← Success Story with Scott D. Clary
Success Story with Scott D. Clary
Michael Sonnenfeldt - Founded A Billionaires Club ($165 Billion) | The Hidden Curse of Early Success
01:23:15
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- [00:00]
Michael W. Seinfeld
Sometimes it's the success of a parent that drives somebody to success, and sometimes it's the lack of success of a parent that drives somebody to success. In my case my father, he did fine, but he did not amass great wealth. I think that pushed me to want to prove that I could do well in my own right.
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Narrator/Host
He's an entrepreneur, an investor and a visionary who's built success across industries from pioneering one of the largest commercial real estate projects in U.S. history to launching.
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Interviewer
Ventures in clean energy and technology.
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Michael W. Seinfeld
One of the problems with first time entrepreneurs who are successful, they assume it's all their skill and they'll just keep doing it again. So there's a false confidence that comes when luck is smiles on you and you have a great first fortune. It just doesn't work out that way.
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Narrator/Host
Michael W. Seinfeld has never stopped pushing boundaries. But perhaps his most impactful creation is Tiger 21, the world's leading peer learning network for high net worth entrepreneurs and investors. Through it, he's helped some of the most successful leaders on the planet navigate.
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Interviewer
Wealth, race, risk and legacy.
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Narrator/Host
His story is about building, giving back, and redefining what true success really means.
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Michael W. Seinfeld
Sometimes children of parents of extreme success are overwhelmed and assume they could never do better than their parents. And it can be demotivating when you're starting something from scratch. When a seller is selling something, the buyer can see something completely different. That's where great opportunity lies.
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Interviewer
Michael, first of all, thank you so much for coming on. This is going to be a lot of fun and you have an incredible story, but I have heard the story of your father and I think that just to tee up, what shaped you as a person and what made you so resilient just living with this man. I think it would be good for the audience to just discuss the man whose house you grew up in, because it's a remarkable story.
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Michael W. Seinfeld
So my father was a German Jewish refugee from Germany during World War II. In 1938, his mother was able to get he and his brother out of Germany to England. They had tried to come to the United States, but we had closed our borders. And as Hitler was approaching, the family literally considered a kind of mass suicide of all of the family members. But my father says that he convinced his mother not to do that and she was by stroke of luck able to get him to England. And then in England, just like we did with the Japanese, the English interned all Germans, whether they were Jewish or not, and sent them to a prisoner of war camp if they were 16 or older. My uncle was 14. So he stayed at the school in England while my father was interned and sent to Australia to a prisoner of war camp in the middle of Australia. This was September 1940. He was 17 years old. And when he got to the prisoner of war camp, within a week, he was able to convince the commandant that in fact he wanted to fight the Nazis, and he was not one. And because he had been in England for about a year, his English was apparently quite good, and convinced him to send him back to England. And the boat that they had come on had 3,000 prisoners of war. And going back to England, it was deadheading back with four people on the boat and the boat, four passengers. And the boat was bombed in the Indian Ocean by an Italian marauder, if you will. Nobody had told the people on the boat that the boat was being used as a decoy to have the Italian boat come out. And then there was an English frigate behind the Italian that they didn't know it, and that's how they were able to take out the Italian pirate boat, if you will. But his boat was hit, and he was let off in Bombay, India, at the age of 17 with nothing. And somehow, it's a longer story, but he was able to become the manager of an electronics factory for six months, if you can imagine that, in 1940, and eventually made his way to the United States. And then his parents, in the meantime, had escaped to Germany, and they were both doctors. And he was able to reunite with them in Baltimore, where he spent a year or two when he then enlisted. The beauty then, particularly with all the issues of immigration today, if you enlist in the army, you got automatic citizenship. And so he became a citizen in 1942. He was a private in the army, but at the end of the army, he was tapped in by General Bill Donovan, the founder of the oss, which then became the CIA. The OSS was tasked with managing the Nuremberg trials. And my father was tapped at the age of 23 to be the chief interpreter of the US prosecution. He was one of the first privates in history to be carrying orders signed directly by the President. He went behind the enemy lines to Himmler's home to gather some evidence. But he quickly became Goering's personal interpreter. Goering was the number two Nazi after Hitler. And the most important part of that was that many people know the history that Hitler came to power when the Reichstag was burned down. And he claimed that it had been the Communists that had burned it down. And that's why he needed to be given Dictatorial powers. One day my father was sitting in the prison with Goering. And Goering said, richard, would you like to hear a little secret? And my father said, yes, Herr Goering. He said, I burned down the Reichstag. Hitler told me to do it. And it changed the perception of history and all that happened because clearly Hitler used that as the pretext for coming to power when Hindenburg abandoned his powers. Well, if that wasn't enough, my father, after Nuremberg, came home, became a world famous engineer, finished color TV. I have the final patents on 17 patents on color TV at home. But in those days he was working for a corporation. It happened to be rca. Unlike today, if you were an engineer, you'd probably get royalties. He was paid a salary, but he got the pleasure of, of finalizing color tv. We had literally TV number one that came off of the production line in our home when I was growing up. He then sent the first satellite into orbit. It was a weather satellite. Became the dean of a business school and for a while was in charge of all of NBC's operations. And then his last invention was something called the video disc. Before DVDs came out, there was a competing product that was tried in the market developed called VideoDisc. It was a technological triumph, but a commercial failure. So with all of that, I had a brilliant father who was a bit of a inflexible German personality. So on the one hand it's nice to tell you the story. It wasn't as easy growing up with him as my father, as the accomplishments might suggest.
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Interviewer
What does that. Was that pressure that's put on you? Is there expectation that's put on you to succeed, to do certain things, to pursue particular career paths out of your father's life and legacy? How did that impact you as a young child?
