I had a conversation with Paige Wiese recently that reminded me why some transitions fail despite perfect financials and flawless legal work. Paige is the founder of Tree Ring Digital, a Denver-based digital agency. Over her 16 years in the industry, she’s developed a framework for protecting digital assets during business transitions. “There’s value in your website. There’s value in your domain names. There’s value in your Google reviews and your social media profiles,” she told me. “But most owners don’t realize those are assets until they’re at the deal
“While the fictional Roy family on the hit TV series “Succession” and the real world NewsCorp empire might get most of the attention, the fact is that most businesses could benefit from paying closer attention to how they hand off a business from one generation to the next. Unfortunately, the statistics bear this out: The business graveyard is littered with unsuccessful generational handoffs. According to Score, 70% of businesses that are passed on to the next generation fail. That number increases to a staggering 88% when businesses are passed on
After 30 years in this work, there’s one statistic that still keeps me up at night. 60% of transitions are going to fail. When I share this number with business owners, the gut reaction is like, well, they didn’t lock down their will enough or they had a bad tax strategy. And so all the money went away and that’s just simply not true. That 60% of transitions failing is actually because the family couldn’t communicate. So it was communication breakdown, missed expectations, people not on the same page. And
What does “fair” look like when you’re buying the family business? I come back to this question often, because in family business succession, fairness isn’t just a spreadsheet. It’s an emotional equation with a constantly moving denominator: siblings, history, legacy, expectation. I recently had a conversation with Mitch Gambert, third-generation owner of Gambert Shirts in Newark, New Jersey, who just completed the full handoff from his parents. He said something that stopped me in my tracks: “There were decisions I didn’t love, but I made them so I could sit
Every business owner knows fear. It shows up differently for each person—sometimes as a tight grip on the financials, sometimes as “waiting for the right moment,” sometimes as silence where there could be conversation. In this week’s solo episode of The Business Transition Roadmap podcast, Elizabeth Ledoux explores how fear quietly stalls even the most well-intentioned family business succession plans—and what it takes to move through it. https://youtu.be/PJeFJrVqUtw Prefer to read? Here’s what Elizabeth covers in this episode. Fear Rarely Announces Itself Fear doesn’t always look like fear. It can
I’ve been working with wealthy families for over 30 years, and there’s one conversation that causes more anxiety than any other: telling your adult children about the wealth they’ll inherit.
Just this week, I spoke with a father—let’s call him Robert—who’s in his late sixties with four children in their late twenties and early thirties. He has roughly $300 million in family assets. His kids are thriving in their careers, building their own lives, finding their own way. And they know almost nothing about what’s coming.
Have you seen the new F1 movie with Brad Pitt? It’s a great reminder that even the fastest driver cannot win without the right team in the pit. Passing the torch in your business is no different. Roughly half of business sales collapse before closing. Not because the numbers don’t add up, but because planning, people, and process aren’t aligned.
A business exit is a high-stakes race. Even the best car will not cross the finish line without the right pit crew. These are the five players every owner needs and the transition approaches that keep relationships intact while protecting the legacy you’ve worked decades to build.
Most business owners approach succession planning with a focus on financial structures, legal documents, and leadership training. These matter—no question. But we see transitions struggle or fail because of something that’s been decades in the making and can’t be reduced to a line item on a balance sheet. It’s reputation. Recently, I had the privilege of speaking with Meghan Lynch, CEO of Six-Point Strategy, on the Business Transition Roadmap podcast. Meghan’s firm specializes in helping multigenerational family businesses navigate growth, succession, and transition through strategic brand positioning. What struck me
What Is Planned Procrastination in Family Business Succession? Family business succession planning doesn’t have to happen all at once. In fact, one of the most powerful tools in successful transitions is something we call Planned Procrastination—the strategic decision to wait on certain aspects of your transition until the timing is right. If you’ve been feeling guilty about “not being further along” in your succession planning, this article will change your perspective entirely. Why Do Business Owners Feel Pressure to Rush Their Succession Plans? After guiding hundreds of family businesses
