E173: Billionaire Michael Loeb on Risk, Innovation, and Never Giving Up

What happens when you get fired from one of the most prestigious media companies in the world at age 36? For Michael Loeb, it meant inventing a new category in subscription services, launching one of the earliest venture studios, and incubating Priceline—one of the internet’s first great successes. In this episode, I speak with Michael Loeb, founder of Loeb.nyc, about how getting fired from Time Inc. led to the $800M sale of Synapse back to Time, his early partnership with Jay Walker to incubate Priceline, and what makes a great entrepreneur. We also dive into how Loeb.nyc works, the role of trust and pivots in building companies, and why pattern-matching VCs often get it wrong. Michael doesn’t hold back. He’s honest, funny, and full of war stories from decades of building companies—and backing founders through multiple lives.

Speaker names marked ? are inferred from speaking time and the show’s known hosts — they are not voice-verified.

• 0:00David Weisburd?

  So you've said that the best thing that ever happened to you was getting fired from Time Warner at the age of 36. Why is that?

• 0:09Speaker 01

  David, I gotta tell you, I never said that that was the best thing that ever happened to me. It's, it's everybody else that said that about me, that it was the best thing. I was 36 and I was feeling really old until I found out that Bloomberg got fired from Solomon Brothers when he was 38. So he's got me beat. And that, by the way, is a regret of mine that I didn't start early. I do think there is an entrepreneurial gene and I had it. The mantra was just don't fuck it up, right? Just don't fuck it up. And, you know, if you had Time Magazine and Sports Illustrated, Money and Fortune, and all the other magazines, if you added the number two and the number three and you doubled it, it was about equal to Time Inc.

• 0:54Speaker 01

  So it, they were, you know, the, you know, the 8,000 pound gorilla in their space. And it was, yeah, just don't screw it up. Don't screw it up. And I was pretty shitty at, at not screwing it up. And invented a lot of things, but I lost my job. That was especially painful for my dad because he was pretty sure that, you know, at 36, that was it for me and I'd be a ward of the state. But I decided that I was gonna use this opportunity to launch something I always wanted to launch,

• 1:37Speaker 01

  which was a redefinition of a subscription, right? And at the time, you bought a subscription and all the time you would be getting paper renewal notices that would be entreaties of, you know, increasing drama to try to get you renewed. And they called that in the trade a positive option. You had to take a positive option to keep the magazine coming. That was always from day one for me, very curious. And I asked that question about 100 different ways. Why do we do it that way? Because to me, that was the business model of a product and not a service. And I thought of the magazine as a service. People wanted to call this automatic renewal.

• 2:21Speaker 01

  That term was a little bit user unfriendly. So we relabeled it continuous service because who wouldn't want continuous service? Or by contrast, who would want an interruption of service? And what it effectively did, David, is take inertia, which was your mortal enemy, and made it your best friend.

• 2:45David Weisburd?

  You reportedly sold for $800 million to Time Warner, and you have an interesting story about that. Tell me about post-acquisition.

• 2:53Speaker 01

  What they wanted to do is make a statement that this is the new Time Inc., that they are going to be inventive and entrepreneurial. And as proof, here's the guy that we cast out. And we bought his company for a whole lot of money, and that's proof positive that we're entrepreneurial. And so tell us about that, Michael. And they brought me around the world and all the convening of executives and trotted me out. And they always had journalists interviewing me. And in one of these convenings was the guy who pulled the trigger, right?

• 3:25David Weisburd?

  Guy who fired you.

• 3:26Speaker 01

  Guy who fired me. And he didn't make any secret of the fact that he was there. And again, this was a lot of years later. And he sat like fourth row, right in the center. And he came up to the DS afterwards, stuck out his hand. He said, "Michael, I want to thank you." And I said, well, his name was Mike. I said, "Mike, why do you want to thank me?" He said, "Well, when the question came up about you getting fired from Time Inc., I'm very happy that you didn't say, 'And it was that motherfucker over there.'" So anyway, so that was a comedic. And he got no stock.

• 4:07David Weisburd?

  You mentioned that you had a disagreeableness to you. Michael Burke, who you referenced earlier, has similar characteristic. Why exactly is that a good trait for an entrepreneur?

• 4:17Speaker 01

  Fundamentally entrepreneurs are unemployable, right? I think that they are insistent. I think they ask why. I think they don't accept no for an answer. I think they have no appreciation of protocol. They're just impolite. I mean, they're just very equipped to say, David, with all due respect, you're not just wrong, you're like fucking wrong. In fact, you're fucking stupid wrong. Okay? So they're in a big rush and they like doing things differently. And there's many examples of entrepreneurs. And I can give you a couple right now that I think are neat vignettes.

• 5:02Speaker 01

  But there was this 17 year old kid in California. And his first name was Dick. And everybody from the beginning dawn of time, whenever we wanted to high jump, we would barrel roll over the, over the bar. And this kid, 17 years old, went backwards, right? And every coach said, Dick, you can't go backwards. You can't go backwards. And Dick said, all I know is that I'm jumping seven feet. Nobody has ever done that before. And that was Dick Fosbury and it was the Fosbury flop, right? And he invented that. Babe Ruth joined baseball at a time that everybody had little tiny gloves.

