Did you know that over 50% of small businesses in the US are owned by baby boomers? They’re retiring at a rate of 10,000 per day—and this will continue for the next 12-15 years.
The shocking part? Over 60% have absolutely no succession plan in place.
Recently, I had the pleasure of joining Abbey Crane on the Unscripted Small Business Podcast to share my insights on succession planning and the challenges facing baby boomer business owners. During our discussion, I drew from what I witness every day in my consulting practice: business owners who’ve spent 35-40 years building something meaningful, suddenly realizing they’re ready to step away—but with no clear path for what happens next.
I shared my perspective on the emotional journey of transitioning a business, the critical importance of documenting tribal knowledge, and why businesses that embrace structured succession planning will successfully preserve both their legacy and enterprise value. I invite you to listen to our full discussion here!
Here’s a Snapshot of Our Conversation:
Abbey Crane: What strategies do you use to support entrepreneurs in navigating the emotional challenges of letting go of their business, and how do you help them identify the right people to pass the torch to?
Georgi Feidler: For many baby boomer business owners, their business is like their baby. This applies across all industries—whether it’s a top cosmetic chemicals company, a custom metal signs manufacturer like Maker Table, a family restaurant, or a professional services firm. The emotional connection to the business transcends the sector. Oftentimes, I’m dealing with second generation business owners. The baby boomer took it over from their parents and then grew it and developed it. So there is a ton of legacy and emotion there. What I’ve discovered with my clients is, it’s not even about the sale price or the money at the end of the day. More importantly, they want to make sure that their team and customers are taken care of.
One of the biggest lessons I’ve taken away from helping baby boomer business owners through the transition process is that tribal knowledge is the enemy of succession. If everything lives in your head, that’s not true delegation—it becomes a barrier to growth and long-term stability. Another important realization is that successors aren’t found; they’re forged. You can’t just decide to retire tomorrow and expect to hand things off after a couple of weeks. It takes time, mentorship, and intentional effort to develop someone who’s truly ready to carry the torch.
Abbey Crane: Have you found any specific strategic tools that have been most helpful for those entrepreneurs where everything just lives in their brain?
Georgi Feidler: We start by identifying single points of failure – we use the “hit by the bus” analogy. If you got hit by a bus, who else knows what you know? What are the things that you are the only person that knows? That’s the stuff that we need to get documented first. It’s not sexy or fun, but it is the work. You have to document to delegate. We bring in AI tools to help make it a little easier – let’s get you set up with Loom and just start recording things as you’re talking to this person. Then let’s put that script into Scribe or Chat GPT, and then we can start to create some documents from that.
Abbey Crane: What advice do you give founders when they are trying to hire that person that is going to take over?
Georgi Feidler: Our first step is always to conduct a thorough assessment of the current talent within the organization. No one person can do it all—it took the owner decades to build that expertise. People aren’t naturally well-rounded, but teams can be. So we ask: who else already knows how to do what you do?
Finding the right successor isn’t about cloning the owner—it’s about building the right fit. It’s a lot like working with commercial real estate experts to sell a high-value property: you’re not just looking for a buyer, but someone who understands both the value and the vision. It’s about legacy, not just the handoff.
Successor hiring isn’t about perfection—it’s about completing the team. Focus on the three Cs: character (you can’t train it), connection (this is a trust-based role), and contribution (how they strengthen the team).
Start Now, Not Later
If you’re a baby boomer business owner thinking about retiring in the next five years, you need to start your succession planning today.
This isn’t just about documentation (though that matters). It’s about creating a mentorship structure, a governance model, and a gradual transition that reduces risk for everyone involved. Much like how SEOteric makes your business visible and effective online, at Hire.Train.Inspire., we make your business’s future visible and secure through proper succession planning—both require expertise and cannot be implemented overnight.
Because retirement shouldn’t feel like failure. And legacy shouldn’t be left to chance.
Ready to turn tribal knowledge into transferable value? Book a free consult today, and let us show you how!