Bruce Sherman: A Grand-Slam Career

The Naples icon reflects on his home runs in the money game and his current role with the Miami Marlins

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Bruce Sherman had a career as one of the most successful money managers in the country. The native New Yorker became a Floridian at heart when he moved to Naples in the ’80s, helping the Colliers build their fortune and starting the successful Private Capital Management. Then he “retired” to a busy new phase of his life that includes family, philanthropy, and the realization of a life-long dream as part of an investment group that purchased the Miami Marlins. Gulfshore Life sat down with Sherman for a rare interview about his career, his many years in Naples and his portfolio of retirement pursuits.

Where are you from, originally?

Our family is originally from a small town in the finger lakes region of upstate New York called Auburn. When we were still young, my father, who was an engineer, packed up my older brothers Peter and Joel and I, with whom I’m still extremely close, and moved us to Douglaston-Little Neck in Queens. I went to public elementary and middle school and graduated from Bayside High School.

Were you a good student?

(Laughs) I wasn’t a great student, but not too bad either. But good enough that I majored in accounting at the University of Rhode Island. I was always involved in extracurricular activities, whether it was intramural sports, or my lifelong hobby of numismatics.

So you started life as an accountant. How did you get from there to becoming a top-tier money manager?

After graduation I received offers from seven of the “Big Eight” accounting firms. I picked Arthur Young, which became Ernst & Young, because they offered the highest salary, $10,200. I was there for eight or nine years and it was a great learning experience. I had great mentors and valued clients in broadcasting, manufacturing, finance. I was on a career path to stay in Manhattan, until one day, the phone rang. I'll never forget it, the caller said, ‘are you interested in a firm that has a small staff with a large asset base?’ But the caller didn't identify the firm, so I went through the executive recruiting process and eventually I met the Colliers.

And that’s when you came to Naples in 1979 to work for the Collier family?

Yes. Until the mid- to late-’80s, I worked for them essentially as a CFO, and also as a financial counselor to the family, and got exposed to what they were attempting to do, not only in real estate, or agriculture or in oil and gas, but also in venture capital and capital markets. In fact, Miles had started a previous money management firm when I got there, and he involved me with that as well. It was a very good hands-on education. Along the way, we formed Private Capital Management. In the early years, it was cause for celebration when we won a $1 million account. That evolved over decades to where, at its peak, we managed close to $35 billion for more than 7,000 clients around the world. We went from being a firm where people would say, ‘We never heard of you, you're in Naples,’ to not having to advertise because people knew who we were.

Meanwhile, you had started a family.

There was always a lot going on. On my recommendation we bought a bank for the Colliers in Oklahoma. I was working six days a week around the clock, going back and forth to Oklahoma and raising two daughters. So it was challenging, but at the same time, it was a valuable real-world education that made me a better banker and financial investor. In seven or eight years we sold the bank and increased the value of the investment almost ten-fold.

After that, Legg Mason acquired PCM in 2001 for close to $1.4 billion. You stayed on to lead the firm and in 2005, financial informational firm Nelson’s named PCM one of the nation’s best money managers. Then the financial crisis hits in 2008 and 2009. Do you regret staying on?

No. I agreed to stay to help ensure a smooth transition and I was honoring that commitment. When we sold PCM, it was a record amount for assets under management, and the record still holds. Legg Mason was buying an investment approach that had been incredibly successful, and leadership is part of that, so that’s why I stayed. Then as you say, the recession came along, and the world was in freefall, and no one was immune. We lost money in newspaper stocks. And of course financial stocks were very difficult. It all made headlines. But looking back, there were 25 years before that where we had some very positive results. Back in the late ‘90s we invested in Apple before the iPod brought the company back. We sold companies to Warren Buffet and, in fact, our performance from 1985 to 2005 was better than Buffet’s, which is something I’m very proud of. So, yes, it was a painful period for everyone involved, but it doesn’t negate a successful 25-year run.

You retired in 2009, but from the looks of it, you stayed busy with local causes and nonprofits. What are some of the highlights?

Well, together with my wife Cynthia, who retired from her career as an accomplished attorney, we became involved in a number of cultural and educational projects. She helped found the Holocaust Museum of Southwest Florida. We both spent time on the board of the Naples Children and Education Foundation. It provides wonderful educational and healthcare support for underprivileged and at-risk children in Collier county. That’s where we also got involved in the Naples Winter Wine festival which is ranked as one of the best in the country. One year, we co-chaired it together, and we raised $12 million. It’s been very special to us. We’re very proud that we participated in this important work for almost 20 years.

We were involved in Artis—Naples as well. When we came to Naples, Myra Janco-Daniels was starting what was then the Naples Philharmonic. Her offices were right below mine and we became friends. One day in the parking lot she approached me with the opportunity to take a look at their investing philosophy. Through this we developed a lot of mutual respect, and I eventually joined the board and together we did a lot of good work for the community.

You’ve started your own national nonprofit to fight Crohn’s disease. Can you tell us a little about that?

