In this interview I speak to the ‘Stoic Capitalist,’ Robert Rosenkranz, Chairman of Delphi Capital Management (an investment concern with more than $40 billion in assets under management) and the founder of a group of investment and private equity partnerships. Rising from working class origins to self-made billionaire and pioneer in private equity, hedge funds, and insurance, Rosenkranz is also an active philanthropist in public policy, the arts, and medical science. A champion of civil discourse and free speech, he launched Open to Debate (an award-winning weekly debate forum distributed as a podcast, online video series, and public radio program carried by NPR stations nationwide). He also funded Impetus Grants to extend human health spans, and is founding Canyon, a New York cultural institution showcasing immersive works of visual art, sound, music, and technology. He is a director of the Manhattan Institute in New York, The Hoover Institution at Stanford University, the Buck Institute for Aging Research, and the US arm of Hevolution Foundation. In Robert’s new book The Stoic Capitalist: Advice for the Exceptionally Ambitious, he reveals how the threads & ancient principles of Stoicism have played an essential role in his success journey.
Q: What has been the role of stoic philosophy in your life?
[Robert Rosenkranz]: I’ve always felt like a natural-born Stoic. When I first read Stoic philosophy, I thought, Oh my God, this is exactly how I’ve been thinking since childhood. It wasn’t a revelation so much as a way to organize the responses that already came naturally to me.
For example, one of the Stoic maxims is the obstacle is the way. My obstacle as a child was extreme financial insecurity—I was acutely aware of it. In response, I took full responsibility for my own life. My mother frequently espoused Marxist ideology, yet it was obvious to me that whatever ideas my parents had, they weren’t working for them. Once again, the obstacle became the way—this time, fostering critical thinking, which proved to be an invaluable quality in life.
Q: How can stoic philosophy help us respond to the most challenging times in our lives?
[Robert Rosenkranz]: I think Stoicism has often been studied, taught, or applied as a way to cope with difficult challenges. What’s unique about Stoic Capitalist is that I aimed to shift those ideas from mere coping to succeeding on a much larger scale.
At its core, Stoicism as a coping mechanism involves reining in emotion and distinguishing between what you can and cannot control. If something is beyond your control, there’s no point in wasting time or emotional energy on it. It’s also about recognizing and accepting impermanence—understanding that things will change, and your task isn’t to resist but to adapt.
Q: How have you formed your approach to risk?
[Robert Rosenkranz]: I’d say that human evolution has shaped us to dislike risk. The Stoic concept of courage is about letting reason prevail over emotion. Risk naturally triggers fear—fear of a bad outcome. But using reason to manage risk means applying a more analytical approach, almost like a mathematical assessment of risk and reward. If the odds are against you, how bad is the downside really? Will you be able to cope? This kind of reasoning helps overcome the fear of an undesirable outcome.
As for how much risk to take at any given time, it comes down to being as rigorous and mathematical as possible—considering the downside, the upside, the odds, and how often you’ll have the chance to take that particular risk. If you had the opportunity to place a 100-to-1 bet on a roulette number at a casino, that would be a great bet. But would you wager your entire net worth on it? Probably not. And your betting strategy would differ if you could place the bet only once versus 100 times. It’s a complex calculation, but ultimately, reason must prevail, and fear—the toxic side of emotion—must be regulated.
Q: How do you navigate the challenge of incomplete information?
[Robert Rosenkranz]: I’d say there are two key responses. First, you have to acknowledge that luck will always play a role in any situation. Unforeseen developments are inevitable, so to the extent that you can build in a margin of safety—one that accounts for risks you haven’t even considered—you’ll have a better chance of coming out okay.
There’s a story in the book about the first buyout I did, which didn’t work out because it was a manufacturer of record album jackets—then the Sony Walkman came along. But another key precept for me is that just because a decision doesn’t work out doesn’t mean it was the wrong decision. If it was based on the best available information at the time, it was still a sound choice. However, if you ignored relevant information that was available, that was a mistake—and you’d better learn from it.
Q: What does wealth mean to you?
[Robert Rosenkranz]: The most important thing to me is that wealth has allowed me to live a full life, rich with experiences. I see wealth more as a means to experience than a way to acquire things. It has also given me control over my own time. I have a lot of help and delegate as much as possible so I can use my time purposefully—almost entirely. To me, that’s one of the greatest benefits of wealth.
