How to Dominate for Decades | Doug Leone, Sequoia Capital

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?

for decades. What's your answer to that?

My partner in India said there are many roads to heaven. Uh and so there are many ways to dominate. Uh take Steve

Jobs. He had really one job and he

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

linear. Those are gifts where you find yourself in the middle of the hurricane and you just want to keep on going because as the world changes your job changes. What's more interesting is how

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

out of date. I mean, if I look back on my career, uh, 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 and I still have that fear at the age of 69.

[gasps] 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,

bottom. So when I came back to Sequoia, they gave me this fancy title of chairman. We were in front of our LPs,

chairman. We were in front of our LPs, our investors, the first time about 6 months ago, and someone asked me about chairman. I I told them it's a bunch of

chairman. I I told them it's a bunch of [ __ ] What I really am is an analyst. I'm a low-level analyst and uh

analyst. I'm a low-level analyst and uh 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 partners asked me and how do you feel after 90 days? I said I feel like

I'm good for nothing. I feel like I've entered an AI has gotten further away from me than when I first started 90 days ago. And so I'm terrified. I told

days ago. And so I'm terrified. I told

one of my partners just an hour ago that if 9 months from now, which is the one year since I return, I feel just as irrelevant. and I'm going to take myself

irrelevant. and I'm going to take myself out. And so I don't know if I can do it

out. And so I don't know if I can do it yet another time. And there in lies the fun and there in lies the answer to your question.

Do you know who Jimmy Aine is?

No.

Okay. Jimmy I he another guy dominated for decades. Uh he was in the music

for decades. Uh he was in the music industry for 50 years. But um a lot of people know him because he's uh had the insight to start building businesses with his artist. So he co-founded Beats with with Dr. Dre. They wind up doing

Beats Music and the headphones. They

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

John Lennon.

John Lennon.

He was an engineer and a producer for showing up on a Saturday and next thing you know Yes.

You love him. He's [ __ ] Italian from New York. Like

New York. Like I know who he is. I I forgot his name.

He's awesome. I did an episode with him, but now we become friends. We talk

[clears throat] all the time. He's he's

a very 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 sat down. He's like, "I don't want to [ __ ] talk about the past. I want to talk about what I'm

past. I want to talk about what I'm doing now." He's like, "There's no

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

I can't even tell you what I did 5 years ago cuz I forgot. I'm worried about tomorrow. It was very interesting. But

tomorrow. It 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

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 tailwind. As soon as I feel it, that

tailwind. As soon as I feel it, that means I have to [ __ ] go forward right now. Yes.

now. Yes.

Right now. Do not think. Step forward.

What's your relationship with fear? How

do you deal with it?

Throughout my life, I felt an awful lots of fear. And it's always been the

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 ft masts that whenever I feel it.

I face it head on. It's almost a challenge. Look, there's a story that my

challenge. Look, there's a story that my partners know. I had to get a tooth

partners know. I had to get a tooth removed. Actually drilled um a tooth

removed. Actually drilled um a tooth drill for for a root canal. And I had to go to a meeting [snorts] right after that. And I told the dentist, "Drill

that. And I told the dentist, "Drill without any Novacaane." 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 a fake

or not. In other words, I'm a fake badass that's has this envelope nobody could tell or I'm or am I really a badass on the inside. And I told the dentist, "Take it out with no

Novacaane." And he drilled and I jumped.

Novacaane." And he drilled and I jumped.

And I told the dentist, I won't move again. And I didn't move again. And I

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.

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. [ __ ] it. I'm not moving." Now I had to go

it. I'm not moving." Now I had to go home and change my shirt because I was a puddle of sweat, but it 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 uh 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 on a side.

Do you remember what you said about this? Yeah, I know exactly what I said.

this? Yeah, I know exactly what I said.

Can you repeat it?

I said, "I'm going to get those [ __ ] later." You know, it was all the rich

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, uh, 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. Uh, 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 [ __ ] later." And I did.

That is such a re like a reoccurring theme throughout like the history of entrepreneurship. I felt it that way.

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 [ __ ] high school. And I remember going to

high school. 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 [ __ ] ton of Dominoes 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 uh this other for my other podcast founders. I'm starting to read

podcast founders. I'm starting to read about uh Mike Tyson a lot and Mike Tyson has a video where he talks about the difference what 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 that the hu the star athlete at school like wow look it's Tracy's so amazing and he goes I wasn't like that he goes what I thought when I saw these people wait till I get my shot

wait till I got my chance I will show you exactly 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 [ __ ] when you're later in life. Don't do unto

others as it was done unto you. So, how

do you take this this incredibly negative experience, make it a positive experience, and then as you mature, uh, use it in a positive way for the benefit of of not only for yourself, but

everybody else around you. Point one.

Point two, how 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

50. 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 to

years. It took a good 30 years to to overcome that weakness, cuz in some ways it is a weakness because it's a false narrative. Those were not bad kids. And

narrative. Those were not bad kids. And

I don't want to live in a false narrative. I finally outgrew it. But the

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. 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'll won't be hungry.

