I was asked to share some thoughts with Kiplinger because, after nearly three decades of conversations at TIGER 21 with extraordinarily successful entrepreneurs and investors, I have become increasingly interested in a paradox: wealth creators who measured almost everything while building their businesses often fail to measure the one financial metric that matters most for long-term wealth preservation once they create a family office—what their capital is actually earning over time. The skills that create wealth are not necessarily the skills that preserve and compound it. In fact, I have long believed entrepreneurial skills can sometimes limit investing success.

READ KIPLINGER ARTICLE HERE

The consequences are not academic. A few percentage points of annual underperformance, compounded over a generation, can quietly consume an extraordinary portion of a family’s potential fortune. Yet many families focus on asset allocation, prestigious managers, access to private investments and increasingly elaborate family-office infrastructure without ever establishing a meaningful scoreboard. I wrote this article because measurement is the beginning of accountability. If you don’t know what you are actually earning—over time, after fees, and relative to the risks and liquidity you have accepted—you cannot know whether all that sophistication is creating value or quietly destroying it.

The timing feels particularly relevant after my conversation Wednesday with Brian Sullivan on CNBC.

TIGER 21 will likely welcome our 2,000^th Member in the next few weeks. Collectively, our Members manage almost $280 Billion in personal investment portfolios. Private equity has grown from roughly 10% to 34%, the most extraordinary growth of any asset class in our 28-year history. Why?

Members have the lowest cash reserves in 20 years. Long term cash holdings were steady for most of the last two decades at 12%, but have fallen in recent years to a current low of 7%. The last time we saw such low levels of cash was right before the financial crisis of 2008 (when cash was 8%). Is this a canary in the coal mine? Draw your own conclusions.

But whatever the allocation of your capital, the question remains the same: What are you actually earning for the risk, fees, complexity and illiquidity you have accepted? Is that reasonable or acceptable?

I wrote this piece for Fortune Magazine, where it was originally published on Sunday, July 19. Many thanks to the publisher for allowing me to share it with you here as well. Read the original at Fortune Magazine.

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I have spent much of my working life among entrepreneurs and business leaders wrestling with a deceptively simple question: when is it time to let go? Twenty-seven years ago, I founded TIGER 21, the premier global peer network of some of the world’s most successful entrepreneurs and executives. I remain its non-executive Chairman, though 18 months ago I ceded control to a new owner, and now spend more of my time managing my own family office.

Over those years, I have watched extraordinary founders build remarkable organizations, and I have also watched some stay too long. Few decisions reveal more about a leader’s judgement than knowing when their continued presence strengthens an institution, and when it begins to weaken it. That same pattern appears far beyond business.

There is a particular kind of failure that history reserves for some of its most admired figures: the failure of people devoted to a cause who, by refusing to step away at the right moment, hand that cause to its enemies. The reasons vary—ego, misjudgment, or the counsel of those invested in proximity to power—but the outcome is consistent: supporters are left with a sense of betrayal when the failure to step aside enables the very outcome they sought to prevent.

Ruth Bader Ginsburg spent her life building a jurisprudence of equality. By 2013–2014, after surviving serious illness, she had a clear opportunity to secure a successor aligned with her values. She declined, confident her health would hold and that the presidency would remain in sympathetic hands. She was wrong about who would name her successor. Trump’s Amy Coney Barrett, who replaced her, helped form the majority that overturned Roe, the decision most central to the legacy Ginsburg sought to protect. Just as important, that appointment contributed to a Court that has expanded the formal powers and protections of the presidency. The consequence is not confined to any single ruling: we now have a presidency willing to test limits and norms, reinforced by a Court that has enlarged its authority. It is the interaction of those forces, not any one decision, that gives the current moment its particular danger.

Ginsburg’s decision was a wager under uncertainty. She bet that she would live for years, remain productive, and that the political environment would cooperate. She was right about the first two and wrong about the third. Such miscalculation is human. She made a political judgment, whether or not she described it that way. She chose to stay, and the bet failed.

Having defeated Donald Trump once, Joe Biden spent four years insisting he was uniquely positioned to do so again. Having described himself as a bridge to the next generation, he might have committed early to a single term and allowed time for a genuine process to produce a successor. He did the opposite. By the time his candidacy collapsed, the time required to mount an effective alternative had largely disappeared. In withdrawing late, he effectively narrowed his party’s options at the moment they mattered most.

