49, Company President
Eddie Taylor Jr. starts Early — like, 5 a.m. early. Without hesitation, the president of insurance brokerage Taylor Oswald laces up his shoes to walk a few miles. Then, the former Allegheny College running back, with strong shoulders that fill out a navy suit, hits body weight, free weight and core exercises. As he gets further from the days of being a two-sport athlete at Elyria West High School, the workouts are about more than just maintaining physical health.
“Clearing your mind is a part of the physical process,” he says with a soft, deep voice. “It is indispensable in terms of trying to maintain the best version of yourself.”
Being his best is important when his days are as packed as they are. At year’s end, Taylor Oswald is busy forecasting, budgeting and planning for a successful 2025. Partnered with Cleveland-based insurance behemoth Oswald Cos., the company is one of the largest African American-owned insurance brokerages in the region.
The hard work started in 1987, after graduating from Allegheny College with a degree in psychology. He worked in retail before jumping into workers’ compensation and insurance at Columbus-based Davis & Associates, becoming the company’s
youngest-ever vice president. In 1997, he founded Integrated Consulting Services, which grew to a dozen employees and more than $1 million in sales in its first two years.
In 2012, then-CEO of Oswald Cos. Mark Byrnes approached him. Byrnes felt his now-130-year-old company and its industry hadn’t done enough to serve women- and minority-owned companies, and he wanted Taylor to help him rectify that. Taylor took the opportunity, forming Taylor Oswald, an independent company that is partnered with Oswald Cos.
“It's a venerable company in this town,” says Taylor, “but that executive had the good thinking to recognize that women and folks of color hadn't been an important enough part of the organization's growth and their look into the future.”
Despite building a customer base from scratch, Taylor Oswald grew faster than most startups thanks to administrative support, processes and expertise. While Oswald benefits from having a partner that can serve companies looking for a minority-owned brokerage (often to serve their diversity, equity and inclusion efforts), the benefit for Taylor Oswald is the ability to run lean by having the expertise, systems and backing of the insurance behemoth and its parent company Unison Risk Advisors. Today, his few dozen employees bring in between $5 million and $20 million a year.
“The secret sauce is that we don't have to necessarily bring on additional staff resources to fill the needs of our many and varied clients,” he says. “While our numbers are relatively few, our reach is greater because of the hundreds of local Oswald employees and beyond that we tap into.”
In the final stretch of his day, Taylor serves or has served in some capacity on an astonishing roster of philanthropic organizations, including The Presidents’ Council, University Hospitals Cleveland Medical Center, the Greater Cleveland Sports Commission, Greater Cleveland Partnership, the Burton D. Morgan Foundation and the Greater Cleveland Chapter of the American Red Cross.
What Oswald is to Taylor, Taylor hopes to be to these organizations: a source of institutional knowledge that allows them to be more agile and powerful — a source of “energy,” he calls it.
“Sometimes shortcuts matter,” he says. “Not shortcuts in terms of the work, but shortcuts in terms of which path will lead to bad outcomes, versus another path where the chances of success are increased significantly.”
Ideally, he likes to set these organizations up for success and then move on to the next one that needs his help.
“There are so many talented people in this community that can serve, and I’m happy when the torch is passed to do that,” he says. “I’m not in any way collecting boards. My goal is to serve because there is a need.”
When his professional and civic duties are done, the father supports and used to coach both of his sons, a sophomore scholar and football player at Hobart and William Smith Colleges and a 17-year-old junior at Solon High School who also participates in track and field, Science Olympiad and speech and debate.
“In the end, it's a day that's varied,” he says. “It's a day that has lots of moving parts, but the component parts together make it make sense. And I love the variation.”
Taylor talks about wanting to bring energy to the people around him, but on these busy days, the people around him and their impact keep him energized.
“More than the big win or the big sale,” he says, “watching people excel and grow is the thing that brings me the most joy in life.”
Meet the rest of the 2025 class of Most Interesting People. >>
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