Michael Loeb - President and CEO of Loeb NYC | Launching Billion Dollar Companies

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➡️ About The Guest
Michael Loeb is a serial entrepreneur and the founder and CEO of Loeb.nyc, a startup investment platform that pairs strategic and executional talent with passionate founders. Michael has a long and successful track record of building and scaling consumer marketing businesses, from magazines to online travel to pharmacy discounts.
Michael started his career at Time, Inc., where he met his longtime business partner Rich Vogel. Together, they co-founded the Synapse Group, which revolutionized the magazine subscription industry with its patented Continuous Service Model. Synapse Group also incubated Priceline.com, one of the most successful online travel companies in the world. In 2006, Michael and Rich sold Synapse Group to Time Warner for over $500M.
Since then, Michael and Rich have launched Loeb Enterprises and Loeb.nyc, where they oversee 18 direct investments in innovative companies across various sectors. Michael is also an avid philanthropist and a creative visionary. He sits on the board of several non-profit organizations, such as the Michael J. Fox Foundation for Parkinson’s Research, the Robin Hood Foundation, and the UJA-Federation of New York. He has also spoken at various events and festivals, such as the Cannes Lions International Festival of Creativity, the Advertising Week, and the SXSW, where he shared his insights and experiences as an entrepreneur.
➡️ Show Links
https://twitter.com/realmichaelloeb/
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➡️ Talking Points
00:00 - Introduction
01:19 - Michael Loeb’s Origin Story
04:29 - Winning Attitude for Success
08:33 - Michael's Persistence Is His Superpower
17:48 - "Burn the Boats" Philosophy
22:52 - Navigating Lay-off Realities
28:12 - Sponsors
30:35 - Synapse: Trials Behind Triumphs
38:23 - Spotting Resilient Entrepreneurs
45:08 - Key Insights From Building
55:33 - Defining Success
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Today, my guest is Michael Loeb. He's a serial entrepreneur and founder and CEO of Loeb.nyc, a startup investment platform that pairs strategic and execution talent with passionate founders. Michael has a long and successful track record of building and scaling consumer marketing businesses from magazines to online travel to pharmacy discounts. Michael started his career at Time Inc., where he met his long-time business partner, Rich Vogel. Together, they co-founded the Synapse Group, which revolutionized the magazine subscription industry with its patented, continuous service model. Synapse Group also incubated priceline.com, one of the most successful online travel companies in the world. In 2006, Michael and Rich sold Synapse Group to Time Warner for over 500 million. Since then, Michael and Rich have launched Loeb Enterprise and Loeb.nyc, where they oversee 18 direct investments and innovative companies across various sectors. Michael is also an avid philanthropist and creative visionary. He sits on the board of several nonprofit organizations, such as the Michael J. Fox Foundation for Parkinson's Research, the Robin Hood Foundation, and the UJA Federation of New York. He has also spoken at various events, such as Cannes, Lions, International Festival of Creativity, Ad Week, South by Southwest, and various others where he speaks on business, technology, entrepreneurship. Welcome to Success Story. I'm your host, Scott Clary. The Success Story podcast is part of the HubSpot podcast network. A quick nod to HubSpots, new tools at the rolling out for your business before we get started. You know that this year is almost done, and if you want to win next year in your business in 2024, you need tech that puts you in the pilot seat that gives you the unfair advantage. This is what the new HubSpot sales hub is all about. It's going to help you close the year strong. This tool does everything. Sales hub allows you to collaborate on every single step of the customer journey. That means when a customer interacts with any part of your business. They have a comprehensive prospecting workspace. They have powerful analytics, data, tools, all to help your team close more sales. Don't let leads slip through the crack. HubSpot sales hub lets you accelerate every single part of your sales operation with precision and they have over 1400 integrations, a ton of ways to mix in new features. Finish out your Q4 strong and gear for an incredible 2024 with HubSpot sales hub. Learn more at HubSpot.com slash sales. So I grew up in Queens and Queens and in hard scrabble Queens. And I would and people don't believe this, but I would get into a fight every day. And I would get into a fight every day because I was one of the shortest kids in the grade. I'm still one of the shortest kids in the grade. And all the big guys would defer to the little guys and say, hey, you two menchets, you fight, right? And so, you know, from that experience of just being the underdog and having to prove yourself every day, I think that has carried over to my life now. I just want to win. And I don't think I am smarter than anybody. I don't think I am better than anybody. What I think I will do is I will hustle you, right? I am working 24-7. And everybody else needs sleep, okay? We call those suckers, right? I'm the guy who never sleeps and I just work all the time. And I try to outthink and outhouse all everybody that I encounter. And that's my path to victory is not talent, right? But, you know, I've got better bladder control. That's how I win. Do you think that, you know, do you think that's a chip on your shoulder or what do you think implanted that mindset in you? Because that's a super powerful mindset. Yeah, I think it's a chip on my shoulder. I mean, I litter. I'm, look, I'm five, three and a half, right? I mean, if you look, you know, if you're grading on a curve, I might be like, you know, five percent, I might be in the fifth percentile, right? So, you know, I always had a punch above my weight. And, you