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

Episode Date: August 30, 2026

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

All right, we were just talking before we were recording, and you just said something that's very interesting. We were 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? My partner in India said there are many roads to heaven. And so there are many ways to dominate. Take steep jobs.

He had really one job. And he dominated in that domain for a lot of years. or Jensen Wong, 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 and prove to yourself

that you're not getting old and you're not going to be at a 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. 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 has 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. 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 return, 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. Do you know who Jimmy Avine is? No. Okay, Jimmy Avine, 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 artist. So he co-founded Beats with Dr. Dre.

They wound up doing beats music and headphones and they sell it to Apple. I think he's the guy that was involved with the Beatles at the very end. John Lennon. Yeah, John Lennon. He was an engineer and a producer for John Lennon. He just showed up on a Saturday and next thing you know, yes. He love him. He's fucking Italian from New York.

I know who he is. I forgot his name. He's awesome. I did an episode with him, but now we've become friends. We talk all the time. He's a very shigered. 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, I don't want to fucking talk about the past. I'm going to talk about what I'm doing now. He's like, there's no trophy room in my house. 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 train myself to make it a tail win. As soon as I feel it, that means I have to fucking go forward right now. Yes. Right now. Do you not think, step forward. Yeah.

What's your relationship with fear? How do you do with it? 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, at that two drill for a rue canal. And I had to go to a meeting right after that.

And I told the dentist, drill without any novacaine. And he says, you're out of your mind. And my whole life, I wanted to see if I was a badass or not. In other words, I'm my fake badass that has this envelope nobody could tell or I'm really a badass on the inside. And I told the dentist, take it out with no novicane. And he drilled and I jumped. And I told the dentist, I won't 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. Now, I have to go home and change my shirt because I was a puddle 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. 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. Yeah, high school and college. And it was across the street from or across the river from a country club? No, it was in a country club. The country club has the yachts, in the water, in the pool, and the side. Do you remember what you said about this? Yeah, I know exactly what I said.

Can you repeat it? I said, I'm going to get those fuckers later. You know, it was all the rich kids. What does that mean? 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 wise through sweating like a pig,

working overtime, and just looking over it, kids my age, having the times of our life. And I said, I'm going to get you all fuckers later. And I did. 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. It's like, no one in my family even graduated in fucking high school. Yeah.

And I remember going to public school and there was this kid that would drive. He had like $130,000 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, which I had no idea were phenomenal businesses. The insight that he had phenomenal business, he did, yeah, me and my dad just went to lunch. They took a helicopter, like 200 miles to lunch. I was like, what are you? I'm working full-time at 15.

Like what are you talking about? And that's exactly how I felt. I'm working on 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 the way he's. 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 so amazing. And he goes, I wasn't like

that. He goes, what I thought when I saw these people, wait until I get my shot. Wait till I got my chance. I will show you when I come around what that actually means. Now, what the trick is, though, is to use that as a motivator by not be an asshole when you're later in life. Don't do unto others as it was done into 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, point two. Before you get to point two, how have you done that? My need to get them back, them kind of ended by the time I got 50 or so on. I mean, 50. Yeah. Well, yeah. It seems like a long time, but it's not.

It took a good 30 years. 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 where 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.

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. How many people that grew up wealthy have that drive that you know? A good amount of kids that grow 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 this twin brother. 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 on Sequoia where we checked in. And one of my partners suggested for the check-in to say, what is the vignette in life that made you who you are? 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 changes life. 40 years later, 30 years later, he still wakes up for 4 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. What was your vignette? 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. I want to tell you about the presenting sponsor of this podcast, Ramp.

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That is ramp.com. You mentioned inducing the importance of inducing misery into your kids' lives. Do you still induce misery into your own? No, I've gone full cycle and I have spoiled myself with material things, realized they don't make me happy at all, got rid a whole bunch of material things. I sold my fancy cars, 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 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 leading the life of a monk. But I have shuddered assets on purpose, just to simplify my life. and if you will get down to the really important things in life, which really at the end of the day is your family and friends.

