The Interview That Never Happened — Part VIII: The Role You Didn’t Know You Were Playing
You don’t scale a business until you understand your role in it
Joe’s question sounds simple: “Who does an entrepreneur need on their team to ensure they are setting up their company for a profitable, valuable sale?” It sounds like a team question, but it really comes down to something else: how you see yourself in relation to the business. Until that’s clear, you won’t build the right team around it.
The Moment It Clicked
There wasn’t a single dramatic moment, but there was a shift I could feel. I came from an engineering mindset—measure everything, optimize everything. That concept worked—until it didn’t.
When I hired the COO who would ultimately help scale the business, he approached things very differently. More first principles. Less optimization for its own sake. The question became simple: could both approaches achieve the same outcome? The answer was yes.
That was the click.
I didn’t need to be the operator anymore. I needed to trust someone aligned with the outcome and let them execute differently than I would. That meant letting go of my version of how things should be done and putting on a different hat.
Curiosity Over Control
People like to frame this as ego or control.
That wasn’t it.
Curiosity has always been a core value for me. And real curiosity means accepting that other people can do certain things far better than you ever will. You can learn from them. You can understand their process. But trying to out-execute them in areas where you’re weak is a losing game.
The job becomes alignment, not replication.
Process vs. Outcome
I learned this the hard way.
Before hiring the right COO, I fired a President. The financials told the real story—we were heading straight into a wall. But if you looked at the org chart, the reports, the visible processes, nothing clearly explained why. Everything looked like a functioning business.
It wasn’t.
The focus was on process—titles, structure, how things were done—instead of outcomes. There was no path to alignment that way. When the focus is on process, you can always debate. When the focus is on outcomes, reality shows up fast.
The Hidden Trap in Growth
There’s a pattern that kills a lot of growing businesses: they don’t change how they manage as they grow. The assumption is simple—if we just work harder at what got us here, it will carry us forward.
It won’t.
I’ve written about this more directly in a previous piece (see: Stages of Business Growth), but the short version is this: the systems, expectations, and people that got you to one level are not guaranteed to get you to the next.
The turnaround didn’t come from pushing harder. It came from bringing in people the business could grow into—people who set clearer expectations, stronger accountability, and higher standards. And the most important part: we did it with buy-in. Existing management saw the path, and most came to the same conclusion—we were heading in the right direction, but they didn’t have the skill sets to take us there.
That’s a hard realization.
But it’s an honest one.
The $100M Question
Joe’s final question in this thread was framed like a punchline: “What haven’t I asked that would be worth $1M, $10M, or $100M to someone listening?”
The answer is straightforward:
Are you building a business that can grow beyond you?
Because if the answer is no, you’ve already capped the outcome.
🌱 Seed Thought: You don’t scale a business by doing more. You scale it by becoming something different inside of it
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