In 1972, Jim Reynolds was less than two months shy of graduating from Chicago Vocational High School, with plans of becoming a television repairman.
Raised in Englewood on the city's South Side, he had been studying the trade for two years when his mother's TV set broke.
Reynolds grabbed his screwdriver, removed the back of her Zenith, looked inside and was stumped about what to do next.
"I didn't recognize much of anything back there," Reynolds says. "I was totally lost, and I realized I couldn't fix televisions."
That realization helped put Reynolds on a path toward earning an MBA at Northwestern University and co-founding Loop Capital, a Chicago-based global investment services firm of which he's chairman, chief executive and majority shareholder.
This year, Reynolds, 58, said he'll consider the first outside investment ever for Loop, perhaps an initial public offering or private equity investment.
When it comes time to find outside backers, Reynolds should have no trouble forging relationships.
He counts President Barack Obama among his friends, having played basketball regularly with the former state senator at the East Bank Club and golf with him at the city's South Shore course.
Reynolds is active in Chicago civic circles, including helping to lead a private, $50 million anti-violence fundraising initiative and serving on the seven-member state board that runs U.S. Cellular Field.
The self-described "health nut" with a 34-inch waist on a 6-foot-3-inch frame snacks on kale chips made by Amy Rule, wife of Mayor Rahm Emanuel.
Reynolds' company helps businesses and governments raise money. If a company wants equity financing, Loop might be the intermediary that sells shares to the public. A big part of Loop's operation is serving governments that want to borrow from the public to build or repair bridges, schools, streets, and water, sewage and public transportation systems. Business with the city of Chicago counts for less than 3 percent of its revenue, Reynolds said.
Loop finished 15th among lead municipal bond managers in 2012, a position unchanged from the previous year, according to data tracker Thomson Reuters. Loop makes its money on fees and commissions.
Loop has about 200 workers in 22 U.S. offices, including 110 in Chicago's central business district, and is coming off of a big win with Pfizer's former animal health subsidiary, Zoetis, which raised $2.6 billion in its recent initial public offering. Loop was a co-manager on the stock offering, among the biggest IPOs by a U.S. company since Facebook.
Reynolds starts the year with a written list of 10 business and 10 personal priorities. A daily list helps provide discipline and structure.
"As an entrepreneur, you begin with a blank canvas," Reynolds said. "You can put a lot of junk on there, and if you're not careful, people can put junk on there for you."
Reynolds grew up around West 58th Street and South Carpenter. Though he, his parents and siblings didn't go hungry, the family just "didn't have any money," he said. His father, who attended school through the third grade, ran a fleet of jitneys, basically unlicensed cabs that served the city's South Side. His mom, who barely got beyond elementary school, was a nurse's aide.
After Reynolds' plans to be a TV repairman fell through, he felt lost. High school graduation was approaching, and he hadn't applied to any colleges. A cousin visiting Chicago from Mississippi encouraged him to apply to the University of Wisconsin in La Crosse because it accepted applications through June.
"I filled out the application — in pencil," Reynolds said. The university accepted him.
"Had that television not broken on that day, I probably would have gone on to graduate and not thought about college," he said over carrot juice during a late-afternoon interview from newly expanded Loop headquarters on the 19th floor of a downtown office building.