Michael Sonnenfeldt. Post-Liquidity Ultimate Wisdom

Episode - 2

Michael Sonnenfeldt. Post-Liquidity Ultimate Wisdom

 
 
 

My guest today - Michael Sonnenfeldt - is the source of ultimate wisdom on the life after a liquidity event. He has built and sold multiple companies and is the celebrity founder of TIGER 21, an exclusive global community of ultra-high-net-worth investors. Michael creates exquisite art, collects photography and runs a venture philanthropy firm focusing on climate change. We discuss the importance of post-exit introspection, how a liquidity event teaches us humility, rules of prudent spending, capital preservation vs angel investing, and how to decide whether to start a new business or focus on passive investing.

What We Discussed:

00:00:37: Introduction of Michael, Founder of Tiger21

00:01:53: Discussion on investors

00:02:05: Challenges of investing

00:02:39: Handling Success and Entrepreneurship

00:04:17: Discussion on Turning into an Investor after Being an Entrepreneur

00:06:44: Setting realistic passive returns

00:18:49: Discussion on Family Offices

00:23:49: Michael's personal motivations and the foundations of his success

00:24:55: Michael's ambition and challenges in the early years

00:27:37: Michael's personal experience of hearing loss and its impact on his life

00:28:53: Reflection on the role of luck in building businesses

00:29:04: Discussing the Role of Luck in Success

00:32:46: Overcoming Responsibility and Trauma After Business Success

00:34:46: Navigating Early Success and Future Ventures

00:39:46: Balancing Entrepreneurship and Introspection

00:43:59: The Intersection of Politics, Philanthropy, and Investment

00:49:02: Discovering Philanthropy

00:55:14: Importance of Travel and Cultural Awareness Post-Exit

 

00:56:22: Passion for Art, Photography and Fashion

00:58:00: Building a Large Photographic Archive

00:58:44: Handling Estates of Important Photographers after they Pass On

00:59:40: Estate Management of Deceased Photographers

01:00:20: Fulfillment in Life

01:01:41: Artwork and Business

01:02:37: Loneliness After Founders Exit

01:03:10: Isolation After Wealth Creation

01:05:10: Inherited Wealth Management

01:06:02: Shift in Wants After Selling Business

01:09:36: Turning Down Family Members' Investment Requests

01:12:07: Generosity Vs Enabling Bad Behavior

01:12:47: Parenting with Wealth

01:14:50: Responsibility Coupled with Inherited Wealth

01:15:14: Preparing Children for Inheritance

01:16:30: Selecting People to Surround Yourself With

01:20:15: Striving for a Life of Meaning and Purpose

01:24:50: Evolution of Tiger Organization and its impact

01:26:54: The Experiences and Learnings from a Long Term Marriage


  • Anastasia Koroleva: [00:00:00 - 00:00:03]

    How to not spoil children with wealth. 


    Michael Sonnenfeldt: [00:00:03 - 00:00:35]

    Love them. If you have early success, if you're young, you really have no idea whatsoever what allowed you to be successful. Many entrepreneurs underestimate the effort it'll take to have another success. The biggest adjustment is setting realistic passive returns. People take a year or two or three of learning about themselves. 


    Anastasia Koroleva: [00:00:37 - 00:00:51]

    Welcome to the Exit Paradox podcast. Here we meet remarkable exited founders to uncover what comes next after selling a business. Did they sustain success and find fulfillment? Let's learn together. Please subscribe to join our community. 


    Anastasia Koroleva: [00:00:57 - 00:01:01]

    Michael, thank you so much for being here with me today. 


    Michael Sonnenfeldt: [00:01:01 - 00:01:02]

    My pleasure. 


    Anastasia Koroleva: [00:01:04 - 00:01:34]

    There is no one on the whole planet who knows more about post exit founder journeys than you. For the past 25 years at least, you've been mentoring and guiding and supporting exited founders with amazing generosity and kindness and grace. For me, as a member and the beneficiary of you creating Tiger 21 in the first place. Given that the name is an abbreviation which includes an investment group, it's the Investment group for enhanced results. 


    Michael Sonnenfeldt: [00:01:34 - 00:01:45]

    Investment group for enhanced results. Not returns. Results. Very important. We don't promise returns, but we do hope for better results. 


    Anastasia Koroleva: [00:01:45 - 00:01:53]

    But I also personally don't necessarily see it as an investment group as much as a community of people who understand each other. 


    Michael Sonnenfeldt: [00:01:53 - 00:02:04]

    We like to say investors sign up and people show up, and we've been catering to the people who show up more than the investors who signed up. 


    Anastasia Koroleva: [00:02:05 - 00:02:39]

    Many people get stuck learning to be investors. They stress out their focus goes all into managing their money. So would it be correct from your standpoint to gently kind of guide those people into investing conservatively and instead maybe going through introspection and then consider channeling their creative energy elsewhere, like building a new business or doing philanthropy or venture philanthropy, whatever it may be. 


    Michael Sonnenfeldt: [00:02:39 - 00:04:16]

    In order to become an incredibly successful entrepreneur, you've had returns on investment that are off the chart. If somebody starts with $1,000 and creates a business worth 10 million or $100 million, they're a better investor than Warren Buffett. But Warren Buffett's done it for 65 years, and the investor might have done it for five years. But typically most entrepreneurs are successful episodically, meaning for a period of time and only the luckiest then get to have another period of time. So I know that in my case, you wouldn't give me a large amount of money and ask me to manage it for you. 

    That's not my particular skill set, but more than a handful of times I've taken very small amounts of money and created significant success from it. When you're building businesses. Many businesses scale because of those magic world words, reproducible and scalable. Many businesses are simply ten times bigger than they were before because they're doing the same thing ten times as much. That's a skill set of an accomplished manager who understands people, processes and systems. 


    Michael Sonnenfeldt: [00:04:17 - 00:06:44]

    In my case, every one of the things I've done is almost completely different than anything else I've ever done. It's like a new territory that's both my gift and my quest. Meaning that's what I enjoy doing is starting anew each time, if you will, there's a decision that every successful entrepreneur whose exit it needs to make. Do I want to be an investor or do I want to be an entrepreneur? 

    So the first decision that a successful exiting entrepreneur has to make is, are they really ready to sign up for another entrepreneurial gig? Because one of the traps that many people feel is, well, I've done this for 20 years, I'll be able to do it with half my time. I'll be able to use my talent, I'll just do it. There are some people who have that extraordinary skill, but mostly, if you sign up for another gig, you're going to have to be all in, because you're going to find out all of the problems that an entrepreneur has. There's no absolute rules here, but I find that many entrepreneurs underestimate the effort it'll take to have another success. 

    And if you were realistic about that, you might say, at this stage in my life, I don't want to do that. Most recently, exited entrepreneurs don't even understand the terms of the question, because they don't really understand where their success came from, how reproducible it is, how applicable it might be to a new venture, and whether they want to be an investor. So some people might sell a business and have the answer to that question the next day. But most people take a year or two or three of learning about themselves and learning about the world. And the other corollary to that is when you've been this entrepreneur earning extraordinary returns, it's almost impossible to appreciate what low returns you should expect as a passive investor. 