know, and I always did that. I always assumed that I was in a, you know, I was, everybody else was at the starting line. And I was like 300 yards behind them. So I had to run faster and run longer. And I, when I do things, I got two speeds, not at all, right? Not at all. Like I do not play golf, right? You know, for those of you out there playing golf, am I allowed to say the word shit? They're scot. You swear as much as you want. I can't. That's a good thing. That's a good, that's a good fucking thing to be able to square. That's a good fucking thing. Shit, right? Fuck whatever you are. Fucking much as you want. But dudes, for those guys out there playing golf, how could you do that thing? I mean, really, you get up at five o'clock in the fucking morning, okay? And, and you don't even walk, right? You don't even get steps, right? On your apple device, because you get a goddamn cart. And then like, you know, somebody tells you what club to use. I mean, how ridiculous is that shit? So no, I don't play golf. Big waste of time. And yeah, so, you know, but whatever I do, whenever I feel the play that I decide to compete in, I play to win. And I played just to get better. You know, success, I find, is not easy, but it's very simple. Oh, really? Scott, that's a new slash. It's not easy. Yeah, the news, but you know what? Hear me out. Hear me out. You call me. Are you calling me? You said success was easy. Okay. God, you get it, though. You get it. This is what I'm talking about. Every single person, if they put 20, 30, 40 years into something, they'd be 10 years into something, they'd be successful at it. Or some, there's, if they have a feedback loop built in, if they iterate, if they learn, they'd be some measure of success at that thing. But I find that I wasn't even going to go into this yet, but we're like right out of the gate. The thing that people have to take home from this, it's that attitude. It's that I'm not fucking giving up till I figure it out or die. Attitude. Yeah, I think you got it, man. I think that, you know, I'm either going to win or I'm going to die on this hill. And the fact of the matter is most people, I mean, like 99% of people don't do that, right? I mean, they get a good job and they worry about, right? They worry about keeping their job. There is an expression, a quote that has stayed with me for a long time, which is eight people hire, eight people and be people hire, see people and be people hire, see people for one reason, which is job preservation, right? Because they know the seas will never, you know, get in their grill and push them. And you know what? Be world class. Be world class. The other piece of advice they can give everybody is that we are all a collection of A's and B's and C's and D's, right? With A's being what we're going to add and C's being what we, you know, we suck at, right? Forget about the C's and the D's. Do not do the C's and the D's. Find your A. Find your A and move it from an A to an A plus and move it from an A plus to a plus plus. And then move it to world class, right? World class. And then you just do that over and over again. Many of your listeners know about Mariana Rivera. He's been out of the game out of baseball for five years. The guy had one pitch. He had a cutter. He was the best in the world to cutter, unhittable. And if you hit it, you broke your bat. And it was as simple as that. And he became the best reliever ever. And he might have been the only guy. I don't know if he was unanimously elected into the Hall of Fame, but he was as close to unanimous as you can possibly yet, right? And he had one pitch, right? And Collins would say the book Good to Great. And that book, by the way, is very interesting. Here is a guy. Here is a dude who sucked as a professor. He got fired all over the place and sucked at everything he did and came up with the book. Good to great. And he talked about foxes and hedgehogs and foxes, right? They're bees and everything, right? They can do everything a little bit. They run fast, but they're not the fastest. They're stealthy, but not the stealthiest. They can, you know, hunt game, but it's got to be rabbits. Can't be big, okay? On the other hand, a hedgehog, which is kind of like a porcupine, or at least I think a zoologist on here is going to bitch at me for that. But, you know, they curl into a ball and they're all quills and they're, they're like nothing can penetrate a hedgehog, right? You're done. That's what you want to do. You want to find out your superpower and you want to build on that superpower and make it the super duper power best in the world power and figure out compensating mechanisms scaffolding, right? To do everything that your bees and season these, forget about the bees and season these. Don't try to take a C capability and turn it into a B or B and turn it into it. It's a waste of time. Become by the way world class in one thing and do that thing all day long like Mariano Rivera. What's your superpower? I told you you're just not listening. Aren't you in the job of listening, dude? Okay. I don't give up. All right. Does anybody know what a helium monster is? No, you don't. Okay. So a helium monster that's in the southwest of the United States. They are the meanest mother fucking snake ever. Actually, they're reptile. So get understand how mean the son of a bitch is. First of all, they got like this pebbly in print, you know, in in pregnant bowl skin, impenetrable skin. And you can, and by the way, they have a poisonous bite, right? And if they bite you and they're hanging from their your leg and you take them as shetty, all right? And you cleave their body off their leg off their head, right? That head doesn't go anywhere. It stays clamped down on your leg. That's a helium monster. I have a helium monster, right? Just, you know, give me any body part. I am like biting your, I'm biting your ass, man. And I'm staying there. And that's what my superpower is. I just will out persist you, out hustle you 24 seven. I'll outthink you, right? I'll outthink you. And part of the reason why I can't outthink you is