That's really the most important thing. Not just shedding material, like inducing pain or misery into your life at this time, at this point in your life. 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. Let's see when you were building, right? Your first few decades there. Did work always feel like work, or is it something like you were addicted to doing that you're obsessed with doing it? No. 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. You've got to spend time with Jamie I being, dude. I'm telling you, I think you would love him. He's been around some of the greatest, you know, people are the most talented people in history. You know, work with John Lennon, Bruce Springsteen, Dr. Dre, M&M, 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, 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 the vibe I'm getting off of you. 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 a partner that

I was homeless. I slept in my car for a week. I showered at 3,000 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 I had some money and I started getting a rental and so on. What was going on in your life that you were homeless? I went through a divorce and 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 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 don't think I've ever told that in a public setting.

I mean, at this point, you can't go any lower than you already are. Oh, no, you can go a lot lower. First of all, I was healthy. Okay, so you can get a lot lower than that. You can be sick with a disease. Good point. And second, I was a partner at Sequoia. Are you kidding me?

My present value, my future earnings were 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 would not have been funny to be homeless for a lifetime. And if you're truly homeless, that's not funny. But in my case, it was I was a partner at Sequoia showering at the sun at the shower and 3,000th and selling a road, parking my car a little bit further away from the office

and sleeping in my car. So go back to, you're saying, the level of discomfort that you felt when you came right now that you're currently experiencing, why did you retire to begin with? And then why did you come back? 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 found that 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. Did you want to step down, though? 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. It was the new king. It seemed to me that being the old king with a 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 nothing to do. 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 it was going to lose my mind.

It turned out the Rulov stepped down. Pat and Alfred took over. They weren't the kings I chose. And 30 days into her, 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 saw. Scrabble. Did you see that coming? They always wondered to me publicly for the two years before, why aren't you around? 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, a surprise visit. I don't know whether they wanted to see me. And I said, sure, right on the spot. It wasn't that long a conversation. Yeah, that's why I asked if you saw it coming because you... No, it was, it was of course. And we agreed that I would attend partners meeting.

I would be 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 investments. I told him I wanted to do nothing for 90 days. I want to get calibrated. And here I am now. Day 91.

Panicked. Yeah, but I mean, 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 come and so many different companies and founders come and go. Like, that's invaluable, invaluable wisdom

to have inside the company. Yeah, except that the world changes. And this change more dramatically through AI. How many different changes have you been through? I understand, but this is the most radical change. This is an industrial revolution kind of change. And so, as I said, I'm 90-day into it.

I feel further away now than when I get 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 didn't know if it was a joke.

I didn't know if the partners wanted to do that to make fun of me. No, because they would do that. Yeah. And it wasn't a joke. And so I've never seen revenue growth at this space. I've never seen prices like this. One could say all you have to do is that three 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. But I don't want to rely too much on the pass. I want to use the pass 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. I would love to know these questions and these heuristics that you ask.

I'm very skeptical because 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 I could actually answer this question for me? It's just seeing a lot more. And so I was talking to Michael Dell about this. And I asked me, I was like, is this time actually different?

And he's like, yes. And then he gave like this, we had like a 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 characteristics that you were mentioning earlier? I have two or three of them. One of them is what I put my kid's 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, 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.

Say more about the bounding of only having 20. There's probably 200 investments that you can make in your lifetime. And a lot of them are going to return two X your money, three X in 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 he was 100 million, then 500, then a billion, then

five billion, then Alfred hit 10 billion, and now Sean hit 20 billion. I told Sean, you fuck her, you kind of ruined it for me. I'm not going to show up now with a $4 billion gain. Was that SpaceX? What was that? Yeah, it's space. We haven't cashed out yet or whatever, but, you know, there's a shot of a $20 billion gain and more.

