Episode 60: The Leadership Principles Behind Enduring Institutions and Family Enterprise with James Rosebush

FBA59 James Rosebush === R. Adam Smith: I am pleased today to be joined by James Rosebush, a senior statesman globally in leadership, governance, and legacy, and whose career indeed spans the highest levels of public service and private stewardship. James, is my friend and just incredible inspirational person. James, great to have you today on the show.

I'm gonna brag about you now and 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 also President Reagan's point person on various topics including philanthropy and public-private partnerships. And 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 the intersections of values, power, communication, and trust, helping steward institutions under global scrutiny, managing sensitive diplomatic engagements, and reinforcing leadership ethos, grounded in clarity, integrity, and long-term responsibility and thinking.

Following public service, James carried these principles into the private sphere where he is today, advising families, family offices, foundations, and enterprises and corporations on various matters, including how to align growth capital and legacy across generations. Indeed, today's conversation is not 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, I'm very honored to have James Rosebush on the show today.

So James, you ready to jump in? James Rosebush: Sure. And thank you for that very, wonderful and information, filled explanation of what I've done and, it's tremendous. I really appreciate your sharing my experience with the audience.

R. Adam Smith: Yes. Well deserved and just a summary, of course. Let's start on leadership formation, talking about stewardship.

The experiences you had in the Reagan era really created a unique ethos for the world in, in the eighties. And obviously we see the impact of that and both economic history and the Cold War. It s also a time of high global tension and scrutiny. I'd like to hear a bit of your experience back then and, you know, talking about some of the discipline and awareness that was essential during that time and such a intense role in the White House.

And of course we know Reagan was all about being a very aware person, knowing when to act decisively. He's also a very good listener an actor, and very high EQ quotient. So, such a fascinating leader for our country also in that regard. So love to hear a bit of your background in that era for the audience.

James Rosebush: Thank you. I'd love to share some unique things about Ronald Reagan as a leader, because I find myself in a position. I have a contractor write for the book about leadership, and now I'm calling it The Complete Disappearance of Leadership. And so I, I think that well, we have had some great leaders in different fields.

The model of Reagan is unique, and I say that because, and I think I've shared this with you before, that Reagan was a person who had zero concern about what people thought of him. This was probably one of maybe a half a dozen ways and strategies that he lived by. This is one of the great gifts of working directly with the president of the United States. You can have interesting conversations, you can have fun.

He's obviously the person that everyone wants to talk to. But, it gave me a lot of opportunities to meet people that are very interesting as well. I mentioned one thing there, that he didn't care what people thought of him. And I thought, well, is that really important?

And the more I saw how important it is, the more I saw that this is a genuine aspect that is absolutely critical to leadership. Obviously we had pollsters, in the Oval Office they'd report every Thursday. We were all interested in the polls, but he wasn't at all. He would go, sit in his chair at the resolute desk and he would just be doing something else.

He didn't really care about his polls, and I thought, well why is this? Because people basically in politics, are absolutely obsessed with their polling status. I had to figure him out. It wasn't easy because I had not come from the entertainment industry in LA, I had not been in politics.

Fortunately for me, there was a company that really ran his campaign and when I was running the foundation of the US Chamber of Commerce, I hired a lot of people and I happened to hire this firm. The day after Reagan was elected, they called me and they said, we'd like you to come work in the White House. If you can believe this, I said no, thank you so much. But I loved my job.

I was the head of the Standard Oil Foundation at the time and that was a great job. But fortunately I slept on it and the next morning someone in my head said. - "Are you kidding?" You turned this down.

So I called them back and I said, is there a chance I could rescind what I told you yesterday? And they were like yeah, no problem. I said, well, what job do you want me to hold? And they said, well just get the Green Book, which has, 2200 jobs that the president can choose people for himself.

So I looked, and I saw there was a role for representing the president to the business community. And I thought that would be ideal. So they said, sounds good to us. Sounds good to us.

So there I was in the beginning of the administration, but I've always felt that you can go several extra miles if you understand the people that you're working with and working for. So let's go back to why it was important, critically important that Reagan didn't care what people thought of him. As a result, Reagan was not tied to any people. For example, that gave a lot of money for his campaign, or were trying to seek his favor.