    Michael Sonnenfeldt: [00:06:44 - 00:08:23]

    The biggest adjustment is setting realistic passive returns. And when you do that, that will help you decide whether you can afford to be an investor or you need to become an entrepreneur. If you don't ask the right question, you can never get to the right answer. So this issue of setting a realistic expectation of what you'll learn as a passive investor is a terribly gut wrenching transformation in the world of entrepreneurs. If you're lucky enough to have a business that would be phenomenal, that's profiting, let's say $3 million a year. 

    You go and you sell that business. And if it's not high tech, but just any kind of manufacturing business or service business, you might get seven or eight times earnings. So you would get $21 to $24 million, let's just say 20. To keep it simple, you pay your taxes in America, I'm not sure, different countries. But you're left with $16 million. 

    Well, for the last decade, if you invested passively, you might have earned two or 3% on that $16 million. So let's say at 3%, that's $480,000. But you were making $3 million a year last year. Now you're making $480,000, and you'd say, where did all my wealth go? And that's probably one of the biggest shocks of the illusion of success, when you lose your platform. 


    Anastasia Koroleva: [00:08:23 - 00:08:34]

    So you're one of the most quoted people in our community, and one of the most popular quotes is about your 2% rule. Could you tell us about it? 


    Michael Sonnenfeldt: [00:08:34 - 00:13:13]

    So, it's amazing if you ask a bunch of 25 or 30 year olds, but it could be any age. You've just inherited a million dollars. What do you think? You could spend a year of the million dollars and sustain it. You get crazy numbers. 

    People will say, oh, I don't know, $200,000 or 100,000 or 300,000 if you spend $100,000. Generally, if you've inherited a million, it might not last much longer than ten years. And then all of a sudden, you wake up in the 10th year and say, oh, my God, I just squandered a million dollars, and I didn't realize it. So the 2% rule is a very tough, very conservative, very disciplining rule, which is in the absence of any other piece of data, because any other piece of data could make a difference. But in the absence of it, if you say, how much money can I spend and preserve my capital? 

    It's about 2% a year. Obviously, the math is simple. If you don't make any money and you don't lose any money, it'll last 50 years. The likelihood is that you'll make money and you can sustain it. But that goes back to the 4 to 6% that I was saying. 

    You should be able to prudently grow your wealth and live on 2% a year, presuming you're just being reasonable in the way that you're doing it now, obviously, 2% over the last 20 years is different than today, where interest rates have started rising. So maybe it's two and a quarter or two and a half percent, maybe it's 3%. Many people's portfolios are not constructed similarly. If you've had a career in a corporate setting, you might have a pension plan, which you never realized how valuable it was, because if you have a $200,000 a year pension, that's like the equivalent of having 10 million of capital at the 2% rule. So obviously, if you have invested, I don't know who would, but all of your capital in a certain kind of government bond that's paying 7%, and those times have happened, you could probably live on a little more than 2%. 

    If somebody says, look, I want to lead a very simple life. I just want to make 15% a year on my investments, and I don't think I need to live on more than 10% a year. You don't have to look at the numbers to begin a conversation, because both of those assumptions are so divorced from any reality that a prudently diversified investor would have. But the financial industry would say the number is closer to 4%. There's something called Monte Carlo models. 

    I don't know if you're familiar with those, but when you go to a wealth manager, they run like simulation after simulation to think of all the outcomes depending on when rates are up and they're down and losses are high and they're low. And very often their Monte Carlo models will say somewhere between 3 and 4%. But observationally, obviously, the wealthier you are, you can still have an extraordinary lifestyle on a smaller percentage. So where Tiger members are, is closer to 2%. And that's the starting point in any discussion. 

    So 3 to 6%, obviously, it's all different. There are some people who have what would be called a barbell approach, where they keep a lot of money in cash, but the money that they invest is high risk because they might have the skill to invest in high risk. But three to 6% is sort of, in itself, a big range, but it's certainly not eight or ten or twelve. And of course, there are investors who make those kind of returns, but generally because they're bringing some kind of distinctive competence. And maybe some of those returns are returns that are not passive returns, but returns on capital in businesses that people are actually working in. 


    Anastasia Koroleva: [00:13:14 - 00:13:28]

    In your experience, the very traits that, personal traits that help us succeed as entrepreneurs are exactly the traits that prevent us from becoming successful investors. I would love you to elaborate on that. 


    Michael Sonnenfeldt: [00:13:29 - 00:14:34]

    Look, every case is different, but as an example, most entrepreneurs focus on a single opportunity as an investor. If you do that, you'll be out of business, because once you start investing passive capital, if you're not prudently diversified, then any one mistake could destroy your portfolio. One of the worst training grounds for being a competent investor is being a successful entrepreneur. And what I mean is that many entrepreneurs, when they're accumulating wealth that are distributions from their business, make investments. But when you have an underlying business that can make profits this year and next year and the following year, it allows you to become a sloppy investor, because you can make investments that you lose money on and you don't think much about it because the next year's profits replenish the well, so to speak. 

    So unless you're incredibly disciplined, the type of investing you do as a successful entrepreneur actually can make, the type of investing you have to do after you've sold, more difficult. The risk tolerance that an entrepreneur has that can replenish funds each year through next year's profits may be a very different risk tolerance than they need to have to make sure that they preserve capital once they've had a liquidity event. 


    Anastasia Koroleva: [00:14:35 - 00:15:15]

    So for someone who recently sold their business and now thinking, what do I do with my wealth? What would your advice be how they organize themselves? 


    Michael Sonnenfeldt: [00:15:15 - 00:16:50]

    Rather than making a sale in January and being fully invested even by December? The best advice I would give, it's not precise, but take three to five years before you are fully invested, because you just don't know what you don't know. So one thing is time, and for sure, the other thing is risk. Most entrepreneurs were successful in part because they found a sweet spot that married their skills and some need in the world. Investors really don't have sweet spots. 

    And entrepreneurs who become investors don't realize how ill equipped they are to be dispassionate, diversified investors. Of course, every entrepreneur faces risk, but when you're in the sweet spot of what you know better than almost anybody else, it's a lot less risky. But when you start investing across multiple classes of assets, multiple types of assets, it's quite difficult to be able to assess risk in any realistic way until you've had enough successes and failures as an investor and you hope that the successes are more important than the failures. 


    Anastasia Koroleva: [00:16:51 - 00:16:53]

    So you would say, stick to what you know. 


    Michael Sonnenfeldt: [00:16:53 - 00:17:41]

    For people who made their success outside of finance, the entire financial industry sometimes is trying to be like a priesthood that has special incantations with acronyms that you have no idea what they're talking about. They don't appreciate what unique skills they have and how to deploy them, even as investors. But very often people cross some threshold and think they're just an investor like everybody else. And so one of the things that I try and encourage people to do is to play off their strengths, even though they need a new set of disciplines as a diversified investor. 


    Anastasia Koroleva: [00:17:41 - 00:18:02]

    Lots of exited founders from the tech industry tend to jump right into angel investing. And if you talk to them about it, they often say that they feel they actually have competence in there, yet they statistically get burnt a lot. What is your view on such strategy? 


    Michael Sonnenfeldt: [00:18:02 - 00:18:40]

    Well, it's the misassessment of risks, because a particular tech investor might have had a software genius around a particular process and was able to build an incredible company around that. And it seems so natural. And they are in denial about how lucky they were. It's just in the nature of human nature, particularly people who've had success have good reason to believe that they have superior skills. It's just not always the case. 


