1:14:53Speaker 01

  They love it to meet new people. Oh my God, another person I have to meet.

• 1:14:57David Senra?

  Yeah.

• 1:14:58Speaker 01

  And yes, I do it. I can turn the, the charm gene on. I can fake it. I can be a cocked up party in order to walk around and network with everybody. But I get home and I'm exhausted from that.

• 1:15:09David Senra?

  Yeah, definitely introverted.

• 1:15:10Speaker 01

  Yeah.

• 1:15:10David Senra?

  I am too. And I think there, there's a very similar, like, you know, I, I think about the opportunity cost. Again, I always quote Munger, where he's like, you know, the way intelligent people make decisions today, it's all opportunity costs. And for me, it's like, I'm gonna spend two hours with somebody new. That's very expensive to, compared to maybe the five true friends that you have in your life, the cop in Italy, or your friends back in New York, whatever. It's like, I'd rather just deepen that relationship that I have than go on.

• 1:15:33Speaker 01

  But I realize though, that putting myself out there and meeting new people makes me happier later. In other words, if I let my instincts of going to the same three restaurants or hanging with the same people, if I do that all the time, I'm less happy. But if I put myself out there, I dare take these minor emotional risks. I find myself happier because I feel more well-rounded at the end of the day. I feel like I've done something.

• 1:15:59David Senra?

  Could you even be in the business that you're in? But not meeting new people?

• 1:16:05Speaker 01

  No, absolutely. Although it's not a social setting, right? It's, it's present, it's work. It's presentation, present, help, assist. Well, you know, I, I, I think the closest friend I have as a founder is Vales. All the other founders are pure business. I don't socialize with spouses or anything with any of my, with any of the founders.

• 1:16:25David Senra?

  But you do with Vales?

• 1:16:27Speaker 01

  Yes, because he was an associate, I hired him. I was, we had kind of a paternal, you know, son relationship.

• 1:16:34David Senra?

  Yeah. Is there any venture capitalists that just made like maybe one or five or 10 investments and then that was it?

• 1:16:43Speaker 01

  Crosspoint Ventures had a hell of a run for seven years and they went away. It's, it's, it's a name you may not remember. Look them up. Now, they still exist, but it's all the partners left after, after just making a whole bunch of investments. There was a venture firm called TVI. You may not remember. Technology Venture Investor.

• 1:17:07David Senra?

  That's the one that bought Microsoft right before the IPO?

• 1:17:09Speaker 01

  They didn't buy Microsoft, but Dave Markward was on the board of Microsoft.

• 1:17:14David Senra?

  Yeah, they got 900.

• 1:17:15Speaker 01

  It was a couple of, one guy started Benchmark with two other persons from another firm.

• 1:17:22David Senra?

  But Dave did, I think, if I remember correctly, from this book called Hard Drive.

• 1:17:26Speaker 01

  He was on the board of Microsoft. He was the only venture investor in Microsoft.

• 1:17:29David Senra?

  The year before Microsoft went public, if I remember correctly, they were doing 140 million revenue with 38 million in profit. And they sold 995,000 shares for a million dollars to him.

• 1:17:38Speaker 01

  No, I don't think, I don't think, I don't know what they did.

• 1:17:41David Senra?

  We're gonna, we're gonna put this in the show notes.

• 1:17:42Speaker 01

  But that was a venture firm that had the keys to the kingdom.

• 1:17:46David Senra?

  Yeah.

• 1:17:46Speaker 01

  And somehow didn't last as a venture firm. Where Crosspoint, they just called it in and, and they all went their merry way. This is a firm that just couldn't coexist, even though they had everything.

• 1:17:59David Senra?

  Yeah, there's something interesting about that. So I can't name who, but it's one of the best entrepreneurs living. And he's like, actually, you know, they were talking about the greatest seed investors of all time. He's like, greatest seed investor is my dad. He made one investment and made $40 billion.

• 1:18:12Speaker 01

  That's it.

• 1:18:12David Senra?

  Didn't invest in anything else.

• 1:18:14Speaker 01

  That's it. That's it.

• 1:18:15David Senra?

  That's awesome. So I asked you, if you're introverted, I want to ask you something that I think Morris is definitely introspective. You don't strike me as introspective at all.

• 1:18:29Speaker 01

  Morris taught me how to listen. Morris taught me how to listen to the exact word that's said, the timing of that word. You really can understand that how to human being by just listening to the adjective and so on. I took the Morris basic training that I got and I used it and I expanded on it. I love listening to people speak and.

• 1:18:57David Senra?

  Wait, what do you, what do you mean? You can, you can learn by listening to the adjective they use?

• 1:19:00Speaker 01

  Oh, the one they use when they describe a situation. Humanity, humans can let, can, can't help but letting it out by, by showing themselves. And how they use the word I versus we when they describe. I can sell you this. I'm thinking to myself as this pretty, he's presenting and said, fuck that. You can't sell me shit. You know, that, that's what I think during the presentation. You know, as I have that stupid grin in my face. But just listen to, to the specific words that are said, when they say it. We often choose a founder without a line of code, without anything, based on a presentation, a clarity vision.

• 1:19:44Speaker 01

  But we also want to get the interpersonal traits. And you can learn a lot if you just pay super careful attention. I mean, Morris used to do it to me all the time. He used to re-quote my words back, back to me or the way I said them. You know, it would drive me nuts. It drove me nuts enough that, that I learned.

• 1:20:04David Senra?

  What was happening there? Why would that drive you nuts?

• 1:20:07Speaker 01

  We used to write memos at Sequoia. And the memo were from and to. And Mike always, Mike pointed out to me that the from puts myself first and the to, the recipient second. And Morris was the first that wrote the memos to and from, to put the other person first and yourself second. I understood that putting the from first and the to second as being a somewhat egocentric move where it comes from you. You had to put yourself first in that memo. And that's one of the minor little things that I learned from Mike Morris. And there were hundreds of things like that.

• 1:20:49David Senra?

  What else did you learn from him?

• 1:20:51Speaker 01

  So Mike was brilliant. Let me tell you, he was a very painful co-head. And I, you know, he knows that. I, I was painful for him. He was painful for me. Like I said, it's, it's, it's a badge of honor for me anyway, that we made it work. But Mike had the ability to dream broadly in ways that I've never seen before. He could answer the question better than anybody I've ever known. What if everything goes right? Not, oh, we're hedges and that. No, what if everything goes right? What can this business look like? And if you look at the companies he's been investors in, it's a spectacular list. You know, look, he had his faults and we're not gonna talk about all his faults here.

• 1:21:35Speaker 01

  But on that dimension, he was by far the best in the world.

• 1:21:40David Senra?

  All right, Doug, I appreciate you doing this. We're gonna run this back because a year from now, you're still going to be doing this. I have faith that you're not gonna quit nine months from now.

• 1:21:47Speaker 01

  Yeah.

• 1:21:48David Senra?

  And if, when you're still around, nine months and one day from now, let's run this back. I appreciate you taking the time.

• 1:21:52Speaker 01

  Thank you.

• 1:21:53David Senra?

  All right.

• 1:21:53Speaker 01

  Bye-bye.

• 1:21:54David Senra?

  I hope you enjoyed this episode. Please remember to subscribe wherever you're listening and leave a review. And make sure you listen to my other podcast, Founders. For almost a decade, I've obsessively read over 400 biographies of history's greatest entrepreneurs, searching for ideas that you can use in your work. Most of the guests you hear on this show first found me through Founders.