• 5:46Speaker 01

  In fact, nobody had their own glove. They just left it on the field and the other team would pick it up. And the players were not nearly as mobile. So basically the way baseball was played is you hit down on the ball. You hit down on the ball, you hope to find an opening, get to first base, hope to steal second, then you hope that somebody, you know, gets something in the outfield and advances you to third. That's how the game was played. It was ABC ball. And Babe Ruth, who was a big fella and was not very fast, said, well, explain this to me. You're telling me that if I hit the ball out of the park, I can go around the bases as slow as I want?

• 6:30Speaker 01

  I can just like trot around the bases if I hit it out of the park? And they go, yeah, that's right. And so instead of hitting down on the ball, he hit up on the ball. And Ruth, and we got to put this in context, but Ruth hit more home runs than whole teams like in baseball. It was transformational and you know, baseball was played for an awfully long time and he just changed the way baseball is played. And that's entrepreneurs, right? They're just insistent, they think differently. And by the way, they, when they succeed, they crow about it. They're awful employees. You really don't want to have an entrepreneur as an employee.

• 7:12Speaker 01

  So I was just that guy who was not content with four or 5% gains every year. It had to be 40 or 50. And I put that to practice in Sports Illustrated, which by the way, got a lot of people, you know, pissed off at me. In Japan, they say that the highest poppy gets cut first because you want a unanimity and you know, in big, comfortable corporates, they kind of want the same thing.

• 7:40David Weisburd?

  So while you were at Synapse and you were growing that, you also incubated Priceline. Tell me about the origins of Priceline. How did that come about?

• 7:48Speaker 01

  I got to step back and describe my partner in Synapse, which it was very, very early in the curve. A mutual friend introduced me to Jay Walker, who I thought was a genius. It is a genius. And Jay had some great patter, which was, hey, I'm a uber-successful entrepreneur. I won't say if that was true or not, but I'm an uber-successful, multi-times entrepreneur and you're just some schmuck who got fired from a mid-level job at a Fortune 500 company, right?

• 8:30Speaker 01

  And you want to be an entrepreneur, you're going to fall flat in your face. And we met, we went back and forth. Jay said, you know what? Best thing is I'll hire you and I'll give you 20% of the company. And I'll finance everything. And I said, you're crazy. You're not going to hire me. Maybe I'm going to hire you and maybe I'll finance everything. Truth is Synapse was bootstrap. We didn't need to finance much of anything. And we kind of met in the middle. It was a 50 50 deal. And I learned the hard way that Jay, like a lot of incredibly brilliant people, are not gifted necessarily when it comes to managing other people.

• 9:13Speaker 01

  You figure out you're the smartest guy in the room by, you know, several lengths. And it becomes hard to, you know, work with, you know, employees. So after a time, it was Jay, you know what? You think of what we are going to do together. And Jay came up with another idea, which is a sabbat every other day. And it wasn't just an idea. It was an idea with a, with a business plan, a 50 page business plan. The man was prodigious when it comes to be able to churn out work. Those things were not particularly attractive or viable, in my opinion.

• 9:53Speaker 01

  But one day it was Priceline.com and that to me made a whole lot of sense. And my, this was a day been in a day that if you wanted to go from New York to Boston, you had to get a travel agent, right? You just couldn't do it yourself. There was no self-serve option. And Priceline was, you know, was self-serve travel. And the Name Your Own Price was all about the fact that there was remnant inventory in travel. And this was a way to monetize that, monetize that, that, that, those seeds.

• 10:35Speaker 01

  And Priceline was the very first of its kind. Jay Walker saw it. He, he.

• 10:44Speaker 01

  He was very prescient and figured out that IP had changed and is now patentable. It used to be that it was widgets that were patentable. And he put all that together and came up with this incredible idea. What Synapse's contribution was that we were the funding source in the beginning. And we were also, by the way, the labor source because we told everybody, instead of getting double the employees and more space, at least in the beginning, we just said to everybody,

• 11:24Speaker 01

  you got two jobs and as long as it was the same pew in a different church, it kind of worked. And even when it became apparent that the appetite for funding of Priceline outstripped Synapse's ability to generate cash, and we had to go to an outside firm, outside source. You couldn't really do that for anything internet because the internet didn't exist. I mean, that's how advanced Jay was in his thinking to do that.

• 12:04Speaker 01

  So Jay sold half of his half of Synapse to give the next shot of capital to Priceline, which was, which brought him to the public offering. So last I checked, Priceline, now bookings, had a $165 billion market cap. So Jay built one of the very first, actually, I think the very first, and big, successful internet companies back in the middle 90s, which was really very early.

• 12:39David Weisburd?

  You've been running a venture studio since 2006, now called Loeb.NYC. How would you describe the venture studio thesis?

• 12:47Speaker 01

  If you wanted to put it into four boxes, you would have a box labeled ideas. You would have a box labeled entrepreneurs. You'd have a box labeled know-how and a box labeled capital. And if you put all those things together, there's a lot of synergies to be had. So we self-generate ideas. We then research those ideas, test those ideas. And if they test out, we put a team of entrepreneurs behind them. Now, you're going to ask me, where do I get my entrepreneurs? Well, the answer is they're entrepreneurs that I've recycled from other projects, right?

• 13:31Speaker 01

  So there's a sale, there's an exit of some sort, then you've got a team freed up. They're accustomed to working with one another. When we have an idea, David, the very first thing we do is research it. We write a white paper. It goes into the freezer. And when a entrepreneurial team frees up, they get to look in the freezer, they see what's there, and they get to take their pick, and then it becomes theirs, right? Now, we complement that with what we call shared services. That's the know-how. So I went through ideas, entrepreneurs, know-how.

