Relentless Pursuit

You started your career in employee benefits. There has been a lot of change since then, a lot more compliance, a lot more cost. Have you seen any improvement in the employer-sponsored insurance system over these years?

I’ve seen a tremendous amount of improvement. I think a lot of it has to do with all the additional things the brokers are bringing to bear for employers. I’ve been in this business for over 40 years, and 40 years ago we were placing product, we didn’t have wellness, we didn’t have compliance, we didn’t have all the reporting that we do today. The changes have forced the common broker today to be able to be more risk management on the benefits side, like they are on the property/casualty side. Now we’re managing that risk on the benefit side so much more. And we bring so many more resources to the employer that it has improved. It’s still the best place to get health insurance—through your employer.

In addition to being on The Council’s board, you’ve served on its Council of Employee Benefits Executives for a long time. What is the group currently focused on and where do you see the most need for attention in the coming year from that group?

First of all, CEBE has done great work over the past couple of years…they have been very focused on transparency, and rightfully so. They are the ones that pushed very hard for no-surprise billing, which was very important. Now they’re pushing very hard on the pharmacy benefit managers (PBMs) and for transparency in healthcare costs, all these things that you’re seeing come to bear where hospitals have to start posting their costs and so on. That’s what CEBE has focused on for the last several years and continues to do, and I think it’s going in the right direction. We just have to keep pushing hard, because there’s a tremendous amount of waste in the PBM world.

In 2020, you led Oswald’s merger with Baltimore-based RCM&D, forming Unison Risk Advisors. Can you talk to us about that decision and the process of making that happen?

Well, the process lasted a long time, but I look at it this way: anytime you can go into business with one of your best friends, it’s a great time. It was a pleasure to partner up with Bob Cawley [chairman and CEO, RCM&D], whom I’ve known for over 20 years. We both had older firms, over 100 years old, steeped in legacy, steeped in being privately held; ours happened to be employee-owned. We live for that, we live for being privately held, we believe in that model. But we both had agencies that had older senior leaders, and the chance for perpetuation was going to be hard. Ours could have perpetuated, but there would have been a lot of debt handed down to the next generation. And it’s not as much fun to run an agency that’s loaded up in debt. You can’t really grow that much.

So we decided the best way to do it would be if we merged the platforms together to create a new platform with both of our agencies and then we recapitalized a part of our company, brought in a minority partner to help us use equity instead of debt to buy out some of the senior debt and try to move on. We’ve created a platform now for the next generation—Bob’s firm is over 130 years old, mine is almost 130 years old—we want to make sure it’s here for another 100 years. This platform is designed that the next generation can continue to perpetuate. We’re 70% employee owned, and we’re going to remain at least 70% employee owned. We’ve got a great partner, and we’re very excited about the future.

Do you think that in this era of consolidation it’s necessary to at least partner in order to survive as an independent agency?

Well, selfishly, I would tell you yes. But no, I don’t think it’s necessary—I don’t think that’s the right word—it’s helpful for some. It all depends on your structure. You have a lot of agencies out there that are passing it on from generation to generation that want to stay in the family and so forth, and that’s reasonable. It’s everybody’s individual situation. But we truly believe our platform allows people to stay privately held, they keep their name, they run their own offices. We just bring additional resources and additional capital to them. We think it’s the best of both worlds. But you don’t have to; you could still stay independent.

You didn’t grow up in a privileged environment. You’re pretty self-made. How has that shaped your view of the world and the work that you do?

It shaped it a lot. I learned at a very young age I had to settle for certain things. I watched my mother have to settle for certain things, as I would call it. And they weren’t first-class things. They were second, third class and down, and you scrimp and you run out of money at the end of the month for food, and you’re trying to figure out what you’re gonna make for dinner until the Social Security check comes in. You watch all those things happen, and of course it shapes you a little bit. I never wanted to do that in my life. So you fight harder to make sure that you never have to settle. I think it pushed me more to say I’m not going to settle, I’m never going to settle, I’m going to make sure my family never has to settle for second best.