I will take disparate things from disparate industries and different disparate experiences. And I'll put it together in unique ways now. What lets me do that? It's the courage to free your mind, right? And if you are in penitrable, impenetrable, okay? If you cannot be defeated, then you get that courage and allows you to think laterally like nobody else. And yeah, that's my that's my skill. I don't give up. I love it. But that wasn't, was that always the case? Or was there something that? No, always the case. So when somebody says, listen, because your superpower is a superpower, the trumps all superpowers. I mean, there's people that are, are specialists in a variety of different things, but the ability to not give up can make you significantly proficient at literally anything you take on. That is almost like a skill that allows you to learn new skills, too, because you just don't give up. I don't give up. That's like saying. I don't give up. That's like saying like, yeah, go ahead. All right, I'll tell you the story about me and tennis, okay? So 20 years ago, I bought this house in the Hamptons, right? And your listeners would like to know this because if any of your listeners has seen billions, I want to show up hands, who have you have seen billions? Oh, a lot of you have. Okay. So that was house. That is the house on billions. And it became the protagonist of the show. And the beach house is what I'm referring to. And there's a whole story, not worth getting into about how that became the billions house. It was not my choice. It found me a friend of mine, Rand's Showtime. And he, well, he kind of begged, he compromised it. He did whatever he had to to get that house. And he was, by the way, paying a little bit too much to film at that house, which was a good thing and all went to charity, true story. But anyway, I never played tennis before. And that was because in college, I was a lacrosse player, but I really was a wrestler. And if you saw, you know, if you saw my, my shoulder to waist ratio, you would totally understand why I'm a wrestler. And anyway, I thought, you know, tennis, the white shit, you know, the white clothes, those funky little rackets, the fufu stuff. I mean, that's, that's not the stuff that wrestlers, right? Right? We're not, we know, we get bloody. Okay? It's like, you know, oh, I broke my notes again. Okay, just put it back in place. I'm back out there. Like we think Rocky, right? Is a sissy. Okay? So anyway, that's what a wrestler is. And I'm a wrestler. And then I bought this house at a beautiful tennis court. And I said, you know what? I really got to try playing. And I learned to love that sport. It's not golf. Right? You pick up that racket. You are running, running around. I do not play with humans only pros. And I am now in the really, really very good category of tennis, right? As an old guy, right? An old half Jewish short guy. I am in the really, really good category. And, you know, I play pros straight up. And the question I always get is, where did you play your D1 tennis? And it was like, no, I didn't start playing until I was 50. Well, first of all, congratulations for that question. That's a pretty damn good question to be asked. That's pretty good. Yeah. It's kind of cool. It's kind of cool. It is very cool. I will play, I will play like a guy who just graduated, you know, from like wherever as a D1 player. And then, you know, he went on the circuit for a little bit. And then he plays me and he said, where'd you get all that? I mean, where'd you, where'd you, where'd you play your tennis? And it's kind of fools. It's cool to have that assumption. But anyway, so yeah, so, but, you know, I pick and choose, right? It's not every sport. It's like that one sport. And, but if I do it, I do it a conquer. And I never, I never lost that. I never lost that. Can I tell you about a friend of mine? I'll tell you about a friend of mine. Yeah. Ready? Okay. Yeah, go. So I have a friend named Stu not going to lose, use last names and Stu had a number and the number was 200 million. Right? If he got to 200 million, he quit. And he was able to quit like 30 years ago. Right? And Stu calls me out twice a year. And I pick up, you know, I answer the phone. And it's Stu. And he says, hey, dumb fuck. I see you're still working. Right? Because, you know, I went over the 200 miles, don't a while ago. But anyway, so hey, dumb fuck, you're still working. That was a Stu's number 200, right? Took care of all the kids that everything you want. And then he says, okay, what do you think? Where do you think I am right now? And I say, well, Stu, you're probably not in your, you know, your mansion in Aspen. I don't think it's past, you know, harvest. So you're not in your winery and tuscany. You're not in your apartment and try Becca because we'd be going out to dinner tonight. So you got to be in Palm Beach. And he goes, bingo, dumb fuck. Okay, what am I doing now? And I said, I don't know Stu. And he says, well, I got my cup of Joe. I'm looking at my waves hitting my beach. But I'm not that guy, right? I mean, I got the toys, but I really like to work. I really like to work. I like to think. I like working with people half my age and twice as smart. And I say that with, I'm not being disingenuous. This is with all humility and humility. I mean, it's amazing what, you know, the people I encounter know and how intelligent they are. But I like being in the game. I like the action. I like me. Yeah. But do you think that's a learn trait? Do you think that's inherent? Do you think when you invest in companies? It's inherent. I really do. I think one of my questions for entrepreneurs is tell me about your lemonade stand. And if they said, I never add a lemonade stand. I said, well, tell me about your paper route. And if they said, I never had a paper out, I said, well, tell me about your lawn care business. And they said, you know what? I never lemonade stand a paper route or a lawn care business. I kind of say, well, you're not an entrepreneur. That presents itself young, right? That the idea of that you can make