I talk to a lot of owners across Ohio, Kentucky, and Indiana who are starting to think seriously about what comes next for their business. Almost every one of those conversations starts the same way: with a number. Valuation is where people want to begin, and I get why.
It’s a fair place to start, even though it’s usually the easiest question in the whole conversation. A number is concrete, it’s comparable, and it feels like something you can control. The harder questions live underneath it, and they’re the ones that actually determine whether the years you spent building this business hold up after you’re gone. If you’re a $3M to $10M revenue owner weighing a sale or a partnership, here are the seven questions I think matter more than the number on the offer.
1. How was this valuation actually calculated?
A multiple on EBITDA tells you almost nothing on its own. Ask what assumptions are baked into that number, what add-backs the buyer used, and whether the number holds up if growth slows for a year or two. Ask how they treat owner compensation, one-time expenses, and any seasonal swings specific to your market. A buyer who can walk you through their math in plain language and defend it under pressure is worth more trust than one who just hands you a term sheet and expects you to take it on faith.
2. What happens to the people who helped you build this, once you’re gone?
This is the question I keep coming back to, because it’s the one most owners forget to ask until it’s too late to matter. Your service manager, your best technicians, the office staff who’ve been there since the beginning, the people who show up every day and make the business what it is. A good buyer should be able to tell you specifically what their path looks like, not just promise that “nothing will change.” Ask about compensation, advancement, and whether there’s an actual plan for developing the next generation of leaders inside the company.
3. Does this buyer’s culture match how you’ve actually run things?
Culture fit sounds soft until you watch it play out in a bad way. Ask how the buyer has handled past acquisitions, how they talk about the teams they’ve inherited, and whether their operating philosophy sounds like something you’d recognize in your own shop. Talk to owners who have sold to them before. The way a buyer describes their last deal will tell you almost everything about how they’ll describe yours in five years.
4. What is this buyer’s real time horizon?
Every buyer will tell you they’re in it for the long haul. Some are working against a fund clock that requires an exit in three to five years, which shapes every decision they make from day one, including how they treat your team and your customers along the way. Ask directly how the capital behind them is structured, how long their typical hold period runs, and what happens to the business when that timeline runs out. The answer will tell you more about your future than anything in the offer letter.
5. What role do you want after the deal closes?
Some owners want out completely, and that’s a legitimate choice. Others want to stay involved for a year or two to help the transition land well, mentor a successor, or keep a hand in the parts of the business they still love. Get specific about what you want before you negotiate, because a vague advisory title with no real authority tends to satisfy no one. Decide your ideal role first, then find a buyer willing to build around it.
6. How will your customers experience this transition?
The people who’ve trusted your name on the truck for years deserve more than a form letter. Ask the buyer how they plan to communicate the change, over what timeline, and in whose voice. Ask whether the brand, service standards, and pricing philosophy you built your reputation on are staying intact or quietly being phased out once the deal is signed.
7. What does legacy mean to you, beyond the number on the check?
The other six questions all point back to this one, because valuation, culture, timeline, and what happens to your people are really just different ways of asking the same thing. A transition can look successful on paper and still cost you the thing you actually cared about most. Get clear on what you want to be true about this business five, ten, even twenty years from now, and let that answer guide which offer you take, not just which one pays the most today.
None of these questions will show up in a typical LOI. They’re the ones that determine whether the business you spent decades building still resembles itself once you’ve handed over the keys, and whether the people who helped you build it are still standing on solid ground.
If you’re starting to think about a transition and want a second set of eyes on the process, I’d welcome the conversation. Reach out at https://g5ventures.com/contact/.