David Kidder: Obsess Over Solving Problems, Not Making Money | E70

book. You're a serial entrepreneur with no experience in business whatsoever. Can you learn to be a serial entrepreneur? Or do you have to be born with the DNA? And what are you looking for, in terms of the traits of a founder? What traits will make an entrepreneur successful when they started a new business?

entrepreneurs are very rare. And even even the rare ones are probably environmentally conditioned at home, honestly, at bed, maybe out of necessity, in many cases, the radical ones, radical necessity, trauma, or parenting, and then for the other ones, probably cultural inside the home entrepreneurial, I'm trying to do it in my own son's if they want to, we just know it's a very, very hard journey, and most most likely, they're not going to be successful because most

entrepreneurs are not. So that's the second part, your question is what makes them successful, is their ability to quickly quickly learn the solutions to the challenges of building the business in service of this factor, which I think is the primary, which is an obsession with a problem. So all it's either a product or service solving a need in the world that's on time. That's basically it. I mean, if you want to dumb

it down. So the question is, is, how long can you sustain the level of effort, and humility it takes to solve the ability of business to solve that problem. If that's if that's not years and years and years and years, typically, eight years of 80 100 hour weeks, you don't care enough, which means don't do it. Unless you are obsessed. That would be my simple version of how to do the calculation whether you should build a company or not.

all cases. So I'm I'm I'm saying this is a very meta level, but for, let's say, 80% of the business problem, most likely any part of the business has, as that you're facing to create your business become undead, as it described, dead undead has already been solved successfully, just not by you.

So if you can assemble those questions of the things you solve in the right order, the right time, right talent, which we talked about the three things, then you can go get the answer, because you can hear it, see it or buy it and then assemble it. So I think the more you're like, I'm going to learn it and do it my way, the more likely you're learning cycles just simply aren't fast enough. And you're unlikely successful. I'd rather find it successfully solved by someone else because

I'm humble and curious. And I'd have I can build relationship and adopt it in the spirit of as Dali once said, Great artists steal. You kind of have to do that. I mean, we you and I've talked about this firm businesses today, at least in the early stages.

that person. Where should money rank in our success and what are the other motivations owners should have and think about when they start their own business.

could start over? And so if he, as he did this, hundreds of times, he learned the answer to this question, which is, the answer was 10 million liquid. And this was gates, or, you know, Bezos, it didn't really matter who it was Cuba, they all basically said, you know, after that amount of money, money didn't matter to me anymore, because I kind of bought my time like I could, I could start over, not lose, if I own my assets and begin again, it was didn't matter really, and, or

lose it all and begin again. And it's the point is like, that, that is a lot of money, let's be honest, it's that small amount of money. It's not a it's not so much that a successful entrepreneur in your lifetime would actually have. So it's, it's completely achievable, relative to your risk and time. But the thing is is like is that people weren't saying like, an order of magnitude bigger. So they're not really motivated by

money above a certain level. And it's not, it's a sort of equivalent to be a question of like, you know, in other parts of the economy, where people say how much money you need to have be happy as an employee, and people are like, I think the answer is like, 75 to 100 grand or something a year, which is a lot less than you realize. So the point is, money is not the primary motivator, but it's still motivating. So that's an

important part of this. But I'd say there's another part of this, that's actually motivating, is the loss aversion to losing it. So like, there's you, you created it to a certain level, and there's all the things that come with that, and then you're motivated because you want to sustain it or not lose it. And you're gonna go back to this different type of energy in yourself as an entrepreneur, to create the next

thing for different reasons. So I said another third, another prism into this, which is, there's no amount of money that you're going to have you're going to ever make. And it's ever going to solve the issue of enough if you don't know what your version of contentment is. So, the point is, you have to determine what content means in your mind and your life, and

decide what that is. And it's what you achieve more or less than that, you know, what it is your self awareness and knowledge defines that version of what money means to you. So these are it's less about a single answer more about dimensions into how to think about that. So let's separate that from the last piece, what you said is that is that truly a

