DOPE CFO

On one of our coaching calls, someone shared a count from a dispensary shelf. The point-of-sale system said eight units. The state compliance system said ten. The box in the back held six.

If you run a cannabis business, you’re probably not surprised. Retail cannabis runs on systems that were never designed to agree with each other. The POS was built to sell and the compliance system was built to satisfy the state, while the books mostly exist to get taxes filed. Each one produces a number, each number looks defensible on its own screen, and on any given day they can all be different.

Richard put it to the marketing coaching weekly call this way: your POS, your inventory system, and your books each tell a different story. Which one does your banker see?

That question matters because sooner or later someone outside the business, a lender or an investor, an auditor or a buyer doing due diligence, picks one of those numbers and treats it as the truth. The moment they notice the numbers disagree, the conversation stops being about your business and starts being about whether anything you report can be trusted.

Getting three systems to tell one story is unglamorous work. It’s reconciliation work and count procedures, plus a chart of accounts that maps to how the operation actually runs. Nobody ever posts a photo of it. But it’s the difference between reports that describe your business and reports that can defend it when money or a license is on the line.

The operators who have this handled aren’t the ones with the fanciest software. They’re the ones with someone on the team who owns the job of making the numbers agree, and who keeps checking. If your systems have never told the same story, that’s usually less a software problem than a seat nobody has filled yet.

Kristi, part of our team, broke down the different kinds of cannabis events on a recent call, because people tend to lump them all together and they reward very different approaches. A conference tends to run at a higher ticket price and looks like a curriculum day: panels, sessions, maybe a meal or two built in that doubles as informal networking. An expo is a different animal, a big auditorium full of booths where you’re walking table to table talking with marketing staff and sometimes the owner-operator themselves. Meetups are looser again, community-first, no formal agenda required.

One of the ones Kristi mentioned is a women-in-cannabis group that gathers at a brand’s headquarters for an afternoon: a taco truck outside, some yoga, once a session making bath bombs. People show up to actually talk to each other.

And the list keeps going from there. The cup competitions and cannabis fairs cover the culture side, where growers compete for medals in front of their own community. There’s legislative and lobbying work, where people mobilize to change the laws in their own state. And there’s a whole informal layer underneath all of it: golf outings, retreats, campouts, river floats. Some of the best conversations in this industry happen somewhere between a fairway and a campfire.

None of these need to cost much to attend well. You don’t always need the full-price badge. Plenty of the value at a big event sits in the happy hours and the hallway conversations around it, and you can often work that social side of an expensive event for fifty or a hundred bucks.

We bring this up because it’s part of how we stay close to what’s actually happening in this industry. Our team shows up to conferences, expos, meetups, and fairs because that’s where the people running these businesses are, and we’d rather hear it from them directly than from a headline.

Follow along here if you want more of what we’re seeing and hearing out in the field.

A week or so ago a longtime colleague of mine, someone who has cannabis clients of his own, emailed me about a situation I think every cannabis business owner should hear about. His client wanted to file refund claims for prior tax years, arguing that Section 280E shouldn’t have applied to them. I understood the instinct. Nobody wants to leave money on the table. But I told him to slow down, because that question hasn’t been decided yet, and the IRS made that very clear just days ago.

Here’s where things actually stand. Medical cannabis was reclassified to Schedule III back in April, and going forward that takes 280E off the table for those businesses. What hasn’t been decided is whether that relief reaches backward into prior years, for medical or recreational operators. Treasury and the IRS have said publicly they’re waiting on the rescheduling hearings before they take a position, and those hearings have now wrapped up, with the judge’s recommendation and formal guidance expected in the next months ahead.

In the meantime, the IRS isn’t sitting quietly. They’re actively pursuing companies that already filed retroactive refund claims assuming 280E wouldn’t hold up, and that list includes large, well-known names along with smaller operators who took the same bet. Filing that claim now, before guidance exists, paints a target on your back rather than getting you a check.

I get why an operator would want to move fast here. Every dollar matters when you’re running a cannabis business under 280E’s weight, and the temptation to act on the first article that says relief is coming is real. But the rule is going to be the rule once regulators actually finalize it, and getting out ahead of that decision doesn’t change where they’ll ultimately land. It just adds risk you didn’t need to take on.

If you’re a cannabis operator with old returns and a preparer telling you to file for refunds now, ask what that’s based on and do you really want the risk of litigation with the IRS? A good adviser will tell you honestly that we don’t have the final guidance yet, and that patience here protects you a lot more than speed does.

One of our newer members sent us a message this week that just said she was lost and didn’t know where to start. Ten minutes later a second message came through. She’d booked a speaking slot at a state cannabis association and had a dispensary owner asking her for a call. Lost, and already out in front of a room of operators in the same week.