money. You can perform a service and make money. And you can repeat it again and again, because if you can do that, it's called the business, right? That it's infectious. If you're an entrepreneur, you get a little taste of that. And that's it. You double down, triple down, quadruple down, you never stop. Because the making of the money is too much fun. And if you hire somebody to help you with that, then you're done, right? It's like, let me get this straight. I can hire somebody, train them. And I get a big on what they do. It's amazing. Yeah. I want to, so on that point, you know, you're asking me, who's listening to this podcast? And I said, well, there's people that are building, but I said, there's people that are in companies trying to build something for the first time. I was talking to, I was talking to somebody. And the general thesis was, if you don't burn the boats, you aren't ready to build. That's a good one. Do you believe in that? Do you believe in that? Well, all I can do is tell you my experience, right? And I followed my dad into timing. So my dad was a journalist of great renown, right? And he really tried, and we talked about the Scott, he changed the arc of history more than once. And he joined timing as a reporter at Time Magazine, he rose to the ranks and became a senior editor. And then almost as a consolation prize, they made him the managing editor of Money Magazine, which he turned into from a failing property into a powerhouse. And then Fortune Magazine, right? So he was the editor of Fortune Magazine for 10 years. And I really wanted to work at HBO at the time. And HBO was you know, in its day like, you know, the Netflix, right? It was unbelievably important and it was in the Vanguard, not so much anymore. And all I wanted to do was work for HBO. And I can never get a job at HBO. And then all of a sudden, Time Ink was starting a new magazine called TV Cable Week officially. The ill-fated TV weight cable week and they were hiring just about anybody. And that's how I got a job at Time Ink. And the rose through the ranks got the opportunity to manage sports illustrated. You may not know this, but I am the inventor of the sneaker phone in the football phone. Look for him in eBay. They're expensive. And then created kind of the idea of a bloopers video as a premium and launched SI for kids had something to do with turning the swimsuit issue into the franchise that it became, which got me labeled as a misogynist. I didn't know what that word meant at the time. I thought it had something to do with misogyn. And was tapped to run entertainment weekly or start launch entertainment weekly, which I did. And that was the job that got me fired. And myself and the editor, the editor was quite the intellectual. And he thought that, you know, stories or cover stories on books and polo would sell. And but not to the masses of America. For me, it had to be about the big three, just like SI is about big three sports. This is had to be big three entertainment. And anyhow got fired and decided that I was going to start the business outside of Time Ink that I was trying to start inside of Time Ink. And so to answer your question, you got to burn the boats, right? You got to burn the boats. You got to cross the Rubikam, which is a whole lot better analogy than burning the boats, right? Cross in the Rubikam, the Rubikam, because that's what Caesar did to get in the room. Okay? And yeah, you got to do that. And you got to have the courage to do that. In my case, I didn't, right? I didn't have the courage to do that. But fate stepped in and said, you know what? You got to be an entrepreneur, right? So we're going to make you an entrepreneur. And here's that. We're going to do it. You're going to have to suffer the humiliation of being fired. Now, the notice of me being fired, because it was the editor of me, both being fired at the same time. You know, that was in, you know, the daily news, the New York Post, the Wall Street Journal, The New York Times. It wasn't about us. It was, is timing going to shutter entertainment weekly? But the derision related to that, right? Because the official stance of timing was, you know, we were telling you that everything was copacetic and entertainment weekly. We kind of fibbed on that. But here was the problem. And we got rid of it. Okay? So now everything is good again. And you know, you got to see your name and print under that context. So the likelihood of my getting a job was not high. So I had kind of no choice. I had to become an entrepreneur and I had to pursue that, you know, that idea that I was talking smack about inside a time ink. I, you know, had to try it outside of timing. What was it happened to work? And I think that it's interesting because every time I've seen somebody laid off, and this is a harsh, a harsh reality that I believe, and I'm sure a lot of people are going to argue me on this and they're dealing with that right now. They don't, they don't think that I'm correct. But every time that I've found that somebody gets laid off or fired or terminated or furloughed, if they have the right mindset, they end up in a better spot. Yeah, that's the key words, right? The right mindset. And what do you have to be in that circumstance? Well, one, you can't be afraid, right? Now, I have, I have an internship program in my company that we call Internatopia. Kind of cool, right? And I put that together because I'd run down the halls when the, you know, when the time was ripe. And I would say, good news, everybody, the interns are coming and I'd get this eye roll. And I'm saying, why the eye roll? And they're saying, well, you know, I don't really have anything for them and they come in and it's a surprise and it's like, I got to find a work. And by the time I got them situated, they're gone, right? So, you know, all they do is slow me down. And I said, you're an idiot because in a year's time, right, you're going to be slitting your each other's throat and Goldman Sachs and McKinsey and everything else to get these guys, right? And what I do know is pick the fruit from