Leadership for him was that he had to be faithful to the American people, not faithful to the people who were funding him or even his friends. He had a lot of friends, obviously from the entertainment industry, and from living in California for so many years. But also, second point, he was the son of an alcoholic. There are many studies about this.

If you have a parent who is a serious alcoholic, meaning, you know, stumbling down on the front lawn and you have to pick 'em up, apparently these people, it's hard for them to open up to other people because they've had a person, a parent who they couldn't trust. So Reagan was very bound in and circumspect about his beliefs and what he would say. Of course, on the other side of it, he was giving speeches maybe three or four days sometimes that people really loved. So I had all of these incredible opportunities to figure out what true leadership is.

So I've given you two of these keys. I would travel with him, for example, to Boston, to the area in Boston where there were all Democrats. We went to a bar one day, I remember, it was just me with him at the bar. And these people, they're all Democrats.

They were all lining up, not just to shake his hand, to kiss him, to thank him, they wanted to be a part of the Reagan brigade. There's another aspect of leadership right there. He embraced without wanting to be popular or wanting to be a person who, opposite of the other things that I just shared with you. So that was another lesson I learned.

That you have these friends and supporters and people that are interested in you and vote for you because they can feel that they trust you and that they understand that you're on their side. It's like when we went to China and I went into the fields, where they were hoeing. They had no equipment, and they called out to the president. I was walking right next to him.

I think it was just the two of us. There was an advanced team in Secret Service, but they said - "Hey, freedom man. Freedom man. Come and talk to us.

We wanna hear about freedom." And, just to have had those experiences and to see the interest and the honor that people placed with Reagan because of how he felt about them and how he wanted to provide a freedom, independence for all people. R. Adam Smith: Thank you so much, James.

That's such a powerful personal window into one of the most fascinating presidents I think we've had in modern history. One of my heroes and I think a powerful core of the Republican Party, Republican platform and ethos. I think referring back to awareness, Reagan showed a very powerful awareness and also empathy, which was kind of ironic coming from his background in a sense we can talk about later. But having someone who had a very difficult household and also was an actor.

It was very interesting that he showed such powerful empathy and awareness, 'cause you get burned by certain things in life. So that awareness, I think is very relevant to the family office community of super wealthy people that have huge impacts and huge wealth in the world. To be aware and to be empathetic, and to not have blind spots of the wealth that can create, greed and ego and limited perspectives. So there, we'll move into let's say moral clarity and integrity.

How you saw integrity functioning within the Reagan White House and how that integrity related to trust, building trust within the White House with his team and also of course, especially within foreign affairs. Talk about how trust is a strategic asset, not just a throwaway term. How it allowed Reagan to have such incredible success as a president. Let's remind people of his tremendous successes, of course, both domestically and recovering from some difficult Carter years, not just of inflation, but also social matters, and also driving the Cold War into another era.

Talk about that integrity and trust within the White house. James Rosebush: So Reagan was a deeply spiritual person, and this was another thing that I had to learn about him. And it came because one day I was up in the family quarters and someone came from the correspondence unit and the president gets, thousands of letters every day. So what they do in the correspondence unit, at least they did in our administration, is they choose maybe every day, like 10 different letters that are addressed to the president.

And of course he wanted to read every one of them, but this was handed to me by one of the members of the staff. And it said - does the President have any favorite hymns, meaning church hymns or Christian hymns. This was another way that I learned about who Reagan really was, because of course he never talked about himself. Around the same time, I said to him, Mr.

President, I'm gonna get you some shirts that have a tighter neck. He looked like an old man. He had shirts on, but it wasn't tight around his neck and all that kinda stuff. He said, oh Jim thank you.

So I went over to a store in Washington, and I got him a couple shirts and a couple ties, and after, oh gosh, three weeks, I said, Mr. President, did you try the shirts that I got you? You know, Jim I did. I thank you so much, but I am a person of.

He said, this is the kind of shirt I wear and I can't change. Not long after that, he was in the hospital and he said, you know, I didn't know I was gonna have to stand another day. Would you mind going into my closet and bringing me some clothes that I can change into for the next day? typically that would be handled by a military aid, but I would do anything for the president.