It’s just built a tenacity in me that there’s no finish line with me. I’m gonna out-hustle you. My father always taught me before he died, never get out-hustled. Somebody might be better than you at something, somebody might be more talented, but don’t ever let them out-hustle you. So I always made sure, since the day I started in this business, you might be smarter than me, you might have more years on you than me, but you will never outthink me, you will never outwork me, because I’m relentless. I’m relentless, and I won’t stop until I succeed. That attitude is what’s propelled my career for all those years. And a lot of it has to do with how I grew up.

Do you bring that to the young talent who work at Oswald?

I try to, man. I try to fire them up every single day. It’s different personalities; different people get motivated in different ways. I love this profession. I still love it 42 years later, and it is a profession. I try to bring that upon people to understand that this is not a job. If you want a job, please go work for one of my competitors. This is a profession. And if you love this profession, you will become good at it. It’s your craft; embrace it every day. We try to teach people “win the day.” Life is made up of a bunch of days. And if you win more than you lose, it’s a pretty damn good life.

You also have seen several transitions in leadership at your time at Oswald, including your own transition to chairman and CEO. What have you learned from these leadership transitions?

Well, I’ve been blessed. I’ve had two great leaders come before me—Jim Pender and Marc Byrnes. They were both chairman and CEO before me. And you learn something from each one; they’re both different. But one thing I reminded folks when I took over: the name might change on the door, people might change, but principles don’t change. What we’re built on, the values we’re built on, what we believe in, those were instilled in me over the years by both Jim and Marc. We believe in being privately held, we believe in employee ownership, we believe in caring for our communities, we believe in integrity in everything we do, those are the values that will never change. The name on the door might change, but those values will never change. I have had big shoes to fill for both of them, but it’s been a great ride.

What did you learn leading through the pandemic?

Leading was a challenge. There was no playbook to lead. It just taught you that you never know what’s around the corner. There’s been lots of things that we’ve gone through over the course of decades. You have economic downturns, you have different things, but we never faced anything like a pandemic. So you learn that you’ve got to lean on other people. There is no one right answer. I don’t think any of us had the right answer. We did what was best for our firms. We learned to be very resilient. My people were unbelievably resilient in what they did. And the coming together was really cool when it first happened, because we all came together and said we’ll get through this somehow, we’ve got to take care of our customers, let’s figure out a way to do this. I learned how important it was for ongoing communication with everyone to keep them informed of what was going on, why we were doing what we were doing—and we didn’t do everything perfect, trust me—but they always knew we cared. They always knew we were trying to do what was best for them and best for our customers. I think all of us learned how to be very resilient, and I think we surprised ourselves and others surprised themselves in how resilient and adaptable they could be.

Now that a lot of companies are returning to the office, we hear all the time from our members at The Council how much they’re struggling with managing a hybrid workforce. What are you doing at Oswald?

My people would laugh if they heard you ask me that question, because I don’t hide my feelings. I prefer the old-fashioned way. I prefer being in a room with people and collaborating and teamwork, and I love the energy of everybody coming together and working together to solve problems and help clients. All of that, I miss that. But I’ve also learned, begrudgingly, that it’s a new world, it’s a new dynamic, and people are still very, very productive. Their quality of life is just a bit better, and they’re still productive. As long as our customers are happy and we’re getting things done, that’s the most important thing. But we can never lose sight of the fact that relationships matter. Relationships at work matter, and relationships with your customers matter. It’s still a people business, it’s always been a people business in all my years, and it will continue to be. You don’t create relationships on Zoom. You create relationships over a cup of coffee with somebody, over having lunch with somebody, sitting across a desk from somebody, and it’s the same in the workforce. So hybrid has got to be hybrid. I don’t believe in 100% remote for everyone; it’s just not our model. I know it works for some people, but I believe there’s times you still have to come together and you have to collaborate. But the old man is learning to adapt.