the tree and not the ground. So we just got to make this internship program work. And so what we do, Scott, is we have three days boot camp and it's in my house in the Hamptons. We have 1,500 applications, you know, for every summer. We look for rising seniors in college. And they come from the great colleges and universities in the United States and, you know, we'll get 100 applications from like London. So in Internatopia, the idea is three-day boot camp, right? I'm going to rearrange your thinking in three days so that you're thinking like an entrepreneur. Now, they're not in until they can make a persuasive argument that they are an entrepreneur. And one of the things they have to do is write a 300 word essay on their best idea, right? Which I promise not to steal from them. And it's really to do several things. One, if they don't have the energy to do that, right? And do it well, then, you know, I'm going to put a lot of energy into them. And if they're not going to do that, then I, you know, I don't want to have anything to do with them. So that's first thing. And second, I want to see the quality they're thinking they can be dead wrong. But if there's logic behind it, and it's well articulated because three inner words, you've got to think about what your business model and your thesis is. And you got to put it to pros. So we accept them. And they have three days. And I have three things that I add that are kind of fun things that, by the way, are helpful if you're an entrepreneur. Thing one is I got a world-class pool player and they teach them how to play pool. And why is that? Because pool is not about, and I don't play pool, right? But pool is about not this shot, but about three shots down the road. So this shot sets up the next shot, which sets up the next shot, which by the way, that's a very important concept for an entrepreneur. The consequences of what you do now are going to affect the next decision and the next year and the next decision and the next year, the following year. And you should know that and you should appreciate that. And you should think that through, right? The next night, we teach poker. What does poker teach you? Detachment. If the chips in the middle, right? In the middle of the table, if that is your life savings, and that is what you're thinking, you will lose 1,000% because the pros who are used to picking up the signals will see the tells and you're done. You're done. And the last day, okay, we have a magician. What does a magician, magician teach you? Okay, the stupidity of the crowd, right? Because what it all is is a big deception. So they make you look at the left hand when all the action is on the right hand, right? So if you only want to follow the crowd, right? You're not going to decode how a magician actually gets it done. Because you want to be the one tenth of one percent and the behave differently, you got to think differently. And that's what magic tells you to do. There we have a very special sponsor for today's episode foundation source. They are all about helping people and companies make the world a better place through giving. 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The point is every bite size 20 minute show comes packed with practical advice from these incredible entrepreneurs behavioral scientists and everybody in between nudges fast paced but very insightful and a must listen if you're a podcast fan, make sure you listen to nudge wherever you love to get your podcasts. Now, you had wild successes when you built synapse. Was there any failures or was this an iteration after iteration after iteration that eventually led to success? Yeah, so let me disabuse your audience about one thing. They call history. Where does the word history come from? Where it comes from? I don't know. It's his story. That's what the word history comes from. His story. There's another thing. The other thing is history is told by the victors. Victories. What do entrepreneurs do? They rewrite history. It's their narrative. So they want you to think it's all up into the right. They're lying. They're lying. It's not up into the right. It's what Mike Tyson said, which is we all go into the ring with a plan and then we get punch in the nose. We all get punch in the nose. By the way, what's very interesting and it sounds like I'm going to be casting a subversion on VCs and I don't mean to, but they are the up into the right crowd. They're the up into the right crowd because when they studied it at Harvard Business School, it was always up into the right. Well, dumb fox, why do you think that is? We wrote that son of a bitch and we made you believe that it was up into the right. It's never up into the right. You always get bloodied. Always get bloodied. VCs don't get that. It's a five year smooth line up into the right. I cannot tell you how many business plans I've seen that year five, you're 100 on the top and you're 20 on the bottom and it's a smooth curve. Never. Never. And by the way, that is the test of an entrepreneur. Not when you're on the horse, but when you get smack mouth and you get and you get knocked off that horse and the courage to get back on that horse is what it's all about. So we write those textbooks, but we're lying because it was bloody. You don't win. You don't win. You don't win with grace. You must lit over the finish line. And you are panicked. Okay, about three quarters of time. I, there is a scene in the movie, hunt for red October. Okay. And that's Sean Connery. Scott, did you see that movie a long time ago with my dad? But I don't remember the scenes. Okay. That's all right. And I want to tell you the scene. I just wanted to know if you're one of the different red October club or not. Okay. So Sean Connery, right, is meeting with a sea suite. Right. Here they are. Great deception. The entire crew, but you know, the half dozen guys that are running the place, the sea suite. Right. And they're, you know, in tight quarters and they're having dinner. And they're talking about, you know, how are they going to and the ideas that they're, you know, they're