Ginsburg misjudged an unknowable future; Biden failed to respond to a visible present. One error was a forecast that proved wrong; the other was a refusal to act on evidence already in view. The latter is harder to defend. Nor was Biden’s failure his alone. Those closest to him had the clearest view of his condition and the greatest influence over what was shown to the country. In protecting the individual, they compromised the cause they believed he alone could serve.

What unites these cases is the indispensability delusion: the belief that the cause requires the individual, and that departure would amount to abandonment. The leader does not say, “I want to stay,” but rather “the institution cannot do without me.” This is the most dangerous form of the error, because it does not announce itself as ambition. Naked hunger for power is visible, and we know to distrust it; the indispensability delusion wears the costume of duty, telling the leader that the discipline of leaving is actually a dereliction, and that one more term, or one more year on the bench, is a sacrifice made for others rather than a comfort taken for oneself.

History is dense with this pattern, and the better cases show the same supporting cast. Woodrow Wilson, having suffered a debilitating stroke in 1919, refused to yield the presidency while his wife and physician quietly hid his condition from the country, deciding on his behalf what the nation would be permitted to know. This helped doom American entry into the League of Nations, the project Wilson had staked his name upon. A similar claim could be made about Churchill’s return to power in 1951, when a stroke two years later was likewise hidden. The principal’s delusion is the visible part. It almost always also rests on a circle of those closest to the leader who are willing to sustain it.

There is a simple test. A leader truly serving a cause larger than themselves should be able to name the conditions under which they would leave, and, crucially, should arrange their departure early enough that the cause has time to produce a worthy successor. In many positions of leadership, leaving is not a single act at the end. It is a process that must be started while there is still runway, because a successor does not appear on demand; an institution sometimes needs years to surface and test one. The leader who waits until the last moment, then announces that no acceptable replacement exists, has usually engineered that very outcome by waiting. The figure who experiences every prompt to begin the process as a threat rather than a relief has confused the cause with the self.

I write this as someone who has heard that voice. I make no comparison between myself and a justice or a president, and the stakes I faced were not remotely theirs; but the phenomenon is not confined to the highest offices. It attaches to every form of leadership, which must eventually come to an end, and that is the only standing I claim. The voice insists that no one understands the enterprise the way you do, that you and the institution are the same object, that stepping aside is a form of abandonment. Recognizing it as a liar is not the same as overcoming it. The work lies in acting against it while the choice is still yours to make.

The discipline this requires is rare, but it is not hypothetical. As the country marks its 250th year, it is worth recalling that the republic exists in its present form partly because George Washington demonstrated that discipline twice. In 1783, having won the revolutionary war, he relinquished his power to Congress rather than use it to ensure his continuation. Then, in 1796, he declined a third presidential term, establishing the principle that the office must outlast the man. He understood that precedent, not tenure, was his most important contribution. His contemporaries called him the American Cincinnatus, after the Roman who laid down absolute power the moment the crisis that summoned it had passed. That the ideal was so ancient, and the examples so few, is precisely what makes the discipline remarkable.

Modern cases confirm the test rather than complicate it. Nelson Mandela served a single term and stepped down in 1999, on a continent where liberation leaders routinely became presidents for life. The restraint was itself the message: the movement, not the man. What distinguishes these figures is that they surrendered power voluntarily, while it was still theirs to keep, at moments when continuation would have been possible or even popular. They treated departure as fulfillment rather than loss.

For those who view recent institutional developments as deeply damaging, the sense of betrayal is acute. The damage was not done only by opponents. It was enabled by those most entrusted to prevent it, acting in the belief that the cause required continuity. We expect our opponents to seek our undoing; we do not expect to be undone by the very stewards who assured us, sincerely but mistakenly, that they were holding the line.

The lesson is not that leaders should distrust their own importance. Some genuinely are, for a time, the right person for the moment; Washington was, as were Lincoln in 1864, Roosevelt in 1932, and Churchill in 1940. Indispensability is sometimes real, which is exactly what makes the test so hard: the sense of being uniquely needed is itself the distortion, weighting the case for staying when the facts do not warrant it, so that self-interest arrives disguised as the cause’s own demand. The more indispensable you actually are, the more carefully you must plan your departure, and the more suspicious you should be of any voice—your own, or those of the circle around you—assuring you that the institution cannot survive your leaving. Washington heard that voice and overruled it. That, more than any battle, is why the office outlasted him.