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

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

twin brother. They were they both attended the same college. They're both

wide receivers on opposite side of the fields. They adore one another and they

fields. They adore one another and they love nothing more than beating the [ __ ] out of one another. So drive comes in many ways. I have a son-in-law who is

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

cheese. I mean, it shows you it shows you these little things. You know, we had a session at 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 uh 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. 40

thing. To him, it changed his life. 40

years later, 30 years later, he still wakes up at 4:00 to work out. I mean,

the 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. Uh, it was the being made fun of in a classroom. It was

being called pasta in high school. All

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You mentioned inducing the importance of inducing misery into your kids' lives.

Do you still induce misery into your own?

Yeah. 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

all. Got rid of a whole bunch of material things. I sold my fancy cars a

material things. I sold my fancy cars a great discount. I just want them gone.

great discount. I just want them gone.

It was one day I woke up. I just didn't want to have cars with vowels on at the end of the name. I just got rid of them.

I just wanted a more simple life. I

wanted to uh 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

sheded 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 I feel that 3 months into it, I'm really good for nothing.

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? You're obsessed with doing it.

doing? You're obsessed with doing it.

No, it 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.

You got to spend time with Jamie Ian, dude. I'm telling you, I think you'd

dude. I'm telling you, I think you'd love him. He's been around some of the

love him. He's been around some of the greatest, you know, people, the most talented people in history. You know,

work with John Lennin, 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 makes them different. And also like the same side

different. And also like the same side of their genius is also their dysfunction. Yeah. And his whole he and

dysfunction. Yeah. And his whole he and he he's like for himself it's the same thing. He's like

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. It ha I have to succeed at it. Very similar to like the vibe I'm getting off of you.

Yeah. Uh look, failure was never an an option in my life. I had no plan B. Uh 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

Road. I was down to no money. I was down to zero zero money. Seoia back then would buy you a car when you made partner. I bought a car. I didn't have a

partner. I bought a car. I didn't have a home. I slept in my car for a week and

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.

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

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 of $400 a month. So, I didn't

have a home uh 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 3 weeks. And

then I had enough money to go buy uh to go rent a to 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 that Sequoa has ever had. I don't think I've ever told

ever had. 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

healthy. Okay. So, you can get a lot lower than that. You can be sick with a disease. Good point.

disease. Good point.

And second, I was a partner at Sequoia.

Are you kidding me? My my present value, my future earnings were going to be terrific. So, I wasn't panic. I just

terrific. So, I wasn't panic. I just

knew it. It was only an inconvenience.

And I saw the humor in that for about a week. I mean, clearly would not have

week. I mean, clearly would not have been funny to be homeless for a lifetime. And if you're truly homeless,

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 uh at the shower in 3000 road,

parking my car a little bit further away from the office and sleeping in my car.

So go back to you're saying that the 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 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 I was a hired gun. So, it seemed to me the right thing

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 Valentiney founded it. He

bat. Don Valentiney 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 I

chose a successor.

Did you want to step down though? It

wasn't a matter whether I wanted it or not. It was the right thing to do for

not. It was the right thing to do for Seoia. And so I chose Ruaf. Uh I I was

Seoia. And so I chose Ruaf. Uh I I was the old king. He was the new king. It

seemed to me that being on the old king with a new king around, you shouldn't be around. You should be removed. And so I

around. You should be removed. And so I stepped out. I I was on 10 boards. And

stepped out. I I was on 10 boards. And

uh 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

working. When a company's working, there is no there's nothing to do. Uh, and so I had a great backlog of companies and I wasn't busy. So I started taking drum

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. Uh it turned out the RUF stepped down. Pat and Alfred took over. They weren't the kings I

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

come back? You're not on 10 boards anymore. You're on six boards. We sold

anymore. You're on six boards. We sold

four companies. There were companies like Whiz and so on [snorts] and I said sure. Uh and we cut a little deal in an

sure. Uh and we cut a little deal in an afternoon and a you know on a single sheet of paper that we scra scribble.

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 Ruof was gone, it was uh much easier uh for me and for them. And so they came over, surprise visit. Uh 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 cuz you No, it was it was of course. And we

agreed that I would attend partners meeting. I would be in a c in the inner

meeting. I would be in a c in the inner circle. I would help them spot crucible

circle. I would help them spot crucible moments, as we say, to figure out how to navigate them. Uh, and make a couple

navigate them. Uh, and make a couple investments. Uh, and I've done

investments. Uh, and I've done everything but make a couple investments. I told them I wanted to do

investments. I told them I wanted to do nothing for 90 days. I want to get calibrated. And here I am now, day 91,

calibrated. And here I am now, day 91, panicked.

Yeah. 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 come and so many different companies and founders come

and go like that's valuable invaluable wisdom to have inside the company.

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

Yeah. But how many how many different [clears throat] changes have you been through?

I understand but this is the most radical change. Th this is an industrial

radical change. Th this is an industrial revolution kind of change. And so, as I said, I'm 90day 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 [snorts] a memo. I won't

weekend. I saw [snorts] a memo. I won't

tell you the name of a startup company that wants to raise money without anything at 10 billion pre. Uh, you

know, it gets my head spinning. I I

didn't know if it was a joke. had enough

their partners wanted to do that to make fun of me. Uh no, because they would do that.

