Family Business Audiocast | Episode 60 | James Rosebush

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R. Adam Smith: I'm pleased today to be joined by James Rosebush, a senior statesman in leadership, governance, and legacy, whose career spans the highest levels of public service and private stewardship. James is my friend and an incredible, inspirational person. James, great to have you today. I'll brag about you first, then we'll dig in.

James served at the heart of the Ronald Reagan White House, including as Chief of Staff to the First Lady and as President Reagan's point person on philanthropy and public-private partnerships. In that role, he helped shape initiatives that mobilized private capital for public good, laying early groundwork for what we now call impact investing and mission-driven capital.

During a defining era of American leadership, James operated at the intersection of values, power, communication, and trust — helping steward institutions under global scrutiny, managing sensitive diplomatic engagements, and reinforcing a leadership ethos grounded in clarity, integrity, and long-term responsibility. Following public service, James carried these principles into the private sphere, where he advises families, family offices, foundations, and enterprises on aligning growth, capital, and legacy across generations. Today's conversation isn't about politics — it's about what it takes to build institutions that last and endure, whether you're leading a nation or stewarding a family enterprise. James, ready to jump in?

James Rosebush: Sure — and thank you for that wonderful, information-filled introduction. I really appreciate your sharing my experience with the audience.

R. Adam Smith: Well deserved, and just a summary of course. Let's start with leadership formation and stewardship. Your experiences during the Reagan era created a unique ethos for the world in the eighties, and we still see its impact on economic history and the Cold War — a time of high global tension and scrutiny. I'd love to hear about the discipline and awareness essential to that role in the White House. Reagan was famously perceptive, knew when to act decisively, was a great listener, and had a very high EQ. Tell us a bit about your experience in that era.

James Rosebush: I'd love to share some unique things about Reagan as a leader. I've had a contractor helping me write a book about leadership — I'm now calling it The Complete Disappearance of Leadership. We've had great leaders in different fields, but Reagan's model is unique, because — and I think I've shared this with you before — Reagan had zero concern about what people thought of him. That was one of maybe half a dozen defining strategies he lived by.

Working directly with the President gave me the chance to meet incredibly interesting people, and to have real conversations with him. But that detail — not caring what people thought of him — is genuinely critical to leadership. We had pollsters reporting to the Oval Office every Thursday, and all of us were fascinated by the numbers, but he wasn't. He'd sit at the Resolute Desk doing something else entirely. I had to figure out why. It wasn't easy — I hadn't come from the entertainment industry in LA, and I hadn't been in politics.

Fortunately, the firm that ran his campaign was the same one I'd hired while running the foundation at the U.S. Chamber of Commerce. The day after Reagan was elected, they called and asked me to come work in the White House. I said no, thank you — I loved my job running the Standard Oil Foundation. But I slept on it, and the next morning I thought, "Are you kidding? You turned this down?" I called them back, asked if I could rescind what I'd said, and they said sure — what job did I want? They handed me the "Green Book," which lists about 2,200 presidential appointments. I found a role representing the president to the business community, and that was it.

I've always believed you can go the extra mile if you truly understand the people you're working with and for. Reagan not caring what people thought of him meant he wasn't beholden to anyone — not major donors, not people currying favor. Leadership, for him, meant fidelity to the American people, not to whoever was funding him, even his own friends, of which he had plenty from his years in California and entertainment.

Second, he was the son of an alcoholic — there's a lot of research on this. Children of a parent who's a serious alcoholic, someone you had to pick up off the front lawn, often find it hard to open up to others, because they had a parent they couldn't trust. Reagan was very guarded and circumspect about his beliefs and what he'd say — even though he could give a moving speech three or four days a week that people genuinely loved.

I'll give you an example of that connection with people. I traveled with him once to a heavily Democratic part of Boston — we went into a bar, just the two of us, surrounded by Democrats. They lined up not just to shake his hand but to kiss him, thank him — they wanted to be part of the "Reagan brigade." That's another aspect of leadership: he never chased popularity, yet people trusted him and felt he was on their side. In China, walking through fields where people were hoeing without any equipment, they called out to him — just the two of us and an advance team nearby — "Hey, freedom man, come talk to us, we want to hear about freedom." Seeing the honor people placed in him, because of how he felt about them and his commitment to freedom and independence for all people, was extraordinary.