We’ll quote you on that.

Some of my people might not agree yet, but I am trying.

How are you keeping good talent around?

I think they see that we have a plan for the future with our merger with RCM&D and creating the Unison Risk Advisors platform and then building a financial capital base to allow us to continue to grow. They want to be with a winning company; they want to be with somebody who’s growing. We’re not stagnant. We’re not just staying in one place and hoping things work out. We’re building a future for our next generation. Everything that Bob and I are doing, and the rest of our partners, is all built around the 30-somethings, the 40-somethings and so on, to say, “Here you’ve got a place now, and you have the chance to have the same equity and wealth creation that we did.” That’s the most important thing. If you like that model, if you’d like to be an owner and not just an employee, it’s pretty easy. We’re the place to be. We’ve got a fun model, and we do pretty well.

You are a leader in Cleveland, where you live, and you’ve served on various boards there. What are some of the community boards that are most special to you?

It’s a tough question, because I’ve served on a lot of boards over the years, and each one has a different place, serves a different part of the community. So it’s really hard to say which one’s more important. I’ll give you two examples.

I’m currently chair of the Greater Cleveland Sports Commission. You say that to somebody, and they say, “Oh, that’s fun, you get to go to sporting events, you get to go to games,” but the Sports Commission is what draws events to Cleveland. All the different amateur events that have gone on—the women’s NCAA Final Four that’s coming to Cleveland in 2024—we have to win those events. We had the NBA All-Star game, we had the NFL Draft. All of those are brought by the Sports Commission along with other things like volleyball tournaments, wrestling tournaments—all of those things that are brought to the community create hundreds and hundreds of millions of dollars of economic development for the community, the restaurants, the hotels, all the other things that survive on that. You forget about that when you just hear “sports”; you don’t realize the almost billion dollars that the Sports Commission has brought to Cleveland since its inception over the years.

There’s also Northeast Ohio Medical University. I was appointed there by the governor. I served on the board for nine years, and I was chairman for two years. I watched great work that the small, urban medical university was able to do. I was also blessed with being the head of the search committee for the new president. We brought him on three years ago, Dr. John Langell, and he has done wondrous things. Watching the evolution of that and how many more young people, especially in underserved communities, are able now to go to medical school, are able to find a way to do that and get back in their communities and treat the people that they grew up with, seeing that stuff, that’s really cool. So, each one serves its purpose. I’ve been privileged to serve on some great boards.

What would be your favorite sporting event that you could bring to Cleveland?

The Ryder Cup. I love golf. And I love the Ryder Cup. It’d be wonderful if it was there.

One more for you. You are the new Council board chair. What do you want to accomplish this year?

Well, I’ve followed a lot of great other board chairs over the years, and it’s an evolution. We’ve had a great leader in Ken [Crerar] for over 30 years now for The Council. So my job is to make sure that we continue to shepherd a very clear vision for the future for The Council as we transition over the course of time that is very clear for the membership and for The Council staff. What does that vision look like as we go forward? As board chair, I believe that I represent the membership and I have to make sure the membership’s thoughts and what they want to accomplish are also represented by myself and the rest of the board.

On a personal note, I am not thrilled with the lack of integrity in our business over the last several years as it relates to organizations not honoring non-solicitation agreements. We see it in the paper all the time. It’s highlighted with all these lawsuits and these lift-outs, and it’s ridiculous. We have contracts, we all sign contracts. We are a profession, OK? We all sign those non-solicitation agreements, and we should agree to them. You want to hire talent from my place or any other place? Go ahead if they want to go, but don’t steal the business. They have a contract. Let’s honor those. I would like to see that come to bear a little more, because I just think it’s a stain on our profession. So personally, that’s something I would like to champion a little bit more. I don’t know how many people will back me on it, but it’s just something that I believe in.