The Business of Kindness: The CEO of the Milken Institute believes capitalism needs therapy

When Richard Ditizio buried his father, he was prepared for grief. What he didn’t expect was the repetition of a single word. “I was struck by how many people came up to me at the funeral and said the same thing: ‘Your dad was kind.’”

Kind.

It’s an unglamorous word — out of step with a culture that prizes disruption, sharpness, efficiency. But for Ditizio, now Chief Executive Officer of the Milken Institute, it came to define his entire philosophy of leadership and humanity. “That word — kind — isn’t something you hear much anymore,” he says. “Somewhere along the way, especially in America, kindness stopped being seen as strength. It became something people could exploit.”

There’s no sentimentality when he says it. Only a studied understanding of what happens when wealth and civility detach from one another — when finance loses its soul.

Before the Milken Institute, Ditizio spent a quarter of a century in private banking at Citi, advising clients whose names were synonymous with dynastic wealth. “Unlike a traditional bank, these clients aren’t coming to you to get wealthy — you already have to be wealthy to be part of it.”

His job was never about accumulation. It was about disposition. “People asking, ‘Now that I have all this wealth, what am I going to do with it?’” He pauses. “But what struck me most over the years was how much unhappiness seemed to accompany great wealth — depression, suicide, drug dependency, failed marriages. The list went on.”

He remembers one year in particular — four funerals, all for the children of clients. “Suicides, overdoses, and so on.”

He began to see a pattern. “When you’re going to inherit more money than you could ever earn yourself, your relationship with money becomes distorted.” Parents, desperate to protect their legacy, hid it behind legal scaffolding. “Lawyers are always around, signing documents the children don’t understand, all under the pretext of protecting the money.”

The result was a generation of young adults who felt owned by their inheritance. “It creates an odd dynamic where it’s hard for these kids to form an independent sense of identity or self-esteem, separate from the shadow of family wealth.”

That was the beginning of Ditizio’s turn — from banker to something more complex. “We leaned into philanthropy as a way to give these kids a sense of agency,” he says. “For once, it wasn’t about what money could buy, but what money could do.”

It was the moment he began to understand that philanthropy, at its best, is not generosity. It’s redemption.

Connection as currency

When he left Citi, it wasn’t burnout. It was evolution. He had served on arts and nonprofit boards for years, but never thought of it as a vocation. The Milken Institute changed that.

Founded by financier and philanthropist Michael Milken, the Institute is a non-profit think tank headquartered in Santa Monica, with offices in Washington D.C., London, Singapore, and Abu Dhabi. It sits at the intersection of financial markets, public policy, and innovation, a place where capital becomes a tool for solving human problems.

“The Institute uses financial markets to address global issues,” he explains. “Our role is to be catalytic — to move things closer to a solution.”

Unlike most philanthropic entities, the Milken Institute doesn’t distribute cheques. It connects. It brokers collaboration between investors, governments, and academics. It treats the system itself as the problem, not the symptoms.

Each office adapts to its geography. “Each has its own nuance, reflecting local priorities, though common themes run across like climate and the environment. These issues are universal, but they manifest differently.”

He gives the example of Africa. “We’ve developed a programme with the International Finance Corporation that has trained about 300 mid-level finance professionals from ministries across Africa. We bring them to the U.S. for a year-long programme with Georgetown University, place them in internships with financial firms, then send them back. They form a cohort — a network that now knows one another and can collaborate to build local capital markets.”

The logic is elegant: build the scaffolding for others to build their own futures. “In many parts of the world, there isn’t a proper stock or bond market, only banking systems that can be antiquated or corrupt. By helping develop financial infrastructure, we create tangible progress: capital can finally flow to entrepreneurs, helping lift people out of poverty.”

This, for Ditizio, is what impact looks like — progress that may never trend, but compounds quietly over time.

No quarterly miracles

The hardest part, he admits, is the absence of a scorecard. “When I managed my previous business, it was very market-dependent. Every day, I could look at data — asset flows, market performance — and know where we stood. Public companies give you a built-in feedback loop; you get a quarterly report card.”

Here, there are no quarterly miracles. “No one comes into my office and says, ‘Fewer people are poor now,’ or ‘That disease is gone.’ The success we aim for is often intangible and long-term.”

So he created his own feedback loops — internal ways to measure motion without expecting conclusion. “Because these problems didn’t emerge overnight; they won’t resolve overnight either.”

It’s a shift from quantitative certainty to qualitative impact and, in some ways, it makes leadership here even more demanding. “But also more meaningful.”

That belief in meaning is what anchors his philosophy of giving. He resists the cynicism that philanthropy is performative. “I think it comes from a sense of generosity — that impulse to fill a gap you see in the world,” he says.

