Will Read, Founder and CEO of CannaPlanners – Interview Series

As the cannabis industry continues to expand, the need for marketing professionals with substantial previous marketing experience with businesses such as Fortune 500 companies also increases. One cannabis professional who wishes to normalize cannabis branding and advertising with successful strategies and styles taught to him during his impactful time with technology giant Apple (AAPL ) (and also maybe partially from his time as a traveling musician) is CannaPlanners Founder and CEO Will Read.

So, what subjects did you study at St. Lawrence, and what important lessons did you learn while attending that university? At that time, did you ever picture yourself founding a cannabis ancillary company?

I was a double major at St. Lawrence, earning a BA in Music and Religious Studies. Interesting combination, right? I was really into music and wanted to pursue it, but at the same time, I felt a little self-conscious. I didn’t want to waste my parents’ time and money. So I figured I should get something more out of my education. Not that I regret it at all. It was interesting! But it wasn’t exactly something you could apply directly to the real world.

And I definitely never imagined myself running a cannabis company. Back then, cannabis was so illegal. This was around the time Tommy Chong was sent to jail for selling bongs. I think California’s medical program had just started, but in upstate New York? It was completely illegal. Honestly, I barely saw myself graduating college, let alone founding a company. And definitely not a cannabis company.

During your traveling musician days, what genres of music did you usually play, and what were some of the most historic venues where you played?

We were kind of a hippie band, playing in the early 2000s, during the era of roots rock, reggae, and college rock. That was our vibe. We were songwriters, heavily influenced by bands like the Grateful Dead, Phish, Dispatch, The Police, and Talking Heads.

As for historic venues, the most notable one we played was probably the Ridgefield Playhouse in Connecticut. We actually opened for Dickey Betts, the guitarist for the Allman Brothers, which was pretty cool. I was the lead guitar player and one of the singers. I co-wrote all of our songs (some on my own) and sang either lead or backup on most of them. And, of course, I played guitar.

How did you first become familiar with Apple technology, and what roles did you hold in the innovative company? What were some of your regular duties while working with Apple?

My dad was always ahead of the curve when it came to technology. We had all the coolest computers growing up, and he definitely bought that multi-colored iMac when Steve Jobs first came back to Apple. We were kind of an Apple family, though we had PCs too, we always had a few Apple products around.

I remember a time when I was on the road with my band, and honestly, I was in a rough spot—probably the first time I ever really felt depressed. My mom picked me up after a tour, and I was feeling down about something. To cheer me up, she took me to Walmart (WMT ) (or somewhere like that) and gifted me an iPod, and I swear, that thing pulled me out of my funk. Up until then, I was still lugging around a portable CD player and 15 pounds of CDs, so having thousands of songs in my pocket was mind-blowing. It was truly revolutionary and classic Apple.

I started at Apple as a retail specialist, just selling whatever to whoever walked into the store. But I quickly moved into a role called “Business Manager” which, despite the name, didn’t mean I was actually a manager. It just meant I was the go-to person for business customers. If someone was buying Apple products for their company, they’d call me, and I’d take care of them. That’s where I first learned how to network and build relationships. I’d capture their contact info, sell them what they needed, and then follow up to make sure they were all set. Over time, that turned into repeat business and bigger opportunities.

When I moved to New York, I took on an extra role as a “celebrity shopper.” Because of my experience with my band, Apple assumed I knew how to interact with celebrities. So I got to sell Apple products to some pretty well-known people like David Blaine, David Byrne from Talking Heads, Jessica Alba, Trey Anastasio, and Phil Lesh from the Grateful Dead. I also worked on teams that helped open new stores, like the one in Grand Central.

What initially sparked your interest in the cannabis industry and eventually forming a company that caters to cannabis businesses?

It all came down to timing. I was at a point in my life where I felt professionally stagnant and knew I needed to figure out how to build something of my own. I just didn’t know what that would be.

At the same time, I noticed several businesses in my city thriving by offering digital marketing services for a specific niche. There were five or six of them, and interestingly, one of the founders of one of those companies now invests in ours. And then there was the fact that cannabis legalization was starting to take off. So, I saw a business model that was working, I was ready for a change, and cannabis was happening. It all just clicked.

