The Story of Dynamic Duo Brent Affolter and Jeb Stephen

Emma Fox

June 10, 2021

Our story begins in Akron, Ohio. The year is 1992, high school junior Jeb Stephen and sophomore Brent Affolter have just met for the first time. Over the next 29 years, the duo would continue to grow individually, professionally, and in their friendship, which eventually led to their partnership at Skylight running their own financial planning practice.

Brent and Jeb both described growing up as “latchkey kids”- a nickname for children who return to an empty home after school due to both parents working full-time jobs. “My key was in my sneaker when I went to school so I could unlock the door when I got home,” remembered Brent. Since they were both raised by working parents, they learned to quickly adapt to challenges presented to them. “I learned at a very young age how to cook for myself. If the smell of food cooking was at home and it wasn’t a result of my efforts, it was considered a special occasion. I even remember preparing a meal before a school dance freshman year for everyone that was going together with me,” shared Jeb. However, it was not only physical skills that were gained during this time. “My brother and I are 17 months apart, so we were really close and essentially helped raise each other,” shared Brent. “Being around working parents, having some level of work ethic was instilled awfully early. You had to work for what you wanted.”

Jeb’s mother was the Vice President of the Smythe Cramer Company, and due to her career in real estate, they moved around the area often. “I changed schools halfway through high school, and that’s what led me to first meet Brent when I transferred to Revere High School for my junior year. We’ve been best friends since then, and I don’t think we’ve lost touch for any significant period of time,” said Jeb.  Even though the two were friends in high school, their personalities and school activities varied. Brent was interested in sports, playing both baseball and football, whereas Jeb was more intrigued by the social scene.

After high school, Brent and Jeb’s paths took them on different routes in life. Brent graduated from The University of Akron in 2001 with a degree in business and communications and completed an internship with a wealth management team at Merrill Lynch. While working at a restaurant throughout his college career, Brent was able to build relationships with professionals in various walks of life. Through his education and relationships, he was convinced he was destined to be an attorney or a financial planner. Once he was ready to graduate, he was forced to decide between the two professions. He could continue his education in law school or dive into the financial services world. The thought of more student loan debt ultimately made the decision easy, and financial planning won out. Brent soon jumped into financial services industry and has never looked back!

Jeb’s journey to the financial services industry was a little more complicated. After high school, Jeb went on to start his undergraduate degree but didn’t finish it right away. He had started working while attending the Ohio State University and ended up leaving school due to the success he experienced professionally at UPS. In 1999, he moved back up to Northeast Ohio to join his mother in her launching their own real estate brokerage, which went very well until the tragic events of 9/11 caused the housing market to crash. “I’d become accustomed to that freedom of time and freedom of money that real estate and being self-employed afforded me. It was at that point where I knew I needed to make a career change to a more recession-proof industry,” said Jeb. “In our area, this meant health care or finance. Being that almost everyone I knew was working in financial services, the choice was easy. I ultimately ended up starting in the same office as Brent and his connection that helped bring him into the business.” After a few years into his new career and now having children, Jeb went back to school and finished his undergraduate degree. “I felt that I was going to, at some point, tell my kids they had to go to school and if I didn’t walk the walk, I certainly couldn’t talk the talk,” reasoned Jeb.

In 2002, Jeb officially joined Brent in the financial services industry. Six months into their careers together, both were placed into management positions. “Everything that we’ve done in our entire career has been trial by fire in terms of learning,” explained Jeb. “No one showed us the way by any stretch of the imagination.” After shadowing a few appointments and watching someone else sell insurance, they were left to their own devices to figure out the rest of what the job encompassed.

During the 2017 merger between MetLife and Massachusetts Mutual Life Insurance Company (MassMutual), Brent and Jeb were welcomed at Skylight Financial Group and presented with a new opportunity. Having worked in management for 15+ years, the two decided to start their own financial planning practice. “We had very few clients before we made this transition as our role in management was often focused on helping new reps in any ways we could, which included giving away large amounts of business. We jumped off the diving board into the deep end when we walked away from management. Both of us had families and lifestyles we needed to protect and going from income to ‘if come’ was a huge risk, especially given the fact that we were starting our practices from square one,” said Brent. “The reality is that we had to dig in deep and go hard because we didn’t have another choice.”

Since the beginning of their practices in 2017, Brent and Jeb have continued to grow and evolve in their roles as financial planners, and they couldn’t be happier with their decision! “Had we known what we know now, we would have done this 20 years ago,” said Brent. “We didn’t know this opportunity existed, so once we got here, it was like our eyes were fully opened to what the possibilities were.” Jeb agreed, “It was the best decision that we’d ever made financially and professionally when we made that transition.”

The team is nowhere near finished either. “Perseverance is a huge part of the reason we’re here today,” said Jeb. “We have handled adversity and we are both in fear of failure which drives us to become more and more successful.” The duo is constantly motivating one another, thanks to some friendly competition. “We can’t do anything without having some level of competition to it,” explained Brent. “I think that one of the best drivers we have for each other is when I see Jeb bringing new clients in and when I see him writing larger tickets, it drives me to find the next one.”

Outside of the office, the two live very parallel lives. Their families are close with one another, and they even purchased a boat together last year! They both enjoy playing golf, have a passion for cooking, and love being out on the water.

“We’re tighter than just work colleagues or business partners. It goes much deeper than that which I think is the epicenter of our trust,” said Brent, “I never have to second guess or consider motives because I know he’s working hard, and he knows that I’m working hard.” This close knit friendship has been the origin of many jokes, laughs and accomplishments. We can’t wait to see what this duo does next!

Thanks for sharing Brent and Jeb!