By the time he stepped down from Aon Plc at age 71, Patrick Ryan had earned a retirement fit for a king.

He’d founded the world’s second-largest insurance brokerage nearly from scratch and run it for 41 years as chief executive officer. But once away from the office, he didn’t know what to do with himself.

“I really felt like I needed another career,” Ryan said in an interview. 

So he decided to do it all over again. 

After leaving Aon in 2008, he started Ryan Specialty Group Holdings Inc. and has pursued acquisitions to build the firm into one of the largest of its kind. Chicago-based Ryan Specialty -- with 3,300 employees and a market value of almost $10 billion -- offers products and services to insurance brokers and agents to help protect against risks, including cybercrime and climate-related hazards. 

Now 84, Ryan took the company public this summer and is its largest individual shareholder with a stake of more than 45%. The firm’s shares have risen about 60% since its July initial public offering and now comprise the majority of his $7.1 billion fortune, according to the Bloomberg Billionaires Index. 

‘Very Stifling’
The son of an auto dealer, Ryan was born in Milwaukee and graduated from Northwestern University with a degree in finance and literature. While working as a life insurance agent in Chicago, he came up with the idea of offering policies to auto dealerships’ customers and persuaded Continental Assurance Co. to back it.

By age 26, he’d started his own firm, Pat Ryan & Associates, according to his Horatio Alger Association profile. The company grew into what would eventually become Aon through a series of acquisitions, including rapid global expansion in the 1980s and 1990s. 

Ryan retired as CEO in 2005, although he stayed on as executive chairman. In the months that followed he made his first serious attempt at semi-retirement, when he took charge of Chicago’s unsuccessful campaign to host the 2016 Olympics at the request of the city’s mayor, Richard M. Daley. 

“That occupied my mind” for a while, Ryan said. “But that was a very frustrating job because for the first time in my life I wasn’t in control of anything. The Olympics committee was in control of everything. And being an innovator and entrepreneur, that’s very stifling.” 

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