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Michael W. Seinfeld
You know, it's interesting because if you look at Tiger, we have 1600 members around the globe and, and some of our members success came because they were competing, if you will, with their parents and wanting to show that they could outshine them. And some of our members success came from because they came from homes that were broken homes and their parents had not amounted to much and they wanted to prove to the world that they could do better than their parents. So sometimes it's the success of a parent that drives somebody to success, and sometimes it's the lack of success of a parent that drives somebody to success. Obviously in my case, my father was, he did fine, but he did not amass great wealth. But he had extraordinary stature and accomplishments and his mind was Quite extraordinary. And, you know, I think that pushed me to want to prove that I could do well in my own right. Sometimes children of parents of extreme success are overwhelmed and assume they could never do better than their parents. And it can be demotivating. So one of the real challenges with anybody who's achieved any kind of success, whether it's material or a great author or cured cancer or whatever it is, is trying to encourage your kids to find their own way to be successful in their own right and not feel that they have the shadow hanging over them of a parent who they could never match. You know, you have it with every president's children and, you know, it's unusual. That's why when, for better or worse, whether you are a fan or not, when, when George Bush came to power after his father had been power. That's a very unusual story of a child, of somebody so successful, being able to match that as well.
- [10:16]
Interviewer
When you think about sort of the path that you took in life, you had a very. I mean, at 31, it was 31. Correct. When you sold Harborside Financial center for over 100 million, those numbers are correct. And that age is correct. That is still remarkably young. I know, I know that there are some people that have built massive amounts of wealth at an even younger age, but I would say that objectively, 31 is a pretty good age to have a hundred million dollar sales. So obviously you were quite ambitious, quite aggressive with your career. Do you think you in particular were doing that because of what your father had achieved over his lifetime? Even if not financial success, but just the stature and just the acclaim that he achieved? Or was it something internal that drove you in particular?
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Michael W. Seinfeld
Well, one of the things that I remember growing up was that I was raking lawns, shoveling snow, I was slinging milk at the local dairy barn, working at the tennis academy. I always was ambitious to want to, you know, earn money that I could do what I want with. And one of the things that stuck with me is sometimes when I would earn a fair amount of money, I would spend it on something that my mother thought was foolish. And I remember my father saying, you don't have a right to tell him that if he earned it fairly and honestly, he can do any damn thing he wants with it, as long as it's honest and okay. And there was sort of this notion that when you have accumulated wealth, it creates options that you might not have without it. And so I think the combination of that sort of being drilled into my head that the road to freedom the road to the possibilities that I would control came from achieving success along with the example that he had set. And by then, by the way, I had married somebody. And her father was also an incredibly successful man. And so having a father and a father in law whose shadows were overshadowing me probably was a pretty powerful motivator, although I think I was pretty motivated even from before that.
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Interviewer
Your first success, that was a $100 million plus exit. Incredible. What did that really teach you about what is required to be successful just based on your own experience? Obviously, a little bit of risk, a little bit of a lot of action. But what do you think allowed you to have $100 million exit at 31 years old, outside of your parents influences?
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Michael W. Seinfeld
First of all, I had a partner, so we had to split that I just should say that. But my partner was twice my age. My partner was actually my father's age, and we were 50, 50 partners. We started when I was 25 and he was 57. And in a sense, he became the father I didn't have, although I had a father. He became the brother I didn't have, although I had a brother. And he became my best friend and mentor too. So probably the most. One of the most powerful lessons from that experience was the power of partnership. Most of the things that I've accomplished in life, I've done in one type of partnership or another. And I think part of that is that I'm aware that I have certain skills that are either unique or in short supply. But I'm also aware that I have blind spots and weaknesses. And when I can find a partner that I can divide and each of us can complement the other, very often that's a one plus one equals three kind of situation. So the first was that I had an amazing partner. The second, which has proven to be true over my life, is you have to have real conviction. You have to have a point of view. When we bought that project, we lost money for the five or six years that we owned it, but we knew we were creating value or we believed we were creating value. And in time and time again, what distinguishes many of the greatest entrepreneurs is, is the ability to delay gratification. Because you have to keep investing back in a business or you have to stop looking elsewhere. You have to just focus on what you're doing. In one case, I owned a solar lighting business for 25 years, and I had a unblemished track record of 25 years of straight losses. But eventually I found a company to merge it with, and then during the next five years, that new, new combined business made up for all those losses and more. But not many people have the Fortitude to wait 25 years to do something so delayed gratification. And the other thing is that for people who've gone to business school or read business literature, there's this notion of efficient markets. And efficient markets says if this was such a big opportunity, the market would have already reflected it. So therefore it must not be a big opportunity. But anybody who's been a successful entrepreneur realizes that they've seen opportunities perhaps that nobody else has seen. And you have to really convince yourself that there's something there. I think the last thing I would say is, is that when you're starting something from scratch, an idea like a Apple in a garage or a Bill Gates or whatever it is, that's what real estate people would call greenfield development. Starting with an empty piece of lot and doing something that's different than buying an existing building. I was buying a building that was the largest building of its type in the world when it was built in 1930. But it was a white elephant as an industrial building. And I think the way that I've tried to explain it to people is I was buying an unfinished office building and the sellers were selling underutilized warehouse. When a seller is selling something because of how they understand that product, and the buyer can see something completely different and see the value, our value was made on the buy because if you figured out what it took to upgrade and renovate an old warehouse, it was a lot cheaper than building the building from scratch in this particular case. And so we were looking at what it would be worth as a finished office building, and what did it take to get there? So very often, particularly in real estate, but not only when you can buy something that the seller isn't selling, they think they're selling one thing and you see another use for it. Sometimes that's where great opportunity lies.
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Interviewer
This is always an interesting conversation because I work with and work with, I interview a lot of exited entrepreneurs and they all more or less echo the same sentiment that, that you've spoken about. Where you feel like after the exit, you feel like the rugs pulled out from underneath you and you try and figure out what's next in your life. And really, this is the, the, the premise for tiger. Obviously, at the time, Tiger did not exist yet. But I'm curious what that walk through for people that are listening, for entrepreneurs that are building. What you experienced when you sold for over 100 million. Obviously, yeah, you split it 50. 50. But still, you know, an incredible amount of. An incredible amount of, you know, wealth is created. All of a sudden now you have more money in your bank than you've ever had before, but you're still going through this transition period. So when that happens, when that transaction happens, what do you feel?