motivator by it? So it's really not a motivator, in the sense that you didn't do it with the qualities of how you think about it, what it can do for you, because, you know, money is in terms of entrepreneurs journey is just sort of like engendered life. It can solve things it can, it can, it could fix things right? My brother in law says a product beside money's not a problem. Real problems are health, and relationship. Things that are in your, in your mind, like those are those are things

that are problems. So cat, knowing what it can solve, but also the absence of money leads to bad decision making too. And it leads to unnecessary struggle, right? So it just leaves you with fewer choices. And if you want if you need a lot of choices, when you're building something or creating something, it can be a tool, not all it was one of the tools to help you accelerate that learning. Elon is one of one in our lifetime, honestly mean cups, even some of the greatest

of all time. But also recognize, like one of his great gifts is he can still tell stories, tactically and market stories. And if I would argue that he's probably raised, I have no idea actually hundreds of billions. I don't know the actual numbers, but let's say it's probably between one and $300 billion is lifetimes my guess. So like, you can make a lot of mistakes, but he's taking on big challenges. So you need to read a lot of

mistakes. So all these things take into account your ability to create something of value depending on how much you know you're obsessed about the size of that problem what you need to go solve it of your own resources, right that of others. So I hope I'm not talking past you hopefully around I'm just it's less of an answer more mindset and how to think about it because it's really not the problem if that makes sense.

with age. Why? Because you have to buy a house, it depends where you live, obviously, in some parts of the world, in some parts of the United States, you can buy a beautiful home 5000 4000 6000 square foot home with two acres of land for a million dollars, I live in LA, you live in New York is very expensive, you can't touch a house on the west side of Los Angeles, a teardown house for $3 million dollars, if you want to live in a nice neighborhood, is $5 million in some neighborhoods

is $10 million. So if you buy a $5 million house, you have to have a lot of wealth behind that, behind that wealth. At some point, you're gonna have a family, you're gonna send your kids to private school, my daughter goes to Cornell, it's at $2,000 tuition there. So at some point, the $5 million after tax, you have to make $10 million, essentially, to have $5 million and have $10 million, you got to make $20 million. So the number does increase. As we age, at least I've seen that in

my career. And as I mentoring people, and in my own life as well.

list. very confidential email list, and you know, some people on the list, but we didn't get it for a long time. And most of us have nothing, right. And over time, like some some of the people unless became, I mean, crazy, crazy, crazy successful, like Lifetime's of capital and a lot of our journey people, people who are very successful economically, but, you know, it took them to startups are three

startups in 2025 years. And that's, that's even in the back boundary of successful entrepreneurs, around the boundaries, I'm out. That's most of the cases, it's, it's actually, it's so rare, it's so rare, you're talking about someone who earns or has exited, after tax of 100 million. It's just, they themselves are a unicorn, it's just all the factors of their perseverance, curiosity, market conditions, capital markets, would have to conspire so perfectly for those

scenarios to happen. That and then they themselves would had a crate lightning in a bottle. It just doesn't happen. Your expectations should be in the outside forces were greater than your we're just fortunate for you. That's my experience, honestly. I mean, with exception, one or two people, that's almost never ever, ever happened. My all my successful friends, just to be specific are, you know, who've had great success, or between the 10 and 50 number probably is my guess.

the same business. So like, if you if you, it's the same reason why 80% of Warren Buffett's wealth has been created the last, what, 10 years, whatever the number is, I can't remember when something like that. But it's like given 2030 years in the same business, and you're winning, there's an inevitability that you're going to achieve that type of outcome just based on law of large numbers and ownership. More,

more of the same better. But very few companies in the world we plan for everyone else, are typically at our age generational type of companies that compound in the same way. Either markets aren't big enough, you can't get your arms around it big enough, you can't dominate somebody that without you know, having to sell a lot

along the way. The conditions, even the arc of those conditions have to be perfect for you to be able to own something sustainably long enough to produce those type of returns. If it's not a meteorite that makes sense.

what I want to do. I want to make a ton of more Only when I'm young, and then I can do whatever I want, I think you'll

not money. It's the journey, and it's the becoming part of it matters the most. And it's all the joys because you're with people, you love solving a problem you love, in a journey you love, and you're honest about it with yourself, and, and you accept the grace that's gonna be imperfect in that. So I try to get out of that, trying to get through that more

quickly. Like, why, like, if you are, if you're fortunate to get through it faster, it's probably not because of you anyways, you're just very fortunate, and therefore hopefully, you can do more with me, you know, this, like, it's amazing you when people try to fight for that.