There is a reason this discipline is so rare, and it is not only ego. Our culture has built a shrine to perseverance. We teach grit as an unmixed virtue and treat walking away as quitting. Annie Duke, in her book Quit, argues that this is a costly confusion: knowing when to fold is not the opposite of grit but its necessary partner, a decision skill most of us exercise too late rather than too early, because identity and the fear of looking inconsistent make leaving harder than the arithmetic warrants.

Entrepreneurs feel this acutely, because the thing they are asked to relinquish is something they often built from almost nothing. To hand it on while you can still picture running it better feels like a small death, and the culture offers a vocabulary for holding on but none for leaving well. Yet the founder who steps aside at the right moment, before decline forces the question, is not quitting. The test does not care about scale. It asks only whether you can tell the difference between what the cause needs and what you need, and whether you can act on the answer while the choice is still yours to make rather than mortality’s, or the electorate’s. To leave at the right moment is not weakness. It is the rarest form of strength, and the one we have been least willing to honor.

The opinions expressed in Fortune.com commentary pieces are solely the views of their authors and do not necessarily reflect the opinions and beliefs of Fortune.

Under the Trump administration, that reversal has been deliberate. Congress repealed the $7,500 EV tax credit; U.S. electric vehicle sales stalled in 2025, with most trackers showing a small decline or flat growth even as global sales rose roughly 20 percent, and BloombergNEF projects 14 million fewer cumulative American EV sales by 2030. The administration halted offshore wind leasing, rescinded 3.5 million acres of designated wind areas, and paid developers nearly $2 billion to walk away, surrendering enough power for over 3 million homes, just as U.S. data-center demand is on track to more than double by 2035. The EPA has moved to repeal its endangerment finding which gives it the authority to address climate change, while the Department of Energy uses emergency orders to keep aging coal plants running, despite research in Science attributing roughly 460,000 excess deaths among older Americans between 1999 and 2020 to coal-plant pollution alone.

For a president who casts himself as the consummate dealmaker, this is one of the worst deals in American history. The new energy economy, EVs, batteries, solar, wind, grid storage, critical minerals, is on track to be the largest industrial transformation since the automobile itself. China already controls roughly 80 percent of global solar manufacturing, 75 percent of lithium-ion batteries, and a dominant share, by some measures as high as 85 percent, of critical-minerals processing, and accounted for fifty-five percent of $1.1 trillion in clean-energy manufacturing investment announced globally between 2019 and 2025. In 2025 alone, U.S. clean-energy manufacturing turned net negative for the first time in over a decade, with roughly $22 billion in cancellations outpacing new announcements, even as China announced another $39 billion in fresh clean-energy manufacturing investment. We are not pausing the transition. We are handing it to our principal strategic competitor.

History rhymes. In 1865, the British Parliament, lobbied by horse, stagecoach, and railway interests, passed the Locomotives Act, popularly known as the Red Flag Act, requiring every self-propelled vehicle on a British road to be preceded by a man on foot waving a red flag. For thirty-one years it was effectively impossible to build a serious automobile industry in Britain. By the time the law was repealed in 1896, Germany had Benz, France had Peugeot, and America was about to have Ford. Britain, which had pioneered the steam engine itself, permanently lost the automobile century. Subsidizing buggy whips while taxing the assembly line is not industrial policy. It is a suicide note written in installments.

And there is a deeper damage. When Mr. Trump lost in 2020, the world treated his first term as an anomaly. Allies returned, capital flowed back. The second term proves the reversal was not an accident; it is a feature and liability of the American system. Even if a future administration wants to get back on track, every CEO and every foreign minister will ask the same question: how do we know the rug will not be pulled out again? A battery plant takes three to five years to build and twenty to pay back. An offshore wind farm takes seven to ten years from lease to first power. Capital and credibility, once burned twice, do not return on the same terms. The perception that American climate policy is reversible every four years is now baked in, and that perception, more than any single regulation, is what will keep the new energy century from being an American one.