    Anastasia Koroleva: [00:18:40 - 00:18:49]

    Yeah. So generally, how do you feel about things like angel investing as a path for people who just exited their businesses? 


    Michael Sonnenfeldt: [00:18:49 - 00:20:45]

    I have a bias because I'm now running a venture fund. When I was making venture investments as an individual, or I had one person helping me, I was totally ill equipped to assess companies because there's so many elements in a company that you have to assess. You have to assess the market, the management, the science, the product, the competition, how long it'll take to scale. Individuals who can follow a rigorous, well informed process of investing will generally, not always the world isn't perfectly round, have superior returns to people who just throw money or darts at the wall. One of the biggest mistakes in angel investing is that people are willing to dramatically overpay or overvalue a prospect because they say either it's going to be wildly successful, in which case if I overpaid a little, it won't matter, or it's going to be a failure, in which case, if I overpaid, it doesn't matter. 

    The purpose of my comments are not to dissuade people from being investors after they're entrepreneurs, but rather to appreciate how difficult investing is and if they can put in the processes themselves, which is very difficult, they'll increase their odds of success. And absent them having the skills or the time or the staff to do it, investing with firms that do have those processes and experience will increase the odds of success. 


    Anastasia Koroleva: [00:20:46 - 00:21:09]

    So given that exited founders usually lack the skill to invest their wealth. How should we go about putting together a wealth team to support our efforts? In what circumstances building a family office is justified and when we should really just invest a little bit of time into learning to do things ourselves? 


    Michael Sonnenfeldt: [00:21:09 - 00:23:28]

    Family offices really have at least two very different functions. One is managing wealth, and the other is providing services. Family offices, as a rule, need a minimum amount of capital. There's exceptions to every rule, and there's no question that somebody could create what you would call a family office if they had 30 million or $50 million. But in this day and age, family offices tend to begin at the 200 million dollar range. 

    Literally 20 years ago, it was closer to 100 million. But today, you'll find that most family offices are starting in the 200 and 5250 range. And if you have less capital than that, it's very hard to justify creating a family office. And above that amount of capital, unless you're willing to develop unique skills, it's hard to justify not giving the money to institutions that have deep benches of talent and can diversify. So it really depends what you want to do. 

    The happiest person could be somebody who's had a liquidity event and been lucky enough to make many hundreds of millions of dollars. I know this is rare air, but still has no family office because they've entrusted the money to some of the world's best managers, and they're playing golf or sailing or engaging in philanthropy or doing whatever they want to do. So this really goes back to that foundational question of, what do people want to do? But there's plenty of evidence that many family offices have no economic justification because they can't perform as well as the professionals, and they're doing it at a much higher cost than you would pay professionals. So my bias would say, in the absence of any information, don't create a family office unless you have an appreciation for how much work it will be. 


    Anastasia Koroleva: [00:23:29 - 00:23:49]

    You obviously achieved amazing feats in your life. You started businesses, you built businesses, you built communities, you created incredibly beautiful art. You dedicated your time and energy to philanthropic causes. I really want to understand what drove you through the years and how your motivation changed over time. 


    Michael Sonnenfeldt: [00:23:49 - 00:24:27]

    In some sense, I'm a product of what's called survivorship bias, meaning for every five or ten people who had the same talent and maybe aspirations and creativity, not all of them end up equally successful. And sometimes that's just luck. But obviously, luck favors those who are prepared and willing to take the risk. So sometimes being willing to do something creates your own luck or creates your own wind is what you. 


    Anastasia Koroleva: [00:24:27 - 00:24:28]

    Absolutely. 


    Michael Sonnenfeldt: [00:24:28 - 00:24:55]

    The thing that always excited me was creating things. It's being in the act of creation. That is what motivates me almost more than anything else. And sometimes it's because I can solve a problem by doing something. And sometimes I can at least try to solve a problem by doing something. 


    Michael Sonnenfeldt: [00:24:55 - 00:27:36]

    So, as an example, today the most constant activity in my life is building a climate fund. And I now have a team of seven incredible people, six in addition to me. And obviously, this is the defining issue of our time. You asked what had changed. And I think when I was growing up, I was just raw ambition. 

    I didn't have a plan per se. I didn't have a particular. It wasn't like I was a tennis player and wanted to be the greatest tennis player in the world. And that would take 20 years. I just had a sense that I wanted to be successful. 

    Maybe it was in the finance area, but I'm not sure that I had clarity about even what that would mean. But there was a raw drive to succeed, you know, one of the things that we focus on in Tiger is all of the reasons children grow into successes. The most common reason is that there's a problem that they have as a child. It could be ADHD, it could be being on the spectrum. It could be a physical issue. 

    It's amazing how many polio survivors from a very long time ago were driven to be successful because of a childhood wanting to show that it didn't stop them from being successful. So among our tiger members, we have people who had extraordinary challenges when they were young or came from abusive parent relations or divorced parents, drug addicts. More often than not, it's not always the case, but more often than not, successful entrepreneurs, as opposed to other areas, because what distinguishes the successful entrepreneur is their ability, quote, to do it on their own. They very often can't fit in an institutional setting of any sort, but they can create something in their own image that plays to their own strengths and maybe their own weaknesses. In my case, when I was, you can see I'm wearing this little gadget, which is an implant in my brain or on my brain. 


    Michael Sonnenfeldt: [00:27:37 - 00:28:52]

    About six months ago, I started hearing in my left ear for the first time in 63 years. I had an ear infection when I was three, and that not only lost my hearing, but it meant when I went swimming, I had to wear a dunce cap to protect no water in my ear. And I really looked like a ridiculous clown with that dunce cap on. And I'm sure it made me very insecure. And I also had a lot of speech issues. 

    Lisp, ssh jrwch. They're all part of a class of speech issues. I don't think I have a list. Now, my family says that when I'm tired, they can hear a wisp of a lisp. But I'm highly sensitive in hearing it in other people because I spent so many years mostly correcting it that when people have a lisp, I have some compassion. 


    Michael Sonnenfeldt: [00:28:53 - 00:29:04]

    But I also wanted to say you could have fixed that if you worked hard enough. That may be a little insensitive sometimes, but I'm just super aware of it. 


    Anastasia Koroleva: [00:29:04 - 00:29:46]

    You mentioned luck, and that's something that I spent a lot of time thinking about and discussing with fellow exited founders. So I agree with you that luck is absolutely always there when we build a business. But there is a problem that I've observed with attributing all your success to luck or other external forces. Because basically what happens when we sell our business, we finally have the luxury of time and wealth to do proper introspection. And this is when all our insecurities ambush us and many of us end up suffering from imposter syndrome or guilt. 


    Anastasia Koroleva: [00:29:46 - 00:30:16]

    And when I tried to dig into this in myself, I came to the conclusion that it's extremely important to attribute your success in such a way that it's empowering for you that you actually have confidence as opposed to all these insecurities. So I would love to hear your view on this, how you attribute luck in a way that you keep your humility and honesty with yourselves, because luck definitely is there without creating this insecurity. 