Uh and it wasn't a joke. Uh and uh so I've never seen revenue growth at this space. I've never seen prices like 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

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.

that. And so I've seen a lot of changes.

I have good instincts. Uh but I don't want to rely too much on on the past.

It's not what I used to pass as a little corner here that I check things against and I have my uristics, my three or four questions I ask myself with each investments. I can discuss those, but

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 heristics 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.

And so I was like, well, who could I talk to that could actually answer this question for me that's just seen a lot more? And so I was uh talking to Michael

more? And so I was uh talking to Michael Dell about this and I asked him, 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

actually different. What are the heristics that you were mentioning earlier? I have two or three of them.

earlier? 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 uh if I don't pass those

investment? And uh if I don't pass those three, I'm not going to make the investment.

And uh 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 a third? And those are questions that

a third? And those are questions that I've always asked myself. Can you

say more about the the 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

lifetime. And a lot of them are going to return 2x your money, 3x your 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

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 Shawn hit 20 billion. I I told Sean, "You [ __ ]

20 billion. I I told Sean, "You [ __ ] You kind of ruined it for me. I'm not

going to show up now with a $4 billion gain."

gain." Was that SpaceX? What was that?

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.

The ones that your best performing invest investments, I'm always curious if like 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 you had thought about or or mostly is 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 uh 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.

years. You should never sell a share.

And you can make way more money holding those cuz if you're compounding a $5 billion gain that can turn into a $50 billion if we held Google and had soul

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. Uh and you know, we own 20% of

that. Uh and you know, we own 20% of Nvidia. Think about that. [laughter] I

Nvidia. Think about that. [laughter] 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 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

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, you obviously he gave it away before it accumulated to his kids. But if you know if it was still in one person, it'd be worth you know half a trillion whatever the number is now. Um and you realize

like he wasn't making a financial decision. He just liked Walmart. It goes

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 cyber security companies. I don't know anything about

companies. I don't know anything about cyber security. I'm on board a financial

cyber security. I'm on board a financial services company. I don't know anything

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 the technology of a company. Meaning that uh

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, the product marketing of the

final 10% of the product so it's salailable. I can help with that. the

salailable. I can help with that. the

product marketing and messaging, the demand gen, the the lead genen and the revenues, and you've got support and accounting and so on. Often time

companies break or they suboptimize that. That's what I get involved in. And

that. That's what I 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

technology. I'm much more interested in in the in helping founders build a business.

Say more about that. So, how do you take a 22year-old that when he comes to us is an outlier in something in life,

probably IQ 150 or above? Uh, all the adjectives that venture guys use in a negative sense, I use in a positive sense. Irreverent, [ __ ] they don't

sense. Irreverent, [ __ ] they don't listen. Love it. Give me those founders

listen. Love it. Give me those founders all day long.

What 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 5 months has gone to sleep and and has woken up 3 hours into his sleep just g can just thinking about the problem thinking of a

solution crystal clear in what they want to build. No one can detract them driven

to build. No one can detract them driven like crazy and so on. That's what I want. Uh but now we got to build a

want. Uh but now we got to build a business. And so who do you recruit as

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 upandcomers?

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 upandcomer people in sales and marketing because the made people are are going to play it a little safer. And so to help

navigate uh all the sets of issues that is what we at Sequoia I think are the very best in the world at.

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 Valz 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

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 Door Dash of Brazil.

Brazil. We are the Door Dash of Brazil.

[snorts] No real novelty. And one we had to make the call, hey Davided, we're now 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. [gasps]

Brazil. [gasps] Minor problem. He wasn't from Brazil. He

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 them 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. [laughter] I took the call from the men's room. Uh and uh you know, we talked it through. Uh he knew

what to do next. He was just all alone.

What [snorts] 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

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

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 uh code rate. So, I

don't know what what what things are worth anymore.

Well, Dev 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?

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 [ __ ] when they say, "Oh, the founder is the star and the founder is the most important." You use this thing where like 0ero to1 is the black magic and like that's the

founder's job. I can't help with that.

founder's job. I can't help with that.

If you need me to help with that, then we're all [ __ ] We're all [ __ ] And he's like, "If the VC could do that, they'd be founders then." And I'm like, you know, Dash from Iconic.

Yes.

So, I just I just He's a killer.

I just had two [ __ ] crazy lunch with him.

He is a sit in our conversations. He's a

kill.

I wish we just recorded that, but I literally just came straight from there and I was talking to him about you and cuz I'm like I actually think Doug believes this. I think when other VCs

believes this. I think when other VCs say this [ __ ] like they're full of [ __ ] 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. I

them. I'm in the service business. I

think you actually [ __ ] 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 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. [laughter]

Great IR, but we didn't make any money really.

Yeah.

Uh and so you want that founder in in the building for as long as possible.

Think of the refounding of Apple.

Your partner I I quote this on my other podcast all the time. Uh Morris has that great so he wrote obviously the Little Kingdom in whatever the ' 80s or '7s whenever it was and then he updated in I think 2009 to the return of Little

Kingdom and that updated forward again.