But these are all ways that you can learn, and I think this has a lot to do with family office management as well. Because I always consider that it's critically important that you understand the good, the bad, the ugly, the difficult. As we all always say, once you've seen one family office, you've seen one family office. So these are all things and ways that in managing a family office, you really need to understand who it is that you are helping and that you're advising and that you're working for.

So in any case I had that experience of seeing how uncomplicated he was. So to go back to the hymns, I said - " they want me to tell 'em, what hymns you like, and just tell me what they are." "Oh, I'll sing you a couple then." I couldn't believe that the President of the United States was gonna sing to me his favorite hymns.

And it made all the difference in my understanding him, and especially because it happened to have been my dad's favorite hymn. So these are just ways I believe very strongly, and this is why not only I had, I started in the family office business at age 18, but I learned that the most effective way to work with families, and many of them are very challenging because they have a lot of challenging issues. But it is, it is about your commitment to them and what you can learn about them.

He always made this statement. - "You have to ask this question every day, at every issue, at every meeting, and that is this question, what is really going on?" Always asking this question, what is really going on? And he locked that inside and that's the way, yes, as I said, he read his briefing books, but the way he thought and parsed it.

He always asked this question, what is really going on? And I think that's one of the most interesting things about him and one of the most interesting things that contributed to his, you know, the leadership that he showed to the rest of the world, and not just to the US. R. Adam Smith: Thank you James.

That's very powerful. Appreciated one of his key takeaway comments. As you said, to look around and see what's going on and like step back and have a bit broader perspective. Actually I talked about this recently in the podcast with David Wordiger, family office global expert, talking about pausing and looking around and considering and not acting too quickly.

This topic of integrity is super interesting for large family offices. As they get bigger, as we know, getting bigger and bigger, over 10,000 in the world, let's say hundreds of them are super massive and collectively they probably control 10, 20% of the global wealth. If not to mention, 70, 80% of global GDP as family businesses. So the family offices that have a super huge.

Family businesses they have brands, and those brands, of course affect their legacy. They affect their economy, they affect their city, they affect their employees, and there's just a lot of complexity there. So talking about integrity I think is really important to keep in mind that these family offices and their businesses. Can really have implications on the many thousands of people, not to mention their, domestic economy and so on.

So integrity is very important to not just be driven financially, but to incorporate integrity and clarity into leadership to position integrity as compounding capital essentially in these family businesses. So moving on to the power of the story. Just as an aside, do you think that Reagan's ability to navigate lots of different personalities and emotional intelligence and navigate like the subtleties of reading people and emotional and soft power, - do you think that being an actor, having gone through Hollywood and being an actor, do you think that helped him?

In being able to navigate like a range of personalities, but also the ability to see change. As an actor you really have to be nimble now and act your way through it. James Rosebush: Well, it certainly gave him a leg up in terms of his ability to communicate and also to tell stories. For example, I invited a bunch of family offices to have a breakfast meeting with the president one time.

He was down at the one head of the table. I was down at the other one. We had the chairman of Pepsi, and you probably remember him. This was a breakfast meeting, and so there were, there were people waiting on everyone, and so he was offered a Coke.

And he said - "Oh no I don't drink Coca-Cola, I only drink Pepsi." And so I said to the servers so other people couldn't hear it. I said, do you think you could run across the street from the White House and get this, get a Pepsi for him? Anyway, it was very funny.

But the President usually started off as he did that day with a very, very funny story about philanthropy. Why would I give anything to you? I don't give anything to these people either. Meaning the people that were in the hospital, his sister, his son, all that sort of thing.

And it just absolutely floored everyone there. I mean, they couldn't stop laughing over that. So Reagan was very good at, so what's the point of that? Right?

That is to open up a personal relationship with your audience. And he was masterful at that. He loved to tell stories. He told a lot of stories and a lot of jokes, for example, about the Russians.

You know, oh, you can buy a car, it'll be available on October 30th, that we don't have any trouble in Russia. Then they ask him, well, which October 30th? Oh, in 10 years from now, October 30th, you'll get your car. He loved to, to do things like that.