The Sherman Prize is something that our family holds very dear. Both my daughters Lori and Randi have Crohn's disease, which are part of a larger family of diseases that can have life-altering consequences and have no known cures. Fortunately, for both of them, the disease is in remission. But in the process of dealing with the trauma of diagnosis, and watching them both go through surgeries and treatment, we began to see an unserved need. We felt if we could give some national recognition to the excellent work being done in the field, we might start a ripple effect that encourages even more success and commitment.

We created the Sherman Prize from a blank sheet of paper in 2016 as a way to give back to the community that had done so much for families like ours, and also as a legacy that could live on in our family for generations. We’re in our fourth year. Each year we award a substantial financial prize and public recognition to three exceptional professionals who have dedicated their careers to helping people with Crohn’s disease and ulcerative colitis. We are just getting started, we want to do even more to encourage better treatment, advocacy, education and of course the medical research that could someday lead to cures. So, stay tuned, there’s more to come.

We haven’t talked about the Marlins yet. Tell us about how you got started in the business side of baseball.

Business aside, baseball has been a love of mine since my dad played catch with me at five years old. I wasn't good enough to play it beyond the middle-school level. I was an outfielder. Good arm, couldn’t hit a curve. I was a huge Yankee fan growing up, but there wasn’t a Major League Baseball team here when I came to Naples. The Marlins came in 1993 and finally I had a Florida team to root for.

And you thought you would just be a baseball fan until you one day when you picked up the Miami Herald, is that how it played out?

That’s right, I went back to fan status until I read that the Marlins were for sale. At the time, there was a consortium of groups looking to buy, among which was the Jeb Bush-Derek Jeter group. I had supported Jeb Bush during his presidential run, so I called him up. We went back and forth, and finally I said, ‘count me in.’

It was a very long and arduous process. There were people that were in the group and out of the group and eventually Jeb left. I spent some time with Derek, and his vision for how the team should be run was spot-on. You build a team from the bottom up. I admired him not only for his stellar career, but he had managed to stay out of the tabloids and conduct himself in an extraordinarily professional manner. Having worked with him for a year and a half, I’d say his reputation is well-deserved. I think he's taught me a couple of things along the way and hopefully I’ve done the same for him. And that's what makes a good partnership. As the chairman and principal shareholder, I hope to bring my skills of financial discipline to the team.

After the purchase, the organization was criticized for trading away some of its best players, including former MVP outfielder Giancarlo Stanton and future MVP outfielder Christian Yelich, for prospects. What’s your reaction to that?

In sports as in life, everyone is entitled to their opinion, and I respect that. However, from our point of view, the best thing we can do for the fans is build an organization that is capable of sustainable success. We've inherited a club that kept buying and selling. They haven't been in the playoffs since 2003. They haven't had a winning record in nine seasons. The old model didn’t work. So you can have the best outfield perhaps in baseball. But does that matter if you’re not winning? Could we have come in and spent $50 million on a couple of pitchers? Sure, but that’s not a cure-all. This isn’t about cost cutting. It's about a sustainable winning strategy.

We went from having the 30th-ranked farm system in baseball to having a lot of depth and some of the top prospects in the game. Eighteen of our top 30 prospects came in the last two years. We signed outfielder Victor Victor Mesa, the top prospect out of Cuba, along with his brother in a very competitive market. We’re now positioned to have all five starting pitchers under the age of 27. This is about building sustainable success. There are teams like the Houston Astros that had 100-loss seasons before winning a World Series. Great teams aren’t bought, they’re built. You have to have a good farm system.

We’re going to have a new TV contract coming up, and we’ve yet to sell naming rights to the stadium. We have a lot of upside opportunity, but we will spend money at the right time.

Given that strategy, how would you characterize your successes so far?

We want to put a product on the field the city of Miami can be proud of, and hence we've re-branded and we have made improvements to every aspect of the ballpark. This ownership group invested a lot of money into this ballpark. We took out the home run sculpture; it was a batter’s eye problem. And we created ‘the millennial zone’ with three levels where people have room to come and go as they please and to mingle during the game. We've also taken the entire premium seating area and opened that up to the stadium; we made Section 305 a place where fans can bring musical instruments.

We are growing our analytics department as well. That’s very important. These are people out of the best schools who could be lawyers and CPAs, but they want to be involved with baseball. I can tell you Mickey Mantle stats from 1956 but they speak a different language today. Cameras are everywhere now. Every dynamic you can possibly think of is measured. And it’s not just for scouting, it’s for players, too, for them to learn and get better.

With all your business responsibilities, do you still find time to enjoy the game?

Absolutely. That never goes away. There is a business to run, and we take the business seriously. I’ll be in my office in the ballpark, and I travel to a lot of away games, to see the ballparks, and to learn. But my greatest joy comes from the simplest things. Attending the games. Watching my grandkids come alive as they learn about baseball, up close and hands-on. I enjoy getting together with other owners and just chatting about the game. And I especially love and appreciate that Cynthia is engaged with the whole idea and has supported it 110 percent. We go to the games together, and cheer for the team like teenagers. When we’re going out like we did last year to Colorado, Atlanta, Boston, Philadelphia, we have to pinch ourselves. There are a lot of other things we could be doing on a hot summer afternoon. But our hearts are with the Marlins.