Bob Hilb, CEO, The Hilb Group

And how did you get your start?
I had been hired by a very large copier company selling this new technology called a fax machine in Iowa, where I had attended school, and I was scheduled to start two weeks after graduation. Then my dad mentioned an opportunity to work at J. H. Minet—now Aon—in London. It was a pretty easy choice—copiers and fax machines in Iowa or insurance in London. I chose London and have never regretted the decision.

Was it not assumed you would go to work with your dad?
My dad never pushed any of my three sisters or me into the business. As it turned out, three of the four of us ended up in the business. Two sisters were underwriters for the Hartford and Kemper, and the other one, who is the smart one in the Hilb family, got her master’s in microbiology. 

So how did you end up working with your dad?
We never really talked about it. One time I was home—maybe it was Easter—I said to him, “Could I ever work for you?” He said, “Yeah, but you’re not going to get any special treatment because you’re my kid.” So I moved to Richmond in 1987 and worked as a producer with Hilb, Rogal and Hamilton. 

But you left the business cold turkey at the end of 2000.
At HRH I never knew whether I was succeeding because of me or because I was my dad’s son. My dad had retired in 1997, and while I loved working for the next CEO, Andy Rogal, it was time to move on. So I exited the business entirely and bought an industrial supply distributor.

Tell me about the Hilb Group.
We launched in 2009. We felt there was a need to provide a mid-market, East Coast agency, and we’ve done that by partnering with great people who want to take some chips off the table but still have a voice in how the business is run. We have 16 offices, about 200 employees, around $25 million in revenue. 

What have you learned from your father about running a business?
If Bob Hilb told you something, it happened. That was the legacy we built Hilb Group on. We’ve been very passionate stewards of the brand my dad built. 

Who were your childhood heroes?
In my senior year in high school, we had to write a paper explaining who our heroes were and why. I talked about three people. My dad, for reasons I just mentioned. I was on the golf team, so I mentioned Jack Nicklaus. And I was an enormous Bruce Springsteen fan, so I wrote about Springsteen. 

Why Springsteen?
When we’re teenagers, we all go through ups and down emotionally. I went through a six-month period listening every night to Darkness on the Edge of Town. The character in “Badlands”—“For the ones who had a notion/a notion deep inside/that there ain’t no sin to be glad you’re alive.” That really resonated with me. I’ve probably seen Bruce over 50 times, and now my kids all love him too. 

What is something people who work with you would be surprised to learn about you?
Most of them don’t know I had a sister die in 2012. Tracey was the middle of my three sisters. She was diagnosed with breast cancer in 2008. It went into remission for a couple of years, but it came back in 2011 and she passed in March of 2012. She and my brother-in-law had two great sons, who are now 31 and 28. 

Who was your most influential business mentor?
Other than my dad, I would have to say Andy Rogal. I was privileged to work around him when he ran HRH. Those of us who worked for him, we would run through the wall for the guy. 

How would the people you work with describe your management style?
I believe they would say I’m a pretty good listener and I am open to lots of different opinions and new ideas. I go back to one of the Andy Rogalisms: “A good idea is a good idea no matter where it comes from.” 

What gives you your leader’s edge in this business?
The Council, as an organization, gives us tons of opportunities, whether it’s the CFO Working Group or the Legislative Leadership Summit. There’s so much opportunity to get up on a bigger stage.