• 14:12Speaker 01

  Know-how is we have different groups. It's a Swiss Army knife of capabilities that do different things. So back office accounting, for example, we try to have all our companies go on our back office accounting rails. And that is because I want lingua franca. I want to have a common definition of burn rate, fume date, you know, gap accounting, yada, yada, yada. I want to pay the bills on time. I want to collect on time. And those are skills that entrepreneurs are in short supply of. I'm in short supply of. I just, you know, give me a pile of bills to code, forget it. I'll never give you any consistency.

• 14:56Speaker 01

  So you, we have that. We have a research group. We have recruiting legal. We have.

• 15:05Speaker 01

  Fundraising, because once we stand a company up, we'll go, you know, several innings with it, some more, some less. The least amount we put into any one of our ideas before we went outside was two and a half million and the most was like, you know, forty-ish. And some, we never raised any capital at all because we went right to a sale, right? Synapse being a good example. So, so in addition to the other shared services that I described, we have tech and we got marketing. So, and we got everything in between. And basically, the young, you know, these young companies, these startups, these nascent companies borrow

• 15:50Speaker 01

  all that resource. We don't charge it out. Our currency is success. And we think our success rate with the ecosystem and with the incentives and our entrepreneurs, it's not as much as the West Coast playbook. I will re-up a team or a CEO as long as it was a quality at bat. Doesn't have to be a winner, just has to be a quality at bat. Not, not every ball that is hit on the screws drops. And sometimes you did everything right and the company, company doesn't work. And you don't want to penalize somebody for that.

• 16:31Speaker 01

  In fact, you know, failure really is a derivative of success. I think it makes you a better entrepreneur. What goes on in VC-dom is they talk about two in 10 working. And if, when pressed, they might get to one in 10 working. And the problem with that is they very quickly do the triage, figure out who is going to be, in their mind, the winner. VCs typically, they, you know, they either went to Harvard or they went to Stanford to get their MBA, but they never ran a popsicle stand. So, they try to run the war from the Pentagon. And unless you've been in the trench, it's really pretty hard to prosecute a war.

• 17:12David Weisburd?

  And as you've seen startup costs go down dramatically, why do entrepreneurs still want to go with venture studios? And talk to me through that evolution of capital and how you've been able to retain the top talent?

• 17:27Speaker 01

  We self generate our ideas, right? So we start, it's our ideas and we got a merry band and we've had enough wins on the board that, you know, people are always there looking for the next one. So, um, so yeah, it's a little bit differentiated from that perspective.

• 17:47David Weisburd?

  You generate your own ideas. Tell me a little bit at a high level, what your process is like to have such a high hit rate.

• 17:54Speaker 01

  Entrepreneuring is like a process of, you know, defying thing. And I'll tell you a little, a little vignette, but about 20 years ago or so, I'm invited up to MIT and MIT had just started its, you know, entrepreneurial incubation lab and they wanted to have me for lunch. And at lunch, and it was me and about 20 people. So we had this, you know, wonderful lunch and then they hand me at the end of lunch, a book, right? A book. And the cover of the book, the jacket said, "The 24 steps to being a successful entrepreneur", right? The 24 steps.

• 18:38Speaker 01

  And all I could think about is, oh my God, I don't check the box on step 13. Does that mean I can't be a successful entrepreneur? And I said to them, you know what? You're missing step 25. And they go, step 25? There's a step 25? I said, oh yeah, there's a step 25. And they go, what's that? And I said, burn this book. Cause you can't, right? Call 1-800-ENTREMENEROR and hope to be one. It just doesn't work that way. And you can't convene a bunch of people at three o'clock every Wednesday and say, give me your best ideas. It is lightning on a bottle and what you do is just put your shingle out and say, hey, look, anybody with a good idea, you put it in the hopper, give it to research and they

• 19:23Speaker 01

  will write a white paper on it. Sometimes they'll spend.

• 19:30Speaker 01

  10 minutes on it because they'll say it's just not viable, right? Or 100 companies have tried this before, they're all dead. With the good ones, they'll go the distance and they'll write, you know, a 20-page paper on it, which outlines, you know, you know, everything you'd like to know. The TAM, you know, the perceived margins, how you would scale it. Is it B to B, B to C, or B to G, yada, yada, yada. So that is kind of the beginning of the process is understanding the research on the marketplace.

• 20:06David Weisburd?

  Two of the most famous dot com busts were Webvan and Pets.com, which later on became Instacart and Chewy in the next iteration. How do you know when a company that's been tried many times and failed, maybe the time has come for that idea?

• 20:23Speaker 01

  David, it gets to something very interesting, which is sometimes the littlest thing, like somehow has an outside, outsized difference. I'm trying to remember, you probably do, the predecessor to Facebook?

• 20:43Speaker 01

  What was the name?

• 20:43David Weisburd?

  MySpace.

• 20:44Speaker 01

  MySpace. I ask this question of people all the time. What was the difference between MySpace and Facebook? I mean, why did Facebook win and MySpace get evaporated? I, I just don't know.

• 20:59Speaker 01

  But it was something, and it was something that was probably pretty subtle, but it was, it was the difference between success and failure.

