The Window Cleaning Millionaire

57: From Prison to $27M: Dave Carroll's Story Is Unlike Anything You'll Hear on This Show

May 18, 2026·48 min
Episode Description from the Publisher

Episode SummaryWhat do you do when you get out of prison at 25 with no work history, no business experience, and a job at a window cleaning company you're terrible at? If you're Dave Carroll, you start your own company six months later and spend the next 16 years building one of the most interesting entrepreneurial stories in the home service space.Dave is the founder of Dope Marketing — a direct mail and data company that went from $2M to $27M in revenue in four years — and he still owns 100% of Lion Share Maintenance, the window cleaning company he started right out of a halfway house. Ryan sits down with Dave for a wide-ranging conversation covering his past, why he hasn't sold Lion Share despite not touching it in seven years, the science of direct mail targeting, the 52 Weeks of Dope strategy, and why the key to getting off the truck is understanding exactly where you contribute at a high level — and where you don't.

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