In this episode of Let’s Match, Let’s Talk About It, Tony Stewart breaks down how legal cannabis became a real-life version of the board game Monopoly — where corporate giants own the board, small growers fight just to roll the dice, and the government plays Banker.
We expose how legalization was marketed as “opportunity,” but quickly turned into a system where a handful of multistate operators (Curaleaf, Trulieve, Cresco Labs, Green Thumb Industries) control licenses, supply chains, and pricing. Tony explains why states like Illinois and Florida only allow a small number of licenses, how lobbyists influence lawmakers, and how cannabis entrepreneurs are boxed out before they even get started.
From license fees hitting $60,000 just to apply…
to vertical integration that forces businesses to buy from the same companies they compete against…
to social equity licenses being bought up by corporations…
Tony shows how the game is rigged — and what it will take for small growers, local farms, and patient advocates to flip the board.
Featuring our session strain of the episode: Jam’n Hemp 🌿
Proof that quality grows from passion, not monopolies.
How cannabis licensing mirrors Monopoly’s game mechanics
Why corporations lobby against home grow and small business licensing
How tax rules like 280E punish legal cannabis businesses
Why consumers pay more in monopoly states
Real examples of communities fighting back (NY, Maine, Michigan)