R. Adam Smith: Thank you, James — such a powerful personal window into one of the most fascinating presidents in modern history, one of my heroes, and a defining figure for the Republican platform and ethos. That awareness and empathy — somewhat ironic given his difficult upbringing, which we can talk about later — is deeply relevant to the family office community: super-wealthy people with huge impact and wealth in the world. Awareness and empathy help guard against the blind spots that wealth can create — greed, ego, limited perspective.

Let's move into moral clarity and integrity. How did integrity function within the Reagan White House, and how did that relate to building trust with his team and in foreign affairs? Talk about trust as a strategic asset, not just a throwaway term — and how it enabled his tremendous success, both domestically, recovering from the difficult Carter years of inflation and social unrest, and internationally, in driving the Cold War into a new era.

James Rosebush: Reagan was a deeply spiritual person — another thing I had to learn about him. One day, someone from the correspondence unit — the President received thousands of letters daily, and the unit would pick out around ten each day for him — handed me a letter asking whether the president had any favorite hymns. That was another way I learned who Reagan really was, since he never talked about himself.

Around the same time, I told him, "Mr. President, I'm going to get you some shirts with a tighter collar" — he looked a bit like an old man in his loose-collared shirts. He thanked me graciously. I bought him some shirts and ties from a store in Washington. Three weeks later I asked if he'd tried them. He said, "Jim, I did, thank you so much, but this is the kind of shirt I wear — I can't change." Later, in the hospital, he once asked me to go into his closet and bring him clothes for the next day, a task normally handled by a military aide, but I'd do anything for the president.

These small things taught me a lot — and I think it applies directly to family office management too. It's critically important to understand the good, the bad, and the difficult about the people you serve. As we always say, once you've seen one family office, you've seen one family office.

Going back to the hymns — I told him, "They want to know your favorite hymns, just tell me what they are," and he said, "I'll sing you a couple." I couldn't believe the President of the United States was singing me his favorite hymns — and it happened that one was my own father's favorite. I started in the family office business at age 18, and I learned early that the most effective way to work with families — many of whom face very challenging issues — comes down to your commitment to them and what you learn about them.

Reagan always said you have to ask, at every issue and every meeting: "What is really going on?" He asked that question constantly. Yes, he read his briefing books, but the way he thought and parsed information always came back to that question — and I think it's one of the most interesting things about him, and central to the leadership he showed the world.

R. Adam Smith: Thank you, James — that's very powerful. I recently discussed something similar with family office expert David Wardiger — pausing, looking around, taking a broader perspective rather than acting too quickly.

Integrity is especially interesting for large family offices as they grow — there are over 10,000 in the world now, hundreds of them massive, collectively controlling perhaps 10-20% of global wealth, not to mention that family businesses represent 70-80% of global GDP. Family offices with major operating businesses and brands directly affect their legacy, their local economy, their city, their employees — there's real complexity there. Keeping integrity in mind matters, so these organizations aren't driven purely by financial motives but treat integrity and clarity as a form of compounding capital in the business itself.

Moving to the power of story — do you think Reagan's Hollywood background, being an actor, helped him navigate different personalities, read people, and adapt to change with the nimbleness an actor needs?

James Rosebush: It certainly gave him an edge in communicating and storytelling. I once invited a group of family offices to a breakfast meeting with the president — he was at one end of the table, I was at the other, and the chairman of Pepsi was there too. Someone offered Reagan a Coke, and he said, "Oh no, I don't drink Coca-Cola, I only drink Pepsi." I quietly asked a server to run across the street to get him one — quite funny.

He usually opened with a very funny story — that day it was about philanthropy: "Why would I give anything to you? I don't even give anything to these people," meaning his own sister and son, people close to him. It floored everyone in the room. That was the point — opening up a personal relationship with his audience, which he was masterful at. He loved telling jokes, including plenty about the Russians — "You can buy a car, it'll be ready October 30th — which October 30th? Ten years from now." It wasn't just jokestering; it served the purpose of building relationship.

I want to circle back, because I love blending this experience of learning great leadership with my work in family offices. One of the big lessons: working in the White House can involve the most glamorous things — I've slept at Windsor Castle, traveled everywhere with the president — but none of that matters when it comes to what families actually need from you.

