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David Kidder: Obsess Over Solving Problems, Not Making Money | E70 · In Search Of Excellence

• 0:00
  David Kidder: Money is not the primary motivator, but it's still motivating. But I'd say there's another part of this that's actually motivating is the loss aversion to losing it.
• 0:10
  David Kidder: The pain in our lives is because we're looking back with regret.
• 0:15
  David Kidder: Or, and we're looking forward with anxiety, right? Your ability to say no to people and very uncomfortable situations be able to terminate people in the first sentence, regardless of what they think of, you know, is probably half your job, honestly.
• 0:36
  Randall Kaplan: You're listening to part two of my amazing conversation with David Kidder, an incredibly successful entrepreneur, investor, speaker and author. If you haven't yet listened to part one, be sure to check that one out. First.
• 0:48
  Randall Kaplan: That's an amazing story. We're going to talk about a lot of the things that you just mentioned a little bit later, including the startup playbook, which is an incredible book, I recommend everybody who wants to be founder of a company or start their own business, read that 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?
• 1:24
  David Kidder: I mean, there are I would say, the Born 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.
• 2:30
  David Kidder: 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.
• 2:41
  David Kidder: Unless you are obsessed. That would be my simple version of how to do the calculation whether you should build a company or not.
• 2:49
  Randall Kaplan: Where does creativity, culture and leadership fit in? As ingredients to build a successful company and be a successful entrepreneur?
• 3:00
  David Kidder: I mean, the whole like, concoction of like grittiness, resourcefulness, creative, all that stuff, hustle, grit, like, there's all I think it all live in this willingness to set down all of your bias with the answers just to find the answer that's going to work. Like it's sort of, you don't have a lot of time or resources. And so the longer you hang on to your absolute belief that this is a way to solve something, the longer it could take, you could be wrong. So most likely, and this is not in 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.
• 3:48
  David Kidder: 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.
• 4:11
  David Kidder: And you're unlikely successful.
• 4:11
  David Kidder: 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.
• 4:31
  Randall Kaplan: So we've met so many entrepreneurs along the way. I've I don't know I've met over 1000 David, I'm sure you've met over 1000 as well, maybe several 1000. And I was asked him what the motivation is and their motivations really are all over the map. But the one that sticks out the most is a lot of founders are motivated by money.
• 4:48
  Randall Kaplan: They read the story of somebody successful like you or me or Mark Zuckerberg, they want to be 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.
• 5:03
  David Kidder: I over the years, for the last 15 years, we go into the TED conference. And it was a there was a guy, brilliant guy named Richard St. John or John said, Richard, I'm blanking. He's wonderful psychologist, any, he'd walk around the conference. And he would ask all the entrepreneurs that this one question, which is, well, many questions, but the primary one was, which is, how much money did you have to create or have before money was not an issue? Like, could you 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.
• 5:41
  David Kidder: 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.
• 6:19
  David Kidder: 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.
• 7:33
  David Kidder: 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.
• 8:44
  David Kidder: 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.
• 9:11
  David Kidder: 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.
• 9:28
  David Kidder: 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.
• 9:44
  David Kidder: 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.
• 9:53
  Randall Kaplan: One of the things I've noticed over the years, David is that at some younger age, you got a number and or it may be a million I usually hear 5 million or 10. I usually hear 5 million or $10 million when I posed this question to somebody, and one of the things that I noticed is that the number always increases 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.
• 11:16
  David Kidder: I mean, it's again, this is while the world your world gets smaller, too. So it's all the fame, it's all relative, right, wouldn't it and you know, as you're going through, I mean, I didn't grow up with any real resources, lots of love. But I mean, I didn't know investment banking was until my 20s, right? Or what real entrepreneur was, but I have a bunch of friends who I've grown up with for the last 25 years who belong to this email 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.
• 13:11
  Randall Kaplan: I'd Mark Cuban on my show. And he says you can't be a billionaire without being lucky. Is that true?
• 13:17
  David Kidder: I think it's more true than not, I think it's mostly true. I ever guess. If they're given given given, given the factor of time, that dependent I mean, Mark marks really young. But like when you if you look at generational, like truly first generation wealth or for Jason SAS, you know, the one factor in all of it, that would influence my judgment of that would just be How long have they been building 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.