Climate may not give a damn about politics, but the fossil fuel industry sure does. The oil and gas industry poured an estimated $445 million into the 2024 election cycle, according to Climate Power, including roughly $96 million directly to President Trump’s campaign and aligned super PACs, after Mr. Trump told industry executives at a Mar-a-Lago dinner that a $1 billion contribution would be a “deal” given the regulations they would avoid. Eighty-eight percent of the industry’s direct contributions to incoming policymakers went to Republicans; for coal, the figure was 97.6 percent. The EV rollback, the wind buyouts, the coal revival, the endangerment-finding repeal: these are not the random outputs of an administration searching for a policy. They are the deliverables that were purchased.

History has a name for this posture: the leader who substitutes his preferred reality for the one his experts describe. In the spring of 1941, Joseph Stalin received scores of credible warnings, from his intelligence networks, his border commanders, and British decrypts passed personally by Churchill, that Hitler was about to invade. He dismissed them as provocations, purged the intelligence officials who delivered the bad news, and forbade defensive preparation. Days later, three and a half million German troops crossed the border. The Soviet Union lost millions of soldiers in the opening months. President Trump is not Stalin, and America is not the state Stalin oversaw; our institutions and our press are, for now, still functioning (but, in my opinion, not fully). But the pattern of denial is notable, and the relevant comparison is the cost. Stalin’s self-deception killed millions of his own people. Mr. Trump’s, if it runs its course, will cost more, because it will not be confined to one country or one generation. Stalin’s mistake was paid for by the people he ruled. Trump’s will be paid for by humanity.

I do not write this as a detached observer. As a businessman, philanthropist, and political donor, I have spent the last twenty years “all climate all the time” across all three realms. For two decades that combination felt sufficient: press on capital, science, and policy, and the rest would follow. Over the last two years I have had to reconsider. Without a fully functioning democracy, the fossil fuel industry will continue to buy government policy on a scale that climate philanthropy and investing alone cannot offset. You cannot out-donate hundreds of millions of dollars when the rules themselves are being rewritten by the donors. Climate and democracy, once parallel concerns, have converged. Defending democracy is now, for me, a climate strategy.

We do not get to vote on the laws of physics. We get to decide how intelligently we respond to them, and whether the people doing the deciding actually answer to us. Climate won’t wait—should we?

I came to the exhibition with an unusual stake in it. My colleagues and I collect entire photographic estates, the complete life’s work of a single photographer rather than scattered prints, an approach that has made the MUUS Collection the preeminent private holder of such estates in the world. Twelve years ago, before the market had fully recognized what was at stake, we acquired the complete archive of André de Dienes, including some 400 images of Norma Jeane becoming Marilyn Monroe, made between the ages of 18 and 24. Many of the works on the gallery’s walls this week came from that archive. I mention this not to claim authority over her story but to be plain about where I stand: the longer I study these photographs, the less they seem to be about a face and the more about a mind.

There is a recurring pattern in American entertainment that is rarely acknowledged. Some of the women who played the most naive or broadly comic roles were, behind the scenes, among the most disciplined and perceptive intellects in the business. Monroe chose to inhabit such a persona, then spent much of her career straining against it. The tension between projection and reality has long framed her story, but it is not the only instructive part.

A moment in 1955, often recalled but insufficiently examined, points in a different direction. The Mocambo nightclub in Los Angeles, then one of the most prestigious venues in America, did not book Black performers. Ella Fitzgerald, already widely regarded as the finest jazz vocalist of her generation, could not secure an engagement because of her race. Monroe intervened. She telephoned the owner and offered a proposition: if he booked Fitzgerald, Monroe would sit in the front row every night of the run. He agreed. She followed through. Fitzgerald later said the engagement changed her career.

What matters is not only that Monroe acted, but how she acted. This was not an appeal to conscience; it was an alignment of interests. Monroe reframed the decision so that doing the right thing also became the profitable one: a full house, guaranteed attention, and Monroe herself in the most visible seat in the room. The perceived risk of booking Fitzgerald disappeared. The ethical outcome and the advantageous outcome became identical.

That instinct stands in contrast to many of our dominant assumptions. Increasingly, power is framed as coercion, and influence as the ability to impose costs. Hard power, whether financial, legal, reputational, or military, is treated as the primary instrument, while persuasion is recast as weakness and mutuality as compromise. An administration that leans reflexively on coercive tools does more than shape immediate outcomes. It conditions allies and adversaries alike to expect ultimatums rather than alignment, producing compliance where it can but rarely commitment. In doing so, it forfeits one of the most durable forms of influence: structuring choices so that cooperation becomes the rational path forward.

