Seven years ago, when supposed retiree Patrick G. Ryan launched what is now the third-largest wholesaler in the United States, no one should have been surprised.

Taking bold decisions and executing on them has been a hallmark of Mr. Ryan’s career.

Whether it be establishing his own specialty agency only four years out of college, cutting the deal for Combined Insurance that provided him with the capital to absorb bigger rivals, the rapid expansion of what became Aon P.L.C. into a global brokerage or his latest venture in the world of specialty and surplus lines insurance, Ryan Specialty Group L.L.C., Mr. Ryan has always been about risk-taking in the world of risk management.

In recognition of his achievements as a brokerage leader and entrepreneur, Mr. Ryan, founder, chairman and CEO of Ryan Specialty and previously the longtime builder and leader of Aon, is the recipient of the first Crain Lifetime Achievement Award, which recognizes an outstanding businessman or -woman in the insurance sector and was established this year by Business Insurance.

Known for his ability to spot industry trends and act on them before the competition, Mr. Ryan has a straightforward approach to capitalizing on those trends.

“When people ask me what’s the best time to start a company, I always say right now, because if you try to wait for the right market conditions you are likely to miss a lot of opportunities,” Mr. Ryan said.

That clearsightedness and a combination of his qualities as a “visionary entrepreneur, calculated risk-taker and world-class leader” have been a big part of his success, said Greg Case, president and CEO of Aon.

“But more than that, it’s his willingness to make a bet — many times on himself, but also on his team. Pat is always there believing that his team is more capable and is able to bring them along and help them do more than they even thought was possible,” he said.

Mr. Ryan’s willingness to take risks, his people skills, sales skills and execution skills produce a powerful combination, said Michael O’Halleran, brought in by Mr. Ryan in 1987 to run Aon’s reinsurance operations and now a senior adviser to the firm.

“He synthesizes something very quickly, brings people around it — he’s a total team player — and then he executes the plan and takes it over the finish line,” Mr. O’Halleran said.

Empowering his team has been important for Mr. Ryan, especially as he has rapidly grown Ryan Specialty, said Diane Aigotti, chief financial officer and managing director of Ryan Specialty Group.

“His leadership style is very empowering and very collaborative, and it’s very easy to feel like you have open access and that you can be frank,” she said.

And his willingness to get involved in every aspect of his businesses has also been key, said Tim Turner, chairman and CEO of R-T Specialty L.L.C., Ryan Specialty’s wholesale brokerage operation.

“The leaders of most big businesses tend to stay at 30,000 feet, but he’s the opposite. He’s very detail-oriented and likes to get into the weeds, so follow-up and executing are key attributes that have contributed to his success,” Mr. Turner said.

Focusing on the details and looking for the right opportunity is where Mr. Ryan started.

Born in Milwaukee, he grew up in suburban Wauwatosa, Wisconsin, and graduated from Northwestern University in 1959. After graduation, he became a life insurance agent for Penn Mutual Life Insurance Co.

“I’d known some people in the industry who had done quite well, and as independent agents they were in effect entrepreneurs with their own business. I didn’t have any capital, and it was clear to me that you could start in the insurance business and build a business selling,” Mr. Ryan said.

Four years later, he started his own business, Pat Ryan & Associates, which was a managing general underwriter for Continental Casualty Co. selling credit insurance and auto liability to buyers of automobiles. He had learned from his father, who was a Ford dealer, that this business was being done poorly. “Prior to when I started, auto dealers didn’t have trained people selling insurance in their dealerships,” Mr. Ryan said. “We set up a professional approach, recruiting talented young people to become licensed professional insurance agents.”

The business started in Chicago but quickly spread nationally. Within five years it was doing about $10 million in revenue, and by 1976 it had grown to $30 million in revenue.

Seeking to diversify, in 1976 the company, which was now called Ryan Insurance Group, bought the financial services subsidiary of Chicago-based Esmark Inc., which had an MGU offering bankers blanket bond and directors and officers liability coverage for medium-size and small banks. The deal also included a commercial insurance broker that did large-account and midmarket business in Chicago.

More acquisitions followed, which helped shape the business. “We had to build a culture that attracted people who wanted to be part of building a business,” Mr. Ryan said.

To build the culture, he set values, Mr. Ryan said. They included integrity, entrepreneurialism, the client is everything, teamwork, a meritocracy, empowerment and inclusion, Mr. Ryan said.

The deal that enabled Mr. Ryan to move to another level came in 1982. Combined Insurance, which was in the supplemental accident and health business, approached Mr. Ryan and asked him to succeed W. Clement Stone, the company’s founder.

After at first turning them down, “it dawned on me that really the opportunity wasn’t just to go into the supplemental A&H business, but that they had a balance sheet and cash flow that was very large and very attractive.”

