- Date: September 3, 2026
How Two Business Transitions Shaped the Second Edition of It’s A Journey
- 7 min read

When a business crosses the $10 million mark, everything about transition gets more complex. More stakeholders. More tax implications. More at risk if the process goes sideways. And yet, the thing that causes most transitions to fail at this level is the same thing that causes them to fail at every level: the people involved were never aligned. If you are looking for a transition consulting firm to help you move through this, here is what to actually look for, what to watch out for, and why the most expensive

Your attorney has a plan. Your CPA has a plan. Your financial advisor has a plan. But do you have one? Not a tax strategy or an estate document. A plan for the people. The conversations. The relationships that will either hold your family together through this process or quietly fall apart while everyone focuses on the paperwork. That is the difference between exit planning and business transition planning. And when only one of those is happening, the most important part of the equation gets left to chance. The

If you run a small business and someone brings up the word “governance,” your first instinct is probably to change the subject. It sounds corporate. It sounds slow. And if you have been making every decision yourself for the last 10 or 20 years, it sounds like someone wants to put handcuffs on you. I hear this from business owners all the time. And I understand the resistance. You built this thing by being decisive. You go home, think about it for a couple of nights, come back, and say,

If you are in the middle of planning a business transition, or even just starting to think about one, chances are someone has already told you to call your attorney. Get the entities set up. Talk to your CPA about the tax implications. Put together an estate plan before a sale or a transition. That advice is not wrong. Those professionals are essential, and every successful transition needs them. Bring smart people together who are specialists in their area and you are going to get a great plan. But here

There is a particular kind of stuck that only shows up in people who have built something significant. They are decisive in business. They can read a market, manage a crisis, and make a hundred calls a day without flinching. But ask them to sit down and plan what comes after the business, and everything grinds to a halt. Dennis Passis, founder of the Family Wealth Library and author of Founder Paralysis, has a name for it. And in a recent conversation on the Business Transition Roadmap podcast, he helped

We work with a lot of families and owners who are carrying a quiet fear. They’ll say things like, “I don’t want my family to fight over this,” or “I just want to protect what I’ve built.” And underneath those words is this belief that they have to choose between keeping their family together and preserving their business legacy. It’s one of the most common things we hear. And I want to tell you: you don’t have to choose. We have plenty of examples where families ended up with both

When business owners start thinking about what comes next for their companies, the conversation often jumps straight to selling. Brokers, valuations, letters of intent. And for some owners, a third-party sale is the right path. But for many of the owners we work with, selling to an outsider was never part of the vision. They built their companies with their families, their communities and their employees in mind. The idea of handing the keys to a stranger, even a well-funded one, feels like a contradiction of everything they worked to create. These owners want

We recently sat down with Marcy McNeal, one of our transition guides and a certified social and emotional intelligence coach, to talk about something that shows up in nearly every family business we work with: conflict. Not the dramatic, door-slamming kind that makes for good television. The quieter kind. The kind that sits in the space between a parent who built a company from scratch and a successor who is trying hard to earn a seat at a table that has always belonged to someone else. https://youtu.be/YgqVU_n_Iro Marcy brought a

I talk to a lot of families and business owners who tell me, “I know I should be thinking about transition, but I’m just not ready yet.” And every time I think, of course you’re not ready. Humans don’t leave something comfortable unless we believe there’s something better waiting ahead for us. And it’s not weakness that causes that. It’s just our normal human wiring. Our brains, our emotions, even our habits. They’re all designed to keep us safe and to stay in what’s familiar. We operate our lives, if