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.
As for the cousin who recommended applying to college in Wisconsin, her daughter runs Loop Capital's equity desk.
Reynolds' oldest son, 20, is a college economics major who works at the firm but is going to Argentina for a semester. His daughter, 18, a college freshman in California, has interned at Loop for the past five years and still goes into a West Coast office after classes. "She loves it," he said. "My daughter seems to have the most passion for it."
A second son, 17, is in high school and plays basketball.
After earning his MBA, Reynolds became a bond trader for First Chicago. He later went on to run Midwest municipal bond sales teams at PaineWebber and Merrill Lynch.
Eventually, Reynolds got an itch to start his own business and in 1997 co-founded Loop Capital. It started as a municipal bond firm but has branched out into other lines of business and is among the nation's biggest minority-owned financial services firms.
Public and private set-aside programs generate business for women- and minority-owned firms, he notes. "We took advantage of a lot of those because when we were starting off, the fact that a small, fledgling investment bank could underwrite bonds for the city of Chicago would not have been possible without a preference," Reynolds said.
But he calls that a "Venus' flytrap" because, at some point, a business wants to vie for a bigger piece of the pie, not just for the limited portion reserved for women and minorities.
"You've got to be careful not to create a business that could be successful in the minority program world but not competitive when you leave," Reynolds said. "They're good for starting you up, but when you want to grow, you've got to run from them."
While not dependent on set-asides from governments, or preferences from corporations trying to be more inclusive, Loop still gets them. In 2012, Chicago-based Northern Trust Corp. picked 15 firms owned by minorities, women and disabled veterans for its stable of equity and fixed-income broker dealers. Loop was among them.
'This is not a loan'
Among Reynolds' early employees was Craig Robinson, a former Morgan Stanley banker and Michelle Obama's brother. In his 2010 biography, "A Game of Character: A Family Journey From Chicago's Southside to the Ivy League and Beyond," Robinson recounted how he was going through a divorce while working at Loop.
Reynolds walked into Robinson's office and gave him a $5,000 check, saying: 'This is not a loan, and don't even try to pay me back.'"
"Jim was a prince of a human being who had been through the divorce mill already," Robinson recounted in his book. And Robinson was also planning to leave his job at Loop for a less-lucrative job of coaching basketball.
In a recent interview, Robinson said he did repay Reynolds when he got a head coaching job about six years later. Reynolds, upon receiving the check in the mail, had no recollection of giving him the money.
Robinson, now head coach of Oregon State University's men's basketball team, said that he has borrowed a page from Reynolds' management playbook with his college staff and players, giving them some room to be creative and independent.
"Jim had a vision and recruited guys who could execute, but he always made me feel like it was my show to run," Robinson said. "A lot of managers, particularly entrepreneurial managers, can't give up that kind of control," especially in the high-finance arena.
Reynolds, married for 21 years to his second wife, Sandy, lives in the Hyde Park neighborhood and also has an Arizona home. He and former Chicago Bears player Richard Dent share a skybox at Soldier Field.
"Here is a person who could have (one of) the first minority firms on a stock exchange," said Dent, whose Chicago-based energy company RLD Resources provides voice and data services to Loop.
Reynolds said he has been friends with Obama since the president was a state senator. Reynolds learned from Obama, on the golf course, that he was going to challenge Rep. Bobby Rush for his congressional seat.
"I ran his campaign then — the only one he lost," said Reynolds, who also helped raise money for Obama's Senate and presidential races.
Having such a high-profile friend can also bring unpleasant scrutiny. In 2008, USA Today ran a story about how Obama and Republican rival John McCain had both relied on fundraisers whose names had surfaced in federal corruption investigations.
"In 2003, James Reynolds, a Chicago investment banker who is a member of Obama's national finance committee, was recorded on FBI wiretaps arranging what prosecutors said was a 'sham' consulting contract with a woman they called the 'paramour' of a mayoral adviser in Philadelphia," USA Today wrote. "His firm later won $300,000 worth of city contracts."
In a statement to the paper, Reynolds pointed out that, after a thorough examination, no criminal charges were ever brought against him. "I can assure you, if the U.S. attorney's office believed that (my company) or I had violated any law, they would have brought charges," he said.