“When I travel, I see all kinds of deficits; health deficits, wealth deficits, opportunity deficits. But the most troubling one I see is a deficit of hope.”

Hope, for Ditizio, is the currency that underwrites civilisation. “When people lose hope in their future, they have very little to lose. That’s when societies fracture — when conflict, extremism, or despair take root.”

He believes this is the true reason people give; not out of duty or optics, but to restore hope in themselves and others. “It’s not always about money. If solving cancer were purely about money, we would have cured it by now given the trillions invested. It’s also about ideas, collaboration, and persistence.”

A pragmatic sadness

There’s something quietly radical in this, to frame giving as a kind of self-preservation. “There’s something deeply human about wanting to take care of others. Giving fulfils that instinct. It makes people feel that they’re part of something larger than themselves.”

That’s the thread running through the Milken Institute’s Center for Advancing the American Dream, which he helped build to address what he calls “the erosion of optimism.” Gallup’s latest numbers are bleak: 18.3% of Americans are either depressed or being treated for depression. Among young adults, the figure crosses 20%. “We are a society that’s depressed and armed. That’s a dangerous mix.”

Ditizio looks at the landscape with a pragmatic sadness. “Gun violence has become an epidemic. This year alone, around 3,000 children and teenagers have been shot. Gun violence is now the leading cause of death for young people. There are more mass shootings in America each year than there are days in the year — and we’ve become numb to it.”

When he talks about it, it’s not political theatre; it’s moral arithmetic. “Because I don’t want to wait until it’s personal or until it’s someone in my family or someone who works for me.”

Ditizio calls this refusal to wait proactive empathy. “It’s surreal when people overseas ask if it’s true that we teach kindergarteners what to do if someone enters their classroom with a gun — and I have to say yes. Parents are buying bulletproof backpacks, and no one blinks.”

He pauses, then adds: “I want to be proactive. If talking about it helps save even one more life, it’s worth it.”

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Ethics as systems design

His language often slips between the moral and the managerial, as if the two were not mutually exclusive. And perhaps that’s his most interesting legacy: he treats ethics like systems design.

“There’s so much idle capital in the world; it just needs to be activated differently.”

At Citi, Ditizio applied finance to philanthropy, creating metrics for social impact. “Take cancer,” he says. “If your only measure of success is finding a cure, your odds of being the one to make that breakthrough after trillions of dollars already invested are infinitesimal. You need other feedback loops to know your giving is productive.”

At Milken, he applies philanthropy to finance, borrowing compassion as a metric for efficiency. “If we’d moved the money earlier,” he says of the HIV/AIDS crisis, “we could have saved even more. People sit on capital ‘just in case,’ when deploying it earlier could prevent catastrophe. We need to move money faster.”

Still, speed isn’t everything. The other word that recurs in conversation is civility.

“I actually think most people want to do good,” he says. “But they first need to feel secure in their own circumstances. People still want to contribute positively, but they’ve begun seeing the world as a zero-sum game — as if helping someone else somehow takes something away from them.”

Civility, to him, is the condition for generosity. “We try to create spaces for civil dialogue where people can bring their whole selves to the conversation. We want to debate ideas, not identities.”

That insistence on conversation — on curiosity — is what makes Ditizio unusual in an age where leaders perform certainty. “If someone feels passionately about an issue, it’s my responsibility to understand why and not to dismiss it. Agreement isn’t the goal; understanding is.”

The moral infrastructure 

He’s acutely aware that fairness is the next frontier — the moral infrastructure on which all of this rests. “What drives me is the belief that all people need is a level playing field, a fair chance. Nobody’s asking for handouts. But when people are excluded because of skin colour, religion, or who they love, it creates an unfair exchange.”

He sees fairness not as charity, but architecture. “Existing systems — corporate, governmental — were often built for one kind of person. As the world diversifies, those systems must adapt. If structures only work for a specific type, we have to rebuild them.”

Even language, Ditizio argues, is complicit. “For decades, the goal was ‘tolerance.’ But tolerance is a terrible word. No one wants to be tolerated — it elevates the person doing the tolerating. Then came diversity, then inclusion. All of these still carry a hidden power dynamic; as if someone’s granting permission for others to belong.”

He points to our own grammar of progress. “Even in history, we say things like ‘In 1920, women got the right to vote.’ From whom? They were citizens. The phrasing itself implies that rights are given, not inherent. Language shapes mindset. Until we reframe that, equality will always sound like concession.”

The two-inch box test

Leadership, for Ditizio, is where philosophy becomes practice. “A leader’s primary dimension is emotional,” he says. “You can have all the tactical and operational skills in the world, but leadership is about transmitting mood — setting the emotional tone of the organisation.”

The pandemic tested this theory brutally. “Suddenly, CEOs who were once distant became two-inch boxes on a screen, as accessible as anyone else. Some handled that shift well; others didn’t.”