Another is the ability to give my children options in life that I felt I didn’t have. In my case, that means the freedom to pursue academia or public service—paths that didn’t seem realistic for me due to the financial imperative of not repeating my parents’ struggles. And, of course, wealth also enables you to give back to society, to address needs you recognize, which naturally leads to philanthropy.
Q: How do you create a legacy without disincentivising the generation who follow you?
[Robert Rosenkranz]: It’s a tricky balance. Warren Buffett had a phrase I really liked: You want to give your kids enough to do anything but not enough to do nothing. I set up a plan to create wealth for them—and I wildly overshot that.
That said, my kids are both constitutional law scholars, they lead productive lives, and I feel very fortunate for that. But one of the key insights from Stoic wisdom is accepting that, to some degree, children are genetic accidents—you can’t have complete control over the outcome.
Q: What is the concept of ‘selfish philanthropy’?
[Robert Rosenkranz]: Because I didn’t have role models at home, I became a voracious reader of biographies as a child. I saw them as how-to manuals for success—and, in a sense, for a well-lived life. I was particularly struck by how early American industrialists like Carnegie and Rockefeller were also great philanthropists, establishing the expectation that if you make a lot of money, you give chunks of it away. But for me, it wasn’t just about the giving—it was about using your talents and abilities to identify and fill a societal need.
Carnegie did this through libraries, Carnegie Hall, the Carnegie Institute for Peace, and Carnegie Mellon University. Rockefeller founded the Rockefeller Institute and helped establish the University of Chicago. My model of philanthropy follows that same idea—a space to apply my own abilities to meaningful societal contributions. That’s why I found the creation of Open to Debate so satisfying. I’m also launching a venue in New York focused on video art and the intersection of art, music, and technology in ways that museums can’t fully engage with. I’ve also initiated a project on human health spans. These are all efforts in which I’ve been actively involved.
The idea of selfish philanthropy is a push against the notion of philanthropy as simply “giving back.” That phrase implies that wealth was accumulated by taking something from society. But if you’ve built a successful business, you’ve contributed to society—you don’t owe anything back. My view of philanthropy is that it should also serve the philanthropist in a meaningful way.
Q: Why does the UK lag so much on philanthropy versus the USA?
[Robert Rosenkranz]: It’s certainly a cultural difference. Britain has long embraced the idea of noblesse oblige—the notion that those in the castle take care of those in the village. There’s a deep-rooted sense in British culture that privilege comes with an obligation to support dependents, so to speak. But this is quite different from the American perspective.
When I titled this book, I thought I was throwing down a gauntlet by including capitalist. But I later realized that ambitious might be just as provocative. There seems to be an ambivalence toward ambition in British culture that contrasts with the American view, which has traditionally celebrated it—at least for most of my lifetime.
If you look at philanthropy in the U.S., every American who has donated over a billion dollars made that money themselves. Big-scale philanthropy and ambition are closely linked in a way that may be culturally distinct between the U.S. and the U.K.
Q: Why did you choose to deploy capital and resource to support public discourse?
[Robert Rosenkranz]: I felt that civil discourse in America was breaking down, with people splitting into two warring ideological camps. Meanwhile, the real issues we face are far more subtle, nuanced, and complex. I believed society needed what I call a contempt-free zone—a space where reason prevails over emotion, a core Stoic principle, and where critical thinking is encouraged—again, a Stoic ideal.
At the same time, this idea aligned with my philanthropic approach. My means are modest compared to the role models I sought to emulate, so finding something small and manageable was particularly appealing. It fit into my vision of a well-lived life, and I wanted to seize the opportunity.
Q: What has been the role of art & culture in your life?
[Robert Rosenkranz]: I was very fortunate to meet a handful of people who became mentors in some way or deeply influenced me. One story I tell in the book is about someone I met before college—a business leader who ran a large insurance company but was also profoundly cultured. He owned Parke-Bernet, which later became Sotheby’s, as well as the largest dealer in French antiquities.
When I visited his office, he had an enormous Louis XVI desk and a massive tapestry behind him. I asked about them, and he spoke with such passion that I thought, Oh my God. He was also a remarkable philanthropist—chairing the United Negro College Fund and the Urban League—and an incredible athlete, the first person to swim around Manhattan Island. His ability to integrate art and culture into a well-lived life left a lasting impression on me.
Inspired by that, in my first year at Yale, I took an art history course. The professor, Vincent Scully, was a legendary Yale figure who taught with such passion and forcefulness that it became the catalyst for a lifelong interest. I later studied architecture with him as well.