Lessons from Selling Two Businesses
Prep, pitch, profit.
The first time I sold a company, I thought I knew what I was doing.
I assumed there would be a clear process: step one, two, three. Instead, it was more like step one, step two…step 109. And because I didn't connect my company’s valuation to others’, when I saw the number investors offered me, I thought it looked pretty good.
Only later, I realized that I missed out on getting the highest possible valuation.
That was one of many lessons I learned during this process.
Looking back, I realize the problem wasn’t a lack of effort on my part, but a lack of awareness. I didn’t have the experience to know what to look for, or where the real leverage points were. I could have done my homework to fill my knowledge gaps.
I got that opportunity during my time in investment banking, where I saw the mechanics behind how deals actually happen. I learned how much weight a clear comparison carries - how buyers use valuation comps, how you’re expected to frame your own narrative, and how important the future story is, not just your past results.
When I sold a second company, the approach was entirely different.
I walked in saying: “This company looks a lot like 1, 2, 3, and 4. Here’s why. And here’s the valuation range they traded at.”
The conversation was much more grounded, intentional, and the outcome reflected that.
To me, this experience reminded me that preparation makes all the difference…but, sometimes, you don’t know what to prepare for until you’ve been through it.
So maybe the right approach is both:
✅ Do the work upfront.
✅ Be okay learning the hard way if you need to.
And if you’re lucky enough to get a second shot, make it count.