About Matt

Matt Bennett is an investor, operator, and facilitator who spends most of his time making real decisions in the real world — and helping others think more clearly about theirs.

Over the last several years, Matt has built and managed a growing portfolio of multifamily properties and short-term rentals, including large Airbnb homes designed for high-trust, high-responsibility use. He has also founded and operated sober living homes, helping create stable housing environments for people rebuilding their lives. After successfully launching and stabilizing three sober living facilities, he chose to exit day-to-day operations — a decision rooted in clarity about where his strengths are best applied.

That pattern matters.

Matt is less interested in chasing scale for its own sake and more interested in alignment — between goals, effort, cost, and the kind of life those choices actually produce. Much of his work now centers on helping people slow down, think honestly, and stop carrying goals that no longer fit who they are or where they’re headed.

He doesn’t teach goals as motivation or aspiration. He treats them as commitments that reveal priorities, tradeoffs, and identity over time. That perspective comes not from theory, but from repeatedly having to decide what to build, what to keep, and what to walk away from.

This workshop reflects how Matt works in his own life: write things down, reduce complexity, face costs directly, and choose deliberately. The goal isn’t to want more. It’s to know what you want — and to respect that truth enough to act on it.