There’s no clutter in Steve DeCarlo’s office in Charlotte, N.C. It has the glass-walled acreage worthy of the CEO of AmWINS, the nation’s second-largest insurance wholesaler, but it is curiously under-furnished. A desk, a few chairs, a laptop. And over on the bookcase, a small statue of a caddy to remind him of his origins. That would be “helping rich people play golf” back in South Plainfield, N.J.

“I’m from the wrong side of the tracks,” he says. “Put me with the caddies, telling stories, telling lies.”

Such modesty is appealing, but it does have a side effect—that feeling of being a kid who’s in over his head. “I’ve been in insurance for over 25 years, and I’ve never underwritten an account, brokered an account, or handled a claim,” he says. “I’m just a finance guy.” But then, he adds, “Impostor syndrome is common in guys who run hard.”

If M. Steven DeCarlo does have impostor syndrome, nobody else can see it. Loquacious and affable, he calls himself “just an accountant” who gets a kick out of building businesses. This is his second such invention. When he took over as CEO of Americana Financial, an insurance distribution firm, in late 2000, the company, with 110 employees and a usual revenue of $20 million, had just lost $13 million in one year. Two years later, he turned it into American Wholesale Insurance Group—AmWINS, for short—and continued to snap up the 16 specialty wholesalers that comprise the company today. By 2008, AmWINS had 1,000 employees and 35 offices nationwide, with combined premiums of more than $3.3 billion.

“I’m not surprised by how fast and how big Steve has grown that company,” says Kathy Aberson, senior vice president at Royal Special Underwriting, Inc. (RSUI), who worked for DeCarlo for 10 years. “He’s a builder, and it can’t be something small. It’s got to be big, and he’ll do it very well.”

The process was painful. When he was first hired at Americana, he says, the company was “doing a lot of things not very well.” In 2001—“the year from hell,” as he calls it—DeCarlo basically gutted the organization, dropped the retail and MGA functions, dismissed all but three employees, and relocated headquarters from New York City to Charlotte. He still feels pain over two former Americana employees in New York who left the company as it failed. They joined Aon and perished in the World Trade Center attack. “If this had been a better company,” he says, “they’d be alive today.”

One of the three employees re-starting the company was Scott Purviance, now CFO. “Steve is probably one of the smartest, pure businesspeople I’ve ever met,” he says. “Some people have risen strictly through sales or marketing, and they don’t necessarily grasp the soup-to-nuts of what happens in a business. This, he clearly does.”

Meatballs and Grits

DeCarlo’s fast talk stands out in Charlotte, but his style was the norm back in South Plainfield, where DeCarlo was an altar boy and “the classic kid who pretended he was good but got away with murder.” His Italian father was the guidance director at his high school, and his mother was from the hills of Tennessee. “I grew up with meatballs and grits,” he says.

South Plainfield was also, notoriously, a golf school. Hard by the Plainfield Country Club, it was the kind of place where “you could get out of high school if the caddymaster called because we needed the money. I could cut a class and make $16.” But it was definitely an underdog job. His sense of the backstairs life was so strong that “the one time I got to play at Plainfield Country Club as an adult, I felt so out of place. I kept wondering if I would get caught and thrown out of the clubhouse.”

Though his sister had been a statewide champion Latin scholar, DeCarlo’s dad discouraged dead languages for Steve. “After two years of Latin, he said to me: ‘I’m thinking…accounting.’”

DeCarlo studied accounting at East Tennessee State University, where his parents had met and which had “great golf programs.” Though he was “barely on the golf team—I was more of a ‘wannabe,’” he says. (Flash forward: At ETSU he met classmate and golf-pro-to-be Mike Hulford, for whom he caddied on the PGA tour in 1985, taking time off from his insurance job. “That was fun,” he says. “I’d do that again anytime.”)

After college, DeCarlo returned to New Jersey and got a job as an internal auditor for Crum & Forster. “I got to travel and meet all these insurance executives from Monday to Thursday,” he recalls. “Then on Friday, I told them what they were doing wrong.”

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In 1984, DeCarlo was offered a job as an assistant vice president at The London Agency, Crum & Forster’s specialty underwriting operation in Atlanta. (The London Agency eventually became part of what is now ACE Westchester.) There he came under the guidance of CEO Steven Smith, who became his boss for 13 years and promoted him to CFO. “He took me places I didn’t think I’d go,” says DeCarlo. “He taught me how to think about the business side of an insurance organization and how each unit, from the support staff to the underwriter to the broker, played an important role in a successful organization.”

Smith, now retired, says he saw in DeCarlo “a guy who could do a lot more than finance. He’s very bright, he’s very organized, and he has an outgoing personality that’s rare in an accountant. We had him doing all kinds of things, including marketing and human resources. He was good with clients as well.”

In 1988, DeCarlo followed along as CFO when Smith and his business partner, Jim Dixon, left to start RSUI, an excess and surplus lines firm that would be 51% owned by the British-owned Royal Insurance, which had U.S. headquarters in Charlotte and in a later merger became Royal & Sun Alliance. In this job, DeCarlo got to interact with the customers, who were all wholesalers, adding quite a few experience arrows to his wholesale quiver. The job also brought him to Charlotte.

Aggressive, Opinionated, Hard-Headed

“I was an aggressive, fast-talking, opinionated hard-headed kid when I became CFO of RSUI,” DeCarlo recalls. (“That’s about right,” says Smith.)

