Eddie Brennan, CEO of Ayrloom- Interview Series

Despite distinct initial differences on paper, the well-established alcohol industry and the burgeoning cannabis industry share many fascinating similarities. Beyond both being highly regulated sectors geared strictly toward adults aged 21 and older, they also share a surprising number of family-owned brands. While multi-generational alcohol brands are nationally renowned and coveted, an increasing number of family-owned cannabis brands are now earning their own prestigious recognition.

For a deeper look into these industry parallels—and to discover what it’s truly like to run a family-owned cannabis business—mycannabis.com had the pleasure of speaking with Eddie Brennan, CEO of Ayrloom.

What subjects did you mainly study at Colgate University? In retrospect, what were the most universally useful courses throughout your career in multiple fields?

I majored in history, which I’ll be the first to admit, has almost nothing to do with running a hard cider brand, a cannabis company, or a 115-year-old farm. I can tell you a great deal about the fall of the Roman Empire. Whether that’s ever made me a better CEO is a question I’ll leave open.

The real education happened on the lacrosse field. That’s where I actually learned the things that have mattered most across every chapter of my career: that hard work is non-negotiable, that relationships are everything, and that the person next to you will define your outcomes as much as anything you do individually. A lacrosse team is a pretty honest mirror, you can’t hide on the field, and you can’t win alone. Those lessons have followed me into every room I’ve sat in since.

What were the most successful retail and store development strategies you learned while working with Bloomingdale’s? How did those strategies become beneficial throughout your endeavors in alcohol and cannabis alike?

Bloomingdale’s taught me that retail is theater, and the consumer is always the audience (and always right). Every touchpoint, from how a product is positioned on a floor to how a salesperson makes eye contact, is part of a story you’re either telling well or telling badly. I learned to think obsessively about the customer journey: what does someone feel the moment they walk in, and what do you want them to feel when they leave?

That lens translated directly into how we built 1911 Established. We’re not just selling hard cider, we’re selling a 115-year-old farm, a family story, a place. The retail experience at Beak & Skiff has to feel like that. And in cannabis, frankly, the bar for retail experience has been all over the map in New York. The operators who will win long-term are the ones who treat a dispensary the way Bloomingdale’s treated a flagship store with intention, with warmth, and with a clear point of view on who their customer is and what they deserve.

What went into the founding of 1911, and how did your family’s multi-generational history with orchards and agriculture play a role in the founding of the company?

1911 wasn’t just a pivot,  it was a survival strategy that turned into a passion. The apple industry faced enormous pricing pressure from commodity markets, and we were sitting on one of the best apple-growing operations in the Northeast with a heritage going back over a century. The question became: how do we capture more value from what we grow? Hard cider was the answer, but not just any cider, a craft cider with a genuine story behind it.  We like to say that 1911 Hard Cider saved the family farm.  Without it, we would not have a business today. 

After so many years in retail and in the spirits industry, what caught your professional attention about entering the New York cannabis industry? Were there any concerns you had regarding joining the industry, especially as someone who co-owns a distillery?

What caught our attention was the size of the opportunity and how early we still were in the real story,  not the hype cycle, but the actual industry maturation. New York is one of the largest consumer markets in the world. We believed the operators who came in with real manufacturing discipline, real brand-building experience, and real roots in the state would have a durable advantage. We worked hard to build a brand, not a label. 

Were there concerns? Absolutely. The federal conflict between cannabis and alcohol is real and consequential, there are financing, banking, and reputational dimensions that you have to think through carefully. And I’ll be honest: there’s still stigma in some circles (even with our legacy customers). But I’ve come to believe that reducing that stigma is part of the work.

How does the experience of owning and operating a popular distillery give you an advantage in your roles and duties as CEO of Ayrloom? What are some transferable skills between operating a distillery and operating a cannabis company?

Manufacturing is manufacturing. Whether you’re running fermentation tanks or extraction equipment, you are managing inputs, yields, quality control, regulatory compliance, and labor, all simultaneously, all with consequences if you get it wrong. This was a strategic advantage we knew we had.  All of the mistakes we made building 1911 Cider & Spirits we could correct with Ayrloom!

What are some of your regular duties as CEO of Ayrloom? How do you ensure that the standard of quality is upheld across multiple product formats, such as beverages and edibles alike?

We have an incredible team of passionate leaders within Ayrloom. From our President Mack Hueber on down the line, we show up everyday with a mission to grow safe cannabis in NY State.  My duties revolve around supporting our team members to ensure they are able to make fast decisions, rooted in data and stay out of the way!

What are the biggest regulatory issues that Ayrloom faced when expanding into other state markets? Did expanding into medical-only markets come with added challenges over markets that were already recreational?

On the adult use side we are only available in NY dispensaries with Ayrloom and we are laser focused on this market currently.  We do sell Ayrloom D9 beverages in 13+ states currently and we are awaiting more clarity on the regulations.  

Similar to the 1911 brand, how does your family’s many generations of agriculture play a great role in Ayrloom’s operations and standards? I would imagine with the company name being a play on the word “heirloom”, that your family and ancestors are a huge influence on the company.

Very intentional. The name carries everything we want to say in one word. An heirloom is something worth preserving and passing down, something that has accumulated value through time and care, not through shortcuts. That’s the ethos of our farm, and it’s the ethos we brought to Ayrloom.  Cannabis is another crop we can add to our 1,000 acre farm and helps us carry on the tradition of farming. 

Given your expertise and experience in alcoholic beverages, what advantages and potential do you think the cannabis beverage market has over other product sectors of the industry, like flower and vapes?

The biggest one is accessibility. A significant portion of adults who are curious about cannabis have real hesitation around smoking or vaping, whether that’s a health consideration, a social one, or simply that they’ve never been comfortable with it. A beverage removes that barrier completely. It fits into familiar rituals. You can drink a cannabis-infused cider at a party, at a concert, on a golf course, and it reads to the people around you as a beverage, because it is one.

What do you envision the next few years holding for the New York industry? Do you think the ripple effects of federal cannabis reform will reach the state industry?

New York is going to find its footing. The early years of the rollout were rocky, everyone in the industry knows that, but the underlying demand is real and the market is maturing. The operators who survived the turbulence with their brands and balance sheets intact are going to be well-positioned as retail infrastructure catches up and consumer habits stabilize.

On federal reform: I think it’s when, not if, though the timeline remains genuinely uncertain. Rescheduling at the federal level would be transformative, it unlocks banking, it changes the tax structure under 280E, it opens up research. And for a state like New York with a large, established adult-use market, the ripple effects would be significant. What I tell anyone who asks: build your business as if federal clarity is five years away, but be ready to move fast when it comes. The companies that are operationally sound, brand-strong, and financially disciplined will be the ones that scale when the federal environment finally catches up to where the consumer already is.

Thank you for joining us, Eddie! For more information on Ayrloom, please visit its website.