What led to the creation of CannaPlanners, and what services does the company provide to cannabis brands/businesses?

We’re a creative and digital marketing agency specializing in the cannabis industry. Our services cover everything from branding and logo design to packaging design and website development. We also handle SEO for cannabis retailers and brands, ensuring they stay visible and competitive online. On top of that, we manage retention marketing, building out campaigns in platforms like AIQ and Klaviyo to keep customers engaged and coming back.

As someone who works with businesses in the Vermont cannabis industry, how would you describe the overall state of the industry? I would imagine it’s a smaller overall industry, but does the state still have some lesser-known advantages?

I wouldn’t necessarily call it an advantage, but it’s definitely unique—just like Vermont. One standout requirement here is that cannabis businesses must use eco-friendly packaging, which isn’t mandated for any other industry in the state—or for cannabis in any other state, for that matter.

While this can be a challenge for small businesses due to the higher costs of sustainable packaging, I think it’s pretty cool that Vermont is leading the way on this. It feels very Vermont-y of us!

When it comes to subjects that are vital to a successful business, such as customer experience and branding in an emerging market, how does your experience with Apple shape or otherwise influence your approach to success in those subjects?

The influence Apple had on me touches everything from my sales approach to how I think about branding and the customer journey. Apple really ingrained these ideals in me, and I welcomed it because it was impossible to ignore the impact of those values. At the end of the day, it just felt like the right way to do things. It led to happy customers, and ultimately, to Apple’s success.

In regards to marketing/advertising for cannabis brands in both Vermont and in the neighboring states, what are the most common or widespread issues that your clients have to deal with?

Cannabis brands and retailers are still dealing with so many restrictions. There’s really no end to the challenges. For example, they can’t freely use social media or run Google ads responsibly without facing limitations. Everything is highly restricted, which forces the industry to be incredibly competitive. But in a way, that pressure creates a well-tuned marketplace where there’s no room for messing around.

Expanding on that, what professional skills did you learn at Apple that surprisingly became useful in the cannabis industry?

Back when the first iPad launched, Apple required its sales associates to offer an unboxing experience.

That meant after selling an iPad, we wouldn’t just hand it over. We’d walk the customer through setting it up, starting with the unboxing itself. We’d carefully peel back the plastic, let them lift the device out of the box, and guide them through turning it on. That moment—when the screen lit up with the Apple logo—was designed to be immersive, letting the customer fully experience the excitement of getting a new Apple product. Every time we did this, you could see the impact. Sure, Apple products were already intuitive (anyone could set up their own device) but this extra step made the experience feel special. It was about going the extra mile to make sure customers walked away feeling like they just had the best day ever.

Now, at CannaPlanners, we’re not selling physical products in quite the same way, though we do create plenty of tangible things. But what is the same is our commitment to crafting that kind of journey for our customers. I want our team to bring that same sense of empathy and human connection to every interaction. At the end of the day, our clients should feel heard, valued, and part of something bigger like they’re not just working with an agency, but with a team that truly cares.

Based on the experiences of yourself and your clients, how would a federal rescheduling change both the operations of CannaPlanners and how cannabis companies are allowed to market and advertise successfully?

I saw a recent post on LinkedIn where someone in cannabis broke down their revenue and how much of it goes to taxes. It was wild: over 60%! Cannabis businesses aren’t just heavily regulated, they’re taxed into the ground. If cannabis were federally rescheduled, it would absolutely help businesses market themselves and operate more efficiently. They’d have more money to reinvest into growth instead of handing so much over in taxes. Right now, cannabis companies’ marketing budgets are a fraction of what businesses in other industries get to work with.

As for marketing and advertising, I don’t think we’d see any major floodgates open. Companies like Meta and Google don’t allow ads for things like cigarettes or alcohol, even though those industries are legal. Sure, you’ll see plenty of DraftKings (DKNG ) ads, but some things remain taboo no matter what the laws say. I don’t expect Meta or Google to suddenly embrace cannabis advertising anytime soon.

Thank you for joining us, Will! For more information on CannaPlanners and its services, please visit its website.