The Interview That Never Happened — Part VII: The House, The Buyer, and The Mirror
Attractiveness isn’t declared. It’s discovered—over time, by the right people
Joe’s next question sounds like two questions stitched together: “When you consider investing in a company, what criteria do you look for and what should entrepreneurs do to make their companies more attractive to acquirers?”
They are related.
But they are not the same.
One is about how you see.
The other is about how you are seen.
And most people treat both as events instead of ongoing practices.
The Rembrandts Are Already There
There’s a concept often referred to as “Rembrandts in the attic”—hidden value inside a business that the owner either doesn’t see or doesn’t present well. The instinct is to think you need to create those Rembrandts.
You don’t.
They’re already there, or they’re not.
The real question is whether you—and others—can see them.
How do you do that?
You talk to people. Not when you’re ready to sell. Not when you need capital. As part of running the business. You talk to companies that could acquire you. You talk to companies you might want to acquire. You listen. You ask questions. You pay attention to what they notice, what they ignore, what they value, and what they discount.
That process doesn’t just inform a future transaction.
It trains your brain.
It’s like learning to draw. The skill isn’t in how you hold the pencil. It’s in how you see the world before the pencil ever touches the paper. Once you see it differently, everything you do reflects that shift—even if you can’t point to a single moment where it changed.
That’s how you uncover the Rembrandts.
The Conversation Before the Transaction
One of the most valuable things you can do is build relationships long before they are needed.
I remember a company we were interested in acquiring. Getting them on the phone was difficult. “We’re not for sale,” click. Eventually the conversation shifted—not because we pushed harder, but because we showed up differently. “Oh, you’re not an investment banker… let me tell you about those.” Then it became, “let’s go golfing.”
Years later, we bought that business for a little over $100M.
What changed?
Timing.
But more than that, familiarity. Trust. Relevance.
Every business will eventually be sold—whether by decision or by circumstance. If you’re not already part of that owner’s world as a peer, a sounding board, or a known quantity, you won’t be the first call when that moment comes.
And first calls matter.
The “Why” That Holds Up
Now shift to the other side of the table.
When I look at a business as an investor, the first hurdle is simple:
Tell me your why.
Do I understand it?
And does it still make sense if the world shifts?
The “why” goes beyond numbers. Financial projections don’t impress me. They look good on paper for everyone. Good ideas can be just as dangerous. I remember someone pitching a business around aggregating remote feeds for high school sports. Interesting idea. But why would someone use that instead of just going live on YouTube?
If I can’t see the behavior behind the business, I’m out.
There’s another version of this that’s just as important: areas where I don’t have knowledge. If you’re building something in a space where I don’t understand the pain points—say, a next-generation HR system—I can’t properly evaluate whether what you’re doing matters.
And you teaching me doesn’t count.
Why’s need to be resilient. They need to survive shifts in behavior, changes in technology, and moments no one saw coming. After 9/11, parts of our business disappeared overnight while others grew. If your “why” depends on a static world, it’s fragile.
Buying vs. Investing
There’s also a distinction that doesn’t get talked about enough: buying a business is not the same as investing in one.
Buying is commitment.
You are allocating time, energy, and responsibility. If you have control, you are the operator whether you intended to be or not. The success or failure of that business sits closer to you than you might expect.
Investing is different. It’s more passive, at least by design. You’re supporting, advising, and providing capital, but you are fundamentally betting on management to execute.
And if they don’t, your money goes to zero.
It’s not like you get to hire better people and “try again.”
The two require very different mindsets.
I learned that the hard way. After selling the family business, I spent time doing direct investments. What I found was that it pulled me back into operating more than I expected. Not formally, but practically. You get involved. You care. You spend time. And over enough investments, that becomes something else entirely.
Now, I look to place capital with people who are leading those investments—private equity funds, venture firms, individual operators running SPVs—people who are already in the seat I would otherwise drift back into.
It’s not about avoiding involvement.
It’s about knowing where you’re most effective.
🌱 Seed Thought: Attractiveness isn’t something you create at the moment of sale. It’s something the market recognizes long before you ever ask the question.