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Michael W. Seinfeld
Yeah. So what I want to say is that for entrepreneurs who have had the good fortune of having a successful exit, something magic happens in the moment that the deal closes. And it's like going through the looking glass, because you go from having 100 or a thousand employees to maybe having an assistant or no one. And as we like to say, everybody used to laugh at your jokes, and now there's nobody to laugh at your jokes anymore. And you go from owning a business to having a large bank account. But all of a sudden, issues of legacy, health, meaning, and what's next all come into being. And what we've created Tiger 21 for is primarily that moment when all of these changes occur. In my case, there's obviously a big difference when you have a liquidity when you're 31 than when you're almost 70. And when I was 31, I wasn't thinking. I didn't have any children. I wasn't thinking about legacy. I wasn't sure. I'm not even sure I'd heard the word wealth preservation. I just assumed if I had had this extraordinary success by 31, I could just keep doing it again and again because how we. How hard was that? Then, of course, life taught me a few lessons. It's not as easy as you think. So one of the biggest decisions that entrepreneurs have to make is after they have one success is do they have another one in them? Do they have a desire to do it again? If you're 65 or 70 or 80, you're not likely to be doing it again. If you're 30 or 35, you might be, but in my case, I just assumed I would keep doing deals and I didn't think much about wealth preservation. So I invested in a couple of deals and one of those deals went south. You know, nobody bats a thousand. And one of the problems with first time entrepreneurs who are successful is they rarely appreciate how lucky they've been. They assume it's all their skill and they'll just keep doing it again. So there's a false confidence that comes when luck smiles on you and you have a great first fortune. So after I had my first fortune in Harborside, I tried to create a new company that didn't work. And after five years, I had to throw in the towel of that company and realize why was I successful in the first case but not successful in the next case? And it took a lot of personal introspection to think about what the products, services, the way I manage people, where my strengths were. And so when I did it a third time, then it was the third time's the charm, because that was even more successful than Harborside. But there's nothing more dangerous than a young entrepreneur who's been incredibly successful, who thinks it came so easy, it'll just keep going easy. It just doesn't work out that way.
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Interviewer
Was there a specific incident or thing that went wrong or investment? I mean, you mentioned your second company didn't work out, but was there a really, really traumatic event that made you realize, okay, I need to create a community for people that have had exits to support each other. Was there like one particular event that led to the tiger? 21?
- [22:32]
Michael W. Seinfeld
Yeah. What happened was I tried to build that second company. It wasn't a real estate company, it was a real estate information company. And if you know what Zillow is today, we basically created something similar to Zillow, but before the Internet. And instead of Zillow, whose customers are consumers who are looking at the price of a home, our customers were the real estate brokers who were serving. So brokers could look up online for much of that information. And the problem was that registered brokers were our customers. And during the Iraq war, the economy went backwards in America. And half of the real estate brokers in America delisted, meaning they weren't making enough money to keep their licenses going. So the real estate brokerage community shrank by half in a one or two year period. Well, our customers were real estate brokers. It's hard to build a business when half your customers go away. So one thing that it taught me is sometimes markets just work against you. It's tough to fight a market. Some, some companies will succeed in anything, but others are dependent on having markets. And many people who have been successful because the market has been kind to them don't realize how lucky they've been to have been doing whatever they were doing in a period where the market was very kind to them. And then all of a sudden it turns and the market isn't as kind. And so that second business, the market turned against us. And, you know, I'm not sure I managed it all that well. I'm not suggesting it was perfectly run. In fact, I learned that I was not as good a manager As I was an entrepreneur, I had a remote business in Atlanta and I didn't have any of the skills that worked for me when I was managing people in person to be able to influence people that were a thousand miles away. And so what happened was I went backwards. I had made a lot of money when I was 30, and now I had less of it by the time I was 35 because I had lost money on this company. And I woke up one day and realized that while none of these things were all that likely to happen, I could imagine 10 things that if they all went wrong, I would have lost most of my money, which, whereas I had just given up a small amount of it and it scared the bejesus out of me. I didn't know what. I couldn't imagine that I would go that far backwards. So I started a company called Ms. Emmes. My initials are Ms. It also means truth in Hebrew. And started buying distressed real estate and built a billion dollar portfolio where we delivered 38% returns to our investors and had an extraordinary success. That was one of my career highs. But when I sold ms, I said, you know, I had that first success when I was 31, and then I went backwards during the middle part of my 30s and now I'm 43 and selling my second success. I don't want to ever have to go backwards again. I don't want to ever have to start a fourth company to try and make up the losses. How do smart people, when they've been smart enough to have a great success, learn how to both pursue new opportunities after they've sold their business, but preserve capital? How do they balance those type of issues? And that was really what Tiger was about. It was trying to learn from people who were smarter than me or it had experiences that I hadn't had. How do we, how do we learn so that I could continue moving my career forward but not jeopardize the wealth that I had created so that I went back to square one?
- [26:50]
Narrator/Host
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- [26:56]
Interviewer
To get 10 answers.
- [26:57]
Narrator/Host
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- [28:59]
Interviewer
It's really interesting because that out of every single person I've spoken to that sells a business, that is such a common sentiment. Just the absolute fear that they're going to screw it up somehow. And it's. It's ridiculous to think that you could screw everything up, but you get in your head about, well, was this a one time thing? Is there a chance that it's going to go to zero? What if I make the wrong investment? And this is. I don't think before tiger21 there was really a group. I think it was very lonely on the other side of an exit. And it's hard for people to understand. It's really hard for people to understand.