History suggests that durable progress more often follows that logic. Arrangements built on aligned incentives tend to outlast those imposed through force, because they do not require constant enforcement to hold.

Consider the founding act of postwar Europe. Five years after the deadliest war in human history, the French foreign minister Robert Schuman proposed that France and Germany pool the very industries, coal and steel, that had fueled their militaries. The arrangement required neither apology nor capitulation; it would make further war, in Schuman’s phrase, “not merely unthinkable, but materially impossible.” Six countries joined in 1951. The Coal and Steel Community became, in time, the European Union. More than seventy-five years later, France and Germany have not fired a shot at one another, the longest such peace between them in a thousand years. Schuman did not extract concessions; he restructured incentives until conflict ceased to make sense.

Monroe’s intervention belongs to a quieter tradition of exercising power. Reframing situations, shifting incentives, and redirecting attention are not the fallback of those who lack leverage; they are a more sophisticated use of it. Wielded well, this kind of influence is not a consolation prize for the weak but the choice of the shrewd, because it tends to produce outcomes that are more durable and less costly than anything force can secure. These techniques are not secondary to power; they are among its most effective forms. Monroe’s gesture at the Mocambo, simple as it appears, reflects a precise understanding of that dynamic. That she reached for it so instinctively may owe something to the fact that throughout much of history, women, denied the physical, social, and financial leverage to confront a problem head on, often had to master these subtler instruments to prevail at all.

The analogy has its limits. A nightclub booking is not geopolitics, and reputational leverage is not state power. Yet the underlying principle, aligning interests to achieve outcomes that might otherwise require force, operates at every scale, and it is now in danger of being disregarded. Soft power, the ability to attract, persuade, and align without compulsion, is increasingly displaced by a governing preference for more forceful tools. That shift carries costs that are easy to defer and difficult to reverse. The European peace did not hold because anyone was compelled to keep it; it held because the incentives were built to make breaking it irrational. That is precisely the kind of advantage a preference for coercion leaves unclaimed.

None of this diminishes the importance of hard power. It remains necessary, and at times decisive. But when it becomes the default rather than the last resort, it displaces subtler forms of influence often better suited to lasting results. Monroe never presented herself as a strategist, nor wrote about power. Yet without formal authority or theory, she recognized the leverage available to her and used it in a way that expanded, rather than constricted, the space of possibility. The question her example raises is not whether such moments still exist. They do. It is whether we remain capable of recognizing them, and willing to act when they arise.

Walking through the gallery this week, surrounded by images of a woman the world thought it knew, I kept returning to a single thought. Monroe did at the Mocambo what too few of our leaders are willing to do at scale: she looked at a conflict others assumed could only be won by force and found the outcome that served everyone, then made it the attractive one. The lesson is not that soft power should replace hard power. It is that leaders who reach first and almost exclusively for conflict or coercion leave the most durable victories on the table. The challenge falls to the rest of us. Where a problem can only be crushed, force may be the answer. But where interests can be aligned and a better outcome made the appealing one, we should insist that our leaders reach for the instrument Monroe understood instinctively, and demand that they learn to use it.

Her image has endured for a century. Perhaps her example can be the model for the next one.

Before I transition from my recent piece in The Atlantic to my latest article in Barron’s on wealth transition and family offices, I want to sincerely thank all of you. The response to the Atlantic essay was overwhelming in the best possible way. I received hundreds of thoughtful comments, messages, and conversations from readers who engaged deeply with the ideas I explored, and I’m genuinely grateful for that.

READ BARRON'S ARTICLE HERE

I also want to acknowledge that this next piece is written for a much narrower segment of my audience. Conversations around investing, wealth creation, family offices, and generational capital planning are not topics everyone spends time thinking about. But for readers who are interested in how wealth is built, preserved, transferred, and stewarded across generations, I believe these conversations are becoming increasingly important. The fundamental insight about which I am quite excited is that returns earned by entrepreneurs follow a “power law” while returns that investors earn follow a bell curve. More or less. Most entrepreneurs either lose their investment or generate relatively modest returns, while a very small number create extraordinary wealth. Investing, done reasonably well, might be a lot less glamorous but a lot more predictable.