He remembers how it forced an intimacy that hierarchy had long prevented. “At the bank’s headquarters, if I stepped into an elevator, junior employees would stiffen up, act formal — they were riding with the CEO. But two hours later, if I walked into a Starbucks, the barista didn’t care who I was. Good leaders know the difference. Bad ones expect the barista to recognise them.”

Ditizio tells that story like a parable; part humility lesson, part mirror test. The subtext is clear: leadership isn’t about power; it’s about calibration.

“Leaders hire in their own image,” he says. “Then they hire people like themselves, and so on. Soon, the company becomes an echo chamber of sameness.” That sameness, he warns, is fatal. “If everyone thinks the same way, no one challenges risk. That’s how financial crises happen.”

He makes a conscious effort to hire people who think differently from him. “That’s what makes an organisation resilient — it can function without you, because it’s not a mirror of you.”

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The price of perspective

There’s a particular vantage point that comes from standing between the world’s wealthiest and its most vulnerable. Ditizio has lived most of his professional life in that corridor. First as a private banker advising the ultra-rich, now as the head of a global think tank designing solutions for those left behind. 

The paradox is not lost on him. He has seen what too much money can do to the soul and what too little can do to the body. And somewhere between those extremes lies the fragile business of being human.

To occupy both worlds is to carry their contradictions. “When you’re advising people who already have more money than they could ever spend,” he says, “outperforming a benchmark by one or two percentage points isn’t what keeps them up at night.” 

He learned early that wealth brings its own vocabulary of suffering — one that rarely earns sympathy. Depression, addiction, alienation: these were the currencies of his old trade. Later, at Milken, the scale changed but the patterns didn’t. Poverty and disease were different symptoms of the same problem: disconnection.

I ask what it’s like to spend a life surrounded by stories of imbalance. He exhales. “You learn to build emotional discipline. Not detachment, exactly, but a kind of stewardship of empathy. If you let every story in, you can’t lead. But if you shut them all out, you stop deserving to.”

It’s a delicate calibration, this dance between care and composure. Most of his days are spent in conference rooms and summits, where the human stakes arrive flattened into PowerPoint slides — a million displaced here, a billion unbanked there. 

Yet when Ditizio talks about fairness or civility, there’s still something stubbornly personal in it, as if the weight of every statistic passes through a single moral filter: could this have been prevented if someone had cared sooner?

He has learned that proximity to power doesn’t guarantee proximity to truth. The higher one climbs, the more abstract people become until kindness itself starts to feel like a rebellion. “Proximity can be dangerous,” he says. “You start mistaking access for understanding.” It’s why he keeps returning to the small, almost domestic virtues: kindness, fairness, honesty. They are the only currencies that hold value no matter the room.

That’s the quiet revelation of his career; that empathy, to endure, must be designed into the system. Policies are only as humane as the people who write them, and even the most brilliant strategies collapse when stripped of compassion. Ditizio has spent decades learning to translate between balance sheets and human needs, and the lesson, he says, is always the same: money is fast; change is slow; people are fragile.

The act of risk

Toward the end of our conversation, I ask him what keeps him awake at night. He answers without hesitation. “Unfairness,” he says simply. “What drives me is the belief that all people need is a level playing field — a fair chance.”

Ditizio pauses as if testing the words, weighing them against the years he has spent navigating systems built for imbalance. Fairness, to him, isn’t charity. It’s infrastructure — the moral scaffolding on which societies either stand or collapse. “Kindness stopped being seen as strength,” he had said earlier. But in Ditizio’s world, kindness is structure — the invisible framework that sustains civility, fairness, and hope.

Before we wrap, he offers one last observation. “One of the biggest mistakes leaders make is assuming they hear the truth. You need to create an environment where truth can surface without punishment. Too many hierarchies are designed to suppress bad news until it’s too late.”

He lets the silence settle before continuing. “If you want innovation, you must allow mistakes. Everyone wants to be innovative, but most organisations are structured for zero risk. That’s incompatible.”

He’s talking about leadership, but it sounds like something larger — a comment on the human condition. We want progress without uncertainty, empathy without cost, safety without sacrifice. Yet every meaningful act, from invention to compassion, carries risk.

That, perhaps, is the quiet thesis of his work: that kindness, too, is an act of risk. It asks us to confront what’s uncomfortable and to see people as they are, not as they perform. It rejects indifference, even when indifference would be easier.

Today, in a time when self-interest is so often mistaken for strength, Ditizio’s conviction feels almost subversive. Because kindness, as he defines it, is not gentle. It is a discipline — one that insists on truth, demands courage, and holds space for imperfection.

And if that sounds radical, it’s only because we’ve forgotten how rare it is.