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

Episode Date: July 18, 2023

Welcome to the second part of In Search of Excellence, featuring an exceptional man and a good friend of mine, David Kidder.David is a serial entrepreneur, active angel investor, advisor to Fortune 500 companies, sought-after speaker, and author of four books, including two New York Times bestsellers, “The startup playbook” and “The intellectual devotional”.David has been a co-founder and CEO of three venture-backed startups, including Clickable, SmartRay, and Bionic, where he is currently a CEO.We are discussing if an entrepreneur is born or made, what is the right motivation to start a business, how to learn from hardships, what is the concept of TOAD, and the concept of Becoming. Tune in to hear more! 00:35 Are you born as an entrepreneur or you can become one?- Born entrepreneurs are very rare- Mostly conditioned at home- Creativeness and problem-solving 09:52 The motivation for starting a business- Those who earn $100 million are rare- You can't be a billionaire without being lucky- Compounding is the secret to long-term wealth 16:51 Extreme preparation and its importance for the success- Extreme preparation benefits greatly- For public speaking, David prepares like hell- Do not love people just to get something from them 23:20 Transition from an entrepreneur to an angle investor- 70% of all of our returns come from 7% of all capital deployed- There are two investment signals- You have to put yourself in a network 27:47 Dealing with difficult people and hardships- You have to have the ability to say no to people- Best books about entrepreneurship- Success is a bad educator- Growth lives in discomfort 33:34 Three most important things to look for in an entrepreneur- Why them? What is their secret? What is their proprietary gift?- Timing, their understanding of the forces within the next 3-5 years- The ability to solve a problem and create an unfair advantage 35:24 Three worst things that an entrepreneur can do- Overconfidence- Ambition, not obsession, as a drive- Urgency bias 37:14 What motivates David to be self-aware and constantly grow?- The Becoming Journey- The second stage is Love Loving point- Mike Tyson – an incredible human being- Toad principle 44:28 What is a toad and how it changes people’s lives?- It's a natural psychedelic that exists in both biological and organic form- The conscious physical reality that we live in is a part of the larger nature of our creation- These are not toys, they're not recreational, they're profoundly powerful- You’d probably want to experience them later in your life, in your 40s and 50s 48:12 Fill in the blank to excellence- When I started my career I wish I had known    - The biggest lesson I've learned in my life is- My number one professional goal is- My biggest regret in life isSponsors:Sandee | Bliss: BeachesWant to Connect? Reach out to us online!Website | Instagram | LinkedIn

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. The pain in our lives is because we're looking back with regret, and we're looking forward with anxiety, right? Your ability to say no to people in very uncomfortable situations, be able to terminate people in the first sentence, regardless of what they think of you. No is probably half your job, honestly.

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. 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 start a new business? I mean, there are, I would say the born entrepreneurs are very rare. And even the rare ones are probably environmentally conditioned at home, honestly. 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've tried to do that with my own sons. If they want to, we, I 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 this, the second part of your question is, is what makes them, um, 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 the problem.

So 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, 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 not years and years and years and years, typically eight years of 800-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

of whether you should build a company or not. Where does creativity, culture, and leadership fit in as ingredients to build a successful company and be a successful entrepreneur? I mean, the whole concoction of grittiness, resourcefulness, creativity, all that stuff, hustle, grit, I think they 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. It's sort of, you don't have a lot of time and 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 and you could be wrong. So most likely, and this is not in all cases, so 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 that you're facing to create your business become undead, as I 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, the 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 your learning cycles just simply aren't fast enough and you're unlikely to be successful. I'd rather find it successfully solved by someone else because I'm humble and curious and I have, I can build relationship and adopt it in the spirit of, as, uh, Dolly once said, great artists steal. You kind of have to do that. I mean, you and I have talked about this for our own businesses today,

at least in the early stages. So we've met so many entrepreneurs along the way. I don't know. I've met over 1,000, David. I'm sure you've met over 1,000 as well, maybe several thousand. And I always ask them 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. 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 that founders should have and think about when they start their own business? Over the years, for the last 15 years, we're going to the TED conference. And there was this guy, brilliant guy named Richard St. John or John St. Richard. I'm blanking. He's a wonderful psychologist. And he'd walk around the conference and he would ask all the entrepreneurs this one question, which is, well, many questions, but the primary one was, how much money did you have to create or have before money was not an issue?