defecting from the Russians. Right. Because they have got this sub that is going to be, you know, the World War three sub. And they're trying to, you know, Sean Connery is trying to steal that sub and hand it over to the Americans because he doesn't want to have World War three. And he meets again as sea suite. And they're talking about the Russians, Russian Russians. And he's eating. And he purposely, he's eating with his mouth open. Right. I mean, I'm sure he's British. I mean, they don't do that written. Right. You know, so he's, he's eating like a troglodyte. And he's kind of gobbling his food. He's like looking nowhere in particular. They're talking Russian Russian Russians. And he's saying, it's not the Russians that you got to worry about. It's the Americans. And then he pauses. And he says, I give our chances about one and three. And he's just eating. He's not noticing anything. The crew goes silent. Right. Is sea suite goes silent. They go slack jog silent. And he looked at them. He didn't notice for about 15 seconds. And he looked at them and he said, what you thought it was more than one and three like two and three. Are you idiots? It's one and three. That's our chances one and three. So being an entrepreneur, right. VCs say chances of success are two and 10. Okay. If you put a drink in them, they'll emit to one and 10. Now, frankly, we got a model. We think we're much better than that. But one and 10, two and 10, that's what you're signing up for. And if you're daunted, right, if you lack that conviction and courage, if you can't give yourself your own pep talk. And if you need one all the time, you're not going out for this. Now, by the way, you can be in the game, being that somebody's number two or somebody's number three, that's fine. They all need support. But don't try to lead it because if you lead it, what you are is a hockey goalie, right, with six bucks on ice and no defense. And all you're doing is block and shit and try to make sure that nothing hits net. And you do that all day. And by the way, you can't share that with anybody because if you do, it is that scene in hunt for red October and your team will be freaked out. So you keep it all inside. You don't tell them that, look, you know what? I'm going to make 10 decisions today. And if I call them wrong, we're out of business. How do you say that allowed? And it takes a special, I was going to use the word courage, but the real word is insanity, a special type of insanity that you get excited about that shit because you got to be so thrilled with your victory, right? Think about that two intent is what VCC say, two intent. So one victory has got to be worth five plus emotionally, financially, one victory, five plus. Who will take those odds, right? If I said to you, Scott, you got a one chance and five that you're going to live. You know, I got six bullets in the chamber. I've emptied one chamber. One chamber doesn't have a bullet. Spin it, put it your head. You're saying, no, no, that's not how roulette works. It's not five bullets out of six. It's one out of six. And you're saying, no, no, no, this is entrepreneur's roulette, right? Right five out of six times. You're going to get your head blown off. Who would take those odds? You got to be an idiot. But that's what entrepreneurs do. And that is because that victory, which by the way, last five minutes, I mean, you will ask me all the time because I got fired from timing, built a company and they bought it from me for a billion dollars nine years later. And they say, wasn't that sweet? And I say, yeah, for about six seconds, then it was off to the next thing. Right. How do you know, you look for one thing that you said you are 100% you have to be, but you said something that was interesting. You said, you know, you look when you invest in companies, I'm sure you have your thesis. It's better than one in ten. You have your two or ten or three or ten or four or ten. And you can you can say whatever your thesis is and how you look for founders. But on on on your site, I think the first thing I saw was we are people first investors. So you got to find the right people fine. You found the kid that had the the lawn care business or the lemonade stand. How do you find for how do you how do you suss out this trait, the ability to operate in isolation dealing with all the bullshit nonstop being mentally okay to deal with it. Yeah, you see, I don't. And this is why that's not the number one. That's the number two. You're describing the cheap operating officer, right, because that entrepreneur, right, they have got to be indefatigable. Number one, number two, they got to be able to be think creatively and out of box because they need to pivot. Right, I have never had a straight ahead business. I have never had the business plan execution billion dollar exit. It doesn't ever happen, right. So, but you got to have a number two. Right, you need two number two. So you need somebody to do the book. You need a CFO and you need a COO. All right. And the trains run on time. And that's what you're talking about. It's got the trains run on time guy. That's not the same guy as the entrepreneur. Now in the beginning, the entrepreneur will do everything. And you know what, let's hope that they don't fuck it up. Right. And let's hope that they have the wisdom to get a COO really, really quick when they can afford it because they will fuck it up. Now, I'll tell you something at sit apps, right. When I started the company. And in the beginning, yeah, to do everything. And I was, it was in the magazine business. And I was the sales guy and like the customer success guy, right. I was great at sales. Why? Because I could promise anybody anything, right. But customers, I was dreadful at customer success. I finally had because you were that kind of sales guy. That's why you're doing all the blowback from all the city promise. Exactly. It was like, you know, I was on the next one already. Right. And if it didn't work after that, I had somebody else to blame. Like, how can you guys be fucking it up after I made the