• 14:17
  David Kidder: 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.
• 14:33
  David Kidder: If it's not a meteorite that makes sense.
• 14:37
  Randall Kaplan: You're talking about the value of compounding and I think that is the secret to long term wealth. growing companies over long periods of time so many founders today.
• 14:45
  Randall Kaplan: They want to get rich quick.
• 14:45
  Randall Kaplan: They read about the story.
• 14:47
  Randall Kaplan: Someone founded a company and a year later they sold it for a billion dollars. What's your advice to all those people sitting out there listening today? There's 1000s of them, who are say gosh, that's really 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
• 15:03
  David Kidder: be, I think you'll be sad, you'd be very disappointed with that life.
• 15:05
  David Kidder: Honestly, I don't know, all the joy is the work it's becoming, it's the grind in the valleys, it's self discovery, it's knowing yourself, know what your team, it's receiving the wholeness and experience of growth. And then it's learning to be in a state of being because you've gotten to a place where you can, so I don't think there is really a shortcut to the happiness that they're all trying to get to, it's certainly 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.
• 16:07
  David Kidder: 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.
• 16:44
  Randall Kaplan: We've talked about some of the things that are necessary for success. But one thing we did not talk about, which has been one of the hallmarks of my successful career has been preparation, not ordinary preparation, I'm talking about something that I've coined extreme preparation going above and beyond doing research or preparation that no one else has ever done before.
• 17:00
  Randall Kaplan: How successful has preparation been to your success in Cuba, some examples of how extreme preparation has contributed to your success. This is
• 17:12
  David Kidder: a place that I really admire you a great deal.
• 17:15
  David Kidder: And it's also the difference between why I was, you know, creative and a designer, industrial thinker, and you went to law school, right?
• 17:26
  Randall Kaplan: Which, which I hated, by the way,
• 17:28
  David Kidder: right. But we both did for different reasons. But when we truly look at the world, from, structurally from a different place, so for example, and I have, I have so much to learn from you about this and the way so it's like, on a spectrum, a continuum of like, on the one hand, probably pathologically optimistic, which is where I began, and irrationally pessimistic on the other end, we probably began an opposite sides of this 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.
• 18:26
  David Kidder: So, but I would benefit greatly.
• 18:31
  David Kidder: 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.
• 19:42
  Randall Kaplan: I always ask myself and I coach people. This is a key question everyone should keep in my mind. Is there any other thing or tidbit or something I could find on page 47 of Google results or after reading through 30 transcripts of different podcasts that I can do to prepare. So I'm the most prepared person that anybody has ever met with. And that's the mentality that I coached people that I think is just critical, how to separate yourself from hundreds of other people
• 20:14
  David Kidder: did that as you open the podcast today with a couple life facts that I'm sure I've sprinkled in a lot of other podcasts, but never cohesively into one. So it was very interesting, you brought those things up. And it also shows that you care, and I, I swear, I love you anyways, but I appreciate you doing it. And it matters because it affects the sort of entanglement and the karma, highlight ships and the the well, you want to do things for people.
• 20:38
  Randall Kaplan: It establishes goodwill and establishes respect, it makes people want to deal with you more than they would any other person. It helps you win deals when you know the material better than anybody else, and helps you get jobs promotion, and helps you hire 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.
• 21:11
  Randall Kaplan: And you can achieve results that otherwise would not have been possible, or seemed impossible without it.
• 21:18
  David Kidder: It's true people people want to be on journeys, where they're going to learn with people who care the most.
• 21:24
  David Kidder: And I, having done some really incredible deep work over the last 810 years, there's this sort of, kind of final piece of this whole becoming philosophy which has been been central to my life, which is this idea that the purpose of all this is to 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.
• 22:04
  David Kidder: 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.
• 23:09
  Randall Kaplan: I appreciate the kind words and you know, have similar love for you and admiration for you. And you've done so much. And you've helped so many other people. So kudos 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?
• 23:51
  David Kidder: I mean, they probably are true. I mean, I know they're true. So. So I've done I didn't update that number. It's over at angel investments now. So I'm an LP and I think six VC firms. You know, I'd honestly, I stopped doing angel investing because it's it's rare now. Because it takes a lot of energy and time.
