Experience that Meets Owners Where They Are
Meet Matt Gillespie
Founder & Executive Advisor
I love small and mid-sized businesses. They are the backbone of America’s economy, cornerstones of their communities, and create real opportunities for hard-working folks of all backgrounds.
I have spent my career leading and strengthening small and mid-sized businesses. For nearly a decade, as CEO, I led a single-family office overseeing more than a dozen operating companies across manufacturing, services, a national consumer brand, and a commercial real estate portfolio. Most of my time was spent shoulder-to-shoulder with our operating partners and business leaders, helping them regain direction, strengthen operations, and rebuild momentum.
Before that, as COO, I led the turnaround and rapid scaling of a diversified manufacturing and service business. I have made the tough calls, balanced risk, and done whatever the moment required – from restructuring teams to operating a forklift at 2 AM.
I founded Rawhide Executive Solutions to help Ohio Valley business owners simplify complexity, strengthen their teams, and get back to a life they truly enjoy.
Because your business should serve your life – not consume it.
Direct. Practical. Focused on What Matters.
My approach blends the strategic insight of a CEO, the operational discipline of a COO, and the hands-on empathy of someone who has lived the realities of leading a business. I distill problems to their fundamentals, eliminate the unnecessary, and build on what is truly valuable.
When I am not with clients, you will likely find me in the air – flying myself across the Ohio Valley to meet with business owners face-to-face. I like to travel the same way I like to work: directly, efficiently, and always moving forward.
“The best thing a human being can do is to help another human being know more.”
— Charlie Munger