And so he ruined it for all of us. The ones that you're best performing investments, I'm always curious if you can actually see it back then. They always surprise you on the upside. Right? Always. They never surprise you when they fail because that was always one of the scenarios you had thought about or mostly as well. 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 great companies, they've compounded 20 years after the IPO. NVIDIA 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. Because if you're compounding a $5 billion gain, that can turn into a $50 billion again. If we held Google and had sold gold, 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. And, you know, we own 20% of Nvidia. Think about that. I mean, you know, we own 10% of Google. And there's many others, you know. Apple, are you kidding me? We were the first investor 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. 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, obviously he gave it away before it accumulated

to his kids, but if it was still in one person, it would be worth half a trillion, or 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. Yeah, exactly. That's exactly right. You 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? It means that I'm interested in the business and the building the business of a company, not in shaping their technology of a company,

meaning that I'm not a product manager type. That's what founders are. In some cases, that's the only thing they know. They're getting younger and younger. They're 23 years old or 20, 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. But then you have the business.

You have the selling of shares, not to selling a product. And in the selling of shares, you have to wrap everything into it, which is the analysis of market, 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 legion and the revenues. And you've got support and counting and so on.

Oftentimes, companies break, oh, they suboptimized that. That's why to 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 the helping founders build a business. Say more about that. So how do you take a 22-year-old that when it comes to us is an outlier, in something in life, probably IQ 150 or above.

All the adjectives that venture guys use in a negative sense. I use in a positive sense. Irreverent, shithead. They don't listen. Love it. Give me those founders all day long. You got to say more about that. Why do you like?

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 thinking about the problem, thinking of 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've 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. That means you have to have an eye for these up-and-comer people in sales and marketing because the made people 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 there.

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 mold and shape and build their business with them? With David Valles of New Bank. 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 committed to Sequoie, 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 door dash 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. And he had a notion of a financial services business, a credit card business in Brazil. Mine a problem. He wasn't from Brazil. He knew nothing about financial services. But he had a heart of gold 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 Rost 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, what do I do now? It was more a, I viewed it more 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 did miss a beat. He didn't miss a single B 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 rate. So I don't know what things are worth anymore. Well, DeVie 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 him, like, what are the founders should I talk to? It's like, this guy is incredible. Is this surprising? So an associate at a venture firm then becomes a world-class founder. Is there other examples that you can think of that follow his pattern? I've seen it the other way. I haven't seen too many associates becoming founders. Yeah.

You're actually one of the few. I think most VCs are full of shit when they say, oh, the founders, the star and the founder is the most important. You use this thing, or like, 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. We're all fucked.

And he's like, if the VC could do that, they'd be founders then. And I'm like, you know, DeVesch from iconic. Yes. So I just had a- killer. I just had two fucking crazy lunch with him. He is a freaking. You sit in our conversations.

He is a, I wish we just recorded that. I literally just came from that. 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.

We are the service business. I think you actually fucking believe it. No, we are. And what the trick is is to retain that founder in a company forever if you can and for as long as possible. because once you lose that founder, you do lose the soul, the company. A company is many refounding type moments, and we saw it 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 I-R, but we didn't make any money, really. Yeah.

And so you want the founder in the building for as long as possible. Think of the refounding of Apple. 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, remember us. 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 phenomenal.

You should have seen his memos internally. His reports to the limited partners were funny as heck. It kills me because I read biographies for a living. And that's 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,

backchon, I was like, dude, I got to fucking do a founder's episode on this. And it came back, absolutely not. I'm like, God damn it. I remember that when I was, there's Mike and I, you know, we both ran Sequoia, a cold-blooded, uh, strict, 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 partisan meeting, he would use a word that you had to know the meaning of because he was the key to the sentence. I remember faking like him, go to the bathroom, going and look it up. Like, what does that mean? 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 and 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. By himself, yes. That even if people don't read the entire book,

which I'd highly recommend reading, just buy the Return of the Lover Kingdom and read the Forward that Michael Moritz wrote. Yeah, yeah. It gives you an insight into this, like, and just how rare the talent that Steve Jobs was. One could argue that Nvidia had a refounding moment. That was a graphics chip company. 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. I found one of my all-time favorite quotes when I was reading the book zero to one.

