After three years of starts, stops, busted deals, re-trades, industry strikes, wildfires, and more plot twists than HBO’s Succession — we closed.
Not the most complex deal I’ve worked. Not the biggest. But easily one of the most hard-earned transactions of my career — and one that taught me more about this business than any deal that went smoothly ever could.
Here’s what three years with a single transaction teaches you:
1. Resilience is an underrated M&A skill.
Everyone talks about valuation, negotiation, and process management. Nobody talks about stamina. Real deals test your emotional endurance. Buyers change. Markets shift. Industries evolve. People leave. New stakeholders arrive with fresh opinions and zero institutional memory. If you’re going to play in the lower middle market, you need a long memory and a short ego.
2. Preparation can revive a dead deal.
“Time kills all deals” is true — but it’s only half the story. The counterpoint: preparation and transparency keep deals alive. When the underlying business is strong, the financials are clean, and the narrative is coherent, deals have a way of coming back from the dead. We saw multiple moments where this process could have ended permanently. Each time, preparation gave us another shot.
3. Buyer turnover is real and disruptive.
Corporate development leaders leave. Teams reshuffle. Priorities change. When that happens, you’re not just continuing diligence — you’re re-selling the deal from scratch, often revisiting terms that were already agreed. The lesson: institutionalize the story so it survives personnel changes on the other side of the table.
4. Structure matters more than headline price.
The deal you close is rarely the deal you first discussed. Terms evolve. Risk gets redistributed. Sellers should focus less on the top-line number and more on certainty of close, quality of buyer, realistic earn-out mechanics, and cultural alignment. A lower price with higher certainty beats a top-of-market offer that was never going to materialize — every single time.
5. Momentum is fragile — protect it.
Deals don’t die in dramatic explosions. They die from lack of inertia. Delayed follow-ups. Lingering diligence items. Scheduling friction. Tiny momentum losses compound quietly until the deal just… stops. Even small wins — closing a diligence loop, locking a meeting, aligning on a draft — matter more than they seem in the moment. Progress creates gravity.
6. The psychological side of exits is real.
Long processes are emotionally taxing. Uncertainty lingers. Expectations rise and fall. Fatigue sets in. At various points, perfectly rational sellers start making emotional decisions. One of the most important roles of an advisor is simply helping clients stay grounded — not overreacting to setbacks, not chasing shiny alternatives, not quitting one yard from the finish line.
7. Every scar is a lesson.
Great exits aren’t just about strategy or timing. They’re about persistence. Markets change. Buyers change. Narratives evolve. But resilience compounds. Stay in the arena long enough — keep the business strong, the story clean, and your clients focused — and the deal that almost died a dozen times still finds a way to close. This one did.
Bottom Line
Long deals are a test of conviction — for the advisor and the seller. The ones who make it to the finish line share one thing in common: they never fully stopped believing the right outcome was still possible.
Next month, I’ll share the other side of the coin — a deal that came together the way it’s supposed to. Competitive process, premium outcome, ten lessons worth sharing.