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Michael W. Seinfeld
Yeah, it's, it's terribly lonely because all of a sudden you might have created a Lot of wealth. And some people may know what you created, but you're having all these challenges and they're really quite daunting. But everybody is saying, oh, I wish I had those problems. Well, maybe. But when you have those problems, those are your problems. And first and foremost is children. How do you not allow your success to screw up your children? And how do you give your children a chance to grow and mature on their own without being overwhelmed by their parents success so that they can enjoy it on their own? So there's. And the other thing is that, you know, one of the things that we've learned over the years is if you're neither an entrepreneur nor an investor, they seem like the same thing. They're just people managing money and assets, making money. It's kind of like the Eskimos have nine words for snow to you and I, maybe it's just that white fluffy stuff. But the Eskimos have real expertise to distinguish between different types of snow. And the difference between an investor and an entrepreneur is night and day. If you're an investor or an entrepreneur, but not to anybody else who is not involved in either. You know, investors are quite dispassionate. They have to be across a portfolio of things. An entrepreneur is generally quite emotionally tied up in the one thing that they're working on. So they over concentrate. But they're lucky enough. Not all entrepreneurs who concentrate on one thing are successful. But most of the successful entrepreneurs have concentrated on one thing and milked it for all it's worth for 10 or 20 or 30 years. So concentration risk is a problem every investor knows. But the most successful entrepreneurs think that's the way to go. And you know, most entrepreneurs who love what they're doing, and that's where the most successful entrepreneurs are, really don't want to sell their asset. Something happens and they might be forced to sell, or there might be a health issue, or it just might be an offer that you can't refuse. But it's a very emotional decision for most investors. They try not to get too emotionally involved in any one of their positions so that when it reaches the level it's supposed to, they say it's time to sell and move on to the next investment. So there are a lot of differences. You know, one of the little secrets of Tiger is that we should really say we take some of the world's best entrepreneurs and turn them into mediocre investors. Because if we didn't, they'd turn out to be terrible investors. As it turns out, we have a Lot of great investors in Tiger, and some of the entrepreneurs have figured out how to be great investors. But on average, the transition of being a great entrepreneur to becoming a competent, if not great, investor is a huge shock. It takes on average three to five years for a really great entrepreneur to become a competent investor. And obviously within there, there's some great investors that come out of that.
- [33:14]
Interviewer
When you, when you speak to an entrepreneur that's had that first exit, what's your advice to them to help them transition from entrepreneur into investor so they don't make foolish mistakes when they join Tiger 21.
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Michael W. Seinfeld
So, first of all, you have to do some personal introspection. It doesn't matter whether it's psychiatry or meditation or whatever it is that allows you to learn more about yourself. But you really have to ask yourself, do I think that the skills that I brought to this entrepreneurial success would allow me to do it again? Or was I lucky enough that maybe I should count myself lucky and now think about being an investor? So you have to know yourself. Do you? First of all, if you're 30, that question might be very different than if you're 70. If you're 70, even if you thought you could do it, you might not want to do it. So this notion of knowing yourself, are you fundamentally an investor or an entrepreneur in your personality type is really important to kind of explore. And the other is to say part of what we're talking about is something that we call sticker shock. Most entrepreneurs overestimate the value of the money that they'll have after they sell. They forget that they'll have to pay taxes. And then they forget that once they pay taxes, they're going to earn a return that's so much less as an investor than they earned as an entrepreneur that sometimes their income literally goes down 50, 60, 70% simply because if you were earning 20% as an entrepreneur and then you pay taxes and you're earning 3 or 4 or 5%, it's obviously an awful lot less income. And your lifestyle changes. So when you sell a business, it's not necessarily to give you more annual free cash flow. It's to take risk off the table. And would you rather have risk off the table, but not as much cash flow. The business doesn't cover your expenses. If it did, it doesn't send you on vacations. If it did, whatever, whatever that was going on in your business. But obviously at different levels, you might have enough. One of the big surprises people learn is that TIGER members, on average, live on about 2% of their net worth. Obviously, there are many different variations because some people have different types of income. But as a rule of thumb, 2% is a number. Well, that's a real shock. If you sold your business for $10 million, you probably were living on an awful lot more than 200,000 a year. But once you have $10 million, if you're living on more than 200,000 a year, you won't be able to preserve your capital. You might spend down. And if you're 70 and you say, I'm going to live to 90 over 20 years, well, maybe you can live on 250,000 or 300,000 and still have a dollar when you die. But it's quite shocking to most people what the change is when you're living off passive income. I'll just give one other example. Being an entrepreneur breeds lousy investors. Because when you own a business and it's throwing off money each year, and then you invest that money, if the investment went bad, you don't care about it because next year the business will throw off more money and you can make an investment. So when you're at a cocktail party, you don't have to tell anybody about the bloopers that you made. You can just talk about the winners as if you're a genius. But once you sell your business and there's no repetitive fountain of cash, when you lose principal by losing money in an investment, there's no way to replenish that cash. There's no business to fill that up. So the skills that many people as entrepreneurs have as investors are sloppy, undisciplined investing. And that's sure to get you in a lot of trouble once you no longer have the business to replenish your losses.
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Interviewer
When I know that you do a portfolio defense with all your members, maybe describe what that is briefly. But also I want to. I want to understand what comes out of that portfolio defense in terms of best practices, percentage allocations, just averages. Obviously, everyone's going to be different. But for the most successful, right, the people that have figured it out, I know that all the different asset classes, right, the crypto, the private equity, the real estate, the everything. I want to understand what the best in the world are doing.
- [38:10]
Michael W. Seinfeld
Yeah. So once a year, if you're a Tiger member, you belong to a group. There's 12 or 15 people in the group you meet once a month. And therefore each month one person does a portfolio defense. They've worked on it for a month. They've pulled all their information together. Many times, people are understanding this information literally for the first time. You can't imagine people don't know what they're worth, what all their assets are, how they're allocated. They often don't share it, excuse me, with their spouse or even their advisors because they don't want their advisors to know what they have or whatever. But in Tiger, this is the opportunity to get 12 people whose agenda there is to share their knowledge with you, to not to not sell you on anything, but to employ the collective knowledge. So when you show a portfolio and you talk about the philosophy of how you've constructed your portfolio, two amazing questions in the portfolio defense. Who is this wealth meant to support? Well, some people say my family. That's my husband or my wife and I. Some people say it's from my wife or husband and I and our children. Some people say, oh well, we're supporting our in laws or we're supporting our sisters and brothers, everybody. And others say it's to support the people in my church or my synagogue or at my college alma mater. People define the purpose of their wealth very differently. And you have to start with understanding what people's purpose is for their wealth. And a second question is, if the markets were to go down or your net worth were to go down 20% or 50%, what would you do? And some people say, I wouldn't change anything because I live conservatively. And some people would say, well, I'd have to do this, that or the other. These are the kind of questions, but basically when you show your portfolio, it reveals in almost every case a bias or a blind spot. Some person might not have enough cash because they're just assuming the equities will be fine. But in a market crash, maybe you need to have cash. That's why Tiger members, on average over the last 15 years carry about 12% cash, very little debt and 12% cash. And if you go back to the 2% I was talking about, that means in the worst of cases, you might have six years of living expenses. It doesn't quite work out that way, probably three or four years in any case. But the point is that history has shown that when you're forced to sell assets to raise cash when the market is down, that's the worst time to sell. And if you can have enough cash to weather the storm, then you're not forced to liquidate at discounts, which really takes a hit to your portfolio. And obviously, if you have cash when the market goes down, you can buy opportunities you could not otherwise buy. So in simple answer our members have 10 or 12% cash. Our members have 28% in private equity, 28% in real estate, and only 24% in public equity. That's a very unusually low allocation. But our members are all the great entrepreneurs, so they made it in private equity or private ownership of businesses or private real estate. So it's no surprise that even after they sell, that's what they want to invest in. But I think the bigger thing that is important is between the 28, 28 and 24, that adds up to 80% of our members assets are in long, biased assets. That's a very long term bullish feeling. Doesn't mean anything about what they think the market will be this year or next. It just says over the long term, owning businesses in real estate is where wealth has been preserved and created.
