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In 2020, right before the pandemic, my family sold our business, a travel technology company my father had founded decades earlier. On paper, it was a success. The brand was respected, the industry trusted us, and the sale gave us a sense of relief after years of uncertainty.
But behind the scenes, it didn’t feel like success. The process was backwards, unfinished, and exhausting.
The sale was motivated by a challenged succession plan, a transition from my father, the founder, to the next generation. Expectations weren’t aligned, and communication broke down long before the transaction. My father saw the business as a responsibility. The rest of us saw it as an opportunity to create something new. We were speaking two different languages.
It was a classic family transition story: a lifestyle business deeply dependent on the founder, run by feel, and built on relationships and reputation more than process or predictability. To make it attractive to a buyer, we had to build systems, bring in the right people, and package something that could operate without my father in the middle of every decision.
We did it, but it came at a cost.
Looking back, I see how much internal conflict I carried during that process. I didn’t know if I was doing the right thing for myself, my siblings, my father, or our employees. I told myself I was pursuing freedom for everyone involved, a cleaner future, less dependency, more structure.
But I didn’t fully grasp the emotional impact it would have on my dad. His sense of purpose was tied to that business. It wasn’t just a company to him; it was his identity, his legacy, his proof of a lifetime’s work.
When the deal closed, I thought I would feel relief. Instead, I felt a hollow kind of uncertainty. I had underestimated how much purpose and identity are intertwined for founders, and how unprepared we all were, not just for the transaction, but for what came after it.
My father never wanted to sell the business. He wanted to pass it down. But he didn’t know how, and we didn’t have the structure, communication, or shared vision to make that possible.
We didn’t know about EOS back then, but I think about how much it would have changed things.
We needed a clear vision for the future, not just for the business, but for the family. We needed a structure for accountability so everyone understood their role and could take ownership without constant handholding. We needed the right people in the right seats, not just the longest-tenured ones.
Our communication was inconsistent. Departments operated in silos. Meetings were reactive. Handoffs were unclear. The entire business depended on the founder’s knowledge and intuition.
If we had EOS, it would have given us a shared language. It would have helped us align on the “why” behind the business and clarify what the next chapter could look like, not just for the company, but for the family that built it.
We might have retained ownership, built value, and transitioned with confidence instead of exhaustion.
When I talk to founders now, I often ask what “next chapter” means to them. Most pause before they answer.
For some, it’s raising capital or finding a successor. For others, it’s stepping back to focus on family or freedom. But for everyone, it’s about choice, the ability to move forward on their own terms.
That’s what EOS creates. It gives founders the structure and tools to design their next chapter intentionally, long before they have to make any decisions.
EOS helps leaders define the vision, build traction through systems that work without them, and develop a healthy leadership team that can carry the torch. It replaces dependency with discipline, confusion with clarity, and burnout with balance.
When those things are in place, optionality appears. You can sell. You can stay. You can transition to family or leadership. You can evolve.
I see this every week now in the session room. Founders come in overwhelmed, carrying the weight of responsibility for their business, their people, and their future.
When they finally slow down to define their vision, it’s like the room exhales. They see what’s possible. They see a future where the business can thrive without them constantly pushing every button.
That’s the moment when real freedom begins, when leaders stop reacting and start building toward something intentional.
The truth is, due diligence doesn’t surface the hardest truths. EOS does. It brings everything to the surface long before you’re in a deal process. It exposes the blind spots that create risk and gives leaders time to fix them with intention instead of urgency.
The hardest part of my own family’s sale wasn’t the deal. It was realizing, too late, that we could have done it differently. We could have honored the legacy, kept control, and created space for the next generation to lead if only we’d had the structure, discipline, and communication to get there.
That’s what EOS gives founders. A way to prepare early. A framework for transition. A shared language that makes succession, growth, or sale less emotional and more empowering.
The best time to prepare for your next chapter is before you think you need to.
If you’re a founder thinking about what comes next, whether that means raising capital, stepping back, or planning succession, start now.
Don’t wait for circumstances to make the decision for you. Build the systems, processes, and leadership that will allow you to choose your future, not react to it.
Your business can run beautifully without you. That’s not loss. That’s legacy.
If you’re ready to prepare for your next chapter, book a conversation with Mark Accomando to learn how EOS can help you build a business that thrives with or without you, so you can move forward on your own terms.
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