The Deals Were Never the Constraint. The Bench Was.

There's a winery on my desk right now.

Off-market seller, owner financing, fair valuation, flexible on terms. The kind of deal you almost never see. And I'm still not sure if I'm going to do it.

I've got about five deals in front of me right now. All good. A robotics play, home services automation, a couple others. But I've got four months left in a five year sprint, and every one of these things adds time, no matter how operational I get.

Here's the filter I've been using for the last four and a half years: opportunity cost versus opportunity ROI. How many hours does this deal need. What's the expected return. How does that compare to putting the same hours into the businesses I already own. I run the math, I weigh it against my market and resources, and I get an answer.

But something shifted on the winery deal. And it's not because the deal itself is better than the others. Plenty of good deals hit my desk.

It works because I already have the person to run it.

Four and a half years of building a high performance culture inside one of my companies means I've got promotable talent I literally can't satiate the need for. The winery isn't a new business. It's a promotion path for someone on my team who's already ready, because I don't have enough seats to promote them into at the rate I'm developing them.

That's the real filter at this stage. Not "is this the best deal." It's "can I afford the hours, and do I have the person who can run the day to day while I give them strategy and architecture."

If you're a couple years behind me, don't do what I'm doing

I ran out of cash about a year and a half ago. I've been fundraising just to finish this sprint.

If I could run the five years back, I wouldn't chase twenty businesses. I'd double down on one, maybe two. I'd operationalize them until I was 90% out of the day to day, with strong and steady cash flow. And I'd build that before I went chasing the next thing.

The deals were never the constraint. The bench was.

Where this actually shows up for you

You don't need five deals on your desk to feel this. You feel it the first time a good opportunity comes along and your honest answer is "I don't have anyone who could run that."

That's not a deal problem. That's a People and Leaders problem. You can have offer clarity, predictable customers, clean financials, all of it, and still be capped, because there's no one behind you who's ready to carry the next thing.

Build the bench first. Then go find the deal.

If you want help figuring out where your bench actually stands and what it would take to get someone ready for the next seat, that's exactly the kind of thing we work through with clients 1:1. Grab time here and we'll dig into it.

What's the opportunity you passed on because you didn't have the person to run it?