    Michael Sonnenfeldt: [00:30:17 - 00:32:45]

    First of all, there are many different flavors of success. Most Tiger members, simply by accomplishment, are one in 10,000. I don't have any belief that whatever success I've achieved is simply because of luck. But to deny that luck played a role would be foolish. In my case, I have certain skills. 

    The things that I've been successful at in the business world, I pretty much lost money until I made it, meaning I was willing to suffer losses for two, three, 4, 5, 20 years, and only at the end did something happen that allowed me to do it. Not many people have the fortitude to suffer losses. While I'm not a great manager, I am a fountain of ideas. So where I can harness my idea generating ability, I can't be sure which of my ideas are good ideas or bad ideas. It's hard to self police. 

    It's hard to be the one who's creative and have the clarity about which are the best ideas and if I can throw ten great ideas in and have a team, say of the ten, this is the best one, and then we execute on that one. That's a much more efficient process of. And it's why so many businesses do have partners. There are obviously exceptions to the rule, and there are people who have different type of skills. But the one that comes to mind is in the fashion business. 

    Very often you have a Ralph Lauren as an example, who has a business partner you've never heard of. But that person apparently is as important to his success because that person is translating his endless creativity, discipline, willingness to put off gratification for a long period of time, and finding a way to channel creativity into operational success with a little luck probably is the key ingredients. 


    Anastasia Koroleva: [00:32:46 - 00:33:49]

    I completely agree with you about the necessity of delayed gratification, but there is an interesting phenomena that happens once you've sold your business. Many of us find ourselves traumatized by years and years of responsibility for our employees and for our partners, by the way. And we don't want to repeat that again. We want things to be easier next time. And what I noticed is that lots of very capable people stop creating value, which is probably what they were sent to this planet to do in the first place, just because they are so traumatized by the idea of having that responsibility again. 

    Or also many people are traumatized by their partners. They end up with lots of arguments during the liquidity event discussions, and then they just don't want to do it again. I made that mistake as well myself. I tried to do it alone, and then I found myself very lonely in my new business. But I would love to hear your perspective on that. 


    Anastasia Koroleva: [00:33:50 - 00:33:53]

    How to overcome that. 


    Michael Sonnenfeldt: [00:33:55 - 00:34:46]

    I sold my first really successful business when I was 30, and my brother predicted that I was a one trick pony. And he lamented that my life would be cresting at 30 and it would be downhill from there because I had this really spectacular success. And he predicted I would never do that again. Most entrepreneurs are lucky enough to do it once and a much smaller number do it twice, and an even smaller number do it multiple times. As I said before, the same sets of skills, ambitions, disciplines, intellect. 


    Michael Sonnenfeldt: [00:34:46 - 00:38:52]

    Without luck, the same person the second time may not be as lucky as the first, even though the effort might be as good. But particularly if you have early success, if you're young, you really have no idea whatsoever what allowed you to be successful. You don't know the limits of your talent. And it's all too easy to assume that when you've had an early success, you'll just be successful again and again. And you march into the second venture not really appreciating the specifics of what allowed you to be successful the first time. 

    Sometimes it's as simple as just not knowing. That's what happened with me. I had this enormous success that as my first project to create the largest commercial renovation in the country, which I may be in the world at the time, which I at 25 thought was the natural order of things, that would be my first project, and I assumed that it would be easy to do it again. So I started another business. And that business was a spectacular failure. 

    And it was only through that second business that I was really ready to understand who I was. Because now I knew something about my best skills and my biggest liabilities, and I didn't repeat that mistake again and was able to have an even bigger success the third time around. Failure is a large part of success. When I hire somebody in a senior operating role, if they haven't failed, I'm not really interested in hiring them, because it's only through failure does one really test the limits of where their best skills can be deployed and where the liabilities they have that should be avoided. But this issue about post liquidity careers obviously is a changing one. 

    A generation ago, people generally had a level of success that I think we're talking about much later in life. The world has changed. And so part of the issue is when you're 59 and you sell a business, you used to be more retired. But when you're 36 and sell a business now, all of a sudden, the notion of retirement is no longer quite as appealing. So one of the reasons there's a lot more people trying new businesses over and over again is we have an economy that allows businesses to scale quicker and people to sell them. 

    There's nothing embarrassing about having good luck. Some people are more successful than others, and some are luckier than others. So when you look at Tiger members as an example, some of the successes that people have had, you have a sense, were because of a kind of extraordinary, unique insight, or a kind of organizational or organizing ability or a kind of brilliance. And others, you have a sense they were a little more at the right place at the right time, and they got lucky. The world isn't perfectly round, so it doesn't mean that the first type of people are automatically going to be more successful. 

    They may be a little more likely, but one of the things that happens with people who are very lucky is a small portion of them learn something that becomes reproducible. 


    Anastasia Koroleva: [00:38:54 - 00:39:20]

    When you advise someone who just exited a business if they asked you, in what priority should I follow things? For example, should I take a break? Should I go deep and in introspection to analyze what happened to me before? Because obviously, we have no time to do it when we are building the business. What would be your advice? 

    To jump straight into action again? Or rather, take the time to think. 


    Michael Sonnenfeldt: [00:39:21 - 00:39:46]

    If you imagine a white laser light, that's like a laser. Like an entrepreneur focused on a single thing. The laser light hitting a prism and coming out a rainbow. The prism is that moment of liquidity. And the rainbow is all the possibilities that comes out of the sale. 


    Michael Sonnenfeldt: [00:39:46 - 00:40:37]

    And what comes out in that rainbow are both problems and opportunities. Anybody who doesn't take the time to sort of disaggregate that single entrepreneurial experience into the rainbow of possibilities is generally doing themselves a disservice. Entrepreneurs, as you say, very often can't be introspective while they're in the act of working 60 hours or 80 hours a week. The indignity of having to wait online to get your own coffee after you've had 1000 people working for you, and the fact that there's nobody laughing at your jokes anymore because you don't have any employees, is both frightening for some, but an extraordinary opportunity for others. 


    Anastasia Koroleva: [00:40:38 - 00:40:54]

    People who did it successfully in the sense that they ended up building a fulfilling lives for themselves and making meaningful impact in the world. Do you see any patterns, what it is they did that others didn't that brought them there? 


    Michael Sonnenfeldt: [00:40:54 - 00:41:47]

    Sometimes you hear people say, well, I'm not very philanthropic because I had such an impact employing people or providing products and services. But I think impact also has to do with gratitude, which is such a key part of a person evolving, for lack of a better way of saying it. I think there's a difference between somebody making a fortune, providing even excellent quality services, and employing people, but keeping all the benefits of that for themselves. That's different than the same exact example where somebody takes those financial benefits and tries to make a philanthropic impact out of a sense of gratitude and wanting to give back. 


    Anastasia Koroleva: [00:41:47 - 00:42:36]

    There is this interesting idea in the ancient indian Vedic scriptures that we can only judge a person based on that person's intentions, never based on the results of that person's actions, because that's out of that person's control. So, to me, for example, when I think about impact, I usually use that mental model, because I think, okay, if someone goes into business with the intention to solve an important problem, and it's a big problem, and they do it through business, because that's their skill. That's how they can make the most impact. For me personally, it's good enough. I don't need them to necessarily achieve a purely philanthropic result. 


