I wasn’t locked up for selling weed.
Not the way people imagine it, anyway — not the cinematic version with armored vehicles and agents. I got locked up through a quieter method the government perfected once cannabis became too popular to crush outright: taxes. Specifically, IRS Code § 280E — a relic from the 1980s, repurposed for a new target. As far as me and my lawyer have been able to document, I’m the only American sent to federal prison using that statute as the spear. And it’s now the federal government’s cleanest way to keep cannabis on a leash.
My name is Ryan Richmond. I helped launch Michigan’s first licensed medical marijuana dispensary. And while I was in federal prison for tax evasion, I wrote an investigative memoir called Capone of Cannabis, because people love the Al Capone comparison. It’s neat. It’s a headline. It’s also accurate. Capone didn’t go down for bootlegging or even murder — he went down for taxes.
That’s the part everyone remembers.
What they forget is the machinery that makes “taxes” a weapon.
Back when Michigan medical marijuana was young, dispensaries didn’t look like today’s sleek yuppie temples. There weren’t glossy buildouts stocked with curated brands from stoner celebrities, and no point-of-sale systems handing out loyalty points and automated SMS promos. They were improvised storefronts with no signage out front—patient lists, rules we invented as we went, and the constant feeling you were doing something both important and dangerous.
Discretion was security. We didn’t advertise. We verified patients. We kept things clean, professional, compliant—because in those early days, “compliance” wasn’t a certificate you printed and framed. It was a posture. A defense mechanism. Reopening after every raid, every smash-and-grab. And writing a whole second set of rent checks—one to the landlord, one to the criminal-defense lawyer.
And still, the machine showed up.
The war on weed has always been a war over who gets to touch the money. The myth is that legalization ends the conflict. The reality is it just changes the tools.
For a long time, the tool was blunt-force theft: raids and civil asset forfeiture—meaning cops could take your money and keep it without ever charging you with a crime. Our clinics were hit so often it felt scheduled — every 26 days, on average, for four years. IIf you’ve never had armed men rip through your business and your home—and then act like the cash they took was morally justified—you don’t really understand how asset forfeiture works.
My time in the industry cost me and my family nearly $1,000,000 — and the U.S. government now demands another $2,777,000 on top of that.
Today things are different.
Cannabis became too popular to crush outright. Too many voters now support it. Too many patients and soccer moms now depend on its convenience. Too many politicians need the tax revenue. America has a talent for converting taboo into taxable — and once that conversion starts, the state doesn’t want to smash the machine. It wants to own it.
So the government found a cleaner method. They stopped taking licensed pot dealers’ money with guns. They started taking it with math.
In the 1980s, Congress passed IRS Code § 280E to stop cocaine dealers from writing off “business expenses.” The rule is blunt: if the feds say you’re trafficking a Schedule I or II drug—cannabis included—you don’t get any normal business deductions.
No rent. No payroll. No security. No marketing. No office supplies. No insurance. No professional services. None of the things every other business in America takes for granted. And in my case, it meant something even uglier: I couldn’t deduct the money that crooked cops and straight cops took during raids, or the money lawyers charged to keep me out of a cage.
You can deduct one thing: cost of goods sold — the inventory itself.
For decades, 280E sat there like an old weapon on a shelf — rarely used, mostly forgotten. Then marijuana laws started popping up across the country. And suddenly it wasn’t just dusted off; it was polished to a bright shine.
So if you operate a cannabis business — even one legal under state law — 280E treats you like a drug kingpin with a ledger. It makes you pay federal taxes on money you never actually keep. Effective tax rates can climb into the 60–70% range. Asset forfeiture was theft with guns—and somehow it still cost less than the IRS.
It’s the most polite form of confiscation I’ve ever seen. And it doesn’t come with drug team task forces. It comes with a letter and a summons to the IRS field office, where a guy with a badge and a checklist pretends it’s a conversation.
This is the part that makes 280E so powerful — and so politically useful. It doesn’t require the government to win an argument about cannabis. It doesn’t have to debate medicine versus vice. It doesn’t need a public campaign. It just needs to look at your books and say, “You can’t deduct that, or that, or any of that.”
In the old days, power had to kick your door in to make its point. Now it can do it with an audit, a notice, and a fossil of a statute. It can do it in daylight, in plain language, and still leave you painted as the villain. Because once the public hears “tax problem,” they assume greed. They assume fraud. They assume you were living large and got caught.
That assumption is the system’s favorite magic trick: making targeted enforcement look like accountability.
And it hits hardest where systems always hit hardest: small operators, early operators — the ones without layers of insulation, without venture capital padding the fall, without a legal and accounting team on retainer to translate every threat into a manageable invoice.
Operators today don’t take the same kind of blunt-hits we took back then — the raids, the intimidation, the smash-and-grab crusaders who robbed us in the name of protecting children. But the sting is still there, baked into the math. 280E functions like a tax, but behaves like a penalty.
That’s what people miss when they treat cannabis as a “culture war” that ended. The culture shifted. The power structures didn’t. They just swapped their methods.
If we’re serious about justice — real justice, not branding — then we should ask something uncomfortable:
What does it say about America that once cannabis started winning at the ballot box, the government’s most effective way to punish it was through taxes?
What does it say that we traded raids and forfeiture for audits and disallowed deductions?
What does it say that the punishment didn’t disappear — it just learned how to look neutral?
Because 280E isn’t neutral. It’s targeted by design. It’s the federal government keeping cannabis on a leash while states pose for photos with the dog and tell you it’s free.
And if you think that doesn’t matter, remember this: a policy that can cage a legal business owner can cage anyone the system decides to redefine as illegal. You don’t need a new law. You just need a new label.
The method is the message.
America forgets fast. It punishes people for building the bridge, then charges tolls once everyone starts crossing. Once the stigma becomes a commodity, the pioneers become expendable — useful for the origin story, inconvenient for the headlines.
The war on weed didn’t end.
It got better branding.
And somewhere along the way, the country convinced itself that “legalization” meant the violence stopped — when in reality, it just moved from the street to the spreadsheet.
That’s what happened to me. That’s what 280E still threatens to do to anyone operating in the space between state permission and federal contempt. And that’s why the Capone comparison lands: not because it’s kitschy, but because it’s the blunt truth.
You don’t have to be a gangster to get treated like one.
You just have to be standing in the wrong industry when power decides it needs an example.
About the author:
Ryan Richmond is a serial entrepreneur and one of Michigan’s early dispensary pioneers, building in the medical cannabis space when the rules were still being written in real time. He’s also the founder of Hemp Well, a hemp-based pet supplement company focused on helping pets thrive. Ryan lives in Michigan with his wife, two kids, and their dog.