• 21:08Speaker 01

  The other one that's worthwhile thinking about or mentioning, and that one was a much bigger thing, is BlackBerry versus the iPhone. Right? So BlackBerry invented it, they owned it, they owned it. But I think what the difference was is BlackBerry thought of this, thought of what they had as a communications device. And what Steve Jobs thought is, I am taking a computer and putting it in everybody's pocket. And

• 21:43Speaker 01

  I wonder about those things all the time and it's entrepreneurial success is very fragile and sometimes, you know, which gets back to you can't program it. You can't say at, you know, three o'clock on Wednesday afternoon, we're going to ideate, you know, it, it is a very, it's like a souffle. It just requires the, you know, the right temperature, the right eggs, the right this, right that to make a good souffle. And so I wished I, I wish I was smarter about it all. Because sometimes I think, you know, that winners don't turn out to be winners and, or what I would predict as a winner and the reverse is true.

• 22:28Speaker 01

  Sometimes we're working on something and it's the little engine that could. And, you know, I say, you mean that's still, that's still around? We, that didn't die yet? That's amazing. And it just grows and grows and then it takes off. It's, it's interesting, but you find, I find a lot that with a company, it, it's not up and to the right for sure, but it will spend a lot of time not doing much of anything and then all of a sudden go vertical. By the way, if you look at Apple, right? Apple for the longest time, for like 10 years, maybe even more, had a $5 billion market

• 23:09Speaker 01

  cap and then a couple of inventions just made it go straight up and it's been straight up ever since.

• 23:16David Weisburd?

  When you have these companies that are kind of middling and then shoot up and straight to the right, is it like an iceberg where something's growing underneath and you can't see it? Or is it just almost probabilistic if you stay alive for a long enough time, you get some flash in the pan and suddenly you're off to the races?

• 23:35Speaker 01

  I would describe it a little bit differently than that. I'd say that it's not just staying alive. It's like continuing to try new things, you know, new combinations of things, new thinking about things. Like maybe this isn't a B to C business, maybe this is a B to G as in government business. Maybe our price point shouldn't be a hundred dollars, maybe it should be 10.

• 24:05Speaker 01

  But you know, just saying that is one thing, then you got to re-engineer the business model so that you can actually make money on ten. So I think it's the constant rethinking of the business model. And sometimes, David, I have, I swapped out teams. You know, a team that was successful in a prior business and is working on something and, you know, and just is not successful. You swap out a team and sometimes it just clicks. Like, somebody saw something. Rumors are really hard to squash.

• 24:45Speaker 01

  And a lot of times, you know, a rumor is, "This can't work. We tried it." Right? And, well, you know, you tried it on Tuesday and not Monday, right? You tried it during the day and not the night. People in teams being what they are, they put things in the, "We tried it, it doesn't work" box, and they tend not to look at that box again, which a new team is just gonna start from, you know, "I don't know a thing I want to learn."

• 25:19David Weisburd?

  I like to say, a four-year-old and the greatest first-principled thinkers on the planet have one thing in common: they ask the question, "Why?" And after they get an answer, they ask another "Why?", until you get to the physics of why something doesn't work or works, and then you could actually have a good answer to whether, "Does this defy the laws of physics? Is it just too expensive, given these factors?" And you have a whole understanding of the entire system behind why something works some way versus just this memetic repetition of why something might not work.

• 25:54Speaker 01

  You're 100% right. And as you say that, I reflect on Synapse, which kind of brings us back to the top of the conversation, which I said, "I don't get this catch-and-release program for subscriptions." We worked really hard to find somebody, and they finally subscribe. And then, we send them renewal notices, and if they don't respond to us, they unsubscribe automatically. Makes no sense to me.

• 26:21Speaker 01

  And I kept on asking, why do we do it that way? And I kept on getting an answer and the answers didn't make sense. And then finally, out of exasperation, the answer I got is, this is just the way it's always been done. Right? And by the way, when you get that as an answer, you know you've won. You know there's something there. Because, you know, it's all about what Robert Frost said, which is, it's about the road less traveled. And in the case of the entrepreneur, the road not traveled whatsoever. There's always that fear of the unknown and the fear of something that's never been tried before, something that has been tried before and rumor has it doesn't work, but you step back and it doesn't make sense.

• 27:05Speaker 01

  It never made sense to me that we'd have the catch and release program for subscriptions. Right? It always made sense to me that it would continue as part of what we would call a negative option. Right? You had to opt out as opposed to opt in. And I intuitively knew that when you flipped the script, you would find that there'd be a huge lift in lifetime value. And indeed, there was. And that was what allowed Synapse to kind of eat the world. We really did become a new, you know, a huge company pretty quickly.

• 27:46David Weisburd?

  When we last chatted, you mentioned that it's all about the people, but you also said something paradoxical that the company almost always pivots. So how do you line up the idea with the market, with the people? And how do you line all those things up to build a large company at that early stage?

• 28:02Speaker 01

  David, and this is an advantage we have. You got to make it safe. You got to make it safe. And when you're dealing with VC money and outside money and you showed them a business plan, okay? And whenever you re-meet with, you know, the board made up of, you know, that VC.

• 28:25Speaker 01

  They always ask the question, well, three months ago, you said this and now you say this, right? And you're off plan. And so you learn about the sanctity of a plan. And so the temptation is to try to get back on plan, to adhere to the plan. And you also get the sense that if you don't adhere to the plan, you're done, right? You're not going to be one of the anointed few that gets to, you know, more capital and gets to, you know, live again. So that's not feeling safe, right? You gotta feel safe. You gotta be able to feel trusted and safe as in, go with your gut. You're here because you got a great instinct, right? And you're here because you're into fatigueable, right?