Like, you could start over. And so 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, Cuban. 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 start over if I own my assets and begin again. It didn't matter really.

Or lose it all and begin again. And so The point is, that is a lot of money. Let's be honest. It's not a small amount of money. But it's not so much that a successful entrepreneur in your lifetime would actually have. So it's completely achievable relative to your risk and time. But the thing is that people weren't saying an order of magnitude bigger. So they're not really motivated by money above a certain level. And it's not it's sort of equivalent to be on a question of like, you know, in other parts of the economy where people say, how much money do you need to 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. And 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 going to go back to a different type of energy in yourself as an entrepreneur to create the next thing for different reasons. So I'd say another prism into this, which is there's no amount of money that you're going to ever make that'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 whether you achieve more or less than that, you know what it is. Your self-awareness and knowledge defines what money means to you. So it's less about a single answer and more about dimensions into how to think about that. So let's separate that from the last piece, which you said is that truly a motivator by it. So it's really not a motivator in the sense that you need to know the qualities of how you think about it, what it can do for you. Money, in terms of an entrepreneur's journey,

is just sort of like engendered life. It can solve things. It can fix things. My brother-in-law says, a problem can be solved, money is not a problem. Real problems are health and relationship. Things that are in your mind. Those are things that are problems. So 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 need a lot of choices when you're building something or creating something, it can be a tool, not all the tools, but one of the tools to help you accelerate that learning. Elon is one of one in our lifetime, honestly, even some of the greatest of all time. But I also recognize one of his great gifts is he can

tell stories technically and market stories. And I would argue that he's probably raised, I have no idea actually, hundreds of billions. I don't know what the actual number is, but let's say it's probably between $100 and $300 billion in his lifetime is my guess. So you can make a lot of mistakes, but he's taking on big challenges. So you need to learn a lot of mistakes. So all these things take into account your ability to create something of value, depending on how much you're obsessed about the size of that problem,

what you need to go solve it, of your own resources, rather than of others. So hopefully I'm not talking past you, hopefully around. 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. One of the things I've noticed over the years, David, is that at some younger age, you got a number and it may be a million. I usually hear $5 million or $10 million when I pose this question to somebody. And one of the things that I notice 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, 5,000, 4,000, 6,000 square foot home with

two acres of land for a million dollars. I live in LA. You live in New York. It's very expensive. You can't touch a house on the west side of Los Angeles, a teardown house for $3 million. And if you want to live in a nice neighborhood, it's $5 million. In some neighborhoods, it's $10 million. So if you buy a $5 million house, you have to have a lot of wealth behind that wealth. At some point, you're going to have a family. You're going to send your kids to private school. My daughter goes to Cornell. It's $82,000 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'm mentoring people and in my own life as well. I mean, it's again, this is... Well, your world gets smaller too. So it's all relative, right? I didn't grow up with any real resources, lots of love, but I didn't know what 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 over the last 25 years who belong to this email list.

Very confidential email list, and you would know some of the people on the list. But we were together for a long time when most of us had nothing, right? And over time, some of the people on the list became, I mean, crazy, crazy, crazy successful, like lifetimes of capital. And a lot of our journey people, people who are very successful economically, but it took them two startups or three startups in 20, 25 years. And that's, even in the boundary of successful entrepreneurs around the boundary you're talking about, that's most of the cases. It's actually, it's so rare. It's so rare. You talk about someone who earns or has exited after tax over $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.