    Anastasia Koroleva: [00:42:37 - 00:42:59]

    And some of these people, I noticed, they also end up working on venture philanthropy, which I think is quite a big trend now, which I think is quite interesting. This is how these people try to combine philanthropy with business. I'd love to talk to you about this, because I'm also very actively looking into venture philanthropy as an activity. 


    Michael Sonnenfeldt: [00:42:59 - 00:43:59]

    I have a particular interest in the intersection of politics, philanthropy, and investment. And what I mean is that in the was interested in international security as a way to educate myself and philanthropically support some activities. And I led peacekeeping inspection teams around to 28 different war zones, as I was also doing some shuttle diplomacy back channel in the Middle east. So I make no judgment about people who have entrepreneurial success in one sphere and then are philanthropic in another. But after 9/11, I started thinking that I hadn't been as successful with my Middle east diplomacy as I had wanted. 


    Michael Sonnenfeldt: [00:43:59 - 00:45:33]

    So I decided a few years later to tackle something a little easier, which was climate change, what I'll call my climate portfolio. I run a venture fund for climate in the last year. In the last couple of years, we created or funded the Yale Environmental Law Clinic, the environmental Protection clinic at the Yale Law School, and funded the creation of the School of Sustainability and Climate change at Bengorian University in the Middle east in Israel. The third initiative would be at MIT, where I'm the co chairman of the Climate Pathways Project. And politically, I've been involved with campaigns around climate as well. 

    We're going to have to rewire the planet over the next years. If we're going to solve climate, we'll spend more money rewiring the energy complex and turning it into an electric distribution system. You could do in medicine. You could imagine people investing in new age drugs, funding research at universities, and figuring out what policies are most conducive. I'm not unique, but I'm lucky enough to be part of a group of people who are pursuing these three initiatives and trying to make one plus one plus one equals five or something. 


    Anastasia Koroleva: [00:45:35 - 00:45:43]

    So basically you choose to do venture philanthropy as opposed to impact investing, which is much more common. 


    Michael Sonnenfeldt: [00:45:43 - 00:48:42]

    I think another term which is used is concessionary finance. There are some people who will take below market returns in investments because of the impact those investments will have. I found that to be a slippery slope, because when you're harnessing people to make investments, if you're not trying to figure out how to maximize return within a legal framework. I'm not talking about theft or pollution. I'm saying within a framework, then the best power of a capitalist system to have the best players who perform the best rise to the top, can be lost. 

    So I had owned a solar lighting business and tried to do just what you were saying, which is to give our solar lights in an emergency setting. I was running a business, and I was trying a business model that said, let me sort of pay it forward. I'll make these contributions, and maybe that'll motivate our employees to feel elevated, and maybe it will bring aid agencies to understand the power of what we're doing and order more lights, more solar lights. It didn't work. My observation was, in many companies that have a large working class population, people's concerns were putting food on the table and shelter. 

    And some of these broader concerns were not as uplifting to some of our employees, understandably, because they had much more immediate concerns. But I didn't get a sense that this lofty purpose I was trying to imbue in the company was being translated into any superior performance. Ideally, you'd like a greater purpose to motivate people, but in the climate business, we're not willing to accept submarket returns. It may happen, but we don't invest because in order to attract capital, we have to have returns that will allow capital to come. Sometimes I say, who am I kidding? 

    Because I pretend I'm not into concessionary finance. So I work like a dog to maximize returns, but then I give away a lot of money. And if you combine the two, you effectively have concessionary finance. We don't have access to capital that I'm aware of that is willing to take a lower return. So we have to be pretty disciplined about what we'll invest in. 


    Anastasia Koroleva: [00:48:43 - 00:49:03]

    If I think about it, as a person who is considering investing into one of those funds, I would really want to see that it's a sustainable business, because I wouldn't want it to disappear tomorrow. At what point in your life did you discover philanthropy and why? What triggered it? 


    Michael Sonnenfeldt: [00:49:03 - 00:49:14]

    My father was the chief interpreter of the Nuremberg trials after World War II for the american prosecution at the age of 23. 


    Anastasia Koroleva: [00:49:14 - 00:49:15]

    Incredible. 


    Michael Sonnenfeldt: [00:49:15 - 00:51:07]

    It's an incredible story. And in a sense, he did that as a public servant. One of the things that happened is I was very lucky to be successful in my twenty s. And when I went around the world, I started traveling quite a bit. I noticed that in certain countries, people were not as surprised by my success. 

    As they were, that there was a country where a young man could achieve so much success. My philanthropic activity really came about because I was profoundly aware of how lucky I had been. Didn't mean I didn't deserve the success. It was more important for me to establish my identity as someone giving back. I've not been immune to acquiring wealth, but I'm actually more interested in starting things, the act of creativity. 

    And that's been much more important to me psychologically than any particular amount of money that I've created. And I found that when I was thinking about my identity, I really wanted to give back in a way that not only reflected the success that I had achieved, but also gave me another outlet to be creative in thinking about creative acts of philanthropy, of being a venture philanthropist, starting new philanthropic activities and watching them sprout and have an impact as well. 


    Anastasia Koroleva: [00:51:08 - 00:51:15]

    So today, your identity is linked to your philanthropy more than anything else. 


    Michael Sonnenfeldt: [00:51:16 - 00:51:36]

    Just like you don't see the foundation of a building when you look at a beautiful building, and yet it's as important as the part above the ground. A lot of my philanthropic activity is sort of foundational to who I want to be. 


    Anastasia Koroleva: [00:51:36 - 00:51:54]

    So would it be correct to say that for you today, it's very important to keep doing what you love, which is being actively creative, right? Including through your beautiful art, which I can't wait to talk about, but at the same time, to feel that you are giving to others. 


    Michael Sonnenfeldt: [00:51:54 - 00:53:20]

    My father grew up in Germany, and Europe has a more socialist bent than the United States in the world he grew up in. Being a good citizen meant you obeyed the law and paid your taxes. But the state created the museums, the state created the hospitals. So, first of all, we grew up in a different time and a different place. I've had the good fortune to have the resources to do that. 

    But there are many people who volunteer and do incredible things with their volunteering. I'm just trying to figure out where a certain amount of energy and a certain amount of dollars can have the biggest impact. So, in that sense, I am on a search for impact that's different than when you use the word impact investing, which has a lot of. But just to be vital and to be impacting the world, I'm indifferent right now at this point in my life, between philanthropic activities and money making activities. Other than that, I have a fiduciary responsibility, both to myself and to my partners, to be very mindful of the dollars that we risk. 

    But emotionally, there are times where I feel I've had an even bigger impact in the philanthropic world. 


    Anastasia Koroleva: [00:53:21 - 00:53:23]

    Do you give money away to charity organizations?


    Michael Sonnenfeldt: [00:53:23 - 00:53:24]

    Every day. 


    Anastasia Koroleva: [00:53:24 - 00:53:43]

    How do you think about it comparing to your own philanthropic activities? Because some people are saying, we only want to do it ourselves. And I think part of it just comes from the fact that most of us entrepreneurs are control freaks by nature, and we simply don't trust somebody else do it for us. 


