Bobby founded the Exit Ready Institute after building his own playbook the hard way. He left a Wall Street career to run his family’s Dunkin’ franchise business, scaled it from 20 to 40 locations and $50M in revenue, and later founded Green Ridge Wealth Planning. He’s also the author of Unchained: The Raw Truth About Entrepreneurship, Family Business and Life Balance, a family-office owner, and a manufacturing business owner. Bobby built ERI to be the program he wishes had existed when he needed it most.
What If the Best Exit Strategy Has Nothing to Do with Selling?
Most of the business owners I work with are not planning to sell anytime soon. Some are five years out, some are ten, and plenty have no intention of selling at all, which I completely understand. I am not building Green Ridge while looking at the door; I am building it because I still enjoy the work, the challenge, and the opportunity in front of us.
Why Whether You Sell Is Beside the Point
But I have also come to believe that whether you plan to sell is almost beside the point. Eventually, someone besides you will have to look at your business and decide what it is really worth. It may be a buyer, a bank, a partner, your children, or even you ten years from now, asking whether the company you spent your life building gives you freedom or still requires you to show up every day. That is what surprises many business owners.
What Buyers and Banks Actually Look For
For years, a strong market could hide a fair amount of weakness inside a company. Capital was cheap, valuations were rising, and growth did not always have to come from operational excellence because there were other tailwinds helping. That has changed. Buyers are more selective, borrowing costs more, and the quality of the underlying business matters far more than it once did.
And by quality, I do not mean whether the company has a good reputation or whether revenue is growing. I mean the things that become obvious the minute somebody starts looking underneath the hood: how understandable the financials are, how concentrated the revenue is, whether the management team can make decisions without the owner, and whether the business continues to function when the founder is not in the room.
I learned how important that last one was in a way I would not recommend.
What My Father’s Business Taught Me
My father built a tremendous business. At its peak, our family enterprise had nearly forty Dunkin’ locations and hundreds of employees, and Dad knew it inside and out — the people, the stores, the relationships, the details. He also believed very strongly that he needed to know what was happening everywhere, and there were signs hanging in the office that read, “Tommy needs to know EVERYTHING.”
For a long time, that may have felt like a strength. Dad had built the company, knew how to solve the problems, and had spent decades developing an instinct for the business. But when he got sick, having all that knowledge concentrated in one person became a problem, because now there was a clock.
The questions that could always be dealt with later suddenly had to be answered. Who makes decisions if Dad is not here? Who knows what he knows? Are the agreements current? Can somebody else understand the financials? Who has the authority to run the company, and what happens to all the relationships that had been built around him?
These were not complicated questions; they were basic ones. The problem was that we were now forced to answer them under pressure.
Exit Planning Is Just Better Business Planning
That experience changed how I think about exit planning, to the point that I do not really think of it as exit planning. To me, it is business planning held to a higher standard.
If you build a company that someone could buy tomorrow, you usually end up with a company that is better to own today. The financials are cleaner because they have to be understood by someone besides you; the team gets stronger because all decisions do not have to flow through the founder; the revenue becomes more predictable because concentration and recurring revenue suddenly matter; and agreements get cleaned up because uncertainty is expensive.
You Don’t Have to Sell to Build a Business That Doesn’t Depend on You
None of that requires you to sell. In fact, the irony is that doing this work often makes owners less desperate to sell, because the business becomes easier to run and less dependent on them.
That is why I keep coming back to the same idea with owners: run the company as if you might sell it in 24 months, even if you have no intention of selling it for ten years. Not because every owner needs an exit, but because every owner eventually must address the weak spots in their business. The only real difference is whether you deal with them while you still have time and control, or whether a buyer, a partner, a family event, or life itself sets the deadline for you.
I lived through the second version, and I can tell you the first one is better.
What’s Coming in the Series
Over the next three blogs, I am going to dig into the areas where I see this show up most often: owner dependence, the quality of the business behind the revenue number, and the gap between what your company is worth and what you actually need it to do for your life. But the starting point is simpler than all of that. It is likely you will have to address these issues eventually, and the advantage you have today is that you decide when.
This is the first part of a four-part series. Click here to have part two sent directly to your inbox.