Dennis Hoffman, founder of The Retirement Strategy, on a snowy ridgeline near his home in Jackson Hole
Dennis Hoffman (and Diesel)
Founder, The Retirement Strategy
Former Dell executive · Harvard MBA
Why this exists

There has to be a better way.

For 22 years at Dell, I ran corporate strategy, strategic projects, and internal start-up divisions. As my own retirement came into view, I could feel the standard playbook wasn't going to be enough. I googled “retirement strategy” expecting to find help — and got financial planning dressed up as retirement planning: when to take Social Security, how to build a portfolio. That was the whole internet on the subject.

So I sketched my own. A house: Health and Wealth are the foundation, People and Place are the walls, Passion and Purpose are the roof — and the whole structure, together, is your readiness. Most “retirement planning” only ever touches the foundation.

I wrote it up, a few dozen people read it, and then I mostly let it sit. For about a year I had a framework and no idea what to do with it. Then, one Saturday in February 2026, I photographed the hand-drawn house, opened an AI tool for the first time, and asked whether it could help me build the thing. The answer became The Retirement Strategy — and I've built it since on my own: no team, no investors, no employees. The kind of one-person venture these tools have only just made possible.

The financial plan was the easy part.