Welcome to the latest installment of “Leading Questions: Wisdom from the Corner Office,” in which IBJ sits down with central Indiana’s top bosses to talk shop about the latest developments in their industries and the habits that lead to success.

Michael Bosway, 52, grew up in a military family with a father who was a career officer in the U.S. Army and once served on the Joint Chiefs of Staff. The family moved 15 times while Bosway was growing up, which helped him to develop keen social skills as he adjusted to each new locale. That talent for empathy and making personal connections helped lead him to a career in the investment banking and brokerage industry. Since 1999, he’s served as president and CEO of City Securities Corp., the oldest and one of the largest locally-based investment brokerage firms in central Indiana.



Since the Great Recession hit in 2007 and the securities markets took a beating, Bosway has been busy leveraging his capacity for calming shell-shocked clients, as well as weary and wary employees.

“In a tumultuous time, we spend more time trying to talk people out of things than trying to talk them into things,” Bosway said. “They all want to run for the hills, whereas we need to look at it as, rather than following the herd, you have to go against the herd [and consider investing]. That’s where the opportunities really lie.”

In the video at top, Bosway discusses taking advantage of those opportunities, and provides a rationale for following the tried-but-true advice of diversifying investments across asset classes (such as stocks, bonds, cash and alternatives such as gold and real estate) and sub-classes (large and small companies, taxable and nontaxable bonds, international and emerging markets, etc.). Spoiler alert: For long-term success, he likes large-cap American companies with healthy dividends and a global reach.

As well as taking a toll on investors’ psyches, the recession also battered brokers (and the brokers’ own bank accounts) at City Securities. As head of the firm, Bosway focused on rallying the troops.

“It’s important to seek help as a group, so that’s what we tried to do—get our arms around everybody here and make sure that we’re OK so that we then can go communicate to our clients and tell them that this will end at some point,” he said. “America is not going to end as we know it. Those are the kinds of philosophical statements you have to make in a period like that.”

While he exudes the cool demeanor of a relationship counselor, Bosway also has a steely nature forged from a childhood spent in athletics and a college career in varsity baseball at University of Dayton. He drew some inspiration from the diamond as he piloted a more aggressive strategy for the firm.

“If you’re happy sitting on the bench, that’s OK, but I’m the kind of kid who wants to get in the game," Bosway said. "And my contention years ago was that City was on the bench and that we weren’t moving forward and taking advantage of opportunities or seeking opportunities that were out there. I didn’t know exactly what we would look like, but we needed to get in the batter’s box.”

In 2006, the firm created City Financial Corp. to serve as a holding company for City Securities and newer, related ventures. The ventures met with varying degrees of success. The purchase of ReCasa Financial Group, which provided loans for the purchase and rehab of small residential rental properties, failed to pan out. (City Financial sold the firm earlier this year.) City Real Estate Advisors Inc., formed in 2001 as a full-service syndicator of affordable-housing tax credits, took off and is expected to account for 35 percent of City Financial’s revenue in its current fiscal year. Overall, revenues for the consolidated firm (for which Bosway also serves as president and CEO) have increased nearly 200 percent over the last decade.

In the video below, Bosway recounts his experiences as an itinerant kid and how a youth baseball coach helped inform his current managerial style. He also expands on his sports metaphor for learning how to take educated, well-informed risks.