Learning Workshop w/Tanner Holmes – From Operator to Empire: Scaling Yourself Across Multiple Businesses

From Operator to Empire: Scaling Yourself Across Multiple Businesses

Most entrepreneurs build their first company through grit, hustle, and personal effort—only to eventually hit an invisible ceiling. This two-part EO Member-Led Workshop is designed for founders asking the next question: why and how do I expand beyond a single business?

Together, we’ll break down the real strategic reasons entrepreneurs choose to move past one company—wealth creation, risk diversification, leverage, personal freedom, and values alignment—then explore the practical paths founders actually take. From holding companies and franchising to partnerships and the shift from operator to investor, we’ll unpack what works, what doesn’t, and the common pitfalls that derail even the most capable serial entrepreneurs.

The objective is simple: help you identify the path that best aligns with you and your long-term strategy.

This session is led by Tanner Holmes, a Chicago-based multi-unit entrepreneur, investor, and EO board member. Tanner has owned and scaled multiple brands across health, wellness, and beauty; exited three businesses; and currently operates and invests in a growing portfolio of multi-location franchised companies. He’s lived the transition from hands-on operator to portfolio builder—and made plenty of expensive mistakes along the way.

Expect real numbers, real stories, and clear frameworks. If you’re feeling the pull toward “what’s next,” this workshop will help you think bigger, move smarter, and build with intention.

RSVP By: 3/31/26

Attendees: EO Members, EOA (Accelerators) & SAPs