    Michael Sonnenfeldt: [00:53:43 - 00:55:12]

    In many cases, I'm donating to organizations that I'm involved with personally and have a deep connection to the people running it or the board or whatever. So there are times where your donation is either anonymous or one of many, where collectively you're achieving something with others that you can achieve on your own. And some people are content with that type of philanthropy, and others, for good or bad reasons, want to be more in control. When I say good or bad reasons, there are times where somebody can spend a small amount of money and have an extraordinary impact because of their entrepreneurial skills. But frankly, there are also times where people's egos have them believe that by doing it on their own, they'll be more effective, and the money would have been much better spent in collaboration with others through an existing institution. 

    And there's no rule, it's a case by case analysis. But there's no question that in some cases, people are starting their own philanthropic activities more out of ego than an assessment. But in other cases, because they did that, they've made a huge outsized difference. So it could go either way. 


    Anastasia Koroleva: [00:55:14 - 00:55:33]

    You mentioned before that you think an exited entrepreneur should take two, three years to do some introspection, to understand themselves and the world. And I also know that you've traveled a lot around the world. Would you recommend those people to go and see other countries and experience other cultures? 


    Michael Sonnenfeldt: [00:55:33 - 00:56:22]

    Well, I always recommend seeing other cultures, because the more global the world has become, the more necessary it is to appreciate the breadth of the world. Very few people really have a sense of the breadth of the world, but there are some people who choose not to travel, and they can lead perfectly healthy lives. But I think the act of seeing other countries and other cultures and trying to place your country and your culture in a context, a global context, is a really mind expanding, healthy thing. 


    Anastasia Koroleva: [00:56:22 - 00:56:26]

    Tell me about your art, your photography and fashion. 


    Michael Sonnenfeldt: [00:56:26 - 00:57:58]

    I've been interested in photography pretty much my whole life. My father was into photography. It's not a coincidence that I'm into photography. I was the photo editor of my high school newspaper in my 20s, late teens, and spent a lot of time behind the camera, just at family events and so forth. And I got married, and one day I was at a family event and realized that I was hiding behind the camera and put my cameras down for many years. 

    I didn't really pick up photography in any meaningful way until my older son started playing first hockey and then lacrosse, and he was a champion lacrosse player at Princeton. In the United States, all college sports are regulated, so parents are not allowed on the playing field. The only exception is if the parent is an officer of the university, meaning a coach or something. So Princeton was kind enough to name me the official volunteer photographer of the lacrosse team, allowing me to be on the team. And for those four years, I filmed every game and then ultimately produced four books from it. 


    Michael Sonnenfeldt: [00:58:00 - 00:58:44]

    And it was that expression of 10,000 hours of doing something. When I think of the confidence I had by the end of those four years, compared to, I had never been really a sports photographer. At the beginning was just a personal journey and a delight, but that morphed into an interest in collecting photography. And over the last decade, I've been building a large photographic archive that now has sort of blossomed into activities. I'm here in London. 


    Michael Sonnenfeldt: [00:58:44 - 00:59:40]

    I have a show right now going on in Madrid with one of our artists, Deborah Turboville, and we just have a new book that we've published that the book party is in Paris in November. The photo work that I do now has a particular passion for a gap in the photo world. What happens to estates of important photographers after they pass on? And for a very small number of the very, very best photographers, their work is of such immense value that it can support a foundation like the Richard Avidon foundation or a few of the other great photographers. But just below that, you have many great photographers who might not have been great business people. 


    Michael Sonnenfeldt: [00:59:40 - 01:00:19]

    And when they die, their entire estate is in limbo, and their family doesn't know what to do with it. And museums no longer have the budgets to be able to acquire or manage those estates. And so we've created an archive that acquires estates of photographers. It took until just now for us to be able to begin a series of shows and books, because it took that long to really disentangle what was just a hornet's nest of materials that are now organized into a professional archive. 


    Anastasia Koroleva: [01:00:20 - 01:00:24]

    Would you say art is your source of fulfillment in life? 


    Michael Sonnenfeldt: [01:00:25 - 01:00:58]

    I wish I could, but I would say that the philanthropic activity and the acts of creativity that I talked about more touch something fundamental for me that's more exciting to me than collecting something. And I love collecting, but being able to create something speaks a little bit more to my passion. 


    Anastasia Koroleva: [01:00:58 - 01:01:11]

    Because when we first met, after maybe two minutes, you were talking about your art and showing me how you created it, and it was beautiful to watch. Your eyes lit up and I was really impressed. 


    Michael Sonnenfeldt: [01:01:11 - 01:01:15]

    I was hoping it was in response to a question you asked me rather than just blurting it out. 


    Anastasia Koroleva: [01:01:15 - 01:01:36]

    But no, it felt very natural and organic. But I had watched quite a lot of videos with you before I met you, and my impression was of very serious investor and businessman. And then I meet you in real life, and you are this amazing artist who has beautiful stories and incredible. 


    Michael Sonnenfeldt: [01:01:36 - 01:01:40]

    I think I was comparing my outfit to the beautiful outfit you were wearing. 


    Anastasia Koroleva: [01:01:41 - 01:01:53]

    Probably yours was better, I'm sure, much more interesting. So what is your plan for your art? Do you have a plan to turn it into a business as well? 


    Michael Sonnenfeldt: [01:01:53 - 01:02:27]

    Absolutely not. I know how to lose money in businesses, but I don't want to start an art business and lose even more money. My greatest pleasure is when I'm able to create, in the area of clothes, something that another person that I like will wear. A number of japanese artists whose work I collect wear some of my shirts, which gives me extreme pleasure. 


    Anastasia Koroleva: [01:02:27 - 01:02:35]

    I'm sure lots of people would love to wear things made by you, but you're not really sharing. Yeah, not yet. 


    Michael Sonnenfeldt: [01:02:35 - 01:02:35]

    Right. 


    Anastasia Koroleva: [01:02:37 - 01:03:10]

    I would love us to talk about the loneliness that exited founders often feel after they exit. And a few years ago, you published a book called Think Bigger, which I thought was incredible. And in that book, you are talking about how relationships are affected deeply. When somebody has a singular success in their social group and nobody else has that success. I'd love to hear more about it. 


    Michael Sonnenfeldt: [01:03:10 - 01:05:09]

    Success and wealth, particularly created wealth, can be very isolating. You're thrust into a world that you were not familiar with. Most people who have entrepreneurial success don't really fully enjoy the benefits of the wealth they've created because it's not free and available. It's tied up in the business until there's a sale, and then all of a sudden possibilities open up. And it's very hard to exactly find the right balance, even in terms of what you want to spend or do with your capital. 

    But all of a sudden, it's sort of like a horse pulling ahead in a race and very often leaving the other horses behind. All of a sudden you can afford things that nobody else that you know can afford. Now, obviously, different communities have different comparative wealth. So if you created your wealth on Wall street, you probably are one of many who've created similar wealth. And the act of wealth creation is very different because you're sort of in the same cohort before and after. 

    But if you grew up in an isolated town and you're the one person who started a business that became phenomenally successful, it's not only isolating, but you have to engage in behaviors that, while being sensitive to your other friends means you're not going on the trips that you could afford unless you're paying for other friends to do it because you don't want to make them uncomfortable. It's very difficult to find the balance of how do you enjoy the wealth that you've created without alienating friends and family who are in a different situation. 


    Anastasia Koroleva: [01:05:10 - 01:05:11]

    So what's the solution? 