I think these distinctions have important implications not only for entrepreneurs but also for anyone guiding their family through wealth preservation, investing, inherited capital, and risk. If those issues are of interest to you, I hope you will find the article worthwhile.

I’m pleased to share a link to my first long-form essay for The Atlantic, published this morning HERE.

For decades, most American Jews felt politically and morally aligned with progressive movements. After October 7th, many experienced what felt like indifference, hostility, or even betrayal from parts of that coalition — while remaining deeply uncomfortable with elements of the right wing agenda, despite Republicans’ strong support for Israel. And lets not minimize the elements on the right that are also hostile to Jews and Israel.

In this personal and at times uncomfortable essay, I wrestle with the historical memory Jews carry, the legitimacy and tragedy bound up in Israel’s challenges with her neighbors and Iran, the resilience of American democracy, and the political and moral dislocation so many are struggling to process in real time. It’s intended less as an argument than as an attempt at intellectual honesty about tensions many feel but are reluctant to articulate publicly.

My thanks to The Atlantic for publishing it. I’d very much value your reactions once you’ve had a chance to read it.

For our 6th and final episode of Season 2, I sit down with Shane Neman, serial entrepreneur, investor, and founder of Neman Ventures, to explore a rare transition: how a great entrepreneur becomes a great investor. After successfully building and exiting multiple technology companies, Shane accomplished something even more uncommon- dramatically compounding his wealth as an investor long after his entrepreneurial success. Drawing on his deep understanding of technology, markets, and human behavior, Shane shares how he transformed from founder to allocator, approaching investing as a craft that required an entirely new level of discipline, humility, and lifelong learning.

LISTEN TO EPISODE 6 HERE

Shane and I discuss why most successful founders struggle to make the transition to investing, how he thinks about asymmetric opportunities and concentrated bets in deep tech and physical products and services, and how the principles of decision making have become just as important as understanding markets. Throughout the conversation, Shane offers a thoughtful perspective on risk, resilience, wealth stewardship, and what it truly takes to compound success beyond entrepreneurship.

Episode highlights include:

• From entrepreneur to investor— the unconventional shifts Shane made to successfully evolve from founder to allocator

• Risk as a learned skill— how repeated exposure to uncertainty trained Shane to evaluate opportunities differently than most investors

• How curiosity compounds— from taking finance courses to studying real estate firsthand, Shane explains why lifelong learning became his greatest investment edge

• Bootstrapping as a philosophy— why Shane believes founders should avoid outside capital whenever possible and the freedom it creates

• Special segment: Michael’s son Isaac turns the tables— hear Michael reflect on reinvention, decision-making, portfolio construction and how entrepreneurs learn to think about risk differently

Have a question for our guests? Message us at next@muus.com.

In the fall of 2024, PBS spent time exploring TIGER 21’s Climate Investment Network (one of 39 such TIGER 21 networks) to document how capital, infrastructure, and renewable energy innovation are unfolding across the United States—not in theory, but on the ground. We were honored they chose to highlight Laura di Bonaventura and me as both TIGER 21 Members and principals of MUUS’ climate investment activities, along with fellow TIGER 21 Member, Martin Hermann, Chairman and Founder of BrightNight Power (www.brightnightpower.com), one of the most innovative renewable power companies on the planet, and one of MUUS’ most important investments.

WATCH 50 STATES OF SUSTAINABILITY HERE

The segment is part of Season 2, now airing nationwide across public television stations. MUUS was the first investor in BrightNight. The PBS segment illustrates how renewable power generation, grid-scale infrastructure, and AI-driven demand are coming together in practice. The show’s producer has graciously allowed us to share this preview directly with you.

Today, the over 30 climate companies in our portfolio represent the core of MUUS’ climate investment activities. The capital allocated across these 30 companies was deployed with the same patience and long-term orientation that has defined our work for more than four decades.

If you want to understand where the climate transition is actually happening, not in press releases, but in factories, power projects, data-driven energy systems, and real balance sheets—I encourage you to watch this clip.

Published March 12, 2026

Is it luck when an entrepreneur hits big? It is not the lottery, but the returns can feel like it.

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 thecollective 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.

This piece was originally published in Fortune Magazine and has been reshared with permission. The opinions expressed in Fortune.com commentary pieces are solely the views of their authors and do not necessarily reflect the opinions and beliefs of Fortune.