And they themselves would have to create lightning in a bottle. It just doesn't happen. Your expectations should be, if the outside forces were greater than your, were just fortunate for you. That's my experience, honestly. I mean, with the exception of one or two people, that's almost never, ever, ever happened. My, all my successful friends, just to be specific, who've had great success are between the 10 and 50 number probably is my guess. I had Mark Cuban on my show and he said, you can't be a billionaire without being lucky. Is that true? I think it's more true than not. I think it's mostly true, I would guess. I mean, given the factor of time, it depends.

I mean, Mark's really young. But like, if you look at generational, like truly first generation wealth or first generation success, 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, it's the same reason why 80% of Warren Buffett's wealth has been created in the last, what, 10 years? Whatever the number is, I can't remember, but something like that. Given 20, 30 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 of the same, better. But very few companies in the world we play in, for everyone else, are typically, at our age, generational type of companies that compound in the same way. Either the markets aren't big enough, you can't get your arms around it big

enough, you can't dominate something like that without 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. You talk 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, they want to get rich quick. They read about the story. 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 thousands of them who are saying, gosh, that's really what I want to do. I want to make a ton of money when I'm young and then I can do whatever I want.

I think you'll be sad. You'd be very disappointed with that life, honestly. All the joy is the work. It's the becoming. It's the grind in the valley. It's self-discovery. It's knowing yourself, knowing your team. It's receiving the wholeness and experience of growth. And then it's learning to be it 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. It's the becoming part of it matters the most. And it's all the joy is 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 you accept the grace that it's going to 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 hopefully you can do more with that. I mean, you know this. It's amazing. You, when people try to fight for that, what it, what it exacerbates is this insight, which is, you know, when they get the success of the money, they're, you know, they're a little asshole. They turn into a gigantic asshole. Like whatever it is, it's going to be the inevitability. It's going to be accentuated so graphically to the world. Like, do you really want to be that person who hasn't solved himself

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. 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 and preparation that no one else has ever done before. How successful has preparation been to your success? And can you give us some examples of how extreme preparation has contributed to your success? This is a place that I really admire you a great deal. And it's also the difference between why I was a creative and a designer, industrial thinker, and you went to law school, right? Which I hated, by the way right but we both did for different reasons but we're 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 in the way so it's like um 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 in 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 learned fact is studied and prepared for, some is experienced, right? So some learned fact is studied and prepared for some is experienced, right? It's like going, there's Dick Costolo, a buddy always says, he goes, my job is to get out of the dark alleys and find the light. So how I get down those dark alleys is our own, our own style. So one could be a thinking and studying and preparation. The other could be like, I can run down a dark alley faster than anyone else and get out of it because I'm honest quickly and get to the same light. Does that make sense? But I would benefit greatly and I'd be a better entrepreneur

if 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 my town halls or building a company, writing the sort of cultural playbooks, I prepare like hell. Like I spend an insane amount of time, even if I know the content, trying to understand who's in the audience, what is the from to, what's the miracle they need, the slides, everything. So when I go in, I do not wing it. I don't wing it in front of my company. I don't wing it in front of my clients or partners.

I don't wing it on stage. I don't wing it in front of investors. I will prepare two to five X more than anyone else because I'm going in there having successfully done it in my mind in the same way Bo Jackson went on his alter ego and did it on the field before he ever ran the play. So different versions of preparation, but all vital to however you organize and manage yourself to get down the field, so to speak. I always ask myself, and I coach people, and this is a key question that everyone should keep

in my mind, is there any other thing or tidbit or something I can 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 coach people that I think is just critical how to separate yourself from hundreds of other people. You did that as you opened the podcast today with a couple of 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, that's why I love you anyways, but I appreciate you doing it. And it matters because it affects the sort of entanglement and the karma of highland ships and the will you want to do things for people. It establishes goodwill. It 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. It helps you get jobs,

promotion. It 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 some 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. It's true. People want to be on journeys where they're going to learn with people who care the most. And, um, I,

