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Episode Summary
You’ve been looking for a business to buy for two years. The list of criteria you wrote on day one is sitting in a drawer, and every deal that comes across your desk is missing a box or two. You’ve started telling yourself those boxes weren’t that important anyway. Bill Cowan evaluated about 25 businesses over six years before he resigned from a college presidency to force the issue. Then the anxiety took over. He compromised on his B2B preference, bought BioLawn (a B2C organic lawn care company), and spent the next nine years living with that one compromise. We got into the six-year search, the moment he realized he’d talked himself out of his own list, why he held growth back to keep the buyer pool wide, the unique performance-based deal he wrote with two suppliers he trusted enough to carry the risk, and how a product defect pushed his three-to-five-year exit plan to nine years. He closed three weeks before the pandemic. Now he runs a Vistage group, and the empathy that makes him good at it came from the part of ownership nobody warns you about: doing the work when you don’t love the work.
Top 10 Takeaways
- A list of buying criteria only works if you have the patience to honor it.
- Anxiety about not closing a deal is the most expensive emotion in any acquisition search.
- Buy a business in an industry you love. You’ll do it 70 hours a week.
- The B2C trap: complaints scale with customer count, and your sleep does not.
- Build for exit from day one. Document processes, separate the brand from you.
- Restraining growth to stay sellable to a wider buyer pool is a strategy, not weakness.
- Trust shapes deal structure. The right buyer lets you carry risk you’d never otherwise carry.
- A less-than-perfect decision made on time beats a perfect decision made late.
- You won’t run a peer group well until you’ve worried about making payroll yourself.
- Stop dabbling in AI. We’re in the brick-phone stage of the next internet.
Sound Bites
“Find a business you enjoy running because you’re going to be doing it a lot. You’re going be doing it 70 hours a week, at least at first.” (@00:58:00) — Bill Cowan
“I would lose sleep over complaints. You cannot run a business without complaints.” (@00:51:08) — Bill Cowan
“I am so much a better chair because I own my own business, and I had the fears and anxieties of running my own business.” (@01:25:00) — Bill Cowan
“A less than perfect decision made timely is better than a perfect decision made late.” (@01:28:07) — Bill Cowan
“AI is the internet all over again. As much as we know it’s going to change everything, we don’t realize how it’s going to change everything.” (@01:32:30) — Bill Cowan
About This Episode
Bill Cowan is a Vistage Chair in the Twin Cities and the former owner of BioLawn, an organic lawn care company he bought, tripled in revenue, and sold nine years later. Before BioLawn, his career arc spanned five industries: practicing veterinarian, director of the largest veterinary technician program in the country, Director of Clinical Studies at Guidant Medical Device (now Boston Scientific), and president of both Argosy University and Brown College. He met Ryan four years ago when Ryan presented to his Vistage group, and reconnected after Bill appeared on Chris Jones’s podcast where Ryan’s name came up. This is Bill’s full ownership story arc: search, acquisition, growth, exit, and the seat he sits in now.
Resources Mentioned
- BioLawn — The organic lawn care company Bill purchased, grew, and sold.
- Guidant Medical Device — Where Bill ran pacemaker, defibrillator, and CHF clinical studies. Acquired by Boston Scientific.
- Sunbelt Business Brokers — The broker Bill ultimately worked with after several others didn’t fit.
- Floyd Edelman / Inner Circle peer groups — Mentor who told Bill he needed to worry about making payroll before running a peer group.
- The Pause Principle — Book Bill referenced on the power of pausing to engage a different part of the brain.
- Chris Jones’s Podcast — Where Bill’s earlier conversation reconnected him with Ryan.
- Bill Cowan’s Vistage Chair page — vistagechair.com
Connections
Phase + Module:
- Module 1 — Ownership Goals — The buying criteria Bill wrote down and then talked himself out of
- Module 9 — Operator Transition — Build-for-exit thinking from day one of ownership
Milestones:
- Milestone 1 — Time & Role Goals — The “what do I actually want” list that anxiety overrode
- Milestone 25 — Operator Transition Plan — Documented processes, brand separated from the owner, team capable of running it
- Milestone 6 — Transaction Value — The performance-based deal structure with trusted buyers
- Milestone 7 — Value Growth Plan — Restrained growth to preserve a wider buyer pool
Concepts referenced:
- The Owner-Operator Trap™ — Bill’s nine-year version: the work itself, not the business, was the trap
- Independence by Design™ — The framework Bill saw Ryan present that stuck with him four years later
- Visionary-Integrator Framework — Ryan’s critique of how the labels obscure CEO accountability
- Value Gap — The space between Bill’s stated criteria and the business he actually bought