Are you motivated by love or greed?

investor profile

November 21, 2025

by an investor from Wesleyan University in Dedham, MA, USA

I was sitting with a friend recently who told me about the day a decade ago when he closed out a single trade for his hedge fund that made him $100 million personally. He went on to say that the impact was completely different than what he had always expected, since he had worked his whole life for that day. "I felt a lot worse, not better," he told me. "My anxiety went through the roof." My friend went on to tell me that he is a scientist and engineer, with a thirst for knowledge, so this experience has shaped his life ever since. In one hour on a particular day, when the wire finally cleared for the trade of his life, everything changed, and what he had always thought was the Holy Grail became something entirely different. A problem. Just before he went out and crushed the field in the British Open, Scottie Scheffler, the best golfer in the world, said something very similar: "This is not a fulfilling life. It's fulfilling in the sense of accomplishment, but not in the deepest places of your heart. That's something that I wrestle with daily. It's like showing up at the Masters every year; it's like why do I want to win this golf tournament so badly? Why do I want to win the Open Championship so badly? I don't know because, if I win, it's going to be awesome for two minutes." Honestly, as I mentor CEOs, searchers, men in recovery, and students in my classes, this has been my primary goal, even if it is often hidden like a Trojan Horse underneath all kinds of more mundane information: to try to dismantle the working myth that most young people aspiring to build business careers subscribe to, which is entirely lacking a deeper understanding of why they are doing what they are doing and what it will feel like if they succeed. In my classes, I bring in guest after guest who have been to the mountaintop. I ask each one what they are proudest of in their careers--and these are people with massive resumes, CEOs, senior bankers, big-time investors--and not one talks about deals, money, or their resume. They talk about love. The people. The relationships. I have a love/hate relationship with Scott Galloway. Perhaps due to his modest upbringing, he often overshares about his wealth and material success, which isn't to my taste. But I do like it when Kara Swisher beats him upside the head because, despite his brilliance, she is 10% smarter than he is. But he gets one thing abundantly right: men in our country have lost their way, and that matters not just for the men but for women too, who are their mothers and their prospective partners. The central issue for men in America, particularly our young men, is friendship. I won't go through the data, but suffice it to say, it is heart-wrenching. Men are dying at startling rates from despair, and young men are falling further and further behind. And at its core, all of this is caused by two things: lack of friends and lack of male mentors. We become so focused on climbing the mountain, greed, that we forget why we are doing it. Or for our young men, the hill that society has erected for them looks so impossible, they turn off, go to the basement, watch porn, and smoke pot, at their peril. These angry young men understandably become radicalized in small and large ways and become capable of the unthinkable. This is for young men at all levels of external accomplishment. I have met students who, on paper, look like they have it all, who are still hollowed out and spending way too much time smoking pot and watching porn to numb out the pain. As Richard Reeves has repeatedly pointed out, the script for our young men has been completely ripped up, and even the highest achievers have no idea who or what they are supposed to become. The most straightforward answer is to become an investment banker and aim to maximize the money. I caution my students again and again, listen to the guys at the end of their careers, and what they say. Just like Scottie Shefler, if you get to that mountaintop, it will last 30 seconds, and then what? It will not fill that hole in your heart where love and people reside. Finally, yesterday I found myself listening to my friend Sean McGraw preach on The Parable of the Rich Fool, with the punchline, "life does not consist in an abundance of possessions." I am not a practicing Christian, but I have gained a great deal of wisdom from reading both Christian and Eastern mystics and from talking to Sean. Part of Sean's homily was about the 10th anniversary of the tragic death of a close friend who was a private equity titan. Beyond his business life, this friend was also a man who quietly helped countless people. The homily did not mention his business success. It was about all the people his friend touched and all of their reflections on losing such an important person in their lives, then and now, a decade later. It was about the centrality of love in faith and life. It brought home to me again at an even deeper level how I have found in my own life that humility and love are the answers I have been looking for all along, even as I chased greed and more culturally acceptable forms of success for much of my life, only to end up feeling empty. I was reminded of the day in 1996, when, at 31, I rang the bell at the New York Stock Exchange after taking my company public. It should have been a crowning achievement. But my best friend at the time and investment banker on the deal, Greg Kelly, and I headed uptown afterwards to meet his wife, to play with his kids at the playground. And I realized that absolutely nothing had changed for me. I had done the unthinkable, overcome crazy odds, and yet I still didn't know why I did it or have any real sense of meaning. Thankfully, in the years that followed, I began to mentor men both in life and in business, I redoubled my efforts as a father and husband, and I built a group of friends who mean the world to me. I am human. There are still days when I wonder why I am doing what I am doing, or what it all means. But I come back to people much more quickly. To love. And I am no longer sucked into the myths our society propagates. And I try to guide those I mentor and teach towards building friendships, towards humility, towards service, even as they "succeed" in the world, as the path to a deep and true fulfillment. I challenge you to keep asking yourself why you are doing what you are doing, and if you succeed beyond your wildest dreams, what will that actually mean to you? Will it fill some essential part of your soul that has been empty, or will it become a problem because you have been feeding yourself a myth the whole time that will be proven in that moment to be a complete lie? Of course, as in Zen, all of life is a paradox, and love is not only the answer in your own heart but also the best way to lead and succeed. By not focusing on yourself, your success, you will succeed. The humble leader, the true servant leader, is the one that everyone wants to go to war with. Saying it's not about you is bullshit if you are using that as a fake crutch for your own greed. But if you actually believe that, if you embrace what the Buddhists call sympathetic joy, meaning that the highest calling is simply witnessing another human being’s joy, not your own. Then you are on the right track, at least as far as I can report from 60 years on this planet, chasing big dreams and achieving a lot of them, despite how problematic that became for me.
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commentor profile
Reply by an investor
from McGill University in San Diego, CA, USA
Great post! Thanks for sharing When I was in grade school, I had an English teacher that taught me how to write an essay. You put your conclusion in the first sentence, and then you have 3-5 supporting reasons for your view. All of that goes in the intro to your essay. Later in life, a mentor told me that I should think of my life the same way I think of English essays. Have a life mission statement (conclusion), and the actions I will take to support that mission statement. That was great advice. I probably absorbed about 50% of that advice at the time, and truly saw the wisdom of his words after I started to binge listen/read Arthur Brooks. He teaches the science of happiness at HBS, and is a best selling author. He also has a YouTube station and podcast (so, a lot of his content can be accessed for free). A lot of your comments would be consistent with Arthur's In parallel, Dr. Peter Attia has a very powerful chapter at the of his book Outlive. The last chapter is about his mental health journey (from the point of view as a patient). He referred to a book called I Don't Want to Talk About it (By Terrance Neal), which turned out to be jaw dropping and one of the most interesting books I have ever read. This book is designed for men between the ages of 20-60. All of this comes back to ETA. If you are searching, and want to be a CEO, the question is WHY? Everyone is wondering it. The seller, the broker, investors... When you show up as the new owner of a business, they too want to know WHY. A great answer not only goes a long way with stakeholders... it helps you live a life consistent with your values. I think it's awesome that you teach this stuff, and mentor others. Getting this kind of advice at a young age is priceless. Keep the great posts coming
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Reply by a searcher
from Texas A&M University in Surprise, AZ, USA
Introspection is important. Carl Jung had thoughts about people having a shadow. Basically a dark side that held people’s inner aspects that they unconsciously hold back. Look up shadow assimilation and there are exercises you can do to become more aware of yourself and your own shadow. Not all bad things. Sometimes there’s potential there.
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