• 24:12
  David Kidder: And also you want to show up for people because that's why you did it, right. It's sort of like sound money just because you 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.
• 24:31
  David Kidder: 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.
• 26:07
  David Kidder: 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.
• 26:25
  Randall Kaplan: You just mentioned something very interesting, which is counterintuitive to people, you'd rather invest in founders that have failed than first time founders. It's also interesting that most first time founders do fail, the probability of success is extremely, extremely low. Do you invest in founders that have failed two and three and four times and are going forward on the fifth try?
• 27:43
  David Kidder: would say the second and not the third?
• 27:47
  David Kidder: Because the second means the first one, the second one, definitely, I've done that many times, I invested entrepreneur who I wrote a check, and he blew up like 100 days later, and he started on my kept going. That was a stretch, but it was like I've done that several times.
• 28:00
  David Kidder: And I have a couple friends I'm not gonna mention there are who've had extraordinary success doing that. So three times means you probably are bad at the 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.
• 28:38
  Randall Kaplan: You mentioned a few minutes ago, the word assholes. And I've
• 28:43
  David Kidder: never said that a podcast before. By the way, that's the first time.
• 28:48
  Randall Kaplan: This is not my first time, but I think it's important to talk about it. It's you and I are very lucky, we have our own capital, we have the ability not to invest in assholes. What is what does that mean, exactly? Who's an asshole?
• 29:04
  Randall Kaplan: And what kind of people don't you invest in? And how important is it to be nice and a good person in our success?
• 29:14
  David Kidder: Ah, that's a really provocative question. I don't really mean all entrepreneurs, to some degree, have to be what we just said. It just is like, you have to have your ability to say no, to people and very uncomfortable situations. Be able to terminate people in the first sentence, regardless of what they think of you. They know is probably half your job, honestly, is still been our Marc Andreessen. Why is there's gonna be a CEO, he says because bad news all day long.
• 29:52
  David Kidder: 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.
• 30:06
  David Kidder: 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.
• 30:28
  David Kidder: 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.
• 30:37
  David Kidder: It's just, it's just not part of the character, if that makes sense.
• 30:40
  Randall Kaplan: Let's flip it a little bit. Not everyone has the ability to work with everyone they want to be most people work for companies. We've all had very difficult bosses in our 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.
• 31:35
  David Kidder: I mean, it's they're doing a service to them.
• 31:37
  David Kidder: Because there's, there's, there's so many opportunities to leave every part of your life when they're bad, right? Often.
• 31:45
  David Kidder: 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.
• 32:11
  David Kidder: 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.
• 32:54
  David Kidder: 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.
• 33:12
  David Kidder: 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.
• 34:24
  Randall Kaplan: An entrepreneur walks into your office, what are the three most important things that you look for as they start opening their mouth and making their pitch?
• 34:35
  David Kidder: Before they start talking?
• 34:38
  Randall Kaplan: During the whole thing? Okay, during the meeting, and then as you're making an investment decision, whether the same and the different, and I guess there's not always the same.
• 34:46
  David Kidder: Okay, so first is why them proprietary gift? Like what is their secret? So the 300 hours I spent with those four entrepreneurs in the star playbook. The number one thing they said over and over again, is they had a propriety. They understood that a secret basically, I knew something and how to solve it, and no one else in the world did. I just saw prop gift as the first one, why them second is timing, their understanding of the forces that like within the next three to 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.
• 35:38
  David Kidder: 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?
• 35:45
  David Kidder: 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.
• 36:16
  Randall Kaplan: What are the three worst things that an entrepreneur can do? That you say, no chance in hell, this is over. And I'm not funding this or being a part of this.
• 36:28
  David Kidder: I would say overconfidence is probably number one, like overconfidence means control bias, means they're inflexible to is there's this, this is the word I would say what is their their drive is, is ambition. Not obsession, like, you can tell like, it's really about them, their career, their success, and not the problem. That makes sense, like the huge obsession versus ambition are very different things, and you can 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.
• 37:26
  David Kidder: 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
• 38:05
  Randall Kaplan: successful people that I know and that, you know, as well think I'm successful, I don't have to do things to work on myself. But one of the things that I noticed about you, David, as we got to know each other is you're incredibly self reflective, you're incredibly self aware.
