Owners ask me this constantly, and it is almost always the ones who have already built a strong team around them. They have a tax advisor they trust, an attorney who has handled their work for twenty years, and a financial professional who knows every line of the balance sheet. So the question tends to arrive with a little hesitation, as though asking it might insult the professionals they already rely on. It never does. What is a transition strategist, or what we call a transition guide, doing that those
A private equity group came knocking on a company doing more than forty million in revenue. The owner had not gone looking for a buyer and had no particular plans to sell. The group opened his financials, spent some time with what they found, and passed. Nothing was wrong with the business. It had grown from around seven million to more than forty million in five years, which is the kind of trajectory that brings buyers to your door in the first place. The problem was the record of that
Founders rarely reach out because the numbers confuse them. They reach out because they have started to picture life on the other side of the business and the picture comes back blank. The company has a plan for almost everything. There is a plan for hiring, and a plan for the equipment that gives out in year seven. Then the owner sits down to think about their own next chapter and finds nothing to work from. Thirty years of energy went into building something, and very little of it went
Five years ago, Elizabeth Ledoux and Laura Chiesman sat down to write a book about business transition planning. They had watched too many owners arrive at the most significant decision of their working lives with no roadmap in front of them, and they wanted to put one in their hands. What neither of them fully knew at the time was how much of that roadmap they would end up walking themselves. Since the first edition, Laura has completed her second transition and Elizabeth is three years into her own. That
When a business owner sits down with me to talk about their transition, they usually come prepared. They can talk about valuation. They can walk me through who might take over and roughly when. Many of them can describe the legacy they hope to leave with genuine feeling, because they have thought about it for years. Then I ask a much smaller question. What will an ordinary Tuesday look like after the transition? I am not asking about the celebration dinner or the trip you have been promising your spouse
Many business owners delay transition planning because they believe it signals the beginning of the end. The opposite is true. A business transition strategy starts creating value the moment you begin, long before any change in ownership or leadership takes place. We call this the multiplier effect, and it shows up in five measurable ways: your people, your business value, your time, your conversations, and your decisions. This post breaks down each one, drawing on Episode 87 of The Business Transition Roadmap podcast, where Elizabeth Ledoux explains what compounds when
After more than thirty years of walking beside business owners through their transitions, I can tell you where most plans actually stall. It’s almost never the valuation. It’s rarely the legal structure or the tax strategy. Those pieces are complicated, but they’re solvable, and there are plenty of talented advisors who solve them every day. The place where transitions get stuck is quieter than that. It lives in the owner’s own heart, and it usually goes unspoken for years. The fear of letting go of a business you built is
Somewhere on your to-do list, there’s a line that says something like “start transition planning.” It’s been there for a while. Not because you forgot about it, but because every time you look at it, it feels like it’s asking you to admit something you’re not ready to admit. So you move it. To next quarter, to after this launch, after this hire, after the busy season. And it sits there quietly while time keeps moving. I want to talk to the owners I think of as still building visionaries.
Most business-owning families can tell you exactly what they spend to protect their company. Insurance, advisors, legal work, investment management, it all adds up to one or two percent a year, tracked to the decimal. But when I ask families what they invest in the family itself, in the relationships that will carry the business and the wealth into the next generation, the answer is usually silence. That question sat at the center of my recent conversation on Your Next Gen Friend with Michael Palumbos, founder of Family Business Flywheel
