Podcast: The $1M-$10M Businesses PE Ignores (And Why That's the Opportunity)

A few weeks ago I sat down with Jack Tompkins on the Scrappy but Successful podcast. I wasn't sure what to expect from my first official podcast interview. What I got was one of the more genuinely fun conversations I've had about our business and my life!

Jack runs Pineapple CF and built Scrappy but Successful around a simple premise: the consultants and operators worth learning from are rarely the ones performing expertise online. He's trying to find the real ones. I appreciated that framing before we even started recording.

We covered a lot of ground in about 40 minutes. Here's a few highlights:

The $1M–$10M blind spot: Private equity largely ignores businesses in this range. Too small to pencil, too established to be interesting to most investors. But these are real businesses, profitable ones, with founders who've built something and have no obvious path for what comes next. That's exactly who we built Warden Strategy for.

"We need more leads" is almost never the real problem: It's usually a revenue operations problem, a positioning problem, or a conversion problem dressed up as a lead volume problem. We spent some time on why chasing top-of-funnel before fixing what's downstream is one of the most expensive mistakes a founder can make.

Why Chief Growth Officer instead of CMO or CRO: The CMO/CRO split creates a structural silo at the worst possible place: the handoff between marketing and sales. A CGO sits above that seam. It's a different job, not just a different title.

We also went back to the beginning and dug up some fun lost memories. We chatted through he donut resale stand, the baseball card operation, bootstrapping with my wife in a 600-square-foot apartment, the hardware startup that took me to China. Some of that was new territory for me to talk through publicly, and Jack made it easy.

If you've got 40 minutes, give it a listen. And if you're a consultant or operator who might be a good fit for Jack's show, I'd point you toward Scrappy but Successful!