What the most successful owners understand that the rest learn too late: a good transition is built, not triggered. For most of my career, I’ve sat across from owners who built something real. A company with their name on it, or their family’s name, or a culture they shaped one decision at a time. And almost all of them arrive at the same moment eventually. The moment where retirement stops being an abstract someday and starts being a question that needs an answer. Here’s what I’ve learned watching hundreds of
Jimmy Taylor has lived the thing most business owners are afraid of. Over his career he built three companies. Two ended in successful sales. One was, in his own words, a colossal collapse. He was a founding partner of Novotus, a Texas recruiting firm that grew into the number one mid-market RPO in the country. And at one point, he and his two partners had no idea what came next. I wanted to start there, because the Novotus story is one of the clearest pictures I know of what actually
They’re not asking for a perfect plan. They’re asking for any plan. Over the last year and a half, I’ve had so many conversations with successors and next gens who are in the middle of family business succession. And I started running some analysis on the patterns showing up across all of them. There are some big themes, but one keeps surfacing more than almost anything else: “I just want to know if there’s a plan.” Not a polished strategy deck. Not a five-year roadmap with quarterly milestones. Just something
Mark Richards has been in the advanced planning and life insurance space for more than four decades. He has served ultra-high-net-worth families, family-owned businesses, and privately held companies. And across that time, he went through not one, not two, but three major business transitions. When Mark joined us on a recent episode of the Business Transition Roadmap podcast, he shared his full story with a level of openness that every business owner can learn from. The thing that stays with me from this conversation is how the values behind his
There is something that almost every successful business owner has in common. You have built the team. You have built up the revenue. You have got your reputation. And you are still building. That is good. That is actually great. But there is one thing most founders never build: a plan for what happens when something changes. Not because they are careless. Not because they have not thought about it. But because when you are still in the middle of building, the idea of planning for what comes next can
Most business owners spend decades building something and then only months trying to sell it. That gap is where value disappears, deals fall apart, and sellers walk away with regret. Tim Vorhoff, founding partner of CreoValo and author of Exit Right: How to Sell Your Company, joined Elizabeth Ledoux on the Business Transition Roadmap podcast to talk about what it actually takes to prepare a business for an external sale. Tim is a veteran of Evercore turned founder and advocate who helps mid-market and family-run business owners prepare for and
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,