They eventually worked out a deal where Ryan Insurance would merge with Combined and Mr. Ryan would be the largest shareholder and CEO. Combined had $500 million in shareholder equity and $100 million in free cash flow, and Mr. Ryan quickly used those resources. About a month after closing the deal, in October 1982, he had agreed to buy Rollins Burdick Hunter Co., which was then the seventh-largest broker in the world.

After several more deals, the name Aon was introduced in 1987, and Mr. Ryan saw the opportunity to create a truly global insurance brokerage.

“We wanted to export the culture and blend it around the world,” he said. In 1987, Aon expanded into the London market with the purchase of Nicholson Chamberlain Colls Ltd. Then in 1991, it bought Dutch broker Hudig-Langeveldt Groep B.V., which provided a platform for greater international expansion, all the way keeping and recruiting local nationals to lead the business units.

Many of the purchases also include reinsurance brokerages, which were teamed with Aon’s existing reinsurance operations, and Aon eventually became the world’s largest reinsurance broker.

The biggest financial purchase was Alexander & Alexander Services Inc., then the world’s second-largest brokerage, which Aon agreed to buy in 1996. Many of the companies Aon bought were “gems,” but some, including A&A, had problems.

“They were troubled at the parent level, but they were gems inside and had very good basic businesses. We cleared out the problems and then they became really well-functioning members of the team,” Mr. Ryan said.

Looking at potential acquisition targets now and then, Mr. Ryan said he first considers whether the companies will fit with the existing operations.

“We’d start with strategic fit, and if there wasn’t a strategic fit we wouldn’t do it, because nobody has enough capital to just do opportunistic deals. Secondly, it had to be a cultural fit and they would have to function as good team members. The third was financial, but that was a distant third to the first two,” he said.

The rapid acquisitions in the late 1990s led to headwinds in the early 2000s as Aon dealt with the difficulties of integrating the acquisitions from a technology perspective.

Then in 2001, the brokerage was rocked by the Sept. 11 terrorist attacks on the World Trade Center in New York. Aon had a sizeable operation in the WTC.

Needing to lead the company’s 50,000 staff, Mr. Ryan switched into crisis mode and set up a communications center for families of the 500 missing Aon employees. Many survived, but 176 Aon employees were killed in the attacks. Aon quickly established a memorial fund to help pay college fees of the lost employees’ children, among other initiatives.

“We lost some incredible people, and I was side-by-side with him as he led us as a company through that tragedy and saw the compassion that he showed for our people and our clients. We would have gotten through it, but it wouldn’t have been the same without Pat Ryan,” Mr. O’Halleran said.

The insurance brokerage industry faced significant challenges in 2004 when former New York Attorney General Eliot Spitzer sued Marsh & McLennan Cos. Inc., alleging abuse of contingent commissions and other practices. The accusations spread and all the large brokers were drawn in.

“What Spitzer didn’t like was the very fact of contingent commissions,” Mr. Ryan said.

All the big brokers settled with Mr. Spitzer in the months that followed.

“The good thing that came out of it was that we also agreed to be transparent, which is to tell our clients exactly what we make,” Mr. Ryan said.

The large brokerages also sold their wholesale units over conflict-of-interest concerns, which would trigger another idea for Mr. Ryan.

At age 68, Mr. Ryan decided that Aon should look for a successor, and the firm brought on Mr. Case from McKinsey & Co. in 2005, while Mr. Ryan stayed on as executive chairman.

“He’s done a terrific job and was what we needed because, with his background at McKinsey, he was very skilled at integration and did a very effective job of taking costs out and has been a very strong leader,” Mr. Ryan said.

After nearly three years as executive chairman, Mr. Ryan retired from Aon in 2008, but retirement didn’t last long. In 2010, he launched Ryan Specialty as a wholesale broker and MGU.

“I’m an entrepreneur at heart, and I like building and like creating … I knew that my next entrepreneurial activity would be to build a specialty lines broker and MGU — a repeat of the culture, a repeat of the strategy,” he said.

With retail brokers dealing with hundreds of wholesalers, he felt consolidation in the sector was inevitable and that there was an opportunity to build a significant wholesaler with the talent that was available. That quickly proved to be the case, and Ryan Specialty now has 19 MGUs and recorded $5.5 billion in premium last year.

Again, attracting and training talented people has been the key to the firm’s success, said Mr. Ryan, who is now 80.

“We bring people in and we train them just like we did in the early days in the mid-1960s … Specialty lines will be ever more important in the industry. The industry itself has been growing at a very modest rate, but there are lots of opportunities,” he said.

ABOUT THE AWARD

The Crain Lifetime Achievement Award was introduced this year to recognize an individual whose outstanding contributions have had a lasting impact on the insurance and risk management sector. The inaugural honoree for Business Insurance’s most prestigious award is Patrick G. Ryan, longtime insurance industry leader and founder of Aon P.L.C. and Ryan Specialty Group L.L.C. The award is named in honor of the Crain family, who founded Business Insurance in 1967.