- [42:30]
Interviewer
Are there, are there any alternative investments that the wealthiest. And actually, you know, it's really good because we didn't even, we didn't even pin a number on it. What is the average net worth of a TIGER member? So people can just really understand the, the amounts we're dealing with here.
- [42:45]
Michael W. Seinfeld
To be a Tiger member, you have to be managing between 20 million and a billion of personal net worth. And the average TIGER member is managing about 130 million of personal net worth.
- [42:58]
Interviewer
Do you see a high net worth, ultra high net worth, investing in alternative assets, like I mentioned crypto before or anything else that, anything else that would be interesting to them?
- [43:09]
Michael W. Seinfeld
Totally. First of all, the fact that 28% is in private equity is out of all proportion to what a typical wealth management firm would recommend. Because our members are entrepreneurs who created wealth. They're more comfortable having the illiquid investments. And within private equity, of course, the biggest part, the reason it grew over 15 years from 10% of our portfolios to 28% is that venture capital has been a growing section of. My guess is 15 years ago venture capital was almost nothing and today it probably is a quarter or a third or a fourth of the total private equity allocation. So percentage wise, it's grown tremendously. So that's one area gold has typically been a 1 to 3% asset. Obviously this year it's done something extraordinary in the last year because of concerns about the dollar and the U.S. economy. And we have some real Bitcoin and digital currency rock stars who are members, some of the members, leading funds that are in crypto and some of the world's leading experts. We have many, many members who have millions and tens of millions and likely hundreds of millions of bitcoin and some of the other cryptocurrencies. But it's still, at this point, as best we can tell, if of the 1600, it would be a small percentage of it who are real devotees. So in the aggregate, it's about a 1 to 3% asset as well. And because our members have about 200 billion under management, you know, at 3%, that would suggest we own about 6% of, I'm sorry, 6 billion of cryptocurrency. Not insignificant. But, you know, there's a race going on now between bitcoin and gold, which is the better storehouse of value. The traditionalists tend to lean towards gold. Probably our younger members, but not only younger members, like the digital features of, of Bitcoin and the fact that you can, you know, put it in a bitcoin wallet, and it's totally portable and is really a way to, to protect against currency devaluations and other state concerns that many bitcoin owners have.
- [45:51]
Interviewer
When you think about coming into a significant amount of wealth, you mentioned, one of the major concerns is, is children. And, you know, how do you. How do you make sure you don't screw up? So I think that what would be really interesting is just to understand for people to have made a significant sum of money from an exit. When you think about family and legacy and children, and even you mentioned before, which I find super interesting, some people don't even talk to their partner or their spouse about how much money they've made or I guess, how they allocate it. What are some of the biggest concerns outside of investment? We've covered investment, obviously that's major. But family, kids, wife, husband, what are people worried about?
- [46:32]
Michael W. Seinfeld
Without doubt, the number one concern across Tiger members is how do I both not screw up and at the same time provide for my children? And those are conflicting. The more you provide, the more you might be screwing up your kids. So what's that? Perfect balance. And it generally breaks down into two very different approaches. One approach is to give your kids very little in their early years so that they can become independent and successful in their own right. And in that philosophy, probably you're waiting till the kids are somewhere between 25 and 30, maybe even older than 30, before you fully disclose to them what you're worth. The philosophy being that if I told them how much I'm worth and how much they're likely to inherit, it would disincentivize them from finding their own path to success. There's not a lot of evidence that that's exactly right. But it might be approximately right. And just to give you an idea, my best guess is about 70% of Tiger members follow that approach because they don't want their wealth to get in the way of their children forming their own identities, their own careers, their own success. About 30% of our members, and it probably skews towards the wealthier end of our membership, say that our kids are going to inherit so much money that I'd rather teach them about money, teach them how to be stewards of the wealth they'll eventually inherit. And you have to start that from an early age because it takes a long time for people to really master the concepts and understand the impact. If you're of the 70%, and you never tell your kids what they're going to inherit, maybe they're making decisions that stop them from becoming a priest or a rabbi or a community service or a researcher or a public servant because they don't have the resources. They don't know they have the resources that would allow them to do that. On the other hand, if you give your kids too much money, maybe it could demotivate them from having the passion to try and create success on their own. So there's no perfect answer. Part of it is your own philosophy, and part of it is knowing your kids. But there's, you know, obviously successes where kids created their own independence and only later found out they were inheriting wealth. And there are also great successes where kids learned what they were going to inherit and that enabled them to make decisions that could benefit society or make their lives fuller and that it didn't in any way stunt their growth. So it really depends on what your philosophy is. But the one thing that we know from kids is that at least in your will, you better be treating your kids equally or you're going to leave some deep emotional scars. If you leave more to one or the other, with one exception, if you have a deeply held family value and you talk about that value over many years with your children, then they can understand why the value overwhelms the equality. So if you want to leave a trust for children who go into the clergy, or a trust for children who become public school teachers, or a trust for somebody who preserves the family farm, There are a number of these kinds of exclusions. Where you talk about our family value is the farm that your grandfather or great grandfather had, or we would love you to become a public servant. The Kennedys were purported to have trust for any Kennedy that went into public service. So if you can do that. But during your children's life, it's not as clear that it has to be equal. Some families say it's each kid according to his need. If one kid wants to start a business and you want to lend them money to start a business, and another one wants to buy a home, each is according to their need. And as long as there's a basic equity and the kids feel that they're being addressed, it doesn't leave the kind of emotional scars that if. If one kid is treated one way and another kid treated another.