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That's apploven.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 Tekem called NVIDIA way, which is kind of a company history of invidio, but it gives you enough biographical background. You can function as a biography of Jensen. And he 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. Yes. You get to the book, he's like, oh, he does that to himself. Of course he does. He tortures himself into greatness. He wakes up in the morning, looks in the mirror,

and asks why he sucks so much. And if you're willing to do that to yourself, people will follow you. And people will torture themselves all the way until the goals back. But you have to be able to do, you have to be willing to do that to yourself. And people see that.

Did you torture yourself? Absolutely. my whole life. That's all I know. So your inner monologue's negative? I'm kind of a miserable soul on the inside. Say more about this. 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. and nothing changes it. My kids.

I have had reprieve when I'm with my kids or my grandkids on some good friends on a golf course. I play golf. I suck at golf. It's the same three guys so we can laugh for four hours. I'm going to interrupt you real quick.

Does this start when you come to this country, you tell the story of being like this precious, like, positive boy. A positive boy at 10. Sweet, sweet boy at 10. Free little boy. And then at 15. Yeah, yeah.

So that divine, Dave Ogilby has this great way to put this. And he says, all great people do grace stuff are divinely discontent. Yes. It's like just never satisfied. 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.

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. Stop talking about yourself that way. No, I'm serious. And you're not quitting either. I don't like this defeat his attitude I've gotten from you. No, I have it.

You're 91 days in. You're not giving up nine months from now. I'm not giving up, but maybe it came through that I'm scared shitless. Good. Yeah. That means you're fucking doing something. I haven't done anything yet. Dude, I've been doing.

You're not ready to be out of the game. So I was never out of the game. Exactly. It's my point. I was never out of the game. Well, one of them I don't think of it as a game. I think it was a business where people on, of our capital comes from non-profits, charities.

So I never thought of it as a game. In fact, when I ran Sequoia, I'd be 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 a business word. But if I take myself out, it won't be done 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 anything, I'm going to be the one that's going to have a look in a 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.

Have you seen anybody in your business stay too long? Stay too long. A million people. Did Don? No. Don stepped down in 1993. I believe, I'm going to guess, he was probably 50, 58 to 60 years of age. He didn't stick around for too long.

Why did he stop? 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 who 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, 0.7.6. 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 chose. There's not even a conversation? No conversation. So I'm a big fan of the way he thinks. He gave a few talks. Maybe he talked to Mike Moritz. Didn't talk with me. I just saw the shoot

of paper. To me, when I think about him, it's like a simple genius to the way he thought and operated. Would that be an accurate way to describe him? I think part of it was accidental. You know, look, I love Don Valentine. And there's not a bad thing 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. How big is that mistake in dollar terms? What's Cisco's market cap at its high might have been half a billion? So like what's a quarter or half a billion?

A lot more than, no, no, sorry. Yeah, half a trillion. Yeah, I understand what you. Half a trillion. A lot of money. A lot more than 90. But look, we all make mistakes. How many of distributions I push for at service now, I left the 10xer on a table, 10x, you know, it's crazy. billions upon billions of dollars, as we all did in a venture industry.

But you know the story. I'm sure that you've heard a story of my review from Don Valentine. I don't know. 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 founder. He left on a table for me to see. I love when ever 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, you know, it was a school of Hard Knocks.

It was a semiconductor day's. 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, 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. 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. Yes, yes, yes. So that's a very, you know, common mistake. 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 ten a cycle, maybe it'll be a lot more in this cycle. If you can sniff one of those and hold down to it for 20, 25 years,

there's really nothing else you have to do in life. Are most of your friends investors or entrepreneurs? Most of my friends are neither. Most of my friends are people that I've 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. Even further back? 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 general, Italy. You know, he's one of my closest friends. So you still able to relate to people even though?

Still, just the notion relate to people. I find that kind of weird. Okay. Let me relate to people. It's almost as a, you're there, I can relate to you. No, but you got this ago. It's like, people started with nothing. They're really successful.