What exacerbates is this insight, which is, you know, when they get the success of the money, they're a little generous, they become even, they become massively generous, but they're equally so if someone's all they care about is that they're like, they they're a little asshole, they turn into a gigantic asshole, like, whatever it is, is going to be the inevitabilities can be accentuated so, so graphically to the world, like, do you really want to be that person who hasn't solved themselves and

let that graphically be you in the world with all these resources? Probably not. I mean, like, it's waiting for you as you become it.

your success. This is

continuum. But we've walked to the middle, which is the rational optimistic view, based on learned fact, right. So some learn fact is studied and prepared for some is experienced, right? It's like going as DeCoster Hello, buddy, it says he goes, my job is to get out of a dark alleys and find a light. So how I get down those dark alleys is our own our own style. So one could be thinking and studying and preparation. The other could be like, I can run down a dark alley. Fascinating. I'll sudden

get out of it. Because I'm honest, quickly and get to the same light, this makes sense. So, but I would benefit greatly. And I'd be a better entrepreneur, if I was, I did greater preparation, except for one area. And I know this is

true about you. And I know it's true is that when I go do what I do, whether it be speaking or meeting with CEOs, or building our town, my town halls or building a company, writing the sort of cultural playbooks, I prepare like how, like I spent an insane amount of time, even if I know the content, trying to understand who's the audience what is the from two, what's the miracle that need i the slides, the everything, so when I go in, I do not wing it. I don't wing

it in front of my company. I don't wait for my former clients or partners. I don't wait on stage and I'm waiting for investors. I will prepare two to 5x more than anyone else because I'm going I'm going in there having successfully done at my mind. In the same way Bo Jackson went on the to his alter ego and did on the field before we ever learn to play. So different versions of preparation, but all vital to however you organize and manage yourself to get down the field so to speak.

better people. And it's true in any industry in any field, whether you're a doctor, lawyer, entrepreneur, any other field professional athlete, I've coached someone with $100 million contracts, in anything you do, it can be critical and a differentiator to your success. And you can achieve results that otherwise would not have been possible, or seemed impossible without it.

love loving each other. So it whether it be the work or individually, but the idea is first is that is the is the deep work to learn that for yourself, which can can get you back to a state of you know, abundance and love and not fear that guide your life because you know your why you know your intention. You're no longer trying to fix yourself from the outside I in fact, I tell my sons is like,

don't fix yourself. Don't be excellent sheep, don't be well rounded, find your need in the world, the forces with your giftedness and just do that all your time. You're good enough, right. But the loving each other part is to not transactionally love people are trying to get something is to just be with them in a loving way, while they hopefully are in the same

journey. And the other the other side of thinking about this way is that the people who are there just to get something from you just the transactional quote unquote, love people, they'll fall away. And they weren't very helpful anyways, in your personal life, your professional life, you really want to fill your life with people who love loving you, they first orders themselves so they can be whole

aligned. So they can walk with you in that same journey shoulder shoulder, that's a really amazing way to think about the journey when I find people like yourself who care the most in preparation, but how they show up. I know that that's the origin of your mindset. And it's very special.

to you on that. And thank you for that I want to talk about your transition from a successful entrepreneur to angel investor, you've invested in more than 40 companies, including Airbnb, Stripe, SpaceX, urban many, many more 70% of all of our returns come from 7% of all capital deployed, you said and Fred Wilson, a famous VC said the only legal way to get 100 times your capital in the world is to make a VC investment. Can you talk about the network effect? And are those numbers really true?