- [51:25]
Interviewer
What about the spouse? Because that's also. Hopefully everyone's happy. But I'm assuming that there's still some. Some things that people have to think about or at least want to think about when they come into a huge amount of money.
- [51:38]
Michael W. Seinfeld
I think what I want to say is that there's no way to answer what kind of information should be shared between spouses. Without getting into how many variations of a marriage or a relationship are there? Because we have many members who have created significant wealth, sometimes before they got married, sometimes after, and their spouses have no idea whatsoever of what they're worth. I was in a portfolio defense of a man who was in his mid-60s and had only told his wife recently that the level of wealth that they had, obviously she knew they had enough wealth to support their lifestyle, but had no way to put a number on it and apparently was never interested to know. That's curious to me. I personally would want to know, but that's my own predisposition. But I hear stories about TIGER members whose spouses have no idea what the scale of their wealth is, and spouses who are 100% partners in the sense that they know everything and they actually jointly feel like the sacrifices they made entitle them both to that wealth. And it's harder for me to draw any perfect conclusions. You all want a perfect marriage, but we know that over half the marriages in America end in divorce today anyway, so it's a little tougher. I know that in my case, my spouse has access to everything that I have, and I have access to everything that she has. That's the nature of our relationship and most of the people I know. But I do see it all over the place.
- [53:28]
Narrator/Host
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Interviewer
Partner.
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Narrator/Host
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Interviewer
To get 10 answers.
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Narrator/Host
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Interviewer
Partner.
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Narrator/Host
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Interviewer
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- [55:37]
Interviewer
It's just interesting. I feel like I, I think the lessons are with a lot of these, a lot of these like learnings because again, there's so much, there's so much variation across the board. But I think the lessons are a lot of introspection and I would say a lot of communication. And I think that those two things are just good habits. I know that you, I mean even, I think at some point in your life you practiced a lot of meditation and, and then you abandoned it, came back to it. But you've mentioned meditation You've mentioned introspection. These are all great tools to understand yourself. And if you don't understand yourself when you come into a massive windfall, a massive amount of wealth, I'm assuming that that is the most dangerous situation when you don't know what you would be happy with, what you would not be happy with, what you'd like to communicate to your spouse, what they want to hear, what. I don't know. I just feel like a lot of introspection is needed. Have you thought about this? Like the psychological work?
- [56:33]
Michael W. Seinfeld
Have I thought about it? That's what I've been doing for 26 years.
- [56:35]
Interviewer
I was going to say, have you thought about that?
- [56:37]
Michael W. Seinfeld
Just give you. I'll give you an example of a member who did a portfolio defense. And when I met him 10 or 15 years ago, it could be any number, but let's say he was worth $10 million. And then he said, you know, I just, for whatever reason, I'd like to be worth 20 million, and then everything will be okay. And when he got to be worth 20 million, all he wanted to be worth was 40 million. And the minute he was worth 40, he was reaching for 100. And, you know, we can all find ourself on that endless rat mill, you know, the, the circle. What's it called?
- [57:17]
Interviewer
The treadmill. Yeah. Rat race.
- [57:19]
Michael W. Seinfeld
Treadmill. Yeah, rat race. And, you know, there's this fundamental question is when is enough enough? And it has nothing to do with the number, because you could leave a great lead, a great life if you had a million dollars or 10 million or 100 million or a billion. And, and I can give you many examples of people who have the hundred or a billion who aren't leading a great life. So it's all about how you think about it. But some of us are sort of programmed for whatever reason that wherever we are, we're just striving for a little more. It's not a bad thing. That's what makes great entrepreneurs keep going.
- [57:59]
Interviewer
Is balance important or are there seasons of your life where it is required to be imbalanced to achieve this level of success? Meaning? I've always thought that at some point it is good to focus on your health and your relationships. But I know a lot of people that don't. While they're in the throes of building, they seem to put everything else to the side just in pursuit of the business goal. Do you see that to be the, the, the norm?
- [58:23]
Michael W. Seinfeld
Such a great. It's, it's such a great question. I think it affects each person differently. You know, you. I hope the analogy I'm going to make makes some sense, because I've known people who were not philanthropic during their life, and yet when they died, they left a foundation, and either their children or their heirs allowed that foundation to do extraordinary good. You know, Warren Buffett for many years said he was going to keep his money because he was earning more than any foundation could. And when he died, he'd leave the money to the foundation. But then his friend Bill Gates convinced him, yeah, but if your money saves a life today, how much more valuable is it than saving another life 20 years from now? And apparently, Warren Buffett gave about half of his wealth. I don't remember the exact number. To the Gates foundation many years ago. So the answer is, you know, a life well lived follows many definitions. But one of those lives is, you know, a relationship. What's the nature of your relationship? I was very fortunate to have a wife whose father was also an entrepreneur. And I worked extraordinary amounts, traveled and wasn't home for dinner and was on the road, and she was incredibly supportive. So one of the big lessons that comes out of the book that I wrote about entrepreneurs is, who's your significant other? If you're pursuing goals one way and your significant other is not digging that, liking that, then that's harder for you to do it. So one of the things you have to look at in choosing a life partner is will that person accommodate to your ambitions and you to theirs? It takes two to tango, obviously. So the. The question that you're talking about a balance. I don't. One of the most depressing things that ever happened to me in a tiger meeting is we were talking to a man who was worth $30 million, and we were asking him about. We talk about philanthropy. We try not to judge, but we try and share information. And when I asked him what his philanthropic budget was, he said, oh, I don't have a philanthropic budget. Philanthropy is for the wealthy people. And I wanted to say, you're worth $30 million. How much more wealthy do you have to be? I know some great philanthropists who aren't even worth a million dollars, but they give a portion of their income and they give a portion of their time. So I think philanthropy in particular, when you're talking about balance, I'm always more interested in meeting somebody who has some element of gratitude, because if they've made it to a tiger table and they haven't achieved some level of gratitude, I don't think that they're appreciating how much good fortune they've had to get to that table. You always meet people who. With a chip on their shoulder. But when somebody thinks that their wealth that they've created doesn't come because they've been helped along the way and because they've had some luck, I find to be sometimes one dimensional. And I want to work with people who have a certain modicum of gratitude and a sense of wanting to have an impact on the community that they're in and appreciate even the workers who supported their success. And that makes for a more whole person in my mind. But, you know, comes with all, all different stripes.