• 29:10Speaker 01

  You're not gonna quit. That's why you're here. And this is not about my idea, it's about your idea and running with it. And I trust you, right? I trust your judgment. I trust your strength and your power and your preserve. I trust all that stuff. And that's not what you typically get in a VC universe because they just can't pivot because they don't have the time to pivot, right? You don't have, you're on the clock, you don't have time, you gotta execute the play. And sometimes with the best of intention, you kind of diagram the play, but the play's not working, it's a broken play. So what do you do?

• 29:53Speaker 01

  What Einstein said in Sanity is doing something over and over again and expecting a different result. And you do see that all the time, that VCs just say, get out there. You say, you know what, I'm trying, it's just not working. And it's like, you know what? You're just, you know, you're just, you're just frail, okay? Go out and, and try harder. And the entrepreneur will know, they'll have an instinct that this ain't gonna, it's just not gonna work. And you do have to pivot, you do have to do something different. And there's not a whole lot of tolerance of that. In VC-dom. And so I think one of the keys are you gotta feel, you gotta feel

• 30:37Speaker 01

  safe and supported, right? Like, you know, talk to me, talk to me. The only thing I demand is equality at bat. It's not success or failure. So, you know, you're, you're trying hard. And what's neat is I do get entrepreneurs, my people in my team, they'll come to me and they'll say, Michael, you know what? This just, this dog ain't hunting. You know, this might be a single, I'm not a singles hitter. Get some young, one of your youngsters and let them sink the teeth into, into this and get one, one victory. And then, you know, they'll get, they can throw off the training wheels the next time and go for something bigger.

• 31:16Speaker 01

  But it's the entrepreneurs who know first. And if you have that environment of support and trust and faith, faith that, you know, you're, you're thinking clearly, face that, safe that you have researched things well, that you're trying really hard. You know, and by the way, you know, come to me for advice all the time, we'll talk it through. But, you know, that, that feeling that you can do that, and nobody's gonna be, you know, won't be a punitive experience is, I think, very important. So that's one of the things.

• 32:00David Weisburd?

  I'm very curious on that. So a serial, a successful serial entrepreneur comes to you, launches a company, let's say, they see it could only be a 10 or 20 million dollar revenue business at scale. And they want to bring, they want you to bring in a new CEO, new partner. Tell me a little bit about how you structure something like that.

• 32:19Speaker 01

  If one of my CEOs were to come to me and say that, then, you know, they got equity in the old company, and they keep that equity. And then if they say, you know, look, let me see what's in the freezer, I want to try a new idea, then they get to do that. I mean, you know, yeah, so it's all with regard, respect, appreciation. I, I actually.

• 32:44Speaker 01

  You know, I actually do thank them and I am appreciative of them coming to me with that.

• 32:52David Weisburd?

  Takes a lot of courage.

• 32:53Speaker 01

  Yeah, it takes a lot of courage and takes a lot of courage. And I appreciate their ambition, right? They, they don't want a $10 million company. They want a billion dollar company. I want that too. So.

• 33:07David Weisburd?

  And those entrepreneurs that end up going to the freezer, picking out another idea that you guys have researched. What, what's the base case there? Do they end up more successful than the people that stick with their businesses?

• 33:20Speaker 01

  To be statistical about it, I need to have like, you know, 500 use cases. I just don't have that.

• 33:26David Weisburd?

  But do you get excited about that use case and design?

• 33:30Speaker 01

  You know, I get very excited. I get very excited about sitting down, you know, with a team. When we're sinking, sinking our teeth into a new idea, new company, when we have some early market evidence of success or failure. And we're trying, we're doing the diagnostics. And you know what? One thing that's very exciting is if you look at something and it looks grim, right? You're looking at all the pieces and you're saying, oh my God, this, this just ain't going to get to the promised land. But then you say, okay, I'm gonna, I, I got an idea. I'm turning it upside down. I got an idea, right?

• 34:15Speaker 01

  And so one idea can reinvent an entire business. And what does he, what does that sound like? Well, it sounds like, you know, saying, okay, I'm, I'm redefining what, you know, how we are going to get paid, right? So the product market fit, right now, the product market fit is not a problem with the market. And it's not a problem with the product. It's a problem with the fit, right? So I'm trying to fit myself into, you know, Lululemons when I really should be wearing a jacket instead.

• 34:58Speaker 01

  So you say, okay, you know what? We're not gonna make. Lululemons, we're gonna make jackets. My brainstorm is if we look at our customer, look at our production, we look at everything, we are better equipped to do that. And the margins are higher and everything else. So you change kind of the field of play. It's stuff like that that gets kind of exciting. But I do have an exciting job. I get to work with people half my age and twice as smart. And it's never been a more exciting and trying time. You mentioned before how you can build a company with a lot less people and a lot less resource, and it's getting more and more compressed.

• 35:41Speaker 01

  And AI, of course, has an enormous impact with all that stuff. And so it's, it's a fascinating time. And what's really fascinating is, you know, the big companies, the big hundred-year-old companies with 10,000 people are just gonna have a devil of a time making that transformation. And so it, I think, kind of like an old analogy, the world belongs to the little mammals that can burrow, you know, and stay out of harm's way when the comet came down. Or I guess it was a meteorite that came down 66 million years ago. When, by the way, when you think about dinosaurs, dinosaurs are totally cool. Okay?