want to be with them. But the portfolio theory around this is really two things to think about. One is if you look back on the portfolio theory, 7% equals 7% of the battle return. So the question is, is why did I invest in the 7% that produce those outcomes? And there's actually two investments signals. The first is conviction, right, which really is kind of describing the understanding the forces, the understanding of the need, and the question of the proprietary

gift, the entrepreneur. There's a really interesting company called Fun defy that uses AI to actually look at how to get from zero to 10x in terms of one 10x in your returns, and it's largely around three boundaries of like the number of investments you make, you have to make up to 25 to 30 investments to even get your money back. The secondary factors were just the amount of time, so you spent less than 10 hours alone, it goes from like

1.5, to 2x. But if you use a network of greater than 20 hours of diversified thinking, you can get to like nine or nine and a half x. So these qualities of the portfolio matter. The second signal is non consensus, meaning you have consensus, something's a good idea, it's probably not a good idea, your portfolio has to

have extreme bets in it. In the same way, it has extreme things that you know, and that diversification, you know, Fred is describing that third, a third, a third, a third will go to zero, a third, you'll get your money back one to 2x. And the other third will be three to 5x. And you might get 100x, his legal question, and that's really the high conviction, not

consensus. So you have to put yourself on network, a lot of investments that I've made are the ones you mentioned that it's come through network effect Founders Fund, in that case, those cases, personal relationships, where founder, I've invested in multiple times, through their failure, I just kept going, and they got good. In fact, the odds of investing in entrepreneur who failed are higher than if you're successful entrepreneurs, because the VCs

know how fortunate you are. So all these factors lead to making good decisions, better decisions and venture.

outside forces. The learning part of it, your bias could potentially be too strong. Your understand that forces you could potentially just be chasing things esteem issues, like, like, you're chasing super fancy technology things and you really have no proprietary gift, because you're afraid of who you are. There's like it just coming from the wrong place. And that's, that's, that's why I think I would tube not three is the simple answer for me.

If it doesn't affect your attitude, nothing well, so like, reread the two greatest books of all time, in my view of entrepreneurship is are both Ben Horowitz, his books, the hard things about the hard things and what you do is who you are. Those books are the Bible. And if you Ben Horowitz right. He was my first book who I didn't close personal friend, but I do periodically once every decade reach out to him. I think he's the greatest living entrepreneur

of our lifetime. He thinks along these boundaries around lob a, he is a tough, tough founder. And that's part of the job. So if people think that's you're an asshole for that, then he's perfectly fine because his mission is bigger than that. So I think it's part of the job. It's just, it's just not part of the character, if that makes sense.

lives. And one of the things that I found David over the years is and I said this yesterday to my interns is work is work, and you're going to have difficult bosses and you're going to have to learn to deal with those bosses and in life because if you can't get along with people who are difficult, you're gonna have difficult customers, clients, whatever the case may be, you can't just walk

away. What's your advice to all of the students, young professionals mid career or late career professionals who want to pack up want to go across the street think the grass is greener. And even the younger people and I get this a lot is they go home, they complain to their parents and their parents say if you're not happy, you should leave, which I think is some of the worst advice you could give your kids.

And again, if you believe, to whatever degree you have been convinced by this or not, in this conversation, that success is a bad educator, that actually the opposite is true, you should actually pursue hardship as early as you can in your life, because it'll shape the quality of all life, the back half of your life when you didn't earn it. So like earning the good life is function of your ability to pursue the hard life early. So growth lives and discomfort

and lives in friction. I've had I've had a number of really well known executives who've who've gone through success and failure probably have I've had the good fortune of sort of coaching just as friends and you know, a couple in particular where their success they're quite famous and their company's success when stripe struggled. I told them my advice was is don't try to get

out of this. Like let the heart Let let the glacial pain of being ground down into basically nothing right now publicly shape you let it break you let it break off all the stuff that doesn't belong there anymore. Let it don't hold up what on the gravity of the weight of this moment to like try to fight it like no like, like, let it break you let it shape you don't get out stay the Bata Valley and, and they were very much like I want to I just want to leave go away whatever it is, you know.