It's like they kind of isolate themselves. No, 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 waterglass down in the morning, put in a dishwasher. I cooked yesterday afternoon. I washed over 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. In the 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. You can't say it's a sniffer. What is the sniffer? 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 it. loss otherwise. But relate, not losing an investment. Because I can see it's, I have a sniffer 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 main skill. And the other thing that I pride myself is I'm a very good soul. In fact, the Sequoia spec, or. 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 and the people we hire. We want people, not like me, but that are willing to do the right thing when it's highly inconvenient for the person doing it, and it's willing to walk through walls in order to win, in an ethical kind of way. How does the people you want to hire differ from the founders you want it back?

Same thing. Same. They need to be outliers. The founders who 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 and 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. 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 founders, I love, I'm very attracted to them, going back to the founder of Newbank, did he have those founder traits? He had a combination of smarts, drive, clarity of thought, toughness, goodness, judgment, mature, way behind his years, look, here's what I have to tell you.

We interview people and Mike Muritz 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 at it and you watch, God, I can't believe, you know, I'm done. And then you have people that you look at your 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 moved. We pulled them right back in.

And Mike met him. And within two minutes, Mike and I knew that we were going to hire this kid. And I had interviewed 10, 15 people. 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 new market. I saw it in India and so on. But they all looked the same. I couldn't tell him apart. And then I met David Veles. And within one hour, I knew for sure that he was going to be the person we were going to hire. Who are some other other the great founders besides him that you partnered

with? Fred Luddy of service now. He was older. But he made everything simple. He came to Sequoite to present, and he told us everything that was fucked up with this company. It was the wildest pitch. Yeah, everything that he screwed up. I mean, if you didn't want to sell shares, of course, you 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 asked 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. And that was the foundation to service now. That was incredible. Incredible.

And then you get into the Israeli founders, which I adore. They are top, you know, keep in mind, they think incoming tech 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. And the conversation with one of these usually men, no, actually there's a woman that She used to be a spy in Iran. She's tough. Now she's a founder? Yeah, she's a founder.

What's her company do? 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 smacked a shit out of one other guy smacks. We had the founder on the show, Dana White's company. And you take it and then the guy, now it's not quite that bad when it is we found it, but there are no holds bar. 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. How do you build trust with the people that you want to invest in?

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 the T's founder when they asked me, how much do you want to own? I said, we usually start being happy. about 100%, but we can go out from there. And I do that on purpose to almost 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

out. 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, and then paving the way for them to ask you the first question, which may come in an email, the first little. 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 to screws with them now. If you're going to turn to screws, do them when their egos 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 boy. It's almost they won Doug Leone,

but they're scared of shit to have Doug Leone. The reason I ask, because you have one of the greatest quotes I've heard, we said trust is the grease that makes all business run. 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 0th one, which is trust. Yeah. 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 putts, in which case I'm not going to trust you. Or I can trust his 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. That's interesting.

I've never heard it broken down like that. What came to mind 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. Yeah, it's necessary in order of a business. And you see these companies with broken culture

with no one trusts one another, and you can't get shit done. And by the time someone here that knows something makes a decision, which is the right decision, to the time to get, to the VP of the CEO, forget it. It's a whole different thing. I'm glad you just said that because I had dinner at his house right before he died. And he told this story where he's like,

Who's this? Charlie. Charlie. The right page of 99 years of. I know. And then I had another dinner scheduled after his 100th birthday. And obviously he passed away that November, previous November, fortunately. He told us a story where it was during like the Enron blowup.

Yes. 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. Yes. And they were wanted to, they, they saw this, I think it was like a pipeline business that Enron owned. Guy Buffett trusted call on Friday and said, hey, this is happening, but you have to wire the money like now. And it was like a couple hundred million dollars to think. I forgot what it was.

Let's call it 400 million. And the Burchard's 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 bonger 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. not risk-free.

Yeah. Because, like, why? Because Buffett trusted the guy that was on the NFL. It's quite interesting because I'm a trusting soul by nature and I've never been screwed

in business. I've never pre-wired money, if you will, as a metaphor, and paid the price. 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. Yeah. It's just you said you're going to do

this. I said, I'm going to do this. We don't even write anything down. You just do it. Well, it's a value of a term sheet. A term sheet is not worth a paper. It's written on. But once you sign it, both sides, I think you have to honor it. You know how many times 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 in a much high price. There's no way. There's no way. No, no, we shook somebody's hand. And people say, well, you have a fiduciary duty to take the higher price. No, I have a fiduciary duty to make sure the culture, the company is a clean culture.

