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Some deals go the distance. Most don’t.
But that doesn’t mean they weren’t worth the time. In fact, the ones that don’t close often teach you the most... about how to listen, how to adapt, and how to earn trust when the answers aren’t all laid out in a deck.
Here’s a few deals I worked on that didn’t cross the finish line. Each one shaped how I show up now, not just as a buyer, but as a human.
This was a family-run photo printing business with long-term customers the seller knew by name. These weren’t just transactions to him. They were relationships... some built over decades... and he wasn’t about to pass them off to someone who didn’t get it.
At first, he wasn’t sure I could take the work seriously unless I ran customer service myself. Instead of pretending, I walked him through how I operate... how I build systems, lean on good people, and ask the right questions instead of guessing.
I offered a seller note with a staggered consulting agreement so he could step back at his own pace. Even before he asked, I sent over proof of funds, bios, background... cause I figured if I were in his shoes, I’d want to know who was at the table.
It didn’t close, but we left the conversation with mutual respect. That mattered more than the outcome.
This one was messy in a different way. The broker bypassed me and called one of my financial partners to see if I was “real.” I don’t blame them, but it put me in a weird spot... having to explain that, no, I’m not the capital guy, but I am the one leading the deal, running strategy, and showing up post-close.
Not the most traditional setup, and not always easy to explain without sounding defensive.
After we submitted an LOI, everything went quiet. Total radio silence. That’s when I had to figure out how to follow up without killing the mood. I didn’t want to come off aggressive, especially since we’d already had a verbal “yes.” So I waited, stayed respectful, and kept communication open.
It didn’t work out, but it taught me when to press, when to wait, and why you’ve got to explain your structure early... before it creates confusion.
This one really stuck with me. Local print and digital media, rooted in a tight-knit community. I wasn’t from Bozeman, and that created some distance right out of the gate.
There was a clear undercurrent... “Does this guy get who we are?”
My financing approach didn’t help either. I was planning to use crowd equity, not something most sellers have heard of. I had to walk through what it meant, how it would still protect the brand, and why it wasn’t some high-risk workaround. Just a different way of solving a common problem.
More than anything, I focused on voice. I didn’t want to change the soul of the magazine... I wanted to keep it intact.
We didn’t close, but I came out of that one with a better understanding of how to talk about money and mission... and how place matters to people in ways spreadsheets don’t capture.
A web hosting and development business. Tight team, niche offering, super loyal customer base.
The seller was clear from day one... no outsourcing, no gutting the ops, no “efficiency” plays that would wreck what he’d built.
I’m not technical. I wasn’t gonna pretend to be. But I took the time to understand the structure, the service, and how it all fit together. And I made sure he knew I was stepping in to run the thing, not flip it or hand it off.
Sometimes just being honest about what you don’t know goes further than trying to sound sharp.
One thing I’ve learned across all these conversations... if a seller doesn’t trust you, they won’t say it. They’ll just stop calling back. So my approach now is simple... earn the second call. Not with flash or big promises, but by being prepared, being curious, and showing up like someone who actually gives a damn.
My structure isn’t traditional. I use a ROBS-funded C-corp. My family are the majority owners. I’m the operator. No private equity, no search fund jargon, just a real buyer looking for a real fit.
Sometimes that takes longer to explain. But the right sellers get it. They’re not just looking for a number... they’re looking for someone who sees the whole picture. And that starts with how you show up... especially when the deal doesn’t close.
