#477: William “Bill” Cowan | Buying a Business Is Easy. Living With It Is Hard.

This conversation with Bill Cowan is a full arc—from career operator to business owner to successful exit to peer group chair—and it surfaces the real lessons most owners only learn the hard way.

Bill shares what it was like to spend six years searching for the right business, why anxiety pushed him into compromises he wouldn’t make again, and how owning a company fundamentally changed how he thinks about leadership, risk, and decision-making. We unpack why passion for the work itself matters more than spreadsheets alone, why building for exit from day one sharpens every decision, and how clarity beats perfection every time.

We also go deep into the mechanics most owners never see: buyer psychology, deal structures, seller financing, earn-outs, trust-based transactions, and how real exits actually get done in the lower middle market. This isn’t theory—it’s lived experience, with the scars and wisdom to prove it.

William “Bill” Cowan is a Vistage Chair and former business owner with a diverse career spanning veterinary medicine, medical devices, higher education leadership, and entrepreneurship. After buying, growing, and successfully exiting an organic lawn care business, Bill now works closely with owner-operators as a peer group facilitator, bringing rare empathy and practical insight shaped by firsthand ownership experience.

Top 10 Takeaways

1. Anxiety can create urgency, but it can also cloud judgment and push owners into compromises they later regret.
2. You should enjoy the work of the business itself, not just the idea of ownership or the eventual exit.
3. Building for exit from day one creates better decisions, stronger teams, and a more valuable company.
4. Passion is not optional—it directly impacts stress, energy, leadership effectiveness, and longevity.
5. A timely imperfect decision is often better than a perfect decision made too late.
6. Understanding how buyers think changes how you run the business long before you ever sell.
7. Documented processes, owner independence, and a capable team are core value drivers—not “nice to haves.”
8. Most lower-middle-market exits require creative deal structures, trust, and flexibility—not just cash.
9. Owner experience creates empathy that cannot be learned any other way.
10. Tenacity matters more than getting every decision “right”—you influence outcomes more than you think.

Chapters:
(00:00) Introduction to Bill Cowan and his business ownership

(02:43) Career path from veterinarian to medical devices to education leadership

(07:40) Six-year search for right business reveals complexity of buying

(16:00) Compromising on B2C instead of B2B despite original acquisition criteria

(27:00) Growing business threefold while intentionally restraining further growth

(36:00) Critical lesson learned: passion for actual work matters more than expected

(42:00) Building for exit from day one shaped every business decision

(49:00) Exit structure required trust-based deal with performance-based terms

(57:28) Transition to Vistage Chair applies hard-earned ownership experience

(01:05:00) Making timely imperfect decisions beats perfect decisions made late

Resources:
William Cowan LinkedIn: https://www.linkedin.com/in/williamcowan-dvm/
Ryan Tansom Website https://ryantansom.com/