You know, that's the whole there's a great book by Martha Beck called the way to integrity. And, and it basically she wrote her thesis is about Dante's inferno of there's no way out, there's only through and in going through is where

all the growth happens. And the way to go through in the beginning, and I want to make sure that I say this publicly, this is a this is not a there's a moral imperfection on my own is that this is an area of growth for myself, which is, you know, the very first rule is tell yourself the truth, don't lie to yourself. You could lie to the world, but at least you you are awake. So that's one area of my life that I last several years I began doing, I haven't successfully did that

everywhere else in my life. But the your life changes learning happens when you begin to tell the truth to the world that you're telling yourself, but it must begin with you. So trying to get out of something is the internally breaks that, that that that definition of integrity right there. So you got to sit in the hardship.

five years. If we do this, it is an inevitable outcome. So it's about being their understanding of their being there when it happens. Right. So why then the force? And then the last piece is really the is the unfair advantage to solve that problem. So like, secret is their understanding of it. The timing of the force is their understanding the force and the third is the problem, right? Their ability to solve it in a way that creates an unfair

advantage. Once those three things happen, you start to see like, okay, this person, there will be a winner in this space, it'll be asymmetrical. And they have every bit of chance to be there on time as, as the top two or three people in the world to do this, they're born to do this. And given the 10,000 Gladwell in hours to pull it off, they're gonna be one of three, that's possible for them to pull it off.

sniff that out. And the third will be I don't really like to feel like false, like, urgency bias, like, if you don't do this will be someone else. Like it's like, you know, then it's probably wrong fit for me. Like, it's like, you know, if somebody comes out like, well, I have five people lined up, and I'd love to have you in the round. But if it's not you, then you can't react this fast apply the

wrong time. It's more like, listen, we have we have we have the round done, okay, fine, we have half 1,000,000,200 grand, and we just want you in, like we'd love to have you in, we don't care if you write a check for $1 or a quarter million, or whatever it is. And we just want you your karma on your network and all the things you can provide in a way that you can be successful, that's in it. Okay, fine. You know, that's fine,

that's fine. But like, if it's like, if it's if it's a concoction is like money, or they just, it's just other people for that. That's just not what I want to do. So many

that? And if you're comfortable talking about this, can you tell us about your experiences with the toad and what it is?

yourself completely. The ability to get below you know, your intentions, know your why and get to a state and that journey is you got to walk amongst the subconscious bottom Oceaneer like to figure out what are the two or three things that happen to you that every decision, your dope your whatever it is your money, sex power achievement that you're trying to feel better from originates from, so

you can move past it. And knowing that, you know, if you start to dig a hole in your life, you can spend 2030 years at the bottom hole, you just blow up your whole life and start digging another hole again, if you don't know know who you are right? Trying to fix

it. And the answer is like it's pretty much pretty wasteful way to spend your life so why not learn why not grow and the becoming that first stage is got nerve cell for the second stages that love loving point, which is you got to learn to reconnect from your soul to your human self, there are different things and receive that love so you can

show up for other people. So the last phase of this is just about the being part is is a you know, if you've read Eckhart Tolle, I'm sure many of you have, which is we really go through his experiences. You sort of realize that, you know, if time is an illusion, which largely is, the more the pain in our lives, is because we're looking back with regret, or and we're looking forward with anxiety, right? And right at the boundary of the looking back, looking forward,

is control. And so to get to give away that pain, to give it to a limited control is really a simple concept, which is just surrendering, right? So if you surrender at the edges, then you're right here in the entire experience, and then you could just work on becoming someone that will inevitably be that person in the future. Like, you know, if there's an inevitability to your life of who you're being every single day, on a compounding basis,