And we do business the correct way. Yeah, at the end of the day, you have to be comfortable with, like, your own health. Absolutely. Absolutely. Absolutely. I'm actually surprised that you're trusting, like default trusting. Yes, I have a roundhead, 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 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. What do you mean? I really like helping others.

It makes me really, really happy. 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. Yeah. 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 we could all win. But you tell me what you need and I'll do whatever I can just to get it done. Deal is how the best

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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. of the world. Deal is trusted by over 40,000 businesses. Learn how they can help your business today by going to deal.com forward slash Senra. That is deal.com forward forward slash Senra. So looking forward, you're on day 91. Like, what is it going to, 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. 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 going to matter what's on

that sheet of paper or 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 got to do this. And I have nothing going on. It just came back from vacation. I don't think I have, I don't think anybody ever said they have nothing going on. I mean, it takes guts the same friend of nine people. I have zero going on. My MIT is to go scrounge. I use that word for deals. 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 want to make in my lifetime. But is that process today different for you than it was when you were at Sequoia previously? 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. This is very interesting to me.

I want to hit on that before I forget, though. 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 us attention. to, like 15 minutes my smart friend just identified in the core of the issue. And so the guy that I hooked him up with, text me, he's like, man, this guy was just fucking nailed that, you understood it.

And I sent him text back. I go, he's my favorite type of person. Very hard to get to, hard outer show. But once you break through, he'll do anything for you. I think that's very similar to what you were saying. It's like, don't be confused by the round head and the booming voice and the fucking everything. Yeah, the ball's round head.

Yeah, the ball of round head. 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 of founders. I have no friends that are not entrepreneurs. Like, I work on founders' podcast during the day, hang out with founders at night. Well, I'm so proud that I'm a founder of a company. I actually love that.

Well, no, the reason I bring that up is because it's 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 meet with my partner and talk to us about it? I'll just have lunch. I don't even give a shit about what you. really give a show about your business, but let's talk. And then I would ask this guy who's been adventurous 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 going to call? You can pick anybody, and they're going to 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.

It's nobody on that list. It's exactly what you're talking about. It's these young kids are identifying a vastly different group of people than the previous generation has done. So that is, is it, isn't interesting. In the ideal world, a 25-year-old says, let me get some experience, let me go call Doug Leone.

It's not, it doesn't work that way. So then, wow, what's the solution? Yeah, what's the solution to that? 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 that you're doing for your business.

Yeah, but like, here's the day. I just talked about DeVesch about this. two, where it's like, I have this fucking uncontrollable obsession. Like, I can't tell you why, since I was a little kid, all I wanted to 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, they didn't tell me that somebody on the team was getting married.

They went to Italy. It 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 going back. I got shit to do. Like, I want to get to work.

So it doesn't even feel like a hustle to me. It's just like this compulsion. I think it's the best kind. Yeah. I mean, it can't feel like a hustle because then you're exhausted. Then you need, you know, Friday, Saturday and Sunday off. No, it's your love. Yeah, but one thing that did change.

You know Brad Jacobs? Mm-hmm. You spend any time with him? Mm-hmm. 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, not hypnotism, his meditation practices, like his, it's all about his mind and stuff, but he's so unbelievably joyful human. 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 divinely disconnected to have. People was like, my inner model, I just wake up every day now focused on what I did. Just like, that wasn't good enough.

You could have done it better. Like it's just super negative. And until he sat me down on 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 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 60 years old when I had this conversation with him. And overnight. Overnight, you changed my inner mom.

No, the things I think about is not all the success I achieve, but all the opportunities I let slip. All the screw-ups I made as an investor. You know, I don't think too much about it 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, I could have done so much better. Look, I've done fairly well.

Oh, that's an understanding. I know both. I'm not saying just financially, but, you know, in things I've done. But all I can think about is how much better I could have 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 learning. for yet on the next founder for his benefit or her benefit.