having done some really incredible deep work over the last eight, 10 years, there's this sort of kind of final piece to this whole becoming philosophy, which has been, been central, um, to my life, which is this idea that the purpose of all this is to love loving each other. So it might 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 guides your life, because you know, your why, you know your intention. You're no longer trying to fix yourself from the outside. In fact, I tell my sons, it's like, don't fix yourself. Don't be excellent sheep. Don't be well-rounded. Find your need in the world, the forces, 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 or try 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 upside 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 order themselves so they can be whole, aligned, so they can walk with you in that same journey shoulder to shoulder. That's a really amazing way to think about the journey. I find people like yourselves 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. I appreciate the kind words. And I 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. There have been many, many more. 70% of all of our returns come from 7% of all capital deployed, you've said. And Fred Wilson, a famous VC, has 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? I mean, they probably are true. I mean, I know they're true. So I've done, I think I need to update that number. It's over 80 angel investments now. And I'm an LP in, I think, six VC firms. Honestly, I stopped doing angel investing because it's rare now because it takes a lot of energy and time. And also, you want to show up for people

because that's why you did it, right? It's not out of the money. It's 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 unbounded returns. So the question is, why did I invest in the 7% that produced those outcomes? And there's actually two investment signals. The first is conviction, which really is kind of describing the understanding of the forces, the understanding of the need, and the question of the proprietary gift of the entrepreneur. There's a really interesting company called Fundify that uses

AI to actually look at how to get from 0 to 10x or 1 to 10x in your returns. It's largely around three boundaries of the number of investments you make. You have to make up to 25 to 30 investments to even get your money back. The second two factors were just the amount of time. So you spend less than 10 hours alone, it goes from 1.5 to 2x. But if you use a network of greater than 20 hours of diversified thinking, you can get to 9 or 9.5x. So these qualities of the portfolio matter. The second signal is non-consensus. Meaning, if 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, Fred is describing that third, a third, a third. A third will go to zero. A third will get your money back, 1 two X and the other third will be three to five X. And you might get 100 X, his legal question. And that's really the high conviction, non-consensus. So you have to put yourself on a network. A lot of the investments that I've made are the ones you mentioned. I've come through network effect, founder's fund in that case, those cases, personal relationships where founder, I've invested multiple times through their failure. I just kept going and they got good.

In fact, the odds of investing in an entrepreneur who failed are higher than if you're a successful entrepreneur. It's because the VCs know how fortunate you are. So all these factors lead to making good decisions, better decisions in venture. 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? I would say the second and not the third. Because the second means the first one. The second one, definitely. I've done that many times. I invested in an entrepreneur who I wrote a check and he blew up like 100 days later and he started another one. I kept going. That was a stretch, but it was like, I've done that several times. And so I have a couple of friends, I'm not going to mention who they 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 understanding of forces, you could potentially just be chasing things, esteem issues, like you're chasing super fancy technology things, and you really have no proprietary gift because you're afraid of who you are. It's just coming from the wrong place. And that's why I think I would tube not three is the simple answer for me. You mentioned a few minutes ago the word assholes. I've never said that on a podcast before, by the way. That's the first time.

This is not my first time, but I think it's important to talk about it. On a podcast. You and I are very lucky. We have our own capital. We have the ability not to invest in assholes uh what is what does that mean exactly who's an asshole 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 uh that's a it's a really provocative question um i don't really i mean all entrepreneurs to

some degree have to be what we just said it just is like you you have to have your ability to say no to people and very uncomfortable situations um be able to terminate people in the first sentence regardless of what they think of you. No is probably half your job, honestly. I mean, our Mark Andreessen, why he doesn't want to be a CEO, he says because it's bad news all day long. If that doesn't affect your attitude, nothing will. Read the two greatest books of all time, in my view of entrepreneurship, are both Ben Hor out to him. I think he's the greatest living entrepreneur of our lifetime.

He thinks along these boundaries around law, but he is a tough, tough founder. And that's part of the job. So if people think you're an asshole for that, then he's perfectly fine with that because his mission is bigger than that. So I think it's part of the job. It's just not part of the character, if that makes sense. 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. 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 going to 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. I mean, it's, it's, they're doing no service to them because there's, there's,

there's so many opportunities to leave every part of your life when they're bad. Right. Um, often. Um, and again, if you believe to the whatever degree you have been convinced by this or not in this conversation, that success is a bad educator, then 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 the life, the back half of your life when you didn't earn it.

