Local businesses deserve a future as strong as their past | Tyler Leverington

Bill was 67. He spent 40 years building a business with his name on the door. The business was where he spent early mornings and late nights, where he stressed about making payroll, weathered recessions, and celebrated finally having room to breathe. The company paid for Little League uniforms, college tuitions, and mortgages. It was part of the community and more of Bill’s identity than he cared to admit.

Bill never expected to sell — most owners don’t — but his cardiologist gave him a talk he couldn’t shake, his wife had been telling him to slow down for years, and his adult children built their lives doing other things. His employees couldn’t qualify for financing, and ESOPs seemed messy and expensive. Bill didn’t see any choice but to sell. A buyer came along and made all the right promises. The leadership team would stay. The headquarters would stay. The name would stay.

Twelve months later, the calls started.

The general manager — after 22 years with the company — saw his role “restructured.” The controller “resigned,” and the operations lead was gone a month later. Decision-making migrated to the coast. By year three, Bill no longer recognized the business he had poured his life into.

I spent 11 years as a business attorney guiding owners preparing to step away from their life’s work and watched a generational wave of business transitions begin to roll across the region. More than half of Montana’s business owners are nearing retirement, and only 30% of family businesses successfully pass to the next generation. With few alternatives, regional businesses are increasingly being sold to buyers who have never set foot in the communities where they were built.

But local businesses aren't just businesses. They are a legacy and an identity. They are where careers bloom, families find stability, high schoolers land their first job, and the booster club gets its checks. They are the lifeblood of our communities. Unfortunately, not all buyers see it that way.

Owners hoping to avoid Bill’s nightmare should begin thinking about potential transitions in years — not months — before retirement. When buyer discussions begin, learn as much about a buyer as the buyer is trying to learn about the business. Press for specifics and note whether a buyer’s enthusiasm narrows or broadens as you do. Professional advisors — CPAs, attorneys, and financial planners — have an outsized role to play. I have watched advisors change the trajectory of transactions by asking what an owner wants for their employees and community post-sale. During my time advising business owners, those who treated due diligence as a two-way conversation and selected a buyer based on more than just numbers consistently walked away the most satisfied and had the fewest regrets post-sale.

Fortunately, people are waking up to the potential consequences of regional businesses no longer being regionally owned. In response, a small set of alternative buyers has begun to emerge: regional buying groups that invest with a longer-term vision, are open to promoting from within, and reinvest in the communities where they buy — rather than executing the short-term playbook that drove Bill’s outcome.

For Bill, the money was good, but too many promises were broken. His name is still on the door, but the decisions and money all flow to a part of the country he’s never visited. Over the next decade, thousands of Montana businesses will change hands. Those decisions will determine not only who owns those companies, but where decisions are made, where profits are reinvested, and whether the businesses that anchor our communities remain deeply rooted in the places that helped build them.