I exited one of the NYC area’s biggest real estate deals at 31. Here’s what I learned

I learned this early. At 31, I exited one of the most successful real estate deals in Metropolitan New York history: the redevelopment of the Harborside Financial Center in Jersey City. At the time, it was the country’s largest commercial renovation. For me, it was my first substantial wealth moment and I had no idea what to do next: What to do with the new capital I acquired and how would I make it matter? 

The more wealth one accumulates, the more fragile one can feel. What begins as a quest for freedom can morph into a fortress mentality. I have seen peers—brilliant, driven individuals—become distracted by the fear of losing what they have built. Instead of leaning into the adaptability that made them successful, they retreat behind walls, both literal and figurative. 

Today we are in a similar societal position: We are on the precipice of the largest societal wealth transfer in history, where an estimated $84 trillion is set to pass down to younger generations over the next two decades. What will we do next? What happens now will define the future of American innovation and entrepreneurship, and that’s why we all should be paying attention. 

For the last 26 years, I have been studying some of the world’s most successful entrepreneurs through my founding of TIGER 21, and I’ve learned a lot about how entrepreneurs find success and how investors create impressive returns. 

Two points are poignant today as we think about our future: One, being a successful founder and entrepreneur rarely ever translates into being an equally successful investor, and two, once wealth is accumulated, the fear of losing wealth can cause loss and inaction. Combined, these two learnings have the potential to shift our entire wealth and societal landscape: It turns out that managing capital is just as important as figuring out how to create it. 

During my teens I tried a dozen different ways to hit the entrepreneurial lottery, from shoveling snow to slinging milk at the local Dairy Barn. Some of my endeavors paid off; others did not. In many ways, that experience reflects something uniquely American: a country structured, culturally and economically, to encourage people to take risks, start businesses, accept failure and accumulate learning as the byproduct of each venture to maximize success the next time around. 

So why do so few entrepreneurs hit it big? The answer lies in how success is spread out. Entrepreneurs often start with very little and build something valuable from scratch. Investors, on the other hand, spread their money across many existing opportunities. Most entrepreneurs don’t make much money, but a tiny number hit it big—so big that they re-shape the entire wealth landscape.

Investor returns, on the other hand, typically preserve wealth with safer investments yielding 8-10% returns, and generally a point or two less for family offices that, unlike most institutional investors, have to maintain cash and liquidity. But even at 10% return over the same 30 years, $1 only grows to $18.  Eighteen times very little is very little, but if you inherit $10 million, that can turn into $180 million at 10% for 30 years, and that’s a horse of another color. 

The key difference is to set expectations based on the shape of likely outcomes, not hopeful pipedreams.  Investor returns tend to follow a bell curve—most people earn around the average. Entrepreneurial outcomes, however, follow a power law distribution. That means a lucky few (Zuckerberg, Gates, Musk etc) earn massive amounts—so much so that they skew the average. It’s like city populations: most cities are small, but a handful are enormous because people flock to them–drawn by opportunity, talent, capital and more—making them even bigger. 

Our country was built on the resilience and creativity of entrepreneurs, people who are willing to take risks, adapt and innovate. Success, in its truest form, is something to celebrate. But there is a troubling shift that occurs when success hardens into excess and gives way to fear, a paradox that emerges all too often. 

Defensive wealth behaviors, however, create ripple effects that weaken social fabric. Communities fracture as inequality deepens. Public trust erodes when resources concentrate at the top. Ironically, the very effort to secure one’s position can destabilize the society that enabled success in the first place.

Why does this happen? Partly because wealth magnifies risk perception. The stakes feel higher, and the margin for error smaller. But the mindset that built success—adaptability, openness and a willingness to embrace uncertainty—remains the antidote. When we lose that, we trade creativity for control and generosity for guardedness. And in doing so, we diminish not only our own sense of purpose but the collective resilience of our communities.

There is another way. Ultimate security does not come from building taller walls or deeper moats. A society can become stronger, more successful and more resilient by strengthening the networks of trust and opportunity that bind us together. That means investing in shared systems—education, healthcare, energy, infrastructure, entrepreneurship—that allow all of us to thrive. We must resist the temptation to see privilege as a prize to defend and instead view success as a platform for meaningful contribution and mentorship. True leadership in this era is not simply about accumulation; it is about stewardship.

As someone who understands the allure of control, I know that the entrepreneurial spirit prizes independence, and wealth amplifies that instinct. But independence without interdependence is an illusion. If we allow fear to dictate our choices, we risk creating a society defined by walls that separate, harden and ultimately collapse under their own weight.

As we look back at the first 250 years of American entrepreneurship and look ahead to our shared future, fear cannot win. We must better understand how we can make an impact, as both investors and entrepreneurs. America’s extraordinary wealth must become focused on creating an entrepreneurial prism refracts into a broader spectrum of responsibility, opportunity and stewardship. This is not a left wing fantasy but centrist reality. When the United States has invested in finding societal solutions, we have all benefitted(social security, education, and even fixing the ozone layer in the 1990s). 

The challenge before us is cultural as much as economic. We must redefine what it means to be secure—not as just owning more, but as belonging to a society that works for all. That requires the same courage that sparked our first ventures to let go of the illusion that more is always better. In the end, resilience is not measured by what we keep, but by what we are willing to invest in others. And the future of our country depends on that choice.

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