• 38:19
  Randall Kaplan: And you're on a journey to constantly improve yourself and your way of life, being a better father, and husband in all aspects of your life. He talked about what motivates you to do that? And if you're comfortable talking about this, can you tell us about your experiences with the toad and what it is?
• 38:39
  David Kidder: Yes, I will share that with you, despite Prince Harry going to, you know, the under going to court order for his visa right now these issues you know, it really again, it goes back to the whole becoming, which is the three stages of this for me. And again, this is not prescriptive, it just is my journey is the idea of knowing 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.
• 41:46
  David Kidder: 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,
• 41:59
  Randall Kaplan: incredible human being.
• 42:01
  David Kidder: I mean, have you ever listened to mortal heart, Muhammad Ali's speak, his intellect, his mind, his heart, how it just, he's just a remarkable human being. And he's courageous in a way that is so rare. And one of the experiences that he went through was this concept of the toad and that journey, but what he what he experienced, and what I experienced is this idea of 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.
• 43:00
  David Kidder: 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?
• 43:50
  David Kidder: 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.
• 44:11
  David Kidder: 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.
• 45:14
  Randall Kaplan: I've debated whether to ask this question as I prepare for the podcast, but I want to ask it anyway. Can you briefly describe what the Toad is? And how it does change people's lives? And I'm also going to say this is not something that I recommend actually, I absolutely do not recommend it to to the dangers involved. But Mike Tyson has talked about it. You've talked about it a little bit as well.
• 45:37
  Randall Kaplan: And if you're comfortable, we briefly share without getting into too many of the details.
• 45:40
  Randall Kaplan: 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.
• 45:54
  David Kidder: Yeah, I try to illuminate that those those ideas that just the prior question, I think it's a it's a natural, psychedelic, that exists in both biological and organic form and of DMT. And it basically is a psychedelic a hallucination that helps you, it breaks down your dimensional awareness. So in the same way, for example, we see you can see you can see colors and light and 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.
• 48:32
  Randall Kaplan: We're at the end of the show. And I want to do two things. First. First is, I want to thank Lesley Newman for setting us up one of my best friends who I love more than life itself. Yes. Gave me the amazing pleasure of introducing us. It's, you know, some of our closest friends come through people we love and close friends. So I think like minds, think like you are the company you keep. So I really want to thank Leslie who's been an amazing friend to me throughout the years. Plus one. Thank you, 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.
• 49:12
  David Kidder: Okay, bring it.
• 49:13
  Randall Kaplan: When I started my career, I wish I had known patients. The biggest lesson I've learned in my life is love loving. My number one professional goal is
• 49:28
  David Kidder: impact. My biggest regret
• 49:30
  Randall Kaplan: in life is
• 49:31
  David Kidder: so long to stare down truth. The one
• 49:35
  Randall Kaplan: thing I've dreamt of doing for a long time, but haven't done is
• 49:40
  David Kidder: writing a book called The Board of life, which I intend to solve.
• 49:46
  Randall Kaplan: The greatest innovation of the next 50 years is going to be
• 49:49
  David Kidder: general AI, or it's already done the super intelligence.
• 49:54
  Randall Kaplan: If you could go back in time, the one piece you would give advice to your 21 year old self is
• 50:01
  David Kidder: slow down.
• 50:03
  Randall Kaplan: If you could be one person in the world, who would it be living? Let's go living and let's go not living.
• 50:11
  David Kidder: I'd probably spend time with Sam Altman right now of open AI. Dad, I would say I would say what I'd say Christ or one of the great Yogi's, like Yogananda or something.
• 50:32
  Randall Kaplan: David, I can't thank you enough for being a guest on my show. You've been an amazing friend. You've had a tremendous career as an entrepreneur, investor. Friend, author. I'm grateful to know you you're one of these guys that I wish he lived next door to me or in a townhouse overseas. Have fun. We Well, we're gonna have a lot more fun for the rest of our lives. Thanks for being here. I appreciate you being on my show.
• 51:00
  David Kidder: incredibly grateful. I love loving you and we'll keep we'll keep doing that.