• 36:27Speaker 01

  Dinosaurs, they were, they were, you know, the tippy-top, right? Of the platagram. And for 200 million years, they ruled, right? It was claws and teeth and muscle and strength and size. And then that could have ruled for another 200 million years. And then, you know, the meteorite came down. And things that can go out underground were the things that ruled the day. And here we are. But, you know, intellect was not one of the things that we, we needed back then. Right? So.

• 37:09Speaker 01

  It's kind of interesting when there is a meteorite-like event that changes all the rules and all of a sudden the definition of success kind of changes.

• 37:23David Weisburd?

  Yeah, do you see the construction of teams evolving in terms of smaller teams that are able to scale more rapidly? And if so, how are you incorporating that into your business?

• 37:33Speaker 01

  We've always started in the very beginning with small teams and we added to those teams. And now I think we're gonna still have small teams, we're just gonna add a little more slowly. So I think that these are very interesting times to be an entrepreneur. They're trying at the same time because capital formation is a little bit more arduous than it was a couple of years ago, but that too shall change. We're addicted to invention in this country and we should be. That's where the intellectual property is and that's where the value formation comes from.

• 38:13David Weisburd?

  There's all sorts of the Silicon Valley folklore in terms of entrepreneurs need to start the idea or else they're not entrepreneurs. They need to risk everything or else they're not entrepreneurs. Do you see a class of people that are naturally just really good at execution but may not want to or have the idea?

• 38:33Speaker 01

  They say that, right? But they also say in the same breath that the biggest determination of success is previous success, right? So they want that multiple-time entrepreneur and statistics bear that out. So that multiple-time entrepreneur is not going to be driving a Volvo with 400,000 miles on it. The thing about an entrepreneur is they come, they just, they come out of the womb hungry. They're just hungry and they're irrepressible. And so I don't think they need the motivation of starvation, right, to be successful. And

• 39:12Speaker 01

  I think it's categorically true that multi-times entrepreneurs have a greater probability of success than first-time entrepreneurs. And I don't think anybody in VC-dom would disagree with that one. So that runs contrary to the notion of they gotta be starving.

• 39:36Speaker 01

  And I will just tell you that, you know, entrepreneurs just they're they're just hungry, irrepressible, and they don't need, they don't need to be first timers and, you know, be living on wonton soup and peanut butter in order for them to have that desire.

• 40:03David Weisburd?

  Thank you for listening. To join our community and to make sure you do not miss any future episodes, please click the follow button above to subscribe. I also think starving is a relative term. If all of your friends started billion dollar companies and you're in that peer group and you sold a company for $70 million, your ego might be as starving as somebody that's 24 year old that's just coming out of college.

• 40:26Speaker 01

  How do we explain Michael Jordan? Right? How do we explain The Last Dance? I mean, that guy was ferocious, right? You know, he wasn't a 1-1 championship. That's good enough. I mean, just a ferocity. Look at Tom Brady, 45 years old, winning a Super Bowl. You know, would you bet on Tom Brady or some rookie?

• 40:52Speaker 01

  This is why entrepreneurs are a species unto themselves because they just, they have that fire. They got that desire. They got that need. And what they say about them is true, that the money is just a way of keeping score. It's not, you know, it's not the it of it, right? The it of it is inventing something. The it of it is having some other entrepreneur have some other smart person look at a company, look at an idea and say, damn, I wished I had that one, right? That could have been mine. That, that was an idea that I should have had and I didn't. And the son of a bitch, he stole it from me without stealing it from

• 41:34Speaker 01

  me, but he invented the company I should have invented. That was mine. That's, you know, high praise. And that's what we all live for.

• 41:44David Weisburd?

  You're in your late 60s. You're reportedly worth a couple billion dollars. What still drives you today versus earlier in your career?

• 41:51Speaker 01

  Do I look like I'm in the late 60s?

• 41:54David Weisburd?

  Reportedly, reportedly.

• 41:56Speaker 01

  Reportedly. They lie. So what drives me? No, it's, it's, it's those very tenants, which is I just want to, I just want to win. I just want to win. I want to make a difference. You know, and I want to win. I want to, there is nothing more satisfying than coming up with the idea, planting a seed and seeing a mighty oak grow. And I will say something else, which is you do the happy dance with a victory for about five minutes. And when you have a loss, you suffer that for five decades. It like never goes away. It's, you want to have the five minutes and you really want to avoid the, you know, the 50 years. So it's, you know, I, I don't know what

• 42:41Speaker 01

  to call it, David, except it's a disease. It's a disease and it's like shingles. It just keeps coming back, you know, you, and there's no, there's no, you know, no amount of, you know, inoculation will prevent you from having your shingles. I'm lucky to live in this country because this country has spawned more than a chair. I did a little analysis a few years ago. It directionally still holds, which was the top 25 tech-centric companies is measured by market

• 43:16Speaker 01

  cap. And of those 25, 19 were American. So we're 4% of the world's population, 76% of the Teslas, the Netflix, the Microsoft, the Facebooks, the Nvidia's, et cetera. Right? So here is where these companies get invented. And

• 43:42Speaker 01

  You know, the question is why? I don't really have an answer to that. Capital formation is one, but I think forgiveness when it comes to failure. There's other countries around the world where, you know, if you're if you're failure, done. That stink, that stain will follow you around everywhere, but not in this country. We kind of wear it as a badge of honor, right? And, you know, it's

• 44:04David Weisburd?