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 on this? 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 and a day. night. You know, he talked to me, let's go out. It's no more complicated in that. And then I'm putting any thought into it. You know, a board is like a mate, a lifetime mate. 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 compliment what you have. 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 want to find a little bit of discomfort. You want to find someone with a very different set of experiences, which means that initially, you're going to talk like this. Initially, you're not going to understand what he or she is telling you. But that's what 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 an elite term sheet. Everybody gets an elite term sheet. 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 them? So 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. An 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 I 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 Schifford, maybe 30% are incompetent. They don't know what they're doing. Another 40% I call them no ups. No damage, no anything. They nod. You know, they nod with a group.

And maybe 30% of fewer, maybe 20% know what they're doing. And that's one overlay. The other overlay is, you know, managing their firms, their statured or their status in a firm. I need a win. I need an exit. What's my partner going to 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, duplically type domain, covers your ass with the partnership and incompetence, 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. The best boards that you've been on are the board meeting is contentious. No, but issues are put in the table. Real conversations are put in a table.

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

It's the same thing at partners meeting. We don't argue, but we have the real conversation. At times, at Sequoia, we have to take a five or ten minute break. Five or ten minute break. We walk around, we go back in a room, the temperature is cooled down by ten degrees. We have the conversation. We come up to an 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. I would say that one of the most interesting things I learned this year from doing the show, Ed Cammell was nice enough to let me come to his house and record a conversation with him.

And he was like, hey, a lot of people don't know that in the 10 years that Pixar was a public company before the acquisition from 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 why he fired him. He's like, because they didn't disagree with me. He was like, they always agree with me. They served no purpose. And he was saying that, you know, a lot of people say they want to get to the truth.

And I think Ed on the episode said, most people that say that are actually full of shit. They're full of shit. Steve actually wanted to get to the truth. They're full of shit. 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 went from Italy to New York City, which was halfway to America and then to California, where everybody told me, yes, give me the, give me. me the feedback, the honest feedback. Nobody wants to hear the honest feedback. Who am I

kidding? Yeah. Everybody's full of shit. But the best founders have to. They have to, and you have to figure out a way to do it in a fashion that it's understood, received, accepted, and acted upon. It's almost an art. It's not just giving it. It's giving in the right way at the right time, with the right tone, with the right words, with examples, and so on. Look, it's like telling a founder your VP of sales sucks. You're not going anywhere. But 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. Okay, this is like inception. Well, I don't know about inception. Okay, so I'm a big fan of Christopher Nolan. I just reread his biography before 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 warm?

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 intercept them with the idea so they believe that they came up with it. Yeah, it's like your kids. What are you going to tell your kids?

All the things they shouldn't do. Good luck. Yeah. Forget it. Are you familiar with the shit sandwich? The shit sandwich. On how to get feedback? I don't know if this is,

this is the art you were talking about. But shit sandwich is like, compliment, the negative feedback, and then another compliment. That's what I called the cheese sandwich. 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 founders are going

to walk away from this thinking he won the freaking lottery. And I don't know to do that. And I was always a mirus of how he could do that. And I'm more direct. I hear people talking to phone for 20 minutes, 30 minutes. My conversations are three, four minutes at most. Hi, what do you need? This and that?

Done. Okay, yes, I got it. All right, I'll let you know. 30 seconds, not even three minutes. Yeah. Most of my conversations are less than three minutes long. Yeah. You know what you think is interesting

that you don't like hang around with other venture capitalists? Why? I don't know. Founders hanging with other founders. I think it comes to the fact that I grew up from dirt and the inside of me

that'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 life. I think humanity and one-on-one relationships are probably the most interesting thing for me. Are you introverted? I'm right on the 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 got to meet. Right? Where, I remember to meet. talking where the extroverts, I'm told, find energy. All they get energy is so gross. They love it to be new people. Oh my God, another person I have to meet.

Yeah. And yes, I do it. I can turn the charm gene on. I can fake it. I can be a cockta party and know to walk around the network with everybody. But I get home and I'm exhausted from that. Yeah, definitely interferer. Yeah.

