My First Podcast: Scrappy but Successful With Jack Tompkins
A few weeks ago I recorded my first official podcast interview, sitting down with Jack Tompkins on Scrappy but Successful. I didn’t know quite what to expect going in. It turned out to be one of the most enjoyable conversations I’ve had about my work and my life.
Jack runs Pineapple CF, and he built the show around a premise I liked right away: the operators and consultants worth learning from usually aren’t the loudest ones online. He’s looking for the people quietly doing the work. That set the tone for an honest conversation.
We went back to the beginning, further than I usually go in public. The donut resale stand. The baseball card operation. Bootstrapping with my wife out of a 600-square-foot apartment. The hardware startup that took me to China. Some of those stories I’d never really talked through on the record, and Jack made it easy to dig them up.
From there we got into the ideas that drive my work at Warden Strategy today.
The first is a part of the market I care a lot about: businesses doing roughly $1M to $10M in revenue. Private equity mostly passes on them because they’re too small to pencil out and too established to look exciting. Yet these are real, profitable companies built by founders who often have no clear path for what comes next. Helping those founders is the reason Colin and I started the firm.
The second is something I hear from founders constantly: “We need more leads.” In my experience, that’s rarely the actual problem. More often it’s a positioning issue, a conversion issue, or a gap in revenue operations that shows up looking like a lead problem. Pouring money into the top of the funnel before fixing what happens downstream is one of the most expensive mistakes I see founders make.
The third is why I believe in the Chief Growth Officer role. Splitting ownership between a CMO and a CRO puts a wall right at the handoff between marketing and sales, which is exactly where deals tend to get lost. A CGO owns that whole seam, and it’s a fundamentally different job from either of those roles.
If you’ve got 40 minutes, give it a listen. And if you’re an operator or consultant with a story worth telling, I’d recommend reaching out to Jack about being on Scrappy but Successful.
Fractional CGO and founder of Warden Strategy. I help category leaders sharpen their growth strategy, align sales and marketing, and build the systems that scale enterprise value.