Today, Reynolds says again that after rigorous examination, "I was not a part of anything they wanted to investigate further."
Remembering his roots
One recent day, Reynolds showed a Tribune reporter and photographer where he grew up.
A house that Reynolds lived in when he was 12 to 14 years old, on the 5800 block of South Carpenter, had busted-out windows.
"The building was in better condition when I lived there," he said. It had been a vibrant block with children playing sports outside. "Everybody up and down this block knew each other."
Later, the family lived in two other houses nearby.
"You'd see people going to work, and you'd see cars in pretty much every space," he said. "It was a lower-middle-class neighborhood, but there was more commerce in the area."
Reynolds then got into his own car, a 2003 BMW 745 with 97,000 miles on it, and paid a visit to an after-school program, By the Hand, at Wentworth Elementary School at 6950 S. Sangamon St.
Loop makes charitable contributions amounting to seven figures a year, Reynolds said, and By the Hand is among the charities it supports.
Reynolds visited with two young program participants, a boy and a girl, in the school and was heartened that both like math. "Stay with math, algebra, calculus," he told them. "That will help you excel when you get to college."
Besides donating money, Reynolds brings kids to Loop offices, hires summer interns and invites them to use the Bears skybox and Loop's suite at the United Center for Bulls and Blackhawks games to show them what is possible if they work hard.
"I'm a big believer in the visual for these kids," Reynolds said. "They have to see it so it becomes real."
In recent years, Reynolds has resigned from some cultural boards and turned down other director invitations to focus on community causes, including the mayor's anti-violence initiative.
Reynolds said the city sowed seeds years ago that have resulted in killings occurring today.
"The leadership of Chicago made a decision 15 or 20 years ago that, 'We're going to develop Michigan Avenue, downtown, have a nice Gold Coast and North Side, but somehow in the neighborhoods on the South and West Side, maybe the resources aren't going to find their way there,'" Reynolds said. "Now, those kids we abandoned when they were 2, 3, 4 are now 16, 17, 18, 19 and 20."
Reynolds remains on World Business Chicago, whose board consists of dozens of Chicago business leaders. Reynolds was instrumental in recruiting U.S. Cellular CEO Mary Dillon to the group.
"We had a meeting to talk about the fact that there are a lot of guys in there, mostly old white guys," Reynolds said.
World Business Chicago Vice Chairman Michael Sacks and Reynolds are friends who discuss family, business, politics and sports. Sacks, whose day job is CEO of Grosvenor Capital Management, said Reynolds has "built a terrific business."
In 2011, Reynolds and the head of his public finance banking group, a key part of Loop, parted ways after what Reynolds had called a disappointing year for the firm. Reynolds characterized 2012 as a "great" year.
Reynolds is also one of three Emanuel appointees to the Illinois Sports Facilities Authority, along with former LaSalle Bank CEO Norm Bobins and Mesirow Financial CEO Richard Price. All three were on the losing end of an effort to oppose Gov. Pat Quinn's selection of Kelly Kraft, a former TV reporter, to become CEO of the authority.
Reynolds said he still considers Quinn "a great friend and a great supporter, as I am of him." As for Kraft, Reynolds said she's a "hard worker" who is "dedicated" and doing "a really good job."
"The first thing she did that impressed me is she called me" after she officially got the job, Reynolds said. The two had coffee, and she now calls him "a wonderful mentor."
Their cordial relationship shows that professionals can move on from conflict with respect, he says.
Still, he's unlikely to join a board unless he feels that he has something to contribute.
Says Reynolds: "There's not a room I'm in or a board I sit on that my presence isn't felt and that my opinion isn't stated."
Jim Reynolds chairman, CEO and majority owner of Loop Capital.
Middle name: None, officially. "They forgot to put it on my birth certificate. It's supposed to be Sylvester, but it never made it on there, which is fine with me."
Hobbies: Works out daily, including in his home gym. "Every week I hit every body part a couple of times. I don't know how you function without a gym."
Office conversation-starter: A photo of Reynolds with former Pennsylvania Gov. Ed Rendell, athletes Julius Erving and Franco Harris, and former Penn State football coach Joe Paterno and his wife, Sue.