Morris is a crazy writer. like his

writing is he's incredible. You should have seen

he's incredible. 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 60page, you know, all these obscure ones that are not people are not supposed to have, they all come to me anyways cuz I do this for a living. And I I sat down and read the

a living. And I I sat down and read the Don Valentine one that he wrote in one sitting and then somebody that's mentored by Morates that I'm friends with, I back I was like, "Dude, I got to [ __ ] do a founders 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 coldblooded

uh strategic Brit and a tactical Italian, gregarious Italian. We had no [clears throat] 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 cuz Mike in a part 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 him go to the bathroom going and and look look it up like what does that mean?

Well, he the writing that he put in there, I think he said, you know, um turnarounds are difficult no matter what. In technology business, they're

what. In technology business, they're doubly difficult. They're almost unheard

doubly difficult. They're almost unheard of. He's like when when has there ever

of. He's like when when has there ever been essentially a refounding of a technology company and in the middle of a turnaround and he and then he has a great line was like and the first time

you know he had a partner he had a co-founder the the second reound he 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 little kingdom and read the forward that

Michael Morates wrote it gives you an insight into the psychology and just how rare talent that uh Steve Jobs was. One

could argue that Nvidia had a refounding moment. That was a graphics chip

moment. That was a graphics chip company. No. And no company up to then

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

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

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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

kids. I was thinking about Jensen because uh there's this book by Tay Kim 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 says something in there

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. And 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 goal is bad. 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 is 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 uh fun to be around. It's not an act, but when in my private moments I'm I'm

pretty unhappy always. I'm pretty

miserable and nothing changes.

my kids.

I have had reprieve when I'm with my kids on my grandkids on some good friends on a golf course. I don't I play golf. I don't I suck at golf. It's the

golf. I don't I suck at golf. It's the

same three guys so we can laugh for 4 hours.

I'm going to interrupt you real quick.

Does this start when you come to this country you you go from the you tell the story of being like this precious like precious positive boy at 10 sweet boy sweet little boy

and then at 15 Yeah. Yeah. So that dis divine David

Yeah. Yeah. So that dis divine David Oggoy has this great um way to put this.

He says all great people do great stuff are divinely discontent.

Yes.

Like just never satisfied.

A word I've always hated that I've learned to like is content. I hated that word until about 2 or 3 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.

You're not over the hill.

And you're not quitting either. I don't

like this attitude I've You're 91 days in. You're not giving up 9 months from now.

I'm not giving up, but I'm scared. Maybe

it came through that I'm scared shitless.

Good. [clears throat]

Yeah.

That means you're [ __ ] doing something.

I haven't done anything yet. I want to Okay. You're not ready to be out of the

Okay. 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 unemployed. 70% of of our capital comes

unemployed. 70% of 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

right words. It's not a game. It's not

money in the ground. None of that [ __ ] 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 done out of fear. be

out of good taste and kindness for my partners. It's not out of fear. I'll

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 the mirror and say, "You're you're done. That you couldn't do it

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 tiptop of my game, but in this one, I have to show it. I haven't shown it yet. And it's all

it. I haven't shown it yet. And it's all in performance. It doesn't matter what

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 a million people.

Did Don?

No, Don. Don stepped down uh in 1993.

Uh I believe I'm going to guess he was probably 60 58 to 60 years of age. He

didn't stick around for for too long.

Why did he stop?

I think he had enough. I think he had enough. He had uh two guys in Mike

enough. He had uh two guys in Mike Meritz and me that he thought uh could take over. He had older people that wanted to take over. And it's

interesting how Don told us we were the guys. [snorts] There wasn't a there

guys. [snorts] There wasn't a there wasn't a big conversation. It was the yellow sheet of paper. Don always wrote in green pen and a yellow sheet of

paper. One day we get um a little note

paper. One day we get um 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 You know the older guys 76 that was division of the carry for the

next fund. DTV done question mark. You

next fund. DTV done question mark. You

figure out what you want to give me. Uh

[snorts] and that's how Mike and I knew we were the two guys that were chos.

There's not even a conversation.

No conversation.

So I'm a big fan of the way he thinks.

Uh the talk he gave a few talks.

Maybe he talked to Mike Morris. He

didn't talk with me. I I just saw this sheet of paper.

[laughter] That's that to me when I think about him there's like a simple genius to the way he thought and operated is was 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 things I can 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 height?

It might have been half a billion. So

like what's a quarter or half a billion?

A lot more than no sorry not half a trillion. Half a trillion. Yeah, I

trillion. Half a trillion. Yeah, I

understand.

Half a trillion. Uh a lot of money.

A lot more than 90.

But but look, we all made mistakes. How

many of distributions I push for at Service Now? I left a 10xer on a table.

Service Now? I left a 10xer on a table.

10x, you know, it's crazy. would left

billions upon billions of dollars as we all did in the venture industry. Uh but

you know the story I'm sure that you've heard a story of of my review from Don Valentine.

So I came out of a presentation with a um 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 that 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

review. That was my review right then and there. And so, hey, that was a

and there. And so, hey, that was a school of hard knocks. It was a semiconductor days. Of course, we

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.

third. It's not that we're Boy Scouts.