sale? So I had a client who said to me, you know what? If I've got to endure you for one more day, one more day, I'm pulling the goddamn business. And that's what I made higher. Right. And that was the difference. So you know, you got some what do you go at the special brand of insanity and the rareness of a bona fide entrepreneur. And it's a very, very different skill than making trains run on time or coding bills or reading contracts. Right. Every great entrepreneur, I know they can do math. They're great at math. They're great at math. I don't know, by the way, one entrepreneur that isn't great at math. Okay. Because you got to be very facile. You got to know unit economics. You got to you can't decision properly unless you're really good at math. And so you got to be really good at math. And you got to be able to hold numbers in your head. And you got to be able to do the type of math that a CFO would vomit on top of because your math, your head math is within five or 10% of the real number. But you do it fast. You know, no CFO would tolerate that shit. Right. So we're not CFOs. We make decisions quickly. We're not COOs. And we can't read a contract because we don't have the patients. And if we tried, we'd only screw it up because we would start to go numb. All right. Like at page two and a half. And we'd like look like we're reading like the eyes are crossing the page. And we would not absorb one goddamn thing. Right. It would say on page three. Okay. You know, three, you know, three little eyes see, sell your mom to me for three cents. Okay. That looks fine. Right. I mean, we just we suck at that shit. So he gets back to what? Sorry, I pressed the wrong button. He gets back to what we talked about, which is take that, you know, that that a talent and turn it into a superpower. Okay. I need to ask this because you said you can beat the average VC. What do you do differently at lobe? What's the thesis? What's the difference? Well, a lot of things is a fast answer. Number one, if you look at the ecosystem, right, what does it take? You need the idea, the entrepreneur, the know how, the capital, four different things. In the real world, those are in four different places. Right. In our shop, it's one place. We have the ideation, we have teams of entrepreneurs that we work with for 15 years. We have the capital. And our know how is that we have a group that we call shared services. And it's free to the companies because we own the preponderance of the equity. And it's everything you need that's with Army knife, every blade. Now, what do you need? You need back office accounting. You need to research. You need analytics. You need AI. You need data. You need a, you need product. You need an in house creative team. You need strategy. The biggest stickiest wickets are technology and marketing. Right. And we put all that together. And it's free. So that way, the entrepreneur can spend 100% on 50% of their time building a business. That's what we do. If you were going to give any last advice entrepreneurs that you didn't go into already, what would be final thoughts for somebody that wants to build something? Well, one of my, one of my mistakes was I started late. Right. I was 36 when I got fired from timing. And I do have a talk, Scott, that I bring to universities when I'm called upon to talk about entrepreneurship. Right. So when I get behind the death, I ask a question, who here wants to be an entrepreneur? Well, I'm sponsored by like the entrepreneur's society. So everybody raises their hand. They all want to be an entrepreneur. And then I say, who here is going to quit school? Nobody raises their hand. And then I have a slideshow. And I show was Zuckerberg. And I said, quit Harvard sophomore year. I show Bill Gates quit Harvard sophomore year. I show jobs quit wherever he went to school sophomore year. All rock and rollers died when they were 27. All entrepreneurs write quit school at their sophomore year. And it's because of what Warren Buffett said. And Buffett said, if the path to riches were founded books, every library ran would be a billionaire. So the problem of college is that it's backwards looking. Right. Those who do not know history are doomed to repeat it. I get it. But entrepreneurs change the future. Okay. And the past doesn't sink to them. And that's why they all quit. Michael Dell. Right. Michael Dell goes to university at Texas finds that the computers are not fast enough. Starts by, you know, souping up a computer just like, you know, a gear head would soup up a car. And then he said, shit, why am I messing around with somebody else's computer? Let me build my own. And what the un, by the way, unintended discovery was that if Moore's law is right, which it is, that in every two years, right, the cost of computing goes down by half. Then you don't want to have one computer sitting on a shelf for more than 60 seconds. Right. And that's what Michael Dell changed. Everything is built bespoke. It's built instantly. And it gets shipped right to the consumer. No inventory. Right. Because if things are going down by half in two years. Right. You know, you can't stock the shelves because by the time you put on the shelves, it's obsolete. So that's, that was the big discovery. That was the big thing. But Michael Dell, you Texas, you know, quit software here. They all quit. They all quit. So I show this slide show of this pantheon of the greatest entrepreneurs. They all quit college. Right. They all quit college. And so I say to them, listen, I made a mistake. I started too late. And if you're really an entrepreneur, now Bezos did graduate and did become a consultant before he came up with Amazon, he's an exception. But none of them, they don't graduate college. And that's because they want to change the future. And you don't find it in the university library. If people want to connect with you, if they want to learn more about lobe.nyc, outside of just going to that domain that I just listed. Where did they go and reach out to you? What's the social? Where do you want to tell them? No, they can't. I get too many