Jeffrey Kay

JIW What subjects did you mainly study at the University of Maryland, and what courses were the most worthwhile for someone working in the financial side of the cannabis industry?

Jeffrey I was actually pre-dentistry for about a week. That didn’t last very long. I switched to marketing and never looked back. Likewise, most of my career has been in marketing, primarily on the agency side working across a pretty wide range of industries. I probably honed my expertise most in CPG, retail and entertainment, but I also spent a fair amount of time working with financial services and B2B businesses.

Today I’m on the financial side of the cannabis industry, but I’m still very much a marketing guy. What has helped me most is having a broad business foundation. Understanding finance, accounting, economics and how businesses actually make money matters, especially in cannabis where cash flow, margins and access to capital can quickly become existential issues.

I’ve also spent a lot of time serving on boards, which forces you to look at a business differently. You stop thinking only about marketing performance and start thinking about the whole enterprise: growth, profitability, risk, capital, operations and ultimately whether the business is creating value.

So, oddly enough, I’d say the most worthwhile education has been learning how all those pieces connect. I’m glad I figured that out before anyone let me near a dental drill.

JIW While working with The Marketing Arm and Eastwest Marketing Group, what were the most useful marketing skills and strategies that you developed?

Jeffrey Agency life teaches you pretty quickly that the answer is rarely just “do more marketing.” I worked across a lot of different industries and brands, so one of the biggest skills I developed was learning how to get underneath the assignment and understand the actual business problem. Sometimes the client thinks they need a campaign when the real issue is positioning, pricing, customer experience, distribution, sales support or simply that nobody really understands what they’re selling.

The other big lesson was understanding the customer. In consumer marketing, that means really understanding the consumer: what they care about, what motivates them and why they choose one brand over another. In B2B, the principle is exactly the same. You’re still trying to understand the customer, their needs, their pain points, the pressures they’re under and what would actually make their job easier.

That sounds obvious, but a surprising amount of marketing starts with what the company wants to say rather than what the customer actually wants or needs.

Agency work also made me comfortable moving across industries and between strategy and execution. You can spend all day developing the perfect strategy, but eventually somebody has to turn it into something that works in the real world and, ideally, sells something.

JIW From your experience, what are some lesser-known marketing-related issues that cannabis brands regularly face? Many are aware of Meta and Google’s disadvantageous advertising policies, but what are some other issues that they face?

Jeffrey The advertising restrictions get most of the attention, and I’m certainly no stranger to being thrown in Meta jail The lesson I've learned is that while those channels can absolutely be useful, they’re not something you want to build your entire marketing strategy around when the platform can decide to shut you down with little warning. You have to diversify and build channels and customer relationships you actually control.

Beyond that, one of the biggest issues is that there really isn’t one national cannabis market. Every state is its own little universe. Different regulations, different product rules, different competitive environments, different pricing, different consumers, and often very different products or consistency. That makes building a scalable brand much harder than it is in traditional CPG.

Retail is another challenge people outside the industry don’t always appreciate. In many dispensaries, the consumer isn’t even physically shopping the product. They may be browsing a tablet, digital menu or menu board, with little or no physical product presence before they make a decision. So your brand may be reduced to a name, a thumbnail image, a price and a few words on a screen. The budtender can have an enormous influence on what ultimately gets purchased.

Then there’s data. In traditional CPG, you get spoiled by having relatively mature market data, consumer research and syndicated reporting. Cannabis data is much more fragmented and inconsistent. Even fairly basic questions like market share, promotional effectiveness or who is really buying a particular product can be harder to answer than they should be.

And then you have price compression. In a lot of cannabis markets, everyone starts competing on price, which makes it incredibly difficult to build long-term brand value. If every conversation becomes “who can sell an eighth for less,” eventually everybody loses.

So cannabis marketing ends up being part brand building, part retail strategy, part analytics, part regulatory navigation and occasionally part survival exercise.

JIW How does Safe Harbor provide solutions to the many financial-related issues that cannabis companies face?

Jeffrey One reason I joined Safe Harbor is that I had already lived a lot of these problems from the operator side, both in CMO roles working directly with operations teams and through my board experience.

Cannabis businesses don’t just need a checking account. They need banking, cash management, payments, access to capital, treasury services, retirement benefits and other financial and business tools that companies in most industries take for granted. The difference is that in cannabis, almost every one of those services has to be built or adapted specifically for the industry.

Safe Harbor has spent more than a decade building infrastructure around those realities. We’ve processed more than $36 billion in cannabis-related funds across 41 states and territories, but I think the bigger story is how the company has continued evolving beyond basic cannabis banking as the industry’s needs have grown. Solving cannabis’ biggest financial pain points has always been part of Safe Harbor’s DNA, so expanding into broader financial and business solutions is a natural progression.

The goal is to help cannabis companies operate more like normal businesses, even though they still operate in a very abnormal financial environment. That resonates with me because I spent years dealing with those challenges firsthand. Banking was harder and often unstable. Raising capital was harder. Payments were harder. Even basic business services could become complicated simply because cannabis was involved.

Now I get to help solve some of those problems instead of complaining about them, which is probably healthier for everyone.

JIW How does your Jewish identity play a role in both your professional and personal life? What are some unique ways that you celebrate and observe Judaism?

Jeffrey I’m Jewish, but I’m not particularly religious. For me, it’s much more about family, culture, tradition and community. Interestingly, I’ve found a version of that within cannabis through Jews in Weed. Their Bagel Bashes around industry events have become something I genuinely look forward to. And despite the name, they’re very much non-denominational. It’s really just a great mix of people from across the industry getting together, and I’ve made some meaningful connections through them.

But if I’m being completely honest, I’m in it for the bagels, and Jordan knows how to pick them!

Kidding aside, I really do value that sense of connection. Cannabis is such a relationship-driven industry, and this has been one more way to meet good people, build real relationships and feel a little more at home when you’re constantly on the road.

JIW What are some of the most important financial-related reforms that are still needed for the cannabis industry? When do you envision those reforms will finally be implemented?

Jeffrey The biggest problem is still the disconnect between state-legal cannabis businesses and federal law. Almost every financial challenge in this industry traces back to that in one way or another. Rescheduling is important, particularly because of what it could mean for 280E and the amount of cash operators are currently losing to taxes. But rescheduling alone doesn’t suddenly make cannabis banking normal.

The industry still needs much greater clarity and protection for banks and credit unions serving legal cannabis businesses, more normal access to capital and payment systems, and eventually a financial framework where cannabis companies aren’t treated like a special case every time they need something that every other business takes for granted.

I’m cautious about predicting when any of this happens. I’ve been in cannabis long enough to know that predicting federal reform is a good way to eventually look stupid. But I do think there's positive momentum. More financial institutions are becoming interested in cannabis, more policymakers understand the problems created by the current system, and the conversation is increasingly about how the financial system accommodates cannabis rather than whether it should.

And even as the rules change, there will still be new rules, new compliance requirements and new operating realities to navigate. Progress won’t eliminate complexity overnight.