It's time we are third but we knew if we do right by founders we'll have great returns of which we'll share. Uh so Don was wonderful. Don was the one when

was wonderful. Don was the one when everybody wanted me out at 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 in like 1915. He's like, "We'd be billionaires in 1950." [clears throat] Yes. Yes.

Yes. Yes.

So that's a very, you know, common uh mistake. Most companies if you hold them

mistake. Most companies if you hold them too long go away because technology changes. But if you have a sniffer for

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

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.

Are most of your friends investors or entrepreneurs?

Most of my friends are neither. Most of

my friends uh are people that I'd met in my early days of life uh who have bluecollar jobs uh uh who uh who are

nowhere near the techno world. I have

maybe two friends in this envir in in this world.

Most of my friends are from high school [snorts] uh and maybe college completely or maybe from Italy even further back. Yeah, even further back. Uh, you know, I just came from

back. Uh, 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 Geno, Italy. You know, he's he's one of my

Italy. You know, he's 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.

Relate to people. It's almost as if ah you're there, I can relate to you.

No, but you know how this goes like Yeah. People start out with nothing.

Yeah. People start out with nothing.

They get really successful. It's like

they kind of isolate themselves.

No, no. I have uh uh thankfully, and that's maybe one of my few good traits, uh I'm still normal.

I I make sure that I lead my life with no handlers. Look, I have everything in

no handlers. Look, I have everything in life that somebody needs, but I have no handlers. I have I have no personal

handlers. I have I have no personal assistant. I don't have anybody who, you

assistant. I don't have anybody who, you know, who who cleans up after me. I I

still take my water glass down in the morning, put in a dishwasher. I cooked

yesterday afternoon. I wash all the pans and everything on my own. Uh those are the things that keep me grounded in this crazy world of ours in which we live

here in Silicon Valley. 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.

You keep saying sniffer. What is on people's sniffer? I have an ability to

people's 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

hear. You know, I really haven't lost an investment in 30 years in Silicon Valley. People have beaten me because of

Valley. People have beaten me because of price, but I haven't lost otherwise.

But relate not losing an I have a sniff of what people want. uh

and that same sniffer takes me through what business is 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 the technology maybe a way to say it's EQ that is really my my main skill and the other thing that I pride myself is I'm a 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 hyperco competitive person with a heart

of gold. That has become our spec and

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 is 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 to back?

Same thing.

Same. They need to be outliers.

the the founders who want to back have to be extreme outliers in something IQ drive. It's kind of the same thing in

drive. It's kind of the same thing in the people. We have all these adjectives

the people. We have all these adjectives when you walk in a sequire office the reverence the outliers and I look at that and to me they're the same adjectives and people that that I that

we want to back and people we want to hire. I think we look a lot like our

hire. I think we look a lot like our founders. We don't give up. So, so when

founders. We don't give up. So, 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

them. Going back to the founder of New Bank, did he have those founder traits?

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

judgment.

mature way behind way way way beyond his years his his years. Look, um, here's what I have to tell you. We interview

people and Mike Meritz had a great line, called them half pages or full pages.

You interview someone, you write a half page, there's nothing else to write. You

you're there 30 minutes, you look at, 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 has gone by and you can't believe it. And David was one of them. And I

it. And David was one of them. And I

remember talking to him. The hour flew by and it was clear to me that we love this person. And he tells the story to

this person. And he tells the story to show you how Sequoia works. I said,

"Yeah, there's somebody else I want you to meet." He makes it to his car and his

to meet." He makes it to his car and his phone rang and it was Mike Morris. He

didn't make it out of the parking lot.

That's how fast we move. 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 and I had interviewed 10 15 people from

Brazil. They all looked the same. They

Brazil. They all looked the same. They

were all these super smart, fine, wonderful uh guys and girls. They all

went in consulting because that that's how you self- select in these in these new market. That's I I saw it in India

new market. That's I I saw it in India and so on. Uh but they all look the same. I couldn't tell them apart. And

same. I couldn't tell them apart. And

then I met David Veles and within one hour I knew for sure that he was going to be the person we're going to hire.

Who are some other other great founders besides him that you partnered with?

Fred Lutia of service. Now he was older.

Uh but he made everything simple. He

came to Sequoia to present and he told us everything that was [ __ ] up with this company. It was the wild.

this company. It was the wild.

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

pitch. Now we all still saw through that and uh 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 me 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

incredible incredible. And then you get into into the Israeli founders which I adore. They are tough. You know, keep in

adore. They are tough. You know, keep in mind, they think incoming missiles are are kind of everyday type of occurrences. Uh, and so they're

occurrences. Uh, and so they're naturally tough. They don't take any

naturally tough. They don't take any [ __ ] Uh, they're smart as hell. Uh,

somehow they know what America needs way over there when they work at 8200, which is one of the units in a government uh, you know, uh, 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

men. No, actually there's a woman that I'm She used to be a spy in Iran. Uh

she's tough as hell.

Now she's a founder.

Yeah, she's a founder.

What's her company do?

