What Makes an Entrepreneur? Reflecting on a Decade of Sponsoring EY’s Entrepreneur Of The Year® Program

It is with great pride that we celebrate a decade of sponsorship of the Entrepreneur Of The Year® (EOY) program. We began our EOY journey as a Midwest Regional Sponsor, supporting companies headquartered in Illinois, Indiana, and Wisconsin. In 2024, we became a National Presenting Sponsor, with participation from all our U.S. offices supporting all 17 regions across the program. As EY celebrates 40 years of growing the EOY ecosystem into the gold standard for recognizing corporate leaders scaling businesses across all industries, it’s impossible to overstate the value of this program.

EOY participants range from bootstrapped founders to leaders of multi-generational businesses. As a National Presenting Sponsor, Cresa has heard participants share their entrepreneurial journeys, including mistakes, pivots, fortuitous timing, disappointments, grit, and pushing through periods of adversity and doubt to accelerate their businesses.

Over the past ten years, we’ve heard stories of negative account balances and leaders sacrificing their own income to make payroll. We’ve heard of partnership break-ups and devastating personal losses. On the flip side, we’ve seen candidates step into daunting roles with a public image of confidence and control while carrying the very real fear of failure underneath, fueled by the inner drive to succeed.

Each year, the definition of “entrepreneur” seems up for debate. We do our best to articulate the shared characteristics of the more than 500 individuals we’ve met since our first sponsorship in 2015. If I had to distill the best of the best, I’d say, “Perseverance and staying true to core values; prioritizing others over self and trusting your team to do more than they believed possible; and a passion for the work paired with a belief that there’s always a way to improve upon what’s been done before.”

These individuals recognize the sacrifices made (not only by themselves, but by their families and employees) and they carry a deep gratitude for the opportunity and trust placed in them.

At the end of the day, many still don’t see themselves as “entrepreneurs,” even after receiving the accolades that come with this program. At Cresa, we view their selfless devotion to service, as well as many other qualities, as further proof they not only meet, but exceed, the standard.