things. I'm in a day. No, no, it's not true. I, I try to take, first of all, I will tell you one thing, which is I think that this is a great country, right? Canada notwithstanding. This is a great country. And I'm going to prove it to you. And it's great for entrepreneurs. When I last looked and I did this research like two years ago, there were 19 companies around the world that were worth $100 billion or more, which likely meant that they were public, $100 billion or more, that were 25 years young or less, right? Only 19. Check that box. Eight were Chinese. And I'm telling you, having build companies in China, that doesn't count, because China is a closed market, right? So you have Amazon dominating the world except for China and it's Alibaba. You have Uber dominating the world except for China and it's DD, right? Close market. Thumb, the authoritarian thumb is on the scales, right? So take eight out of the 19 off the board that leaves you with 11. One is Canadian, right? One is Canadian. And one is European and the rest nine are American. So we are the world's bright light, right? When it comes to entrepreneurship. And so I'm a patriot. And I believe that part of my responsibility and by the way, Scott, I am lucky beyond any description because all I was was this kid from Queens that started work in timing and got fired, right? And everything came after age 36. And I don't think I could have done that in too many places in the world. And I believe that it is not only important, but it's an act of patriotism, right? There is a seminal paper that was written by a guy recently passed away, famous economist, Lester Throw, professor at Harvard for many, many years. And the title of the paper was, should Michael Jordan cut his own lawn, right? The absurdity of Michael Jordan cutting his own lawn. And the answer of course was no for two reasons. One, not high as an invest use. He should be doing three throws, right? Practice. And God forbid he cut off a toe. So that was a metaphor. And it was a metaphor for the United States, which is it's okay that we don't make our basketball sneakers here. What we do is design them and we put the Michael Jordan label on them, which makes them worth 10 times as much. That's what we do here. So we have to be highest and best use. And this country, this ecosystem, and part of it, what are the part of it? It's one cutting edge technology, the infrastructure to support that. But the two or three things are being able, the capital formation abilities, right? To be able to raise money for new ideas and to to find the people who have the courage to jump on board in a new company, which by the way, you need a psychology of its okay to fail. And a lot of places in the world, it's not okay to fail. And I have been in many, many forums of entrepreneurs who are successful because of all you did is fail. You can't talk about your failures. Get boring. But they talk about their failures. And they talk about it with the reverence, the same reverence of every one of their successes. And it's, you know, it is kind of a culture and a continuum and an ecosystem that really reinforces what we're able to do in this country. And so I take it as an obligation, right, to help young entrepreneurs and to help young people thinking about entrepreneurs, because if you want this country to be as fabulous for your children and your children's children as it was for you, then you've got to pick up that mantle and do your duty as a citizen of this country. And I'm not talking about being a magma Republican or anything like that. I am just talking about being a human being and doing what's right and helping others think through those problems. And it gets, gets me great satisfaction. And it does happen a lot when people do come to me and say, Michael, this is my business model. What do you think? And I'll say, you know what, you're off my one beat, but that one beat is going to kill you. You got to move at 10 degrees to the right or 10 degrees to the left. And then you'll be successful. Am I always right about that? I don't know. Well, no, I do know. Most certainly not. But it is what Malcolm Gladwell said in Blink, right? And that is that experiences of many, many, many years of experiences will shape an instinct. And you can see something and have an instinct about whether or not it'll be successful. So I am happy to entertain, you know, smart people or willing to put the energy in because, you know, I am not going to put in one ounce of energy unless you put in 10. But I will put in that one ounce of energy. And I'll try to help with, by the way, everybody knowing that I don't have it right all the time. I have it right some of the time, but enough of the time that people do ask me the question. I love that. Thank you. Welcome. If you were going to look at your life now, I wrap up again the bespoke experience. I wrap up every podcast the same way I'm so sorry, but it's a good question. If you were going to look at your life now and you're going to have to and you will have to answer the question, what success means to you? What does it mean to you now? How has it changed? Well, the first answer is it hasn't changed, right? So what it means to me, what it means to me is that I made a difference, right? That I had an idea. I put it into a marketplace. It got adoption, it got enough adoption that it was able to enrich not only the people who bought it, but the stakeholders that bet on me either by working at the company or putting money into the company. Again, I'm so fine, I answered, but eventually I go to VCs and that's very gratifying. And by the way, I say about birthing a company. It is the second most remarkable birth, okay, that you can birth except for human birth, which is the most astonishing birth of all. But I take as the ultimate praise somebody looking at something that I've done or an idea that I have had and looked at that idea and said, I wished I had that idea. That by the way is the most sincere form of flattery I can ever get. So that by the way is remarkably reinforcing.



