It's a cyber security company, but not with her. Although a little with her.

with her. Although a little with her.

[snorts] It's almost when you talk to these founders. Have you seen those uh I

these founders. Have you seen those uh I don't know what that sport is where you smack the [ __ ] out of one another guy smacks. We had we had the founder on the

smacks. We had we had the founder on the show Dana Dana White 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 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.

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 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 uh having the look

with that. and then uh 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 bind they find

email. The first little bind they find themselves in. And if you rush in and

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 when they're down. 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 of [ __ ] to have Doug Leone. The reason I

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

It's accelerate. I created the tenants of Sequoia. One was performance, two was

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."

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 putt, 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 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 read uh when I heard that quote from you is like quote from Charlie Mer 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 to have a business and you see these companies with broken culture where no one trusts one another and you can't get [ __ ] 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 it's a whole different thing. I'm glad you just said that cuz I had dinner with at his

house right before he died and he told this story where he's like this Munger Charlie and um the rip age of 99 years of age.

I know. And then I had another dinner scheduled after his 100th birthday and obviously he passed away that nove previous November unfortunately. He said

he told us a story where it was during like the Enron blow up. 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 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 I think I forgot what it was let's call it $400 million

and uh the Bersard'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 um Mer 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 risk-free.

Yeah.

Cuz he's like, "Why?" Cuz Buffett trusted the guy that was on the other end.

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.

Mhm.

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. 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. We just

do it.

Yeah.

Well, it's a value of a term sheet. A

term sheet is not worth the paper it's written on. But once you sign it both

written on. But once you sign it both sides, I think you have to honor it. You

know, many times uh where where I'm on the board of a company and we signed a term sheet with an investor and then 3 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

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.

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

Absolutely.

Yeah. 100%.

Absolutely.

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

Yes. I have a round head, a deep voice, and people are scared shitless of me and uh 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. Uh it's

ever met. It makes me feel good. Uh it's

a very selfish thing on my part. I I

don't do it for you. I kind of do it for myself.

What? 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 adviser and older brother. He

says he finds it intoxicating to be dependable for his tribe.

Yeah.

That's the way he puts it.

Yeah. Yeah. Look, I ran Sequoia for 26 years. I never viewed it as running

years. I never viewed it as running Sequoia. I viewed it as working for all

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 you don't work for me. I mean, yes, I get to make a decision here and there, but the decision I make is so we could all win.

But you tell me what you need and I'll do whatever I can just to get it done.

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So, looking forward, you're on day 91.

like what do you what is 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 a koi during a crucible type moment and so on as I said it's going to 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 got to do this and my I have nothing

going on. I just came back from

going on. I just came back from vacation. I don't think I have I don't

vacation. I don't think I have I don't think anybody ever said they have 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 scrge. I use that word for [snorts] 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 Sequoa previously? It was because I was more in

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. [snorts] I don't have a network of 23 year old age friends.

This is very interesting to me. I I want to hit on that. Uh before I forget though, I really uh I remember setting a friend of mine up with an one of the smartest people I know. uh he had two businesses running trying to figure out

which business he should give his attention to. Within like 15 minutes, my

attention to. Within 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 [ __ ] nailed.

He understood it." And I sent a text back. I go, "He's my favorite type of

back. I go, "He's my favorite type of person. Very hard to get to, hard outer

person. Very hard to get to, hard outer shell, but once you break through, he'll do anything for you." I think that's very similar to what you were saying, like don't be confused by the round head and the booming voice and the [ __ ] bald round head.

Yeah, the bald round head. Um the the other thing um it's very interesting to me uh I've had a couple like I don't hang out with venture capitalists like I just hang out with founders like I have

no friends that are not entrepreneurs like I work on founders podcast during the day hang out with founders at night and well I'm so proud that I'm a founder of a company. I actually I actually love

a company. I actually I actually love that. Well, no. The reason I bring that

that. Well, no. The reason I bring that up is because it there's been 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

everything. Can you just like meet with my partner and like talk to us about this? Have lunch." I was like, "I

this? Have lunch." I was like, "I [ __ ] like you. We'll just have lunch.

I don't give a [ __ ] about you really give a [ __ ] about about your business, but let's talk." And then I asked this guy who's been in adventure his whole life, which is interesting to me. Uh,

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

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, 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 they than the previous generation has done. So that is is an

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 how to find them? 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 all that you're doing for your business.

Yeah. But like here's the I just talked with Dev about this uh too where it's like I I have this [ __ ] uncontrollable obsession. Like I can't tell you why.

obsession. Like I can't tell you why.

Since I was a little kid, all I want to do is [ __ ] sit in a room and read books. That's never stopped, right? And

books. That's never stopped, right? And

then once I found podcasting, I just can't stop [ __ ] thinking about it. I

get sad. This whole crew that you see here, all these [ __ ] cameras and stuff.

They didn't tell me that somebody was on the team was getting married. They went

to Italy. They took two weeks off. I was

like sad as [ __ ] I went to Italy for like what, 3 days, Rob? How long was I gone? They're like I'm like, I'm going

gone? They're like I'm like, I'm going back. I got [ __ ] to do. Like, I want to

back. I got [ __ ] 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 I think it's the best kind.