For Episode 5 of NEXT, Michael sits down with Joe Neiman, a serial entrepreneur in the automotive technology space, to explore the inner journey behind Joe’s success—one shaped by a drive to confront fear, challenge limiting beliefs, and continuously reinvent himself. Joe shares how his early experiences flipping cars and understanding dealer pain points led to the creation of ACV, a platform that revolutionized wholesale vehicle auctions by increasing liquidity, transparency, and speed—ultimately scaling to over 50,000 cars sold per month and reaching a $5B+ market cap.

LISTEN HERE

Joe also reflects on how a childhood marked by underlying anxiety became a catalyst for growth, pushing him to seek discomfort and think bigger—an approach that now informs how he leads, learns, and makes decisions. He shares insights on personal transformation, nurturing family relationships, and how a deeper commitment to introspection has shaped his post-exit learning style, motivation, and overall well-being.

Episode highlights include:

• The psychology of marketplaces — trust, reputation, and why perceived risk changes price more than the asset itself

• Motivational study — how Joe came to better understand what truly drives him—and how it led to personal self-transformation

• Why speed beats perfection in marketplaces — the power of 20-minute auctions and urgency-driven design

• “Roughly right vs precisely wrong” — how Joe makes tough choices and sold his second business, DealerClub to Cars Commerce after 3 months

• Special segment: Michael’s son Isaac turns the tables — hear Michael reflect on key lessons from the Joe Neiman conversation

Have a question for our guests? Message us at next@muus.com.

It is important to state this clearly at the outset: Concern about the current war is not rooted in denial of the Iranian threat, nor in a reflexive aversion to the use of force. Iran is not an abstract problem. It is a dangerous, revisionist state whose actions have already cost many lives.

I also want to express my deepest sympathy for Israelis who have been wounded or killed, and for those who have lived under relentless rocket and missile fire for weeks. Israel did not choose this adversary. Its citizens have borne extraordinary physical and psychological costs, and any serious discussion that fails to acknowledge that reality is morally incomplete.

Where my unease lies is not with the decision to confront Iran, but with how this confrontation is being framed, and perhaps misunderstood. Much of the praise for President Trump’s decision to strike Iran rests on the claim that he showed courage where his Democratic counterparts would never have acted. But courage is not simply the willingness to act. It is the capacity to understand the nature of the conflict one is entering, the kind of adversary one faces, and the limits of what force alone can achieve.

The United States appears to be approaching this conflict as a war of military might—a domain in which it enjoys overwhelming superiority. Iran, by contrast, understands it as a war of wills: a prolonged struggle over endurance, legitimacy, and political resolve. These are very different contests. History suggests that when adversaries are fighting different wars, the side with greater patience and tolerance for pain often prevails.

This distinction matters because what Israel and the United States are ultimately seeking is not merely military degradation of Iranian capabilities, but a reordering of the regional balance of power. Any Iranian regime that survives—regardless of its internal legitimacy—will resist that outcome as an existential matter. Opposition to a U.S. and Israeli backed regional order is not incidental to the regime’s identity; it is central to its claim to rule.

That reality has been articulated openly. Mohammad Bagher Ghalibaf, a senior Iranian figure close to the Revolutionary Guards, recently stated: “The US doesn’t know how to start or to finish a war in this region. We are not going to sit here and let the Zionist regime and the US establish a new order.” This should not be dismissed as propaganda. It is a statement of strategic intent.

President Trump appears to believe that he can decide when this war ends. But unless the objective is full regime change—an undertaking with an appalling historical record—there is little reason to believe the Iranians will grant him that outcome. Iran is not a brittle adversary. It has spent decades preparing for precisely this type of confrontation: absorbing punishment, retaliating asymmetrically, widening conflicts through proxies, and waiting out opponents whose political systems reward short time horizons.

Years ago, after roughly fifty trips to the Middle East that I had taken in loose coordination with Prime Ministers Rabin, Peres and Barak, and the Clinton Administration, visiting with leadership in Lebanon, Syria, Jordan, Egypt, Gaza, the West Bank, Afghanistan, Pakistan and Saudi Arabia, I had lunch with Karl Rove, President Bush’s senior advisor as he was helping to formulate the soon to be launched Iraq war, who had reportedly visited the Middle East exactly once. He confidently predicted that U.S. troops would be welcomed by Iraqis into Baghdad with flowers in the barrels of their rifles. That belief was not born of malice; it was born of ideology, overconfidence, and a profound underestimation of how adversaries and local populations would actually respond. The failure in Iraq reflected the belief that military superiority and conviction could substitute for a serious understanding of political will, social dynamics, and postwar realities.

