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Episode Summary
You’re not burnt out on the work. You’re burnt out on the pace. Twenty years of running 110 miles an hour, seven days a week, with the laptop on the hotel desk in Disney World because one phone call paid for the trip. Tom Heller hit that wall around year 18 and made a decision a lot of owners avoid: he was 47, his kids didn’t want the agency, the boomers were aging out of the buyer pool, and the math on waiting another decade didn’t work. So he sold. I had Tom on because his story is the unvarnished version of what most owners only hear about in fragments. He bought a company in 2005, doubled revenue in two years, landed Honeywell, ran debt-free, and eventually realized he was never going to be the $20M Minneapolis agency he once thought he wanted to be. The honest part is what came next: picking the wrong broker, sitting across from three very different buyers, signing a two-year employment agreement with an earn-out, and learning what it actually feels like to work inside a company with your name on the wall but somebody else’s signature on the check. We got into all of it, including the fact that his brand color was orange because of a shirt he wore when he was three, and how he had to start buying blue clothes to begin separating himself from the company he’d become.
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## Top 10 Takeaways- If your income depends on running 110 miles an hour for 20 years, you don’t own a business. You own a marathon.
- Your kids may not want it. The boomers are aging out. The buyer pool you assume exists may not be there in 10 years.
- The vision you started with may not be the business you actually built. Make peace with that before you go to market.
- Picking a broker who only gets paid when the deal closes is not the same as picking a broker who fights for your terms.
- Three offers in front of you are not three versions of the same deal. Investor, lifestyle buyer, and strategic each price you differently.
- Value-based pricing makes your business more sellable than hourly billing because contracts and relationships transfer. Time sheets don’t.
- Your two-year employment agreement is part of the purchase price. Negotiate it like the money it is, not the formality it isn’t.
- The buyer is not buying you. They’re buying whether the clients stay after you leave. That’s what the earn-out is really paying for.
- Your identity is woven into the brand, the color, the clothes, and the relationships. Start unwinding it the day you decide to sell, not the day you close.
- The right amount of money up front is whatever lets you walk away the day the relationship with the new owner stops working.
Sound Bites
“It’s tough. You know, I think, again, statistics, 85% of small businesses fail because people give up. It’s really easy to give up. We made the go for 20 years and finally came to the conclusion that it’s not that we wanted to give up, but we’ve done what we needed to do or wanted to do, and we were ready to move on.” (@TBD) — Tom Heller
“It feels like I’ve been running a marathon for 20 years. And that’s exactly how I felt in the moment that I decided to really seriously consider and talk to my wife about putting our company up for sale.” (@TBD) — Tom Heller
“He later told me, he said, well, if you hadn’t agreed to a two-year employment agreement, I probably wouldn’t have ended up purchasing your company.” (@TBD) — Tom Heller
“Since its inception, the company was so closely linked to my own personal identity that when I decided to sell, I had to almost immediately start to create a separation from it.” (@TBD) — Tom Heller
“Neil, whose name is on the wall? I’m like, it’s not mine. That’s my problem. Not yours.” (@TBD) — Ryan Tansom
About This Episode
Tom Heller is a Twin Cities entrepreneur who started his marketing and creative agency in college, ran it for 20 years, acquired another company in 2005, landed long-term contracts with Honeywell and others, and sold the business after a deliberate multi-year decision process. Tom and Ryan share mutual contacts in the Minneapolis business community (including Derek Sussner, who connected them through a LinkedIn thread). Tom now leads operations at his church and is exploring entrepreneurial ventures inside that role. His story is one of the more candid third-party sale narratives on the show, especially around broker selection, earn-out structure, and the emotional unwinding of identity from the business.
Resources Mentioned
- Implementing Value Pricing by Ron Baker — The book Tom had every employee read before he transitioned the agency off hourly billing.
- EOS / Traction by Gino Wickman — Tom self-implemented EOS five to six years before the sale.
- GEXP Collaborative — Ryan’s firm at the time, with guides on business valuation and exit options. — gexpcollaborative.com
- Tom Heller on LinkedIn — Best way to reach Tom (TomadArtGuy).
Connections
Phase + Module:
- Module 1 — Ownership Goals — Tom’s decision to sell came from clarity on time, role, and what the next chapter looked like, not from a financial trigger
- Module 5 — Predictable Revenue — Long-term contracts and value-based billing made the business sellable
- Module 9 — Operator Transition — The two-year employment agreement and earn-out as the operator transition mechanism
Milestones:
- Milestone 1 — Time & Role Goals — The “20-year marathon” realization is a Milestone 1 conversation
- Milestone 13 — Strategic Plan — Tom’s eventual peace with being a boutique agency vs. a $20M shop
- Milestone 15 — Revenue Systems & Forecasting — Three, six, twelve, and twenty-four month contracts as the revenue architecture
- Milestone 25 — Operator Transition Plan — Earn-out and employment agreement as the transition vehicle
Concepts referenced:
- The Owner-Operator Trap™ — Identity, brand color, and wardrobe all tied to the business
- Value Gap — The gap between what Tom thought the business was worth and what the buyers offered
- Independence by Design™ — Selling early, debt-free, with capital pulled off the table to fund the next chapter