But again, it had a purpose. He wasn't just trying to be a jokester, but that's how he developed his relationship. And I wanted to go back to a minute, because I love this conversation by the way. And I love the fact that we're kind of blending this experience that I had of leadership and learning what great leadership is and my work in family offices.

One of the big lessons I learned, or I don't know if I had to learn this, but when you are working in the White House, you may be doing the most glamorous things. You know, I've slept at, at Windsor Castle. I've slept at, you know, all, all these places and gone all these places with the president. But it doesn't matter when you get down to what you really need to do with the families you're working with.

That is one of the things that I admire so much. If you're running a whole family office or a division of it or whatever, You're there to make them. I'm not gonna say successful, you could say that in the investment area, but there are a whole lot of other areas where their need is even greater. I remember one night, I'm not going to mention any names, but I had a family for four and a half years in California and the wealth creator was a very difficult person.

And I had to live with that. His whole family had to live with it and he knew that he was a difficult person. One afternoon, he said to me - "Jim, do you think that we could go to, I'm not gonna tell you which club it was, but could you go to the club with me? And just have dinner, the two of us."

And I said, absolutely. So we go to the club and basically he sits there not really saying much. I didn't say much either because I wanted him to be the one. And he said maybe about after an hour in at the dinner, this is all he said.

He was saying nice things about the work I'd done for him, but that wasn't the point. He said, "I have a lot of problems, and I looked at him and I thought, this is an incredible breakthrough, that he feels comfortable enough to say to me that he was a difficult person and he very difficult for his kids and so forth. To me, this is really the most important part of running a family office or advising a family office is to help them in ways that are, even investment strategy can be affected by personality.

The person who goes to run a family office. And spend time with them. Like I've had great opportunities through the years to work with many families. You have to be willing to really say, what is really going on, what is really going on?

I think that a lot of people have this vision of running a family office is something glamorous. Well, if that's really true, it's very different than what experiences I've had. But I never, I had a family, they were the fifth generation, in one industry, the biggest company in the world. But by the time they got to fifth generation, all they had was real estate.

They had no cash and there were five of them, and they hated each other. All of them, two of them died while I had them. They refused to go to the hospital and recognize their brother. So I had to do that.

I mean, there are things that you have to be willing to do because you know that they need help. Little last story I'll tell you related to that, I was giving a speech probably on family office work in Bermuda. I had my phone on the little stand where I was on the stage and I had it turned off in terms of sound. I was giving the speech and I happened to look down and one of their major estates was burning to the ground.

Underneath it says you have to get here as soon as possible. I said, "Well, that's not gonna happen because I'm in Bermuda working." But these are just things that are both fascinating to me, and yet I think are not really understood by the family office industry for several reasons. But it's a view that I take that these people need not only your best investment advice, and management, and integrity as you mentioned, but you may run across a family that's absolutely perfect, but that would be very rare.

R. Adam Smith: Right. Thank you for the storytelling, about the storytelling. The narrative of family offices can be very important for the family, for their brand and their reputation.

Again, as they get bigger or if they care about their brand. There are, you know, people in the family offices market, CMOs or branding agencies, crisis management firms. Of course, board of directors building a brand like an MSD or Pritzker or Perot or, Waltin family, these are major families. So for them to endure over time we talk about legacy often on the show, these institutions have to have a coherent story that's also like professional and repeatable, and being very present with that storytelling.

So in that sense, legacy requires meaning that can be told by others, not just a internal viewpoint. So I think it's important to think about the Reagan story. He and his administration did a great job in communicating both the Cold War battle with Russia. The tearing down the wall was in such a pivotal moment, but also I think that in today's era of sort of short term memory and media, people forget how powerful the economic recovery was in the Reagan era.

And so that story also was told very effectively. We're gonna wrap up with a conversation on, stewardship and succession and looking longer term. So the Rangan era was obviously defined by very successful leadership. Again, I think both domestically and internationally.