Yeah.

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.

Sunday off. No, it's your love.

Yeah. But one thing that did change, you know, Brad Jacobs, he was spending time with him.

Mhm.

I mean this in a beautiful way. Weird

cat [laughter] unique. And just read his book, How to

unique. And just read his book, How to Make a Few Billion Dollars. Half of it's on his like his like uh not hypnotism, his meditation practices, like his it's

all about his mind and stuff, but he's a unbelievably joyful human. Yeah. And he's the one that

human. Yeah. 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 these divinely discounted people was like my inner model like I just wake up every day now focus on what I did. It's like that

wasn't good enough. You could have done it better. Like it's just super

it better. Like it's just super negative. Until he sat me down one day

negative. Until he sat me down one day and he's like this doesn't serve you anymore. It's like that got you to where

anymore. It's like that got you to where you started to where you are now. But

now your your drive is generative. Your

drive is that you [ __ ] 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 changed my inner moral.

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. Uh, you

know, I I don't think too much about rebuilding my life or redoing my life, I should say. Uh, [snorts] but all I think

should say. Uh, [snorts] 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 understatement.

No, no, both. I'm not 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 I 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 learnings 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

with that. So many of my founder friends just have completely [ __ ] up their boards. Don't know how to run one. Don't

boards. Don't know how to run one. Don't

like the one they have. Like what advice do you have for on this?

Choose to architect your board the same way you architect your product.

[snorts] 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.

You know, he talked to me, let's go out.

It's no more complicated than that. And

then don't put any thought into it. You

know, a board is like a mate, a lifetime mate on the there you mate for the next five, seven years. I bet you most marriages last probably five, seven years these days.

uh 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. Uh and

compliment 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 comfort. 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. Uh, but that's where the learning

you. Uh, but that's where the learning comes. And so, I find people, they don't

comes. And so, I find people, they don't do it at all. I got a term sheet. How

many times have I heard, I got a term sheet. I got a lead term sheet. So,

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.

So, talk about some of the mistakes you've seen in board construction, man.

Is it just that? Is like this person volunteered and I took them? 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. An experience, uh, you

domain skill. An experience, uh, 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.

cycle. And then there's personal needs.

Out of 10 venture folks, and I've said this, and I've taken Shiffford, maybe 30% are incompetent. They don't know what they're doing. Another 40% are I

call them no ops, no damage, no anything. They nod, you know, they they

anything. They nod, you know, they they nod with a group. Uh, and maybe 30% or fewer, maybe 20% know what they're doing. And that's one overlay. The other

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 going to say? So, you don't really have the board

say? So, you don't really have the board member there. You have the shadow. You

member there. You have the shadow. You

you have the interpreter 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, that's the worst of all

kind. I see that all the time. I see

kind. I see that all the time. I see

that all the time. Just completely, let me put it in your terms. Completely [ __ ] clueless. Completely [ __ ] clueless to a damage, not a no-up stage,

a damaging stage.

The best boards that you've been on are the board meetings contentious. [snorts]

No, but issues are put on the table.

Real conversations are put in the table.

But you're willing to argue forcefully.

You you you're willing to have the real conversation. The argument implies

conversation. The argument implies 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 we're willing to get the real job done. I

won't concede the the the word argument.

Interesting.

It's the same thing at at partners meeting. We don't argue, but we have the

meeting. We don't argue, but we have the real conversation. At times at Sequoia,

real conversation. At times at Sequoia, we have to take a 5 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°. We have the conversation. We come up to an answer.

conversation. We come up to an answer.

We're all in. We 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.

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 Caval 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 from Disney that Steve Jobs fired two of our board

members. And they might know that they

members. And they might know that they fired him. They don't know why he fired

fired him. They don't know why he fired him. And so I asked him one day like why

him. And so I asked him one day like why he fired him. He's like cuz 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

truth. And and I think Ed on the episode said, "Most people that say that are actually full of shit."

Full of [ __ ] Steve actually wanted to get full of [ __ ] Here in California, more than the East Coast, people don't like the direct conversation. I had to learn that first

conversation. I had to learn that first coming. You know, I I I I I went from

coming. You know, I I 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 Nobody wants to

feedback." The honest Nobody wants to hear the honest feedback. Cool. Are you

kidding?

Yeah.

You know, are you Everybody's full of [ __ ] But the best founders have to.

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, and

acted upon. It's almost an art. It's not

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, uh, with examples and so on. Look, it it it's

like telling a founder, your VP of sales sucks. [snorts]

sucks. [snorts] You're not going to get 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 just um I'm a big fan of Christopher Nolan. I just reread his

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, uh is it, you know,

parasite?" You know, uh is it, you know, bacteria? Is it worm? It's like it's an

bacteria? Is it worm? It's like it's an idea. And the whole thing is like, but

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

gave you. You can't say, "Doug, you should believe this." You have to incept 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 [ __ ] sandwich?

The [ __ ] sandwich on how to get feedback. I don't know if this is this is the art you were talking about, but [ __ ] sandwich is like compliment what you the negative feedback and then another compliment.