- [62:19]
Interviewer
No, I agree. I mean, you're very, you worded that very nicely. I also, I also really dislike when people consider themselves self made because that means that they didn't have customers or investors or friends or peers or. And it doesn't. In my opinion, that doesn't exist. It doesn't exist. There's always someone else who's been part of your journey. But if you think about, you know, forget the people.
- [62:47]
Michael W. Seinfeld
I'm sorry to interrupt.
- [62:48]
Interviewer
No, no, you're fine.
- [62:49]
Michael W. Seinfeld
I'm sorry. When you talk about part of your journey, one of the greatest lessons that I've learned is the role of mentors. And if you take 100 people in any profession and line them up from least successful to most successful using any reasonable definition of success, money, number of papers, published, friends, I don't know what it is, any reasonable. The half that are most successful will overwhelmingly have had mentors in their life. And the half that are least successful will overwhelmingly have excuses for. For why they don't have mentors in their life. And something you just said reminded me that when you asked me before about some of the lessons that I learned, I've been blessed with five or six or seven mentors in my life. That every one of them sort of lifted me up one rung on the ladder in terms of my ability or my perspective. And I try and do that with younger people as well.
- [63:56]
Interviewer
How would you, for somebody who's listening right now, how would you advise them on finding mentors? Do you recommend they find people that are far more advanced, people that are, have just accomplished what they're looking to accomplish, People that are, you know, kind of in their peer group that are on the same level to hold them accountable? How do you look at mentors and peers?
- [64:17]
Michael W. Seinfeld
Mentors come in all stripes and all colors and all flavors, but basically it's generally within the human spirit to want to have a mentor and to be A mentor. And what people say when they can't find a mentor, they just haven't been looking. Because I think that if you're somebody who. Yourself, who you are, a decent, honorable person of integrity and ambition and kindness, for lack of a better way of saying it, it's almost inconceivable that if you ask two or three or four reasonable candidates, one of them won't, in one way or another, want to become your mentor. And that's just the nature of the human experience. And mentors can make all the difference in a person's life. I. I always mostly had mentors that were very approximately my father's age. Whether that's a coincidence or not, I don't know. But I was looking for people who had achieved some kind of success in some field and had some Persona to me that felt balanced or insightful or kind. And I just wanted to know what made them tick. But I was looking for people that had really different kinds of success that I could learn from. And I just think it's one of the most. One of the least understood, most important phenomenon of almost any young person's success. Young are old. You're never too old for a mentor. I have a close friend of mine who's 96 years old, and I'm going to be 70. We met because we were both on the board of an organization called Business Executives for National Security that was trying to help frame our national security. And I can't do the math, but when I was 30, I guess he was 56, and we spent the weekend on an aircraft carrier sharing a bunk. And Here we are 40 years later from that weekend that started on a bunk. And I still go out to see him every couple months to be showered with his perspective and wisdom. It's been a source of inspiration for many years for me.
- [66:54]
Interviewer
First of all, how important is meditation for an entrepreneur, somebody who's trying to be successful? And if not meditation, then what other practices do you think are very useful?
- [67:05]
Michael W. Seinfeld
I think you have to start with a kind of perspective of the way our minds work. It's when somebody Sundays, I'm of two minds, or there was a very famous book by Danny Kahneman, who's a Nobel Prize winner, called Thinking Fast and Slow. The way we've evolved is our brains are actually the combination of a reptilian brain that evolved into a mammalian brain and then human aspects. So there are different parts of our brain. Sometimes it's the conscious and unconscious. But the point is, most people, there's some aspect of their Thinking where there's a process going on in the background where you're kind of thinking about problems, but it's not in the foreground and the two are quite separate. But when you can find ways to connect that background or that unconscious to the conscious. And sometimes it happens through meditation, sometimes it happens through therapy. Very often it happens when people are taking a shower. Have you ever heard the story, oh, I was in the shower and an idea came into my head. There are different ways to some people do it with exercise. And so the point is that anything that allows you to connect the different parts of your brain into a functioning whole sometimes is like a bridge that connects two ideas. When I'm meditating, it's not like I'm thinking about a problem. I'm trying to have my mind blank. But that blankness opens a door to that part of the brain that's thinking about that problem that I wasn't even aware of. And a solution comes in to a problem that I'm working on, but not at that moment, but in my life. It's no different than somebody says, I had an idea for a new product in the shower. Well, in the back of their mind, their, their brain was working. So it doesn't really matter whether it's you take a hot shower every morning and spend a half an hour just relaxing or you're meditating or you're in therapy. Some people say there's some aspect to it for a runner's high when the endorphins occur. So there's lots of ways to access the whole mind. Most of the time we're conscious, we're just in the conscious mind. And that's not where our best thoughts or our deepest connections come from. And when you can access that deeper connection, sometimes you're able to have levels of creativity or problem solving that wouldn't otherwise occur to you. And I found that there's another aspect in meditation that probably is elsewhere too. The Buddhists have a term called the observing mind. And that's when you're in an experience. Most of us are in it at the moment, but a well trained Buddhist is both in it and observing it. And sometimes you experience an emotion. I'm sure I'm not the only person that sometimes comes into a room and for one reason or another feel a little insecure because people there are more successful than me or better looking or more accomplished or whatever it is. And that creates a nervousness and I start talking, blah, blah, blah, blah, blah, blah, blah. An observing mind says, are you aware that you're behaving in a way that is consistent with insecurity and when you can name it, it tends to dissipate. So this notion of having an observing mind in interactions, when you're talking to people, when you're with people, is just a way to allow people to master their emotions so that their emotions don't drive them to behave in ways that might be seen as counterproductive.
- [71:21]
Interviewer
Do you feel like that is something that you've developed at a, at a later stage in your life, or is this something that you've pursued purposefully to help sort of optimize your cognitive performance? Your reaction?
