Laura Sherman, Lowry Baldwin and Elizabeth Krystyn never thought they’d end up in the insurance industry, yet their unique paths brought them together to establish Baldwin, Krystyn, Sherman Partners.
The $1.2 billion firm has rebranded its affiliated Baldwin Risk Partners, or BRP Group, to The Baldwin Group, to align with its ongoing transformation and expansion. The changes will be done in phases and include transitioning its nearly 40 regional retail brands to The Baldwin Group, by early 2025.
Bridgette Bello, chief executive officer and publisher of Tampa Bay Business and Wealth, interviewed Sherman, Baldwin and Krystyn in front of a live audience at The Baldwin Group, in Tampa. This transcript has been edited for brevity and length.
Photos of this CEO Connect can be found here.
What has it been like being on the cover of TBBW?
Baldwin: My friends lit me up, as you might imagine. It’s a great honor and I really appreciate you all investing the time and energy to tell our story.
Sherman: I actually heard from a lot of people, even my economics professor who now lives in Lebanon. So, you’re now global. I had a lot of friends, colleagues and business associates who really appreciated me sharing my upbringing. So, thank you. It was a real honor.
Krystyn: Got a lot of compliments on that dress and you’re going to be seeing it a lot. It was outside the budget.
You guys had a business baby, right? You lived it, breathed it, bathed it and now it’s being referred to as a unicorn. When you saw that in print the first time, or the second time, or this time, what did that feel like?
Krystyn: It was really nice for just a small group of us to think back, fondly. We just remembered some of the fun of it.
Sherman: And we would be remiss if we didn’t mention that we have a lot of those people [in the room]who took a huge leap of faith and joined us when we didn’t even have printers. I remember, in fact, Frankie Baker’s not here, unfortunately. He was our first official colleague and he, literally, ran from floor to floor, and across the street, looking for a typewriter. We had to issue evidence of insurance. And the last thing we wanted to do is tell our clients, we don’t have a typewriter to issue it. But so many of you are here, all of you amazing people. We wouldn’t be here without all of them.
Baldwin: I think entrepreneurship is all about constantly dreaming about what’s next and what can be achieved. How to create outcomes that would not have otherwise been possible, without our presence or without our collaboration.
Krystyn: To that point, it was a really late night, or early morning, depending on how you look at it, and we had a big goal and I said, “Trevor, do we really think we can do this?” He goes, “Someone has to.”
Sherman: And that’s something that when we were talking with Bridgette, we all admitted, that we would’ve never dreamed this big. So, we’re thankful to Trevor and the executive team that they did dream this big and they kept pushing.
It seems like rainbows and butterflies, right now. You guys are such good friends. Was it always like that?
Baldwin: There are distinct stages of company evolutions in entrepreneurship. What was occurring, and what was necessary, when we were a startup, versus what is required, from a talent systems technology value proposition standpoint, today is completely different. And you have to evolve as you scale.
Krystyn: We kind of did every job. Because Laura and I are female, we answered the phone in a fake reception voice because one of the things we were going to do is have real people answer the phone, but we were them. So they would call and they would ask for me and I would say, one moment please. And then I would come back and my voice became lower.
Sherman: This [story] gave us a great opportunity to kind of reminisce, because we’re always looking at the next new thing. There were so many countless nights. I’m sure as many of you all are entrepreneurs, you put your life savings in, you mortgaged the house. I had a line of credit twice the size of my mortgage. So I would just say don’t give up on your dream because it’s amazing what you can accomplish.
One of the ironies that we realized was that we were three founders going to interview three founders. It was a very cool moment. We thought back to the moments where we had to figure out the division of labor. How did you guys handle that?
Baldwin: Communication is the bane of every relationship. We are three, very different individuals. At times there was overlap, friction, et cetera. But having a successful long-term partnership is essentially having a successful marriage. And what often goes unsung, in successful entrepreneurship, is the role the spouses play. I would come home, spun out so many nights and Jennifer (Baldwin’s Wife) would give me some good counseling, advice and love. And I don’t think you can be a long-term successful entrepreneur without having that support from your spouse and having the kind of relationship that we enjoyed. And we had some really incredible fights. I mean we’d go to war over what was the right answer for the company.