Driven by a power of a personality but also he had a great cabinet. Ultimately, as you said, he was more focused on doing the right thing. And I think it's very interesting that doing the right thing, in business, let's say for a family office can be quite difficult if they're looking at short term needs financially or culturally or with their children. So ultimately love to hear your thoughts on this anchoring longevity as, as intentional design.

What was that like within the Reagan office? James Rosebush: I think that's very well put the way you described that. So here's the thing, coming up to his speech about Mr. Gorbachev take down this wall, I was with him in Geneva for the first meeting.

So he and I were just sitting in front of a big roaring fire and I said to him, " What do you think Mr. President, will really bring down the wall? Will it be some intervention? How do you think it's gonna happen?"

He said, "It will all end because of the people's desire to be free." If you remember, when he heard about the pope, this was before Reagan was elected. He was in his living room in California. He turned to them and he said, now this is a man I can work with.

We had several meetings with the Pope that was especially wonderful. And it meant a great deal to all of us, 'cause he blessed us. But Reagan took this view that if he could work with someone like the Pope, he could do more than just demand that the wall come down. But he had to understand who Gorbachev really was, because most people who are not in the intelligence business didn't know much about Gorbachev.

So the president demanded that this be a one-on-one meeting. And they were really fuming about this. George Schultz was very unhappy. But look, this is how Reagan did it.

He wanted to get into the soul of the people that he wanted to come to his side, and see how they could work together. So when we're sitting there in this fire and I ask him how it's ultimately gonna come down, he said, "It's because it will only come down because of the people's desire to take it down." And I thought, I have to think about that. How is it gonna happen?

And you know how it happened. It was brought down by people who decided they were gonna march to the wall. It was time and they started doing it, and Gorbachev did not stop them. Now you see, that was like nine months, I think, after Reagan's term.

But when we went to the wall and he said, Mr. Gorbachev, tear down this wall. It's important to understand the inflection of how he said this. Typically for proper reading, you would say, "Mr.

Gorbachev tear down this wall." He said, "Mr. Gorbachev, tear down this wall." He was very specific about what he wanted Gorbachev to do, and it happened.

They didn't want him to say that at all, but he had conviction that was beyond a briefing book. Today the amount of wealth in the world needs, to have people running it and managing it, who have integrity. And frankly, they care more about the people that they're serving than themselves. Just to wind this up, I think that there is a parallel there how Reagan treated these tremendously difficult issues and how he viewed and understood what the possibility could be.

And with family offices because there's a tremendous amount at stake. I'm just so unspeakably grateful that after the White House I got to continue my work, on the South Side as well, but working with families all over the world because I feel that more people need to approach it in that way. R. Adam Smith: One more topic, looking at next generation, our children, our grandchildren, and how that relates to today's media heavy skeptical, like non bipartisan world, right?

Which has been marginalized and compartmentalize within politics. Obviously it's a pretty extreme moment in this country. But also we see, a bit of institutional breakdown in a lot of our key countries, especially in OECD we saw some changes. Today in Japan we see changes in the political landscape.

Also in Italy and France. Of course in the UK, of course in the US and also in other countries such as Brazil and peripheral, OECD and emerging markets countries. A lot of change politically, a lot of change in the next gen and voting and moving left, moving right. Putting aside the sides, I see a lot of, let's say de-institutionalization and the next gen, especially millennials, anyone in their thirties and twenties, they are just kind of fed up with a lot of the politics and a lot of the extremism and short-termism.

So I think what I like about the Reagan era is that he brought a balance of humility, but also ambition to the White House. Maybe he got lucky, of course. He had a big turnaround, the economy came from the doldrums. And Gorbachev also was a major sort of aberration in Russian history.

So there was elements that, affected the Reagan experience besides Reagan himself. But I liked the fact that he balanced ambition with humility and brought character to the White House, which is also personality trait. I'd love for you just to wrap up on talking about this focus on responsibility, not just transactional matters, and just maybe share some wisdom on optimism and why optimism is important even in today's world of, dirty and messy politics. James Rosebush: Well, you know, our first two years in the White House, it didn't come as fast in terms of turning the economy around as we all had hoped.

