33. The $1M-$10M Businesses PE Ignores (And Why That's the Opportunity) with Charlie Warden

Charlie Warden is the Managing Partner of Warden Strategy, a revenue strategy and venture-building firm based in Denver. He's a fractional CGO (Chief Growth Officer), not a CMO or CRO, and he joins Jack to talk about why that distinction matters, why he started a second fractional firm instead of scaling his first, and why he'd rather turn down growth than chase it. From running a donut resale stand and a baseball card business in middle school to founding his first agency on campus with free university software, Charlie's entrepreneurial roots run deep. He shares the early days of bootstrapping with his now-wife in a 600 square foot apartment, the hard lessons from a venture-backed hardware startup that took him to China, and how he eventually landed on the Chief Growth Officer model that breaks down the marketing, sales, and customer success silos most businesses get stuck in. Charlie also opens up about Warden Strategy's deliberately narrow ICP (the $1M-$10M B2B service businesses that fall below the private equity threshold), why "we need more leads" is almost never the real problem, and how he and his team built a studio arm for side projects they're genuinely passionate about. Then Jack and Charlie wrap with a scrappy versus sophisticated lightning round covering inbox habits, dryer sheets, and airport efficiency. Chapters: 00:00 - Scrappy or sophisticated: Charlie's take 03:43 - The donut stand and baseball card hustles 09:08 - Launching Lion Head Productions in college 14:11 - Bootstrapping on $80 grocery weeks 18:12 - The venture-backed hardware startup and the move to Denver 23:03 - Building Warden Strategy and the studio arm 26:11 - Why "Chief Growth Officer" instead of CMO or CRO 30:20 - The lead generation myth and what's really broken 33:18 - Defining (and defending) a narrow ICP 35:48 - Scrappy vs. sophisticated lightning round Connect with Charlie: LinkedIn:   / charlie-warden   Company: http://www.wardenstrategy.com Connect with Jack: LinkedIn:   / jack-tompkins   Consulting: https://www.pineapplecf.com AI Analyst Product: https://www.pineappleanalyst.ai/ YouTube:    / @pineappleconsultingfirm