I once worked with a family in California for four and a half years where the wealth creator was a genuinely difficult person, and he knew it. One evening he asked if we could go to dinner, just the two of us, at his club. We sat mostly in silence — I wanted him to speak first. After about an hour, he said, "I have a lot of problems." That was an incredible breakthrough — him feeling comfortable enough to admit he was difficult, and difficult for his kids. That, to me, is the real core of running or advising a family office: helping in ways that go beyond investment strategy, since personality itself can affect investment decisions.

I worked with another family — fifth generation, once the biggest company in the world in their industry, but by the fifth generation all that remained was real estate, no cash, and five siblings who hated each other. Two of them died while I was working with the family, and the others refused to visit them in the hospital or even acknowledge them — I had to step in and handle that myself. There are things you have to be willing to do because you know the family needs help.

One more story — I was giving a speech on family office work in Bermuda, phone silenced on the podium stand. I glanced down and saw one of the family's major estates burning to the ground, with a message saying I needed to get there immediately. I obviously couldn't, being in Bermuda at the time. These are things I find fascinating, but which I don't think the family office industry fully appreciates — these families need not just great investment advice and integrity, but real understanding. Occasionally you find a family that's simply wonderful, but that's rare.

R. Adam Smith: Thank you for that storytelling about storytelling. The narrative of a family office matters enormously for the family's brand and reputation as they grow, or as they come to care about their brand — hence the rise of CMOs, branding agencies, and crisis management firms serving this market, and boards helping build a brand like MSD, Pritzker, Perot, or Walton. For these institutions to endure, we often discuss legacy on this show — it requires a coherent story, professionally told and repeatable, that can be told by others, not just held internally.

Reagan and his administration did a masterful job communicating both the Cold War struggle with Russia — tearing down the wall was such a pivotal moment — and, something people forget in today's short-memory media era, just how powerful the economic recovery was under his administration. That story was told very effectively too.

Let's close on stewardship, succession, and thinking longer term. The Reagan era was defined by very successful leadership, domestically and internationally, driven by personality but also a strong cabinet — though ultimately, as you said, he focused on doing the right thing. Doing the right thing in business, for a family office looking at short-term financial or cultural needs, or decisions involving children, can be genuinely difficult. Share your thoughts on anchoring longevity as intentional design — what was that like in the Reagan White House?

James Rosebush: Well put. Here's the thing — before his "tear down this wall" speech, I was with him in Geneva for his first meeting with Gorbachev. We were sitting by a roaring fire, and I asked him, "What do you think will really bring down the wall? Some kind of intervention? How do you think it'll happen?" He said, "It will end because of the people's desire to be free."

You may remember, before he was even elected, he was sitting in his California living room when he heard about the new Pope and said, "Now this is a man I can work with." We had several meetings with the Pope, which meant a great deal to all of us — he blessed us. Reagan believed that if he could connect with someone like the Pope, he could do more than simply demand the wall come down — he had to understand who Gorbachev truly was, at a time when most people outside intelligence circles knew very little about him. Reagan insisted on a one-on-one meeting, which upset a lot of people — George Shultz was very unhappy about it — but that's how Reagan operated: he wanted to reach into the soul of the person he needed on his side.

Sitting by that fire, when I asked how it would ultimately come down, he said it would only happen because of the people's desire to tear it down themselves — and that's exactly what happened, roughly nine months after his term ended, when people marched to the wall and Gorbachev didn't stop them.

When he actually delivered the line at the wall — "Mr. Gorbachev, tear down this wall" — the emphasis mattered. It wasn't read the "proper" way; he placed distinct stress on "tear down this wall." He was deliberate about exactly what he wanted Gorbachev to do, and his aides didn't even want him to say it. But he had a conviction beyond anything in a briefing book.

Today, the sheer amount of wealth in the world needs people managing it with integrity — people who genuinely care more about those they serve than about themselves. I see a real parallel between how Reagan approached these enormous, difficult issues and how family offices need to be run, given how much is at stake. I'm deeply grateful that after the White House I got to continue this work with families all over the world, because I think more people need to approach it this way.

R. Adam Smith: One more topic — looking at the next generation, our children and grandchildren, and how that relates to today's media-heavy, skeptical, hyper-partisan world, with institutions fracturing across many OECD countries — Japan, Italy, France, the UK, the US, and emerging markets like Brazil, all seeing political shifts, left and right. Setting aside the politics, there's real de-institutionalization happening, and a lot of next-gen frustration — millennials and those in their twenties and thirties are fed up with extremism and short-termism.