Reagan paid a price for it in the media, of course. But I think the most challenging thing today is a lack of not just unity, but this whole idea that is, by the way, it's not just political, it's in finance and other areas as well, where it's a lot about my views, his views, her views all this sort of thing. It's been brought into our culture that each of us should have an independent view, and not necessarily happy one with people that we didn't agree with. But it's important that we do honor people who have different viewpoints because it makes our country stronger.

It makes our communities stronger, it makes our families stronger. I think that the issues have become because of people who wanna control things politically the way they want to, and they have a tremendous amount of money to do it, it, becomes very scary. So you have now, a whole movement let's say in the US in particular, but not only, with people who have large sums of money being able to influence policy. And that's not the way it was meant.

It's interesting and it's clever, and we need people with money, a lot of money to invest and fix things that we need to have fixed. But if they're doing it just for a purpose to increase their own assets or to change the political thermostat, that's one of the most difficult things. Across the street from our house is the former US ambassador to NATO from several administrations ago. We moved in here, he lost no time telling me straight out that he hated me.

I thought, what a sad thing. He goes around telling people that he hates him. But I wasn't gonna get into it, so it was just, okay. He would walk his dog and make sure that the dog went in our gardens, that kind of thing.

So, one of the podcasts that I've been in quite regularly, I enjoyed doing it, and he said to me one day - "would it be okay with you if we added someone and have a third? Now I'm sure you don't know this guy." But I mean, he said his name, I was flabbergasted and I didn't say anything to him because I wanted to see what happened. So the next podcast we did, this gentleman was in it.

And you know what happened? We agreed on 90% of all policy issues and he started talking to me, telling me how much I was his brother, how much he loved me, telling me how much we were alike. And this is the man who looked at me in the face when we moved here and said, I hate you. I thought, what an interesting story that it just happened.

But, what happens is you don't have the width, or the wit to listen to another person's point of view, and that is just one story in my life that I'll never forget. That even though someone appears to be troublesome and hateful and so forth, that there could be meeting points. And that's really important. I'll never forget that, how that happened.

R. Adam Smith: Thank you for that story. Just to wrap up here because we're out of time - Reagan's personality, his empathy, his awareness, his emotional intelligence his affableness, his optimism, was super unique. I think many people, especially in their fifties and around the fifties, I think I'm personally nostalgic about that powerful sense of optimism.

So I appreciate you reflecting on some of these softer points of your experience with him and how these softer elements of power and personality, integrity are very relevant to the family office world within these larger organizations and their impact on their own cultures and their impact, within their communities and the world at large. So we talked about again, integrity, stewardship, awareness, and you reflecting on what legacy means. I really wanna thank you for sharing these personal thoughts.

It's very rare to have this type of access and quiet time to discuss these. Of course you're writing a book, again, and you talk about the Reagan era, but it's great to have you on this particular show. Thank you so much. James Rosebush: Oh my pleasure.

Thank you for inviting me. I appreciate it. R. Adam Smith: The conversation reminds me again about leadership and whether it's, a family business or a nation is anchored in that stewardship of that leadership, and that there's a whole range of factors that matter - growth and money and leadership and intensity and learning and continuous improvement.

But ultimately, I think the legacy is built through, discipline as well and the responsibility of looking beyond yourself to outlast the short term. And any one leader any one moment or any $1 billion and to look, to looks more broadly. So thank you again for sharing your experience around these topics. James Rosebush: Do you have one more minute for me to just add something at the end of that?

R. Adam Smith: Let's do it. James Rosebush: So Reagan's very last speech was to the people of America. So in the oval, there were two women in there and, one was a producer and then I guess the other was a camera.

She said when she got in there, "Is he okay? Is he okay?" He had his head down on the desk and this other woman said to her - "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 these things about the promise of America. He went on like that and it was so remarkably gorgeous in thinking, timing, and depth. I thought, here's a man who is totally more devoted to his country and to his countrymen than himself or anyone else.

And he had the ability to communicate it, not reading a speech, but reading his heart. R. Adam Smith: Wonderful. Thank you so much for your experience, James.

This was amazing talk today. This is R. Adam Smith signing off. Please stay tuned for the next episode of the Family Business Audiocast.