So earning the good life is a function of your ability to pursue the hard life early. So growth lives in discomfort. It lives in friction. I've had a number of really well-known executives who've gone through success and failure publicly. I've had the good fortune of coaching just as friends. A couple in particular where their success, they're quite famous and the company's success struggled.

I told them, my advice was, 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, 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 in the bottom of Valley. And, and, and, and they were very much like,

I want to, I just want to leave, go away, whatever it is, you know? And you know, that's the whole, there's a great book by Martha Beck called the way to integrity. And, um, and it basically, her thesis is about Dante

Zafirno of there's no way out. There's only through and in going through is where all the growth happens. Um, and the way to go through in the beginning, and again, I want to make sure that I say this publicly, this is a moral imperfection of 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 can lie to the world, but at least you are awake. So that's one area of my life that over the last several years I began doing. I haven't successfully did that to everyone else in my life, but your life changes and learning happens when you begin to tell the truth to the world that you're telling to yourself, but it must begin with you. So trying to get out of something internally breaks that definition of integrity right there.

So you got to sit in the hardship. 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? Before they start talking? During the whole thing. Okay. During the meeting and then as you're making an investment decision, whether they're the same and they're different.

And I guess they're not always the same. Okay. So first is why them proprietary gift? Like what is their secret? So the 300 hours I spent with those 40 entrepreneurs in the startup playbook, the number one thing they said over and over again is they had a proprietor. They understood. They had a secret, basically. I knew something and how to solve it.

And no one in the world did. I just. So prop gift is the first one. Why them? Second is timing. Their understanding of the forces. Within the next three or five years, if we do this, it is an inevitable outcome. So it's about their understanding of their being there when it happens.

So why them, the force, and then the last piece is really the unfair advantage to solve that problem. So secret is their understanding of it. The timing of the force is their understanding of 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 the top two or three people in the world to do this.

They're born to do this. And given the 10,000 glad welling hours to pull it off, they're going to be one of three that's possible for them to pull it off. 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? I would say overconfidence is probably number one. Like overconfidence means control bias, means they're inflexible. Two is, and this is the word I would say, is their drive is ambition, not obsession.

You can tell it's really about them, their career, their success, and not the problem that makes sense like it's a huge obsession versus ambition are very different things and you can sniff that out and the third would be um i don't really like to feel like false like urgency bias like if you don't do this it'll be someone else like it, like urgency bias. Like if you don't do this, it'll 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 in 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. It's probably the wrong time. It's more like, listen, we have, we have, we have the round done. Okay, fine. We have half a million, 100 grand,

and we just want you in. We'd love to have you in. We don't care if you write a check for a dollar or a quarter of a million or whatever it is. And we just want your karma and your network and all the things you can provide in a way that you can be successful with us in it. Okay, fine.

That's fine. That's fine. But if the concoction is money or... There's other people for that. That's just not what I want to do. So many 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 and you're on a journey to constantly improve yourself and your way of life and being a better father and husband in all aspects of your life. Can you

talk 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? Yes, I will. I will share that with you. Despite Prince Harry going to, you know, the under going to court order for his visa right now on 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 ocean of your life 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 if you start to dig a hole in your life, you can spend 20, 30 years at the bottom of the hole, you can just blow up your whole life and start digging another hole again if you don't know who you are, right? Try to fix it. And the answer is like, it's pretty, pretty wasteful way to spend your life. So why not learn? Why not grow? And the becoming that first stage has got to know yourself. And the second stage is that love,