Even under assumptions favorable to the war’s advocates, military strikes can degrade facilities but are unlikely to permanently eliminate Iran’s nuclear capabilities absent regime change. Scientific knowledge cannot be bombed away. Facilities can be rebuilt, programs dispersed, and stockpiles concealed. If Iran retains enriched nuclear material or the ability to reconstitute its nuclear weapons program, today’s tactical successes may simply set the stage for a more determined nuclear effort tomorrow—one pursued under the banner of national survival.

This is where the distinction between courage and bravado becomes decisive. Courage accepts constraints. It values dissent, respects process, and prepares for outcomes that are uncomfortable and uncertain. Bravado treats war as an extension of personal will—assuming that force, properly applied, can compel adversaries to accept an imposed reality. American experience in the Middle East offers little reassurance to leaders who confuse the two.

What worries me most is that President Trump’s governing style—highly personalized, impatient with virtually no institutional checks, dismissive of expertise—undermines the qualities required to manage a long, ambiguous, and dangerous conflict. Wars in this region rarely end when their architects declare victory. They end when adversaries decide they have lost—or when escalation produces consequences no one intended. The reasons we hold Washington, Lincoln, Roosevelt and Churchill in such high regard are not because they had the courage to start wars, but because they had the wisdom, character and fortitude, against seemingly intractable odds, to see them through over long periods of time.

For investors and entrepreneurs, the analogy is painfully familiar. The greatest damage rarely comes from risks we fail to identify. It comes from overconfidence, from dismantling safeguards before replacements exist, and from believing that conviction can substitute for disciplined process. Bold moves can create extraordinary value—but only when paired with humility, sequencing, and respect for second- and third-order effects. Otherwise, they compound risk rather than reward it.

Iran posed—and still poses—a grave threat. That fact should not be minimized. The harder question, and the one that will determine how this war is remembered, is whether the United States has correctly understood the nature of the conflict it has entered. If this is a war of wills rather than merely a contest of weapons, history suggests the outcome may depend less on who can strike hardest, and more on who can endure longest.

That is the fear beneath this argument. And it is a fear shaped not by ideology, but by experience.

This Substack will be my attempt to share my sense of the extraordinary moment we are living through: geopolitical conflicts that could reshape global stability, political decisions whose consequences may echo for decades, and the broader question of how entrepreneurs, investors, and citizens might navigate a rapidly changing world. Occasionally, I might comment on something far afield that I find especially interesting, as I have done in the past regarding my photography archive and what I find most interesting in that medium.

We are all trying to make sense of the complex world we find ourselves in, and sometimes we find insights in unexpected places. The moment we find ourselves in is bewildering and yet, at times, exciting—perhaps less so for some of us. I can only pledge to offer the best insights I can summon and hope you will engage from time to time in the conversation.

This morning Fortune published an essay I wrote reflecting on a pivotal moment in my life: selling one of the largest real estate developments in metropolitan New York at age 31 (almost 40 years ago)—and how the entrepreneurial prism refracts into broader questions of social responsibility, opportunity, and stewardship: what to do with the capital and responsibility that success creates. Fortune was one of the first publications I started reading in business school 50 years ago, so there is a deep personal satisfaction in seeing this article published there.

You can access today’s Fortune article here: https://fortune.com/2026/03/12/entrepreneur-wealth-success-fear-investment-tiger21/

At the same time, a second article, “Trump’s War,” has been evolving since the war began two weeks ago, and it was scheduled for publication today. Rather than overwhelming you with two articles of substance, we will send out this second piece in the next day or two, but generally we expect 2-4 mailings each month.

I’m calling this Substack MUUSINGS: reflections from an entrepreneur trying to make sense of the world, and invite you to follow along and weigh in. One advantage of Substack is that readers can comment and be part of a dialogue. I hope you will engage from time to time.

These are stressful times; hopefully these writings will bring some clarity—or at least a momentary diversion from the challenges of your day.

Best,
Michael