- [71:34]
Michael W. Seinfeld
There's obviously many successful people who don't meditate and haven't been to therapy. And again, there's many unsuccessful people that have. So there are no absolutes. But I believe that the people who I know who try and access these subconscious, unconscious, hidden thoughts and integrate them into, into their behavior and their thinking are generally happier people are people who have more gratitude and I'm not going to say more successful, but I'd like to believe that it aids in success. It certainly has for me. If I tell you the number of times I happen to be a almost daily meditator, I often get up at 4:30 in the morning not to meditate, I, I just get up and I can't go back to sleep, so I'll go meditate for 45 minutes. And during those sessions, I can't tell you how many times I've been on that for about the last 15 years, I think, and I can't tell you how many times I've been working on a problem, but not that day. It wasn't even on my mind when I was meditating. But out of the blue a solution comes and I say, oh my God, why didn't I think of that before? That's so clear. And you know, it could be, do I take this direction or that direction? Or I'm in a negotiation and I can't break it up and get it going. And it just, it's happened dozens and dozens of times. And when I say dozens of dozens of times that mean it doesn't happen every day, it doesn't happen every week, sometimes it doesn't happen every month. But I've had so many breakthroughs in getting such perfect clarity that whether again, it's meditation, which works for me, analysis, it's a form of therapy. I've done that as well for many years. Different people do it for different reasons, but I find it's Just a way to be in touch with who I am and maximize my performance.
- [73:43]
Interviewer
Have you ever fallen into the trap of having your identity so wrapped up into your business that it actually hurts your. How do you and what's your recommendation for entrepreneurs that do have their identity wrapped up in their financial success?
- [74:00]
Michael W. Seinfeld
I've had my identity wrapped up in every business I've been involved with. At Harborside, I used to think of the word Harborside with a vine growing around it. That was my identity because that's how wrapped up I was in it. And the, you know, at Tiger, it's different because I'm lucky to be surrounded by a team of 150 people of extraordinary talent, 1600 incredible members. But I'm the face of Tiger. I'm the one who does the TV and most of the news shows and podcasts as well. And so I'm associated with Tiger a lot. But I am finding that when I was 30 and I was tied up with Harborside, which was the largest commercial development in the country at the time, I thought appropriate for my first real estate project. I found that a real loss of identity when I sold it. Tiger, while I'm very involved with feels different. I'll be 70 in October. Feels differently when I think about all the things that I've done. Although Tiger is probably the one that will have the most lasting legacy, of course, other than my children. But the this issue, most entrepreneurs are tied up because as I said before, they're emotional. This is their baby, they're wrapping themselves around it. And the only thing is, just like any love affair, it can be healthy and it can be unhealthy and trying to figure out when that identity that's tied up is healthy because it's making the business more successful while making you feel better about yourself. That's good. But if it's, you know, if it's sucking the lifeblood out of you and causing you to do bad things or counterproductive things or unhealthy things, then it's not good. It's all very case specific and it's a trap that's too easy to fall into.
- [76:18]
Interviewer
What are the biggest regrets of the members of Tiger 21 when they look back on their life?
- [76:26]
Michael W. Seinfeld
You know, I'm sure that there's, it's fantastic question. I think that what I would say is I hate to use the word regret. If you second guess what the mistakes were, you can't ever know whether history, if you did the thing you forgot you did or you wanted to do, whether it would have been turned out better or not. Life is unexpectedly. Good things happen and bad things happen and you have to make the best of it. But when somebody asks me, I don't ask many people about regrets, but for me, I don't have any. Because if I told you I wish I did this or I wish I did that, I actually have no basis to know that it would have turned out any better. I'll just give you one example. I am an entrepreneur. I'm a small time entrepreneur that's been successful a couple times, but each time I start, I restart with planting a new seed. I don't buy large companies. I start something over and over again. And what that means is I pretty much sold every business I ever built too soon because once it grows into a tree, I'm not that interested in pruning trees. I'm interested in planting seeds and growing new trees. And another way of saying it is that my particular passion is around the act of creation. What I love to do is to create things, to have an idea that people say couldn't be done. I'm like many entrepreneurs and to prove them that it can be done. Tiger was an example. People can't imagine you could build a business off of what we do, and bankers said it wouldn't happen. When I did that first project, it was an old warehouse in an abandoned area and nobody believed you could turn it into a modern office complex. So my point is that sometimes people say, you know, if you hadn't sold each of those businesses, you'd be a lot wealthier today. And I'd say, maybe that's true, but I wouldn't have had the quality of life I've had and I wouldn't have had the ability to start the next thing and have the pleasure and the pain of starting things and seeing what's successful. So I think there's just so many situations where regret is just a counterproductive thing that you have to weed out. Wherever you are. You can make the best of where you are and look forward, not backwards, because that's all you can affect.
- [79:08]
Interviewer
I love it. Where I know that your book Think Bigger, that's available everywhere you can get books, Amazon, et cetera, et cetera. If people want to connect with you, where would you want to send them? Any social website that we can put in the, in the show notes below.
- [79:22]
Michael W. Seinfeld
You know, the tiger21 website. I don't do a lot of social media per se. I barely have enough time to brush my teeth at the end of a day. And I'm. I'm. I'm not of that ilk. I. I also think that I have some questions about whether all of social media, particularly among teenagers, but also among voters, is a productive force in our society. And as a personal habit, I don't engage in a lot of social media. But I'm at, you know, www.tiger21 and I'm easy to get a hold of. I'm googleable.
- [80:06]
Interviewer
Last thing I like to ask. You've given over so much today, so thank you for coming on. I really appreciate it. I always like to ask the last question. Out of all the things that you've learned in your life, say you could only pass on one lesson to your children. It's the most important lesson that you've ever learned. What would that lesson be and why?
- [80:22]
Michael W. Seinfeld
What comes to mind is it's sort of be grateful. Find the, the wonderful things that you can, you have, can and can benefit from and be true to yourself. I think that. I think so many people imagine that there are truths that are independent of who they are, as opposed to who they affect them. Each of us is different. Each of us has an identity. And the extent to which we can know ourselves and then act accordingly, I think is a pretty great guide for moving forward.