  It's part of your narrative.

• 44:06Speaker 01

  Part of the narrative. And also, when you get a group of entrepreneurs together, and, you know, we get a, you know, a drink in us or two, then we sit around the campfire, and we say, you know, I, I don't know what I was thinking with that one. I mean, you know, at the time, I thought I was so clever. And then I put it in the marketplace. What an idiot, right? I really thought that one would work. What a dummy. And I spent all oodles of millions doing that. So shame on me.

• 44:37David Weisburd?

  We spoke in the beginning of the interview, how your parents came from the depression area, and when you were fired at 36, they were they were a little bit worried about you.

• 44:47Speaker 01

  Yeah.

• 44:47David Weisburd?

  Did the fuel and the source of your motivation fundamentally change before and after synapse, before and after a price line to today? Or does it still feel like the same type of motivation?

• 44:59Speaker 01

  No, it feels like the same. I'll tell you one thing that I no longer have, which is, you know, don't don't get me wrong, I worry all the time. But you, you know, you had the patina of fear in the very beginning, because one false move, and you're like, done, you're bankrupt. And in the beginning, where you had about nothing, and you're betting it all, betting all of it, right, on the come line. And if it if it comes up, you know, red, not black, you're just done. That's a fear that, you know, I no longer have.

• 45:41Speaker 01

  It's more calculated that it's still, don't get me wrong, hurts like hell when it doesn't work. And I still have a lot of anxiety about all that. I think that's part and parcel of all this. But it's, it's not as present as it used to be.

• 46:03David Weisburd?

  When I first met you, you told a story about this friend that calls you every six months telling you from the beach and telling you to retire and go enjoy yourself. Is there some middle line where you could be half in and vacation or is it truly in or out? And why is there no middle line?

• 46:25Speaker 01

  I don't know. I was hoping that you were a therapist. You're not a therapist, are you?

• 46:31David Weisburd?

  I have a master's psychology, but not a clinician.

• 46:36Speaker 01

  Yes, I do have that friend and I'll tell you that parable kind of right now, which is he does call me twice a year. He does. He used to try to have this conceit where, you know, he got me to pick up a landline phone, but now he doesn't even bother with that. But I get a phone call from him twice a year. And, you know, I see who was calling and I say, "Hey, Stu." And he says, "Hey, dumb fuck. I see you're still working." And I say, "Yes, Stu." And he says, and Stu had a number, the number was 200 million. When he got to

• 47:15Speaker 01

  200 million, that was enough. And dumb fuck, guess what I'm doing now? And I said, "I don't know, Stu." He said, "I'm drinking a cup of coffee." Where am I drinking the cup of coffee? I said, "Gee, I don't know, Stu." I said, "It can't be in your vineyard in Tuscany because it's, you know, not that type of year. It can't be in your, you know, castle in Aspen because, you know, it's no longer, you know, snowing. Probably too cold for, you know, your mansion in Connecticut. You must be in Palm Beach." And he goes, "Bingo, dumb fuck. What am I doing?" And I said, "I don't know, Stu." He said, "Well, I told you I had a cup of coffee. I'm nursing my cup of coffee. I'm standing on the beach, my beach, looking

• 48:00Speaker 01

  at my waves at my house in Palm Beach." And he said, well, what's next? I said, I don't know, Stu. He said, I don't know either. Uh, I, um, I don't know if I get a massage. I don't know if I play around the golf. Uh, you know, I got, you know, the trophy wife. I don't know if I do that, but I said, Stu, too much information. Right? So anyway, that's, that's the conversation I had with the guy. Love him. He's brilliant. But I, I'm just not that guy. And, um, just not that guy. I don't know why. You're the, you're the psychology.

• 48:36David Weisburd?

  Uh, uh, uh, on the brighter side, you have this compulsion of this entrepreneur shingles, as you call it, uh, which, which has led you to be, to be a billionaire and to be very successful. How has that changed how people treat you every day? And how did people treat you before and after?

• 48:51Speaker 01

  Right. Um, I, you know, might have something to do with the fact that I make them call me czar. No, I'm kidding about that. So, um, I, you know, I, I, I don't feel like I'm treated any differently. My wife still says, you know, I'm dumb from time to time, actually more than time to time. Uh, but, um, I don't, if there's reverence around here, I don't, um, I don't feel it. I, by the way, encourage discourse, um, disagreement as in different point of views. How about that? I, um, think that's, uh, very, I think that's very healthy, healthy. And I do encourage that.

• 49:31Speaker 01

  And nobody, uh, loses points for thinking that an idea I had is not a very good idea. In fact, the research department does that routinely. You know, they kind of say, uh, Michael, you know, you, did you really suggest this? Cause what were you thinking about this one? This is pretty dumb. But, um, I don't, um, gee, I don't, maybe I'm being naive, but I don't sense that. I don't encourage that. I don't, um, uh, I, I kind of like, I appreciate hard work, good thinking. I don't need sycophants around me. Um, and I know people who do, but I just, you know, I just don't need that. I, um,

• 50:15Speaker 01

  I have, you know, I got, I got triplets and again, they routinely say, Dad, what, what, Dad, what are you doing? I mean, that's like, you know, that's like, you're a nincompoop. So, no, I don't, I, I, I guess they probably do, but

• 50:36Speaker 01

  outside of stockbrokers, right?

