#361 James Hilovsky: From Pro Athlete to Franchise Matchmaker—Part One

What happens after the cheering stops?

For James Hilovsky, it meant trading his baseball uniform for business ownership—and helping other athletes do the same. In Part One, James shares how his short-lived pro sports career led to 25 years in restaurant franchising, including scaling Pieology from one store to over 100.

Now, as a franchise consultant, James works with NFL and NBA players looking to invest wisely, build generational wealth, and transition from the field to the franchise world. He explains how the mindset of elite athletes—structured, coachable, and risk-tolerant—makes them natural fits for franchise success. If you’ve ever wondered what it takes to make the leap from sports to business, this episode is your playbook.

Key Highlights of Our Interview:

From Dugout to Dining Room

“My playing career ended fast—but the restaurant world gave me a new team and a new game to master.”

Scaling Pieology: A Fast-Casual Success Story

“We went from one location to over 100 franchises. That’s where I really learned what franchisees need.”

Helping Athletes Avoid Bad Deals

“I saw too many players get pitched sketchy investments. I wanted to be a safe, informed resource.”

What COVID Taught Us About Franchising

“People were stuck at home, rethinking their jobs—and ready to bet on themselves.”

Sports Teams and Franchise Systems: More Alike Than You Think

“Both have playbooks. Both have coaches. And success comes from following the system.”

Why Athletes Thrive in Business

“They’re used to risk, coaching, and performance pressure. That’s the foundation of good franchisees.”

Case Study: From NFL to Mental Health Franchise

“A retired Super Bowl winner found purpose building a clinic network for athletes dealing with post-concussion trauma.”

Case Study: A Family Franchise Plan in Atlanta

“A former MLB player launched a dog grooming business—with his wife and kids running the first store.”

The Top 3 Qualities That Make Athletes Business-Ready

“Risk tolerance, coachability, and natural leadership. That’s the winning combo.”

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Host: Vince Chan | Guest: James Hilovsky

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