    Michael Sonnenfeldt: [01:05:11 - 01:06:02]

    Being sensitive to the fact that when you have different resources than other people do, it's not exactly possible. In other words, if you come to my apartment, obviously the apartment I live in is different than the apartment I would be living in if I didn't have the success that we've had. But there's a way to include people in your wealth where they feel embraced. So sometimes it means being the host for a trip that friends or family couldn't take on their own. It's very circumstantial, but clearly it starts with some sensibility about your good fortune and not wanting to make others feel uncomfortable because of it. 


    Anastasia Koroleva: [01:06:02 - 01:06:28]

    I've observed that when we build our businesses, we tend to want more and more of everything. More money, more success, more attention, more people. Once we've sold the business, a shift happens, and we often want less. We become very picky with whom we want to spend time, with, how we spend our energy, what we invest in. Is it your observation as well. 


    Michael Sonnenfeldt: [01:06:28 - 01:07:17]

    When you are so focused, as many, but not all but many people are on creating success? You don't want to be distracted, both for the good and bad, by things that might be getting in the way of your success. Unfortunately, sometimes marriages fail, children's relationships are put on hold, relationships with parents, brothers and sisters, friends, health, physical health, mental health. All of these things, in variations, can be subordinated to the singular goal of success. But once you've had the sale, you now have time to be looking at all of those. 


    Michael Sonnenfeldt: [01:07:17 - 01:07:48]

    And that may seem very picky, but it also could be discerning. So there's two different sides to the same coin. But people naturally can be spoiled and can have unrealistic expectations. And when you have great wealth, sometimes you can indulge those unrealistic expectations without realizing how far afield you've come. 


    Anastasia Koroleva: [01:07:48 - 01:07:57]

    But do you think that also, when we satisfy our desires, especially for material things, we just stop enjoying them anymore. 


    Michael Sonnenfeldt: [01:07:57 - 01:09:17]

    So I think it's sort of an issue of personal evolution of what's important. As people become more successful. A lucky few realize their time is worth more than their money. But most of us are tyrannized by the fact that our money is worth more than our time, particularly with people who've been very successful, who might have come from much more modest beginnings. Sometimes it's hard for them to spend money on things that in the scheme of things, if they spent the money, they might be able to spend a day with their children. 

    But it can all be a trap as well. My point is that very often when you're single mindedly focused on creating wealth, the meaning of it and the ways in which you might spend it, you're not spending a lot of time thinking about. And as you begin thinking about it, what you realize is, for many, the creation of wealth was an illusion that is shattered, not because you don't have the money, but because the money isn't buying you any more fulfillment or happiness. 


    Anastasia Koroleva: [01:09:18 - 01:09:36]

    So when we find ourselves more successful in monetary terms than our family and friends, we inevitably start getting requests from them for money and investments. And, you know, in the Tiger community, it's one of the most common question, how do you say no without damaging the relationship? 


    Michael Sonnenfeldt: [01:09:36 - 01:09:43]

    Actually, that's the reason we created Tiger, so that you can say to your family member, my group won't let me invest. 


    Anastasia Koroleva: [01:09:43 - 01:09:45]

    I didn't know that. 


    Michael Sonnenfeldt: [01:09:45 - 01:12:06]

    In a trading business, sometimes young traders are given money that they're likely to lose, but the learning from it will make them better traders later on. It's very difficult, particularly in family matters. But each family is different when one person is incredibly successful to understand what your responsibility or obligation is to the rest of your family. And there's no absolute because different societies have completely different rules. So envy is almost one of the most basic human emotions. 

    I would be inhuman and lying to you if I denied that I was envious of some others, and I would be blind if I didn't see that some people are envious of me. And it's very easy to blind yourself to both of those realities. And when you can appreciate both of them, it allows you to be a little more realistic in your assessments of relationships and responsibilities. If my success is luck, do I deserve it and can I keep it? Or do I have to share it because I was the one who got the luck on behalf of my family? 

    If I believe that my success is only because of my hard work and I deserve every penny of it, whatever that means. Some people become very constricted and parsimonious. Others would say, well, even if it was because I earned it, I was still lucky to have had the skills that allowed me to be able to earn it and are more willing to share. But this issue is constantly evolving. It's very difficult to exactly find the right balance. 


    Michael Sonnenfeldt: [01:12:07 - 01:12:43]

    I think the people who think about these issues are trying to balance even when they want to be generous with when is certain types of support enabling bad behavior, because it can breed a kind of dependency. And how do you balance your desire to be generous without wanting to somehow enable bad behavior? It's a very difficult balance to find. 


    Anastasia Koroleva: [01:12:43 - 01:12:46]

    How to not spoil children with wealth. 


    Michael Sonnenfeldt: [01:12:47 - 01:14:50]

    Love them, when wealth is a substitute for loving involvement with children, many parents think by showering kids with gifts or toys or cars or clothes or trips that that makes them a good parent. In the end, most kids want contact with their parents. And I think that if parents create an environment in which kids can flourish and feel that their parents are a meaningful part of that flourishing, that the wealth aspects are relatively less important. That doesn't mean children who have, obviously children at any economic level can have loving, involved parents. And at any economic level, those children that have loving, involved parents, on average, will do better than those who do not. 

    One of the really amazing things one Tiger member said was, I'm not giving my kids anything. And I thought, oh my God, here comes another story about how hard it was for me to earn money and I want to make it just as hard for my kids because otherwise they won't ever fulfill themselves. But as I was thinking about that in my mind, he said, no, you don't understand. I'm not going to give my kids anything, but I'll invest everything in them. And I think while it's not a perfect way to think about it, the notion of investing in children's futures is very different than just allowing them to be part of the lucky sperm club that inherited this extraordinary wealth. 


    Michael Sonnenfeldt: [01:14:50 - 01:15:14]

    And I think also imbuing in kids a sense that if they inherited wealth, it comes with responsibility, not just to manage it, but to give back to society from which the wealth was created. I think those are important aspects of a healthy relationship with kids and money. 


    Anastasia Koroleva: [01:15:14 - 01:15:32]

    So there seems to be two popular school of thoughts on the subject. One is to get the children involved as early as possible, prepare them for the inheritance. And the other one is actually not even telling them that they have money, so they don't expect anything. What's your view? 


    Michael Sonnenfeldt: [01:15:32 - 01:16:29]

    Just anecdotally, about 70% of Tiger members tend to want to be less disclosing with their children for fear that if their children knew the extent of their wealth, it would demotivate them and they wouldn't have the chance to struggle and succeed. And about 30% believe that if there's significant wealth, the sooner you start teaching kids to be prudent stewards of the wealth that they will inherit, the longer you have to work with them to transfer skills and knowledge and to prepare them for the responsibilities that wealth creates. I'm in the latter category, not the former, but I respect both views. 


    Anastasia Koroleva: [01:16:30 - 01:16:33]

    How do you select people you want to surround yourself with? 


    Michael Sonnenfeldt: [01:16:33 - 01:19:58]

    So no human is an angel? And even the biblical figures were deeply flawed. There were liars and adulterers and who knows what. Some people are not value driven per se, and they hang out with people who they just have an attraction to for some reason or another. I happen to admire creativity. 