• 50:39David Weisburd?

  Wealth managers.

• 50:40Speaker 01

  Exactly. Not too many people treat me differently. So.

• 50:43David Weisburd?

  You have a lot of really interesting things going on, business, politics. What would you like our audience to know about you, about low dot NYC or anything else you'd like to share?

• 50:53Speaker 01

  Well, number one, you know, you got a great idea, send it to me. I promise not to steal it. By the way, everybody's petrified of that and they really shouldn't be. And they put the idea way in their pocket. And these days, the half-life of an idea is like six minutes, right? Because world is changing so fast. I mean, just go back six months ago, nine months ago, look at the actors in AI and a lot of them are totally different. If a listener has a great idea, I'm open to listen to your great idea. I will take it seriously. I'll give you advice. I'll give you my honest opinion about these things. And

• 51:37Speaker 01

  the only thing I request is that folks appreciate that. I'm, I'm very fallible. I make bad calls all the time. So, but I will share with you an opinion. If it's something that I, I know something about, if it's something I don't know anything about, like, don't talk to me about a biotech company. I won't be helpful or a new chip, I won't be helpful, but. If it's in one of my spaces and we got a pretty broad palette of things that we're involved in, I'll try to be helpful.

• 52:16David Weisburd?

  You have your strike zone, the companies that you've built. What's your hit rate?

• 52:21Speaker 01

  I think we're at least 50%.

• 52:25Speaker 01

  And part of it, David, is when do you count and how do you account? If we have a research paper, white paper done, and I put a team of two or three people on it and spend a few hundred thousand dollars chasing it down, and they come back after six months and say, you know, there's nothing here, I don't count that as a failure. Maybe I should, but I don't count that as a failure.

• 52:50David Weisburd?

  And I know you also partner with VCs. Your wife doesn't let you invest every dollar in your own companies. What kind of VC partners are you looking for?

• 52:59Speaker 01

  A lot of times where a VC, they're a lot of times are pattern thinkers and A, you know, in a different, you know, field of play. It was a different football team in a different field, and they ran this play and it worked. And they just think that it can always work in every circumstance. And sometimes that drives a company into a very bad way. And I've certainly seen that a good time, a good deal before.

• 53:32David Weisburd?

  No one is immune to this memetic copying. Richard Dawkins popularized this term in 1976 where we copy these patterns. The craziest example of that was Elizabeth Home with Theranos. She literally started dressing like Steve Jobs. And I think even Rupert Murdoch, biggest investment he's ever made was in Theranos. I know that we're both really focused also on the New York City mayoral race. So tell me about that. TLDR, what's going on in the New York City mayoral race and specifically the primary?

• 54:05Speaker 01

  Yeah, so thank you for that. So primaries have an outside importance because you can get the fringes who tend to vote in big numbers and the mainstream just assumes that everything is going to be adjudicated in the general election. So we have in New York Cuomo, who is a guy I'm supporting. I think he's certainly very competent and certainly really understands the job. And I think that's desperately needed. The number two guy is, you know, has a lot of vitriol.

• 54:44David Weisburd?

  As a resident of New York City, and of course, famously, AOC won her seat against a 10-time incumbent because of this primary voting. You have the same thing in San Francisco that that used to happen as well. Andrew Cuomo's opponent is literally part of the Democratic Socialist Party, which, you know, it's not a label people put on on him. It's a label he puts on himself.

• 55:08Speaker 01

  Right. And he wants, you know, minimum wage to go up to $30. Now, I believe everybody should have a living wage, but you got to think of the consequence of, you know, our various service providers, our restaurants, and just about everything else when you when you have that. You know, of course, about Uncharted, and we have about 2,500 entrepreneurs in our little tribe, and about a quarter of them, about 700, 800, convene at our summer summit at my house in the Hamptons for a day. A lot of content,

• 55:52Speaker 01

  good food, yada, yada. But the whole mission behind Uncharted was to say to entrepreneurs, you know what, as a group, we're smart enough, connected enough, rich enough, have enough good ideas that we could self-determine. We can self-fund. We can, we don't have to be totally dependent on outside capital. How about generating our own capital and coming up with our own ideas and do that as something of a collective? So I am trying to put all that together, have a, if you will, a pitch club. It's going to be called Uncharted Pitches. And I'm seeking quite a few members.

• 56:39Speaker 01

  And they will, they will have a small membership fee for the year. But the other obligation is that they got to put $10,000 a year to work. And I hope to show them hundreds of companies.

• 56:53David Weisburd?

  You're kind enough to take Jessica and I in your magnificent Hampton's place. It was straight up from the show, Billions. It was the home you used there. So if anyone's wondering how you, how 700 people in a, in a single home come out to Uncharted. And Michael, this has been incredible masterclass on how to found multiple billion dollar companies. Thanks for taking the time.

• 57:16Speaker 01

  Thank you, David. Appreciate that. And thank you all the listeners for, and my sympathies for you to wade through all this tedium. So, but I do appreciate it.

• 57:28David Weisburd?

  Thanks for listening to my conversation. If you enjoyed this episode, please share with a friend. This helps us grow. Also provides the very best feedback when we review the episode's analytics. Thank you for your support.