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
A few weeks ago, Andrea Carpenter and I sat down with Family Business Magazine for a live webinar on preparing the next generation for ownership. We were joined by two people who know this journey from the inside: Laurie and Brad Irish-Jones of Irish Family Companies, a fourth-generation family business that has been serving Western New York since 1932. Laurie is the prior CEO who led her family through the transition from the third generation to the fourth. Brad is part of that fourth generation, now helping lead the business
Because movement and direction are not the same thing. Every transition has a destination. But most business owners start moving long before they actually know where they’re going. Dates get set. A valuation gets pulled together. Legal documents start circulating. And somewhere in the rush toward execution, nobody has stopped to ask the harder question: where are we actually headed, and does everyone agree? This is the gap I see most often in family business transition planning. Owners jump straight to the mechanics, the price, the structure, the timeline, without
For thirty years I’ve watched owners assume the people coming after them will simply be ready when the day arrives. They’ve built something worth passing on, they’ve worked hard for it, and somewhere along the way they let themselves believe that readiness would sort itself out. Then the day comes. They look over their shoulder, and the person they hoped to hand the business to isn’t standing where they pictured. Here’s what I’ve come to believe after all those years. Most owners leave a little too soon and start the
There is a moment in almost every family business transition where you look across the table at someone you love and realize you want a different thing than they do. Not in a small way. In a way that can make the whole deal feel like it might not work. And it can be a gut punch, because this is not an adversary across from you. It is the parent who raised you, the sibling you grew up with, or the partner who built this thing alongside you. The only
Most of the owners I’ve worked with knew something was shifting long before they were willing to say it out loud. It didn’t show up on a balance sheet or in a valuation, and it almost never made its way into a transition plan. It showed up as a feeling. A little restlessness. A quieter sense that the energy wasn’t quite where it used to be. Something small enough to talk yourself out of, and most owners do, for years. I recorded a solo episode of the Business Transition Roadmap
Most of the next gens I talk with are not afraid of responsibility. They are afraid of the gap between what they will one day carry and what they were ever actually taught. Nobody hands you a manual for this. At some point you realize, often all at once, that there is a whole world of governance, ownership, and family history you were never let into, and now part of it is yours to understand. https://youtu.be/RPBM7jilNJU That gap, and the slow work of closing it, is what I want to