    Number one, I would like to think I'm more, rather than less attracted to people who've done some kind of personal work to understand purpose and meaning. I'm not attracted to people who say one thing and do the other. If you're too discriminating, you'll have no friends because nobody can meet any standard that you set. There's no perfect human being. Everybody has shortcomings. 

    And if you're interested in surrounding yourself with people of high quality, high morals, what you'll find is everybody's made a mistake, including me. I'm a curious student of the human condition. I've been in a situation where people who I have the absolute highest regard for because of their philanthropic activity, the type of parents they are, the type of community members they are, the type of leaders they are. Every once in a while, I find that they've done something that either is shocking to me or surprising to me. And you have to say they're human, what came out of it. 

    But if you're not trying to be discerning about people, you're just going to hang around with a bunch of creeps. I would say that I'm aware of the qualities, and I'm interested in the qualities of most of my friends. They're very different. I probably have more entrepreneurs as friends simply because the journey that we share of the kind of risks and rewards are different than others. But on average, I'm more attracted to people who want to make a difference. 

    I like nice people. I probably am more attracted to people who are nice, even though nice was not in the lexicon of what I grew up. I grew up in a world where nice guys finish last. That was the expression. And very often if somebody would say, are you happy? 

    Like, happy, what the hell is being happy but fulfilled is a form of happiness. And within some bound, I'd like to judge people less, not more. I think most of the people that I spend most of my time with are people of very high character who want to give back to society and do it in immensely creative ways. 


    Anastasia Koroleva: [01:19:59 - 01:20:04]

    But it also sounds like you've become more forgiving and accepting of other people over time. 


    Michael Sonnenfeldt: [01:20:05 - 01:20:15]

    You'd probably have to ask my wife or family members whether that's in fact the case, but that's what I feel. 


    Anastasia Koroleva: [01:20:15 - 01:20:21]

    So you mentioned meaning and purpose. What do these words mean to you? 


    Michael Sonnenfeldt: [01:20:23 - 01:22:12]

    I like both of those words. I'd like to live a life of meaning and purpose, like to make a difference, but I also would like to like life. In other words, when I'm a meditator, I meditate in the morning most mornings, not every morning. I'm not sure there's any quote, meaning or purpose to meditation, but it clears my head and gives me a perspective and accesses a part of my brain that sometimes I lose touch with. Very similar to people getting idea in the shower because the water and the hot water and being alone and allows things to pop into people's heads. 

    I'm not in any way a religious person, but I do have a sense that every person has potential that is mostly unfulfilled and that the arc of life is to try and understand what that potential is. So when you talk about meaning and purpose, it's very easy to be quite narrow minded and not take the time to look at the broader context. So what looks like meaning and purpose through one lens, when you zoom out a little, could have a little different context. Clearly, those people who are trying to have more meaning and purpose are more likely to find it or enjoy it than people for whom that's not a motivator. 


    Anastasia Koroleva: [01:22:13 - 01:22:33]

    To me, meaning is about this sense of self realization. Doing something that you were designed to do in this world and discovering this is quite a long journey, but purpose is more about what you give to others. 


    Michael Sonnenfeldt: [01:22:33 - 01:24:50]

    Many years ago, we had a member at Tiger who did his portfolio defense, and he was very successful and very wealthy. And he described himself in a way that said, I have so many children. This is what I'm doing. I've had my liquidity event. I'm an incredibly generous person. 

    This is what I'm doing. Da da da da, and going through it. And when he said, I'm an incredibly generous person, an alarm bell went off just because I've sat through a lot of portfolio defenses. And when I saw the amount of money he was giving away in relation to his wealth, it seemed like an incredibly small amount of money. And yet he characterized himself as an incredibly generous person. 


    And I'm not there. People don't join Tiger to be judged. My purpose was not to judge him. So I had the discipline. I thank my lucky stars to know. 

    I'm just curious. You mentioned that you're incredibly generous, so I'm using your words. I'm not characterizing. Can you relate the amount of money that you give away to your definition of incredible generosity? And he said, oh, sure. 

    I give away more every year than my parents gave away in their lifetime. It's an amazing conception. I said, well, just for what it's worth, looking at your financial situation, given that you want to be an incredibly generous person, I'm simply observing you have a lot of financial capacity to give more based on your circumstances. He didn't say much. A year later, he came back for his portfolio defense, and he brought the picture of a building that was now under construction at his alma mater, because he had given in that year a commitment of I don't remember how many millions of dollars that were ten or 20 times what he was giving away annually. 


    Michael Sonnenfeldt: [01:24:50 - 01:25:28]

    My point is, I'm not sure that my life's purpose is to have been fulfilled by that single act. But when I think about the meaning of the impact that organizations like Tiger can have on its members, that's one of 20 examples I could give you, where, by creating an environment where people can explore issues of identity and purpose and meaning, they can realize potential that they didn't know they had. 


    Anastasia Koroleva: [01:25:28 - 01:25:33]

    Is it how you envisioned a Tiger when you just created it? 


    Michael Sonnenfeldt: [01:25:33 - 01:26:52]

    Nobody plants a seed of a tree they're not familiar with. It's one thing if you take an acorn from an acorn tree and you see the tree and you plant the acorn in the same tree. Some variation. But if somebody sent you a pack of seeds from a faraway place, and you planted a seed and you had no idea exactly what it was that you were planting, but you knew it was a seed of a tree and it would grow and you would nurture it, in some sense, it would be unimaginable 25 years ago to think of all of the collective creativity that's come out of the team and our members to create this kind of self creating organism that would be just impossible to have predicted. So many random things have happened. 

    But on the other hand, the vision which permeates it all is the power of peers to learn from one another, and that when peers can share in a trusting environment, extraordinary things can happen. So that part is what I envisioned. The details I had no idea of. 


    Anastasia Koroleva: [01:26:54 - 01:27:10]

    I'm very curious about your marriage, and I wonder what it is you learned from your marriage and through all the different experiences that you have had in life and staying in this union and partnership with your wife. 


    Michael Sonnenfeldt: [01:27:10 - 01:29:14]

    So I'm married 47 years. I think that's a statistical anomaly. I've had the good fortune to have someone who supports me and partners with me and in her own right is a beautiful person. And it's a bit of opposites attract because we're very different people, and yet life is dramatically better because of the different things. At least I hope she feels the same way. 


    We have four kids, and my wife was a much more natural mother than I was a father. She grew up in a family. I like to say, from the neck down, it was all heart. I grew up in a family. From the neck up, it was all head. 

    Our children's connection to us more closely follows in the line of her connection to her parents. We're in many respects incredible partners, and to put up with me for 47 years probably is an act of kindness. But you learn to accommodate over 47 years. There's something that clearly people might learn when they've had failed relationships that they can try better the next time and see if it works. But there's also something that happens in a 47 year marriage of melding and accommodating to one another. 

    That's quite different than serial relationships would afford. 


    Anastasia Koroleva: [01:29:14 - 01:29:16]

    How do you want to be remembered? 


    Michael Sonnenfeldt: [01:29:19 - 01:29:30]

    What popped into my head would be an epitaph of he gave a damn. That would be enough. 


    Anastasia Koroleva: [01:29:30 - 01:29:35]

    Wonderful. Michael, thank you so much for being with me today and for sharing all the wisdom them. 


    Michael Sonnenfeldt: [01:29:35 - 01:29:36]

    My pleasure.


 
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