That's why I call it the [ __ ] sandwich.

Well, I don't know how to do that. If

anything, the mistake I make is I'm too direct. I remember uh there was a

direct. I remember uh there was a venture guy, Jim Brier. I heard him turning down an investment once. And I

said, "Oh my god, the 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 I was always

admirers of how he could do that. And u

I'm more direct. Uh, I hear people are talking the phone for 20 minutes, 30 minutes. My conversations are 3, four,

minutes. My conversations are 3, four, 3, 4 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.

30 seconds. Not even 3 minutes.

Yeah. Most of my conversations are less than 3 minutes long.

Yeah.

Don't you think it's interesting that you don't like hang around with other venture capitalists?

Why?

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

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 are probably the most interesting thing for me.

Are you introverted?

I'm right on the line. According to

MyersBrigg, I'm right in the middle. I

do not like meeting new people in general. In fact, every time I I have to

general. In fact, every time I I have to meet somebody new, the thought and it's kind of nasty that goes through my mind is [ __ ] another [ __ ] I got to meet.

Right? [laughter]

where I remember talking where where the extroverts I'm told find energy. They

get energy so they love it to meet new people. Oh my god, another person I have

people. Oh my god, another person I have to meet.

Yeah.

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

Yeah, you're definitely an introvert. I

am too.

And I think there there's a very similar like, you know, I think about the opportunity cost. And I always quote

opportunity cost. And 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 2 hours with 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 realized 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 wellrounded.

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 it's

present. It's work. It's presentation,

present, help, assist. You know, I I I I think the closest friend I have as a founder is Valz. 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 with the less.

Yes. Because he was an associate. I

hired them. I was we had kind of a paternal, you know, son relationship.

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

Cross Point Ventures had a hell of a run for 7 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

investments. There was a venture firm called TVI.

You may not remember technology venture.

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

They didn't buy Microsoft, but Dave Marquart was on a board of Microsoft.

Yeah. They got 900.

It was a couple of one guy uh started benchmark with two other person from another firm.

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

He was on the board of M. He was the only venture investor in Microsoft the year before Microsoft went public.

If I did, they were doing 140 million in revenue, 38 million in 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 we're going to We're going to put this in a venture firm that had the keys to the kingdom.

Yeah.

And somehow didn't last as a venture firm where Cross Point, they just called it in and and they all went their merry way. This is a firm that just couldn't

way. This is a firm that just couldn't coexist even though they had everything.

Yeah, there's something uh interesting about that. So, I can't name who, but

about that. So, I can't name who, but it's one of the best entrepreneurs living. And he's like, actually, you

living. And he's like, actually, you know, uh they were talking about the greatest seed investors of all time.

He's like, greatest seed investor is my dad. He made one investment. I made $40

dad. He made one investment. I made $40 billion. Didn't invest in anything else.

billion. Didn't invest in anything else.

That's it.

That's it.

That's awesome. So, I asked you um if you're introverted, uh I want to ask you something that I think more is definitely introspective.

You don't strike me as introspective at all. Mars taught me how to listen.

all. Mars taught me how to listen.

Mars taught me how to listen to the exact word that's said, the timing of that word, you really can understand

that a 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

wait, what do you what do you mean you can you can learn by listening to the adjectives?

Oh, the way they use when they describe a situation.

Humanity humans can let can can help by letting it out by by showing themselves and how they use the word I versus we.

Uh when describing I can sell you this.

I'm thinking to myself as this he's presenting and said, "Fuck that. you

can't sell me [ __ ] You know that that's what I think during the presentation, you know, as I have that stupid grin in my face. Uh but just listen to to the

my face. Uh but just listen to to the specific words that are said when they say it. We often choose a founder

say it. We often choose a founder without a line of code, without anything based on a presentation, a clarity vision, but we also want to get the interpersonal tricks. And you can learn

interpersonal tricks. And you can learn a lot if you just pay super careful attention. I mean, Morris used to do it

attention. I mean, Morris used to do it to me all the time. he used to recquote my words back back to me. Uh or the way I said them, you know, it would drive me

nuts. It drive me nuts enough that that

nuts. It drive me nuts enough that that I learned.

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

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

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

yourself second. I understood that putting the from first and the two second as being a somewhat egocentric move where it comes from you. You had to

put yourself first in that metal. And

that's one of the minor little things that I learned from Mike Morz. 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 I, you know, he knows that

co-head. And I, you know, he knows that I I was painful for him. It was painful for me. Like I said, it's it's uh it's a

for me. Like I said, it's it's uh it's a badge of honor for me anyway that we made it work. Uh, but Mike had the ability to dream

broadly in ways that I've never seen before. He could answer the question

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 looks like? And if you look at the companies he's been an investors in, it'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, he was by far the best in the world.

All right, Doug, I appreciate you doing this. We're going to run this back cuz a

this. We're going to run this back cuz a year from now, you're still going to be doing this. I have faith that you're not

doing this. I have faith that you're not going to quit 9 months from now. And if

when you're still around 9 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

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sure you listen to my other podcast, Founders. For almost a decade, I've

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

your work. Most of the guests you hear on this show first found me through founders.