I am too. And I think there's a very similar, like, you know, 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 going to spend two hours for somebody new.

That's very expensive to compare to maybe the five true friends that you have in your life, the cop in Italy or your friends back in New York or whatever. It's like, I'd rather just deepen that relationship that I have than go out and... 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 that if I put myself out there, I there take these minor emotional risks. I find myself happier because I feel more well-round that at the end of the day. I feel like I've done something. Could you even be in the business that you're in, but not meeting new people? No, absolutely.

Although it's not a social setting, right? It's work. It's presentation, present, help, assist. Well, you know, I think the closest friend I have as a founder is, is Veles. All the other founders are pure business. I don't socialize with spouses or anything with any of my, with any of the founders. But you do it with the less.

Yes, because it was an associate. I hired them. We had kind of a paternal, you know, son relationship. Yeah. Is there any venture capitalists that just made like maybe one or five or ten investments, and then that was it? Crosspoint Ventures had a hell of a run for seven years. seven years and they went away.

It's a name you may not remember. Look them up. Now, they still exist, but it's all the partners left after just making a whole bunch of investments. There was a venture firm called TVI. You may not remember. Technology venture investor.

That's the one that bought Microsoft right before the IPO? They didn't buy Microsoft, but Dave Marquard was on the board of Microsoft. Yeah, they got 900. It was a couple of, One guy started benchmark with two other persons from another firm. But Dave did, I think, if I remember correctly from this book called Hard Drive.

He was on a board of my... He was the only venture investor in Microsoft. The year before Microsoft went public of our market company, they were doing 140 million in revenue, 38 million of profit, and they sold 995,000 shares for a million dollars to him. No, I don't think, I don't think, I don't know what they did. We're going to put this in a shout-outs on venture. That was a venture firm that had the keys to the kingdom.

Yeah. and somehow didn't last as a venture firm. Where Crosspoint, they just called it in and they all went there, Mary Way. This is a firm that just couldn't coexist, even though they had everything. 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, they were talking about the greatest seed investors of all times. He's like, greatest seed investors, my dad, he made one investment. I made $40 billion. That's it. Didn't invest in anything else. That's it.

That's it. That's awesome. So I asked you if you're introverted, I want to ask you something that I think Moritz is definitely introspective. You don't strike me as introspective at all. Morris taught me how to listen. Morris taught me how to listen to the exact word that said, the timing of that word, you really can understand about a human being

by just listening to the adjective and so on. I took the more basic training that I got and I used it and I expanded on it. I love listening to people speak. Wait, what do you mean you can learn by listening to the adjective they use? Oh, what do you mean? When they use when they describe a situation,

humans can help by letting it out by showing themselves. And how they use the word I versus we when the script, I can sell you this. I'm thinking to myself as this, he's presenting

and said, fuck that, you can't sell me shit. That's what I think during the presentation as I have that stupid grin in my face. But just listen to the specific words

that I said, when they say it. We often choose a founder without a line of code, without anything, based on a presentation, a clarity of vision, 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 requote my words back to me or the way I said them. You know, it would drive me nuts. It drive me nuts enough that I learned. What was happening there? Why would they drive you nuts? We used to write memos at Sequoia. And the memo were from and...

and two. And Mike pointed out to me that the from puts myself first and the two, the recipient second. And Morris was the first that wrote the memos to and frung to put the other person first and yourself second. I understood that putting the from first and the two second as being a somebody 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. What else did you learn from him? So Mike was brilliant. Let me tell you, he was a very painful co-head. And he knows that I was painful for him. It was painful for me.

Like I said, 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'm 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 an investor that's a spectacular list. You know, look, he had his faults and we're not going to talk about all his faults here. But on that dimension, it was by far the best in the world. All right, Doug, I appreciate you doing this. We're going to run this back.

because a year from now, you're still going to be doing this. I have faith that you're not going to quit nine months from now. Yeah. And when you're still around, nine months and one day from now, let's run this back. I appreciate you taking the time. Thank you. All right. Bye-bye.

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. Thank you.