What I admire about the Reagan era is the balance of humility and ambition he brought to the White House — perhaps aided by good fortune, an economic turnaround, and Gorbachev being something of an aberration in Russian history, but still, that balance of ambition and humility, and real character, stood out. Share some thoughts on focusing on responsibility rather than purely transactional matters, and why optimism still matters, even in today's messy political landscape.

James Rosebush: Our first two years in the White House, the economy didn't turn around as fast as we'd hoped, and Reagan paid a price for it in the media. I think the most challenging thing today is a lack of unity — and this isn't just political, it shows up in finance and other areas too — this idea that it's all about "my view," "his view," "her view." Our culture has instilled the notion that everyone should hold an independent view and not necessarily get along with people who disagree.

But it's important to genuinely honor people with different viewpoints — it makes our country, our communities, and our families stronger. A lot of today's problems come from people wanting to control things politically exactly as they wish, backed by enormous sums of money, and that becomes genuinely scary — a whole movement, particularly in the U.S. but not only here, of wealthy individuals influencing policy in ways that weren't originally intended. We do need people with significant capital investing in fixing real problems — but if the purpose is purely to grow their own assets or shift the political thermostat, that's one of the most difficult dynamics we face.

Across the street from our house lives a former U.S. ambassador to NATO from a past administration. When we moved in, he wasted no time telling me directly that he hated me. A sad thing — he'd walk his dog and make sure it went in our garden. I didn't engage.

On a podcast I appear on regularly, the host once asked if it'd be okay to bring on a third guest — and named this very man. I said nothing, curious to see what would happen. On the next episode, he joined us, and we ended up agreeing on about 90% of policy issues — he started telling me how much he loved me, how alike we were, how I was practically his brother. This was the same man who'd looked me in the face and said he hated me. What an interesting story — it just goes to show that when you don't take the time to actually listen to someone else's point of view, you miss the common ground that's often there. I'll never forget that.

R. Adam Smith: Thank you for that story. As we wrap up — Reagan's empathy, awareness, emotional intelligence, affability, and optimism were genuinely unique. I think many people around my age feel a real nostalgia for that sense of optimism. I appreciate you reflecting on these softer dimensions of power, personality, and integrity, which are so relevant to the family office world and the impact these large organizations have on their own cultures and their communities.

We've covered integrity, stewardship, awareness, and your reflections on legacy. Thank you for sharing these personal thoughts — it's rare to have this kind of quiet, candid access, especially while you're writing a new book on the Reagan era. Wonderful to have you on the show.

James Rosebush: My pleasure — thank you for inviting me.

R. Adam Smith: This conversation reminds me that leadership — whether in a family business or a nation — is anchored in stewardship, and a whole range of factors matter: growth, money, intensity, learning, and continuous improvement. But ultimately, I think legacy is built through discipline and the responsibility of looking beyond yourself, beyond any single leader, moment, or fortune, toward something broader and longer-lasting. Thank you again for sharing your experience.

James Rosebush: Do you have one more minute for me to add something?

R. Adam Smith: Let's do it.

James Rosebush: Reagan's very last speech was addressed to the American people. In the Oval Office, there were two women present — a producer and a camera operator. One asked, "Is he okay?" — his head was down on the desk — and the other said, "Oh yes, that's how he starts every speech." He went on to say, "You've heard me talk about America and the light of the American cause — I don't think I've ever told you what I saw when I saw the promise of America." It was remarkably beautiful, in thinking, timing, and depth. Here was a man devoted more to his country and countrymen than to himself, with the ability to communicate not by reading a speech, but by reading his own heart.

R. Adam Smith: Wonderful. Thank you so much for sharing your experience today, James — this was an amazing conversation. This is R. Adam Smith, signing off. Please stay tuned for the next episode of the Family Business Audiocast.

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Explore the strategic intricacies of family business success with the RAS Family Business Audiocast. Join R. Adam Smith as he delves into exclusive discussions with global leaders shaping the future of private wealth and enterprise. Each episode offers a rare glimpse into the core decisions driving prosperity in high-stakes markets. Tune in to gain expert insights and innovative strategies that empower family businesses to thrive across generations.

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