Krystyn: I think when we all agreed on stuff right away, then we were like, this must not be the right answer if we didn’t even do a knockdown, drag out on it. As someone who did a lot of the unglamorous operational stuff in the beginning, it was Lowry, Laura and others that would say, okay, you might be the best of the three of us to do payroll, but you’re not the best payroll person. I did payroll so we could get a receptionist, but I think it was the another [person] saying, you’re not the best at this. When we had more options, we could go find help that would allow for us to do things that were a better use of our time.
Lowry, this question is specifically for you. Starting a business with female co-founders is something that you’re really passionate about. What would you say to all the wonderful men in the audience who are thinking of starting a company and, specifically, why should they consider establishing it with women?
Baldwin: I didn’t set out to create the company, per se, by selecting women. I wanted to select individuals that I had an incredible amount of confidence in, that I thought were compatible with my value system, my principles, that had the requisite expertise, et cetera. Elizabeth and I had worked together in a prior iteration, and that iteration too was led by women leadership. Elizabeth and I met Laura after Wachovia acquired my first insurance and risk management firm. If you spend 10 minutes with Laura, you’re in love with her because we call her the woo. She just is an incredible relationship builder. So it worked out that I wanted to start this business with two individuals who happened to be women.
What does it feel like to give control of this baby to someone else?
Baldwin: I’m just speaking for me, it was a natural evolution. When we started discussing how to fund the company’s acquisition strategy, we visited with a number of different capital sources to discuss taking the company public, going with private equity for capital with a sovereign fund or pension fund. And when we elected to take the company public, I remember Trevor and our CFO, at the time, walked into my office and said, “Hey, we’re taking the company public. Do you want to be the CEO of a public company?” It took me 90 seconds to say, no. Most of our leadership is half my age. Their processors are better. Trevor is on the road, constantly. The leadership team is on the road. And that’s just not something I wanted to sign up for.
Krystyn: I mean we have 4,000 colleagues. We are relational people. We don’t know 4,000 people. I mean Laura does because she’s the woo, but I know half the front row over here and the people that I work with in the back that are standing. So I think it’s fine to say this next step, this is not where I’m best. I’m gritty and I like to know everybody. And that’s kind of a smaller company mentality, which is critical when you’re growing an organization, when you get it to scale as The Baldwin Group has, you need a different skill set and a faster processor.
Sherman: I was the last to move into a founder role and I was a little bit more of a control freak. It was a little scary to give up the baby. I think, as women, we don’t want to have to choose our children or a career. And I oftentimes had to put the firm first. I remember, literally, delivering my first child and I was pushing and the phone rang and it was a client. And the claim went sideways and I was like, I have to take that call. And they’re like, you’re delivering a baby. I’m like, I don’t care. This is the claim going sideways. And we still joke about it when I talk to this client. I have a 14-year-old and a 16-year-old son and I get to spend so much more time with them. I get to give back to the community that I love.
Baldwin: I think the big takeaway is that at different evolutions of your stages, you have to look around and honestly, be objective about assessing whether you have the right talent, whether you’re still providing the right leadership in the right role, et cetera. We were generalists, we did everything for the first four to six years, but as you scale, you have the luxury, the balance sheet, the P&L to afford really good talent.
Sherman: Or partners that are willing to tell you the ugly truth. ♦
ABOUT ‘CEO CONNECT’
TBBW’s “CEO Connect” series is an exclusive, invitation-only, event that brings together the Tampa Bay area’s top business leaders to meet and mingle. BankUnited, CLA, Kimmich Smith Architecture and Nperspective were presenting sponsors. The host sponsor was The Baldwin Group.
TBBW’s video partner is Empowering Creative.
The evening begins with a cocktail reception for about 120 guests, followed by an interview with that month’s cover CEO.
Partnering with TBBW provides an opportunity to network with the area’s business elite, generate new business opportunities and increase brand awareness.
For information about event sponsorship opportunities, email Jason Baker at
[email protected].