Smith and Dixon, “took me under their wing and guided me,” DeCarlo says. “They allowed me to build a technology platform that supported the entire organization. We are trying to duplicate that model again here at AmWINS.”

When seven years later the team sold their share of the business to Royal & Sun Alliance, DeCarlo stayed on with RSUI as senior vice president for business insurance until 2000.

That was the year that Americana Financial, in terrible trouble, was looking for someone to lead the firm back into the black. “I was interested,” says DeCarlo, “because it was wholesale and technology combined with the need for finance skills. It sounded right up my alley.”

At the time, the company was a combination of what DeCarlo calls “three great wholesale distribution firms and several retail brokerage firms.” But it also had “a bloated corporate structure that was severely hurting the profitability of the firm.” Besides that, “the technology they built was not effective and we never utilized any of it,” he says. “The firm was initially capitalized by a private equity firm and at the time I joined, that private equity firm owned over 95% of it.”

DeCarlo joined Americana Financial as both board member and CEO in December 2000, took a breather over the holidays, and then spent 2001 purging the company of people, real estate and its brokerage firms. By the end, the company consisted of DeCarlo and two employees.

Rebuilding began at DeCarlo’s home library in Charlotte, where he interviewed and hired help until an office could be rented. In 2002, poised as a wholesale insurer bearing the name AmWINS, the company began an aggressive acquisition program to swallow up wholesalers in brokerage, benefits and underwriting. One insurance publication at the time compared the buying streak to “a race car driver zooming from zero to 100 miles per hour in first gear.”

“There wasn’t a lot of competition for acquisitions at the time,” says DeCarlo, “because most of the wholesalers out there were still family businesses and didn’t have the capital to expand. The larger wholesalers were all owned by large retail firms and weren’t focused on growing their wholesale operations.”

Once the companies are in the stable, says DeCarlo, “we value the entrepreneurs in these organizations. When we acquire a company, the entrepreneurs don’t leave. We want them to continue running the business, and we support them with technology and other services. We have a very decentralized business model.”

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As the divisions keep selling, the Charlotte office “can provide support services on a bigger scale and more economically. So we let the principals keep doing what they do so well. We don’t sell from the center. Basically, the seventh floor in Charlotte is all coneheads who don’t make money—we just spend money.”

Wholesale, Plain and Simple

In aggregate, AmWINS’s specialties now include maritime employers, woodworkers, beer and wine wholesalers, underground storage tanks, solid waste haulers, physicians, private schools, child care centers, fire sprinkler contractors and an armored car cash-in-transit program. One AmWINS division has also long been the wholesaler for Domino’s Pizza, a company with a high exposure because of its use of privately owned delivery cars.

One important selling point for AmWINS is its independence. Most wholesalers are owned by retail brokers or a bank that owns a retail brokerage. This one is an independent wholesaler that doesn’t compete on the retail side.

“We’re not trying to be all things to all people: an insurer, a retailer, a reinsurer, an M&A firm,” says DeCarlo. “We’re totally focused on what we do: being a wholesaler for retailers.”

Collecting companies—each with its own philosophy, culture, products and regional markets—and putting them all into the same corporate pot is no easy task. “When you bring 40 or 60 people into a culture,” DeCarlo says, “you have to impose unity so they’re not always talking about the old firm.” At producer events, DeCarlo uses especially impish ways to get people together. “Last year I gave them all poker chips and told them to keep them on their persons at all times because that was important. They assumed there would be prizes. Nothing.”

That same night, DeCarlo had 16 “leader” volunteers come up on stage. The next day, during a team-building exercise in the desert, the 16 competed in a fear factor contest that involved eating strange things, jellied pigs’ feet among them. “At the end, we gave them all a big hip hip hooray, but…no prizes,” says DeCarlo. “I’m known for ‘ya never know.’”

The point of such random puckishness, he says, is “to get them to spend time with each other, know each other, and learn to like each other. I’m giving them common experiences to talk about. It promotes unity.”

He admits, “Part of my shtick is to make fun of myself.” At RSUI, he ran the client golf tournament at Pebble Beach, and “everybody knew me as an honest guy, a fun guy, a lively guy. And it matters! It’s a people business!”

Aberson agrees. “Steve is probably one of the brightest human beings I’ve ever met,” she says. “He’s got the intellect, a great gut instinct, great people skills, and he creates a lot of loyalty.”

And that education he attributes to caddying. “I learned a lot of life lessons carrying those two bags for eight years,” he says. “How to treat folks, and how not to, and what it means to work hard.”

Lague is West Coast Bureau Chief Louise.Lague@LeadersEdgeMagazine.com

TheDeCarlo File

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Steve DeCarlo

Home: Charlotte, N.C., “a fantastic place to raise a family.”

Married: For 22 years to Lee Ann, whom he “met and married in 90 days.”

Children: Jenna, 21, Reid, 17, and Nick, 16

Ride: 2008 Toyota Tundra and “no toys!”

Teams: Carolina Panthers; Charlotte Bobcats

Do-Gooding: Urban Ministry, Charlotte Soup Kitchen

Business Memberships: The Council Board of Directors, American Institute of Certified Public Accountants, Charlotte Chamber of Commerce

Big Brag: “Making the cut at this year’s Pebble Beach Pro-Am. Only 20 make it.

There will be 80 celebrities, 99 important CEOs and one insurance accountant.”