loving point, which is you got to learn to reconnect from your soul to your human self. They're different things and receive that love so that you can show up for other people. So the last phase of this is just about the being part. If you've read Eckhart Tolle, I'm sure many of you have, which is when you really go through his experiences, you start to realize that if time is an illusion, which it 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 and looking forward is control. And so to get, to give away that pain, to give it, eliminate the 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 and your why and your attention and your work and behavior, your thought, and how you show up in the conscious lens of the world around, if that becomes the quality and your behavior, your thought, and how you show up in the conscious lens of the world around, if that becomes the quality of your person, then everything will be inevitable. And the more we surrender to it, the more that's possible. So the experience with, as you described, the toad is really the beginning of that journey. And we were talking about this because you did an

interview with Mike Tyson and, you know, obviously someone who's dealt with extraordinary trauma and in his life, which was one of his 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. Incredible human being. I mean, like if you ever listen to Muhammad Ali speak, his intellect, his mind, his heart, how he 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 experienced and what I experienced is this idea of being one. And as you, I'm not, I'll paraphrase this very briefly, but it's as if all of your conscious energy of your life is moved out of yourself and rises. And as it's rising, it's almost the velocity of its ability to rise is where the concept of dimensions and time start to tear away. It's almost as if we're on this podcast right now, if I put a frame around your head, Randall's head, Randy goes from 3D to 2D, right? Instantly. That's what dimension is. So imagine that dimension is this over our head, 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 rise into it, there's 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 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 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, then 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 in your youth as you're becoming, and I'm not counseling anybody to go through these experiences if they don't want to. Also, I'm not even counseling to do that while they're young, because it takes half your mind

to become friends with your mom, half your life to know yourself. You wait until you know yourself. But these are questions of fear and control and expectation. And I'm not saying they didn't serve me in my own journey for anything, but it's not something that would sustain any part of my life going forward because it's 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 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. I've debated whether to ask this question as I prepare for the podcast, but I wanted 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 due to the dangers involved, but Mike Tyson has talked about it. You've talked about it a little bit as well. And if you're comfortable, will you briefly share without getting into too many of the details? People can look this up on their own if they 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, and many, many people's lives as well? Yeah, I try to illuminate those ideas, just the prior question. I think it's a natural psychedelic that exists in both biological and organic form and of DMT. And it basically is a psychedelic, a hallucinogen 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 in light and in dimension, right? So we see primary and secondary colors in dimensions that we can understand in our, in our, in our four and five D 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 we, 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 as a result of that, the interdimensional nature of the questions you're going to ask and the journeys you experience, you realize that our conscious physical reality that we live in is a subset, is part of the larger nature of our creation and what it's actually made of. And a lot of these

tools, not the least of which is DMT, are tools to open those dimensions up, open up experiences to know that. And I would say this last thing, which is, I would over-communicate this, which is, these are not toys, they're not recreational, they're profoundly powerful. And they're also something you probably want to 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, um, 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 thirties about starting over again, lifting myself out of that, you know, thorn road 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. We're at the end of the show. And I want to do two things first. First is is I want to thank Leslie Newman for setting us up, one of my best friends who I love more than life itself, who 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 alike, 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 some more open-ended questions. I call this part of my show, fill the blank to excellence. You ready to play? Okay, bring it. When I started my career, I wish I had known. Patience. The biggest lesson I've learned in my life is... Love loving.

My number one professional goal is... Impact. My biggest regret in life is... It's so long to stare down truth. The one thing I've dreamt of doing for a long time but haven't done is? Writing a book called The Board of Life, which I intend to solve. The greatest innovation of the next 50 years is going to be? General AI. It's already done. The super intelligence. If you could go back in time, the one piece you would give advice

to your 21-year-old self is? Slow down. If you could meet one person in the world, who would it be? Living. Let's go living and let's go not living. I'd probably spend time with Sam Alban right now. I have open AI.

Dad, I would say I would say Christ or one of the great yogis like Yogananda or something. 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 you lived next door to me or in the town next door so

we could hang more in person. I do too. We'd have fun. Well, we're going to have a lot more fun for the rest of our lives. But thanks for being here. I appreciate you being on my show. Incredibly grateful. I love loving you. And we'll keep doing that.