James Reynolds, Jr.


Founder/CEO/Chairman, Loop Capital

What an office – a literal visual feast! Mr. Reynolds’ office has a panoramic view of downtown Chicago. Then there’s an authentic African sculpture (a gift from the Chicago Urban League) and a display case filled with autographed Chicago Bears paraphernalia, plus photos of family and friends…including Barack Obama.

“Let’s do this,” urges Mr. Reynolds, who looks like he just walked out of GQ. His style is effortless. A testament, he says, to a trio of fashion experts: “One of the greatest personal shoppers, Morris Gearring at Neiman Marcus, shops for me quite a bit. I also have a lot of custom suits from Albert Carroll, and I buy pieces from Syd Jerome.” The man clearly oozes success, but it wasn’t always that way.

Pausing to reflect on life before Loop Capital, Mr. Reynolds says his path to finance started after a failed career attempt. He believed that he was destined to become a TV repairman and studied the trade at Chicago Vocational High School (now Chicago Vocational Career Academy) in the ‘70s. “While you received a general education, you also learned a trade. So some folks went college, while others straight to the trade,” he explains. “I was in a hurry to move out of my family’s home and make money, so I didn’t apply to college.”

As fate would have it, his family television broke during his senior year. Since he studied TV repair for two years and was on the verge of graduating, he offered to fix the broken set. “I took my tools out to work and froze,” recalls Mr. Reynolds. “I couldn’t fix it. I didn’t know what I was doing.”

Panicking about his future, Mr. Reynolds turned to his cousin who, in turn, helped him apply to a college still accepting applications, the University of Wisconsin-La Crosse. “Once I graduated from there, I joined First Chicago then finished my MBA in 1982 by attending night school at Northwestern.” And after 15 years working in finance as a trader and a bond salesman, he co-founded Loop Capital with Albert R. Grace, Jr., its current president.

“I never thought I’d be an entrepreneur,” reflects Mr. Reynolds. “But I kept seeing things that I thought could be done better and structured differently. I’d talk to my managers and say, ‘We should do it this way.’ They’d respond, ‘Jimmy, if you’re so smart, why don’t you just do it yourself?’ After a while, it slowly started to resonate and I saw opportunities for a boutique firm.”

“Folks think you’re at a disadvantage when you’re smaller,” observes Mr. Reynolds. “You have less money, less breadth, you’re not global. You don’t have 150,000 employees…or even a lot less. But you don’t need that to be competitive in targeted businesses.”

Loop Capital’s motto is: “To provide client service beyond expectations.” And while Mr. Reynolds is aware that this and other phrases like “put the client first” almost sound cliché, he’s noticed a growing number of companies just don’t do it. “Whether you call your cable company, credit card company or interact with your bank, you might not feel like you’re their highest priority,” he says. “What I set out to do is actually live up to our credo. Whether it’s through bond deals, stock deals, a corporate finance assignment or global finance assignment, we sit down with clients to understand what their goals and objectives are. We listen exceptionally and then try to exceed those expectations.”

“I make a lot of mistakes, because I take a lot of chances,” admits Mr. Reynolds. “Newsflash…if you take a lot of chances you’re going to make mistakes. And if you’re not making mistakes, you’re not doing enough.” Optimistically, he says that he’s never made a big, fatal mistake in losing everything. “I’ve made a bunch of little mistakes,” he explains. “I lost all the money I put into one investment; I made money on another investment; I’ve hired bad people; I’ve hired great people; I’ve had a terrible girlfriend; I have a great wife. I’ve done a lot and learned along the way.”

And when he’s not working? Finding time for fun and family isn’t hard for the 60-year-old finance executive. In fact, Mr. Reynolds planned a summer safari in South Africa with his wife, Sandy, and their three kids: James Reynolds, III (who works for Loop Capital in New York), Kendall (a junior at University of Southern California) and Miles (a freshman at St. Louis University).

He’s also a big Bears fan. “I’m at every home game,” he says, glancing at the footballs in a display case that indicate his company is a suite holder. “The ‘85 Bears – Richard Dent, Otis Wilson, Mike Richardson, a lot of those guys – are some of my best friends. And…I write. Actually, that’s probably the one thing most of my friends would be surprised to learn about me. I’m a frustrated writer.”

Before he “stumbled into investment banking,” Mr. Reynolds explored the streets of Paris and, inspired, wrote fiction. “Then I tackled this investment-banking thing and never got back into writing,” he explains. “But I plan to write more. I’m working on an op-ed that Crain’s Chicago Business will probably print, talking about my views on economic development here in the city.”

And what tops his bucket list? “I want to heli-ski,” he proclaims proudly. Seeing that he’s an investor who’s not afraid of taking risks, it’s no surprise he’s determined to go off-trail, downhill skiing on a mountain only accessible by helicopter. “I was going to do it in San Paolo once, but the weather was bad that the helicopter wouldn’t fly. You can either jump out [of the helicopter] or they find a place to land so you can get out and go. But they don’t stop to get you. Once you commit…you’re in.”

Nima Taradji Photograph


About Carrie Williams

Carrie Williams is TCW's managing/digital editor. She manages day-to-day editorial operations of the monthly print publication, website and social media outlets, contributes to a variety of feature articles and directs a team of interns, freelance writers and bloggers. In early 2013, she led the redesign of TCWmag.com/restructure of TCW's brand strategy. Her blog, "Carrie On," is a blog of reflection and discovery, discussing how to push through life when you’re handed one too many curveballs. And finally, Ms. Williams is also executive director of the TCW Foundation, a 501(c)(3) non-profit supporting underfunded women's and children's organizations.