that's what will happen. When you really deeply, deeply think about who you are, your why your attention and your work, your behaviors, your thought, and how you show up and the conscious lens of the world, the world, if that becomes the quality of your person, then everything will be inevitable. In the more we surrender to it, the more that's possible. So like the experience with, he described, the toad is really the beginning of that journey. And we were talking about this because you did a

interview with Mike Tyson. And, you know, obviously, someone who's dealt with extraordinary trauma and his life, which mode was was primary energy sources. And now, I mean, as his soul has been revealed, I mean, in the world, he's a very, very, very special human, very special,

being one. And as you, I'm not gonna paraphrase this very briefly, but it says if your, all of your conscious energy of your life is moved out of yourself, and arises. And as it's rising, it's almost at the velocity of its ability to rise is where the concept of dimensions and time start to tear away. It's almost as if, if we're on this call, we're on this podcast right? Now. If I put a frame around your head, Randles head, right, ready goes from 3d to 2d, right? Instantly.

That's what dimension. So imagine that dimension as this overhead, we're rising into this dimension that goes from 3d to 2d and we move into it, we become into that plane into that picture of reality. And when you're, as you arrive into it, there is no longer a you there's only one thing, and what that one thing of which you're part of says is now you know. And that piece of the past all understanding is the nature of love God the universe as a

single thing. And as you leave that and you return to reality, you no longer have a question of like, Where do I come from? Where am I going? Because they're all the same. I'm right here. And everything that bounds this experience together, is the nature of our being, which is love. So if I know that, and I receive it, and I can be it, that I can be with you in your journey to discover that too. And that's what love loving

means. It's the power of that idea is the boundary between your wholeness and your suffering. So a lot of things you're talking about when you're youth as you're becoming, and I counseling anybody to go through the experiences, they don't want to also known Councilman do that while they're young, because it takes half your mind become friends, your half your life, to know yourself, Wait. So you've noticed that, but these are questions of fear, and control

and expectation. And I'm not saying it didn't serve me and my own journey for him. But it's not something that was would sustain any part of my life going forward. Because no longer in concert with who I am and who I'm becoming, if that makes sense. So much longer

conversation. But what I do hope is that people's people who are listening, their commitment is to doing the work, so that no matter where they end up, that they're happy that they chose that journey, and their definition of where they arrived.

People can look this up on their own if they want to really want to go into the detail, but can you explain what it is and how it has changed your life Mike Tyson's life in many ways Many people's lives as well.

dimension, right? So we see primary and secondary colors and dimensions that we can understand in our, in our, in our four and five, the world that we live in today. But if you were to open the spectrum of light, what is light, right, we see primary search, tertiary, you know, if you give it enough continuum, you know, X rays are

light. Obviously, photons are like the dimensions of light that are available to us relative to what we can see in our physical reality versus our subconscious reality are radically different. And these tools, open the continuum, the spectrum of our ability to see all of them, depending on your

journey. And result of that, the the interdimensional nature of the questions you can ask the journey, as you experience those, you realize that our conscious physical reality that we live in is, as a subset is part of the larger nature of our creation. And what is this what is actually made of, and a lot of these tools, that least of which is DMT is our tools to have those dimensions up with up

experiences to know that. And here, I say this last thing, which is, you know, I would over communicate this, which is, you know, these are not toys, they're not recreational, they're, they're profoundly powerful. And they're all something you probably won't experience later in your life in your 40s and 50s, as you become friends with yourself, so to speak. And I think they're important because they, they allow you to set down old truths to know the origin old truths

and to pick up new truths. And like, like I described in my 30s, about starting over again, lifting myself out of that, you know, thorn row that was getting destroyed by starting over again, this is not unlike that it just was a different. It was beginning a new road, it was beginning a new chapter, a new journey to begin again. And we have to begin again, you always have to commit to starting over sometimes to renew a life that's committed to growth and becoming.

Leslie. Thank you, Leslie. And I always conclude my podcast. By asking you some more open ended questions. I call this part of my show, fill the blank to excellence, you're ready to play.