That is what showing up actually looks like, and it rarely feels the way people expect. She was nervous the whole time, and she’ll tell you she still is. What she didn’t do was wait to feel ready before she started talking to people.

We see this pattern constantly. The finance professionals who build something real in cannabis are rarely the most polished person in the room or the most naturally outgoing. They’re the ones who go to the event, join the group, and have the conversation while their stomach is still in knots. As Richard put it on a recent call, if walking into a room full of strangers feels completely natural to you, you’re the unusual one. Almost everybody is nervous. The people who get somewhere just don’t let that stop them.

It helps that this industry is unusually welcoming. Newcomers tell us the same thing over and over: the people already in cannabis are generous with their time, quick to make an introduction, and far more collaborative than competitive. You don’t have to arrive as the expert. You have to arrive willing to learn and truly interested in the people building these businesses.

That’s the part we care about most. The operators who need good finance help aren’t looking for the flashiest résumé. They’re looking for someone who shows up, listens, and keeps showing up. Nervous and consistent beats polished and absent every time.

Spend an afternoon at a cannabis event and you notice who the operators remember afterwards. It usually isn’t the person who spent the day talking about themselves, it’s the one who took a photo of a founder on stage, tagged them, and wrote a couple of honest lines about what the talk got right.

There’s a habit among the finance people who’ve lasted in this industry, and it has almost nothing to do with selling. They treat their LinkedIn feed as a way to keep up with cannabis rather than a billboard for their own services. They follow the operators near them, the trade groups, the industry press like Ganjapreneur and MJBizDaily, and then they actually engage with what comes through. A comment here, a repost there, sometimes a note to someone whose work they admire.

Most of what they post points at other people. Someone gave a good talk, so they say so publicly and name them. A brand won something at a harvest competition, so they share it. An operator wrote something thoughtful about the market, so they add a point of their own underneath it. None of this is about them, and that’s exactly why it works. The owner who gets recognized in front of their own network remembers the person who did the recognizing.

It matters because the businesses that last in cannabis tend to be run by people who care about more than the margins, and they can tell the difference between someone who’s paying attention to the industry and someone who’s just arrived to sell into it. The professionals who end up mattering to those owners are the ones already in the conversation, celebrating the wins, learning the product, treating the community as something worth being part of rather than a list of prospects.

You build that standing the slow way, by showing up in the comments and the rooms long before anyone needs a number run.

Every state with a legal market seems to have a cup. In California it's the Emerald Cup, running more than twenty years now, alongside the Mendo Cup for Mendocino County and a Farmers Cup down in the San Diego area. None of them started as industry events. They started as a handful of growers getting together at the end of harvest to try each other's product and argue over who grew the best, bragging rights among people who take the craft seriously.

Those informal gatherings have turned into real industry gatherings in their own right, and they've spread. Most legal states have their own now, sometimes several. On awards day at the California State Fair you'll find around two hundred operators under one tent for the better part of five hours, mingling the whole time while the judging plays out. Over in New York there's Piffcon, a competition and culture gathering built around the art of haze and piff. Different corner of the country, same idea.

What makes these worth paying attention to is who turns up. The people milling about aren't working a booth or trying to close anything. They're the owner-operators, there because it's their harvest on the table and their community in the room. They've come out relaxed, proud of what they built, happy to spend an afternoon talking about it. That's rare. Most of the time you have to track business owners down one by one; here a few hundred of them have gathered on their own, in good spirits, on their own turf.

We pay attention to this because the cannabis businesses that last tend to be run by people who care about the plant and the craft, not only the margins. The finance professionals who end up mattering to those owners are the ones who show up to the same rooms, learn the product, and take the community as seriously as the operators do. That standing gets built in the tent, over the afternoon, alongside the people who actually built the businesses.

Follow DOPE CFO for more from the people working inside this industry.

Kristi sits on the board of three cannabis organisations. One is for networking. One keeps her connected to her clients' industry. The third is a cannabis prisoner advocacy group.

She described that third one in a way that stuck with everyone on the call: "They really paved the path for us and this industry wouldn't be here without the sacrifice they've made."

Her advice to anyone looking for an organisation to join: find a cause that heals your heart. If you really care about the work the organisation does, you'll stay involved even when you're busy. You'll show up to the events. You'll volunteer for the committees. And the people you meet there will be people who share something real with you, not just a professional transaction.

The referrals follow naturally from that kind of involvement, but that's not the point. The point is that you're doing something meaningful in an industry that has a complicated history, and the people who've been in cannabis from the beginning can tell the difference between someone who cares and someone who's there for the business cards.