Ep 22: Why Cannabis Brands Need Better Stories — The Shift

with Kyle Rosner · The Shift, a podcast by Headquarters

Kyle Rosner of High Times joins The Shift to explore how authentic stories and strong communities help cannabis brands build lasting connections.

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Auto-generated from the episode audio and lightly edited for readability.

0:08 So today on the shift, I'm joined by Kyle Rosner. Kyle's career in cannabis has taken him through almost every side of how this industry tells its story. He originally entered the space through film making and video production, including an early chapter with High

0:27 Times. He later helped build 420 Interactive, working directly with cannabis companies on media, branding, strategy, and how they connect with consumers. And today, his career has brought him full circle. He's back at High Times, this time as a director of

0:46 partnerships, helping shape what's next for one of the most recognizable names in cannabis culture. So, I wanted to talk to Kyle about what he's learned from seeing the industry from so many different angles, how cannabis media and branding have changed, what high times

1:06 means in a very different cannabis industry than the one he originally entered, and what almost a decade in this space has taught him about the business behind the culture. So, Kyle, welcome to the shift. And how

1:24 did I do there? Thank you, Filip. Very well researched. You You nailed it on the head there. Okay. I love that. Um, so this is obviously, you know, you're pretty much everywhere. You have a lot of experience. So, I'm pretty confident we're going to um have a lot of fun

1:44 today. Uh, especially with the knowledge that you can share, uh, with the audience. So, right off the bat when when I sort of got this up for for the podcast, um, immediately what I thought was that

2:04 your relationship with High Times is interesting because this isn't your first chapter there and you originally came in through video production. That experience ultimately helped lead to 420 Interactive and years later you've come back as a director of partnerships.

2:22 When you look at High Times now versus the company you first walked into around 2018, let's say, what has actually changed both inside the company and in what High Times needs to be for the cannabis industry today?

2:41 Absolute legal disclaimer. This is a separate entity than the previous uh iteration of high times. Um you know as a filmmaker storytelling has always been part of my DNA. You know that's why I obviously you know loved cannabis and really wanted to bring my skill set video media production to the cannabis

3:00 industry. So you know I was I just graduated from college. I was randomly applying to jobs online, looking in the legal cannabis space and saw somebody looking for a video editor. Um, that's how I wound up meeting my now two business partners at 420 Interactive. They had rang me up and said, "Yo, we're

3:18 over here at the High Times office." The previous owners of High Times were in the middle of a public fund raise looking to use the Regulation A uh strategy to raise public funding and help grow the company. You know, really good intentions definitely to start there. High Times is just one of those iconic brands and you know I snuck see

3:38 some High Times in my dad's closet growing up. It's just instantly recognizable to people outside of cannabis. You know, you don't have to be a cannabis expert to recognize High Times. It's been around since 1974. It's penetrated the cultural ethos of of you know the globe. So super recognizable

3:56 name. It got me frothing at the mouth. This is you know exactly what I've been looking for. They liked my video editing work and flew me out to the LA office where, you know, I was spearheading, you know, since, again, the company had just been acquired by the previous owner. So, the teams were still in flux and they were looking for somebody to definitely

4:14 spearhead video production. So, I was there working with my partners at 420 Interactive um spearheading the regulation a fund raise, made a lot of cool fun videos for that. learned all the strategies of public fundraising, uh, email marketing, SEO, media buying, all you know, really a crash course on

4:33 all the things while there for my six month, you know, 9 month stint at the, you know, old iteration of high times. Got it. And so when you look at it from from from your perspective right now,

4:52 what would you consider being like the biggest change that happened? What would you like cultural ethos? You know, was owned by previous more VC oriented people, let's call it. So they were looking at this as more of a traditional business model versus the culturalformational icon that it was. You know, media

5:11 companies in this day and age are tough unless you're, you know, David Ellison, you know, with multi-billion dollar backing. It's hard going out there and pitching businesses to advertise with you and and, you know, showing value where you can while also trying to pay the bills and keep your lights on. So, being acquired by Josh Kesselman and the

5:30 RAW team brings, you know, a real business behind the media company. you know, he treats this definitely as a cultural icon first and is just happy that it's been revived and, you know, injecting some more outside of the box ideas and a whole new team energy behind this this new iteration and bringing it back to its roots again of, you know,

5:48 journalistic integrity, telling Gonzo journalistic stories and popping up in cool ways, you know, outside of of the traditional cannabis business, you know, arenas. Got it. So pretty much it's like a full perspective that has changed.

6:07 Absolutely. Got it. Okay, that makes sense. And now it like when we switched to because this is also very important. 420 Interactive. So when you and your partners built 420 Interactive, you weren't looking at cannabis from the perspective of one brand. You were getting exposure. We wanted to work with with all brands. You

6:26 know, our again our crash course uh at High Times kind of brought us together and gave us the idea like, hey, you know, we can execute this for other people and bring, you know, a valuable skill set that a lot of these cannabis operators are missing out on. You know, storytelling and having that marketing fundraising engine as as part of your team, which you need. you know, you

6:45 could be the best cannabis cultivator in the world, but if you don't know how to market yourself and storytell and, you know, get your business flowing in the right ways, then you're not going to get anywhere, you know. So, so would you say that building cultural relevance while, you know, is extremely relevant as itself?

7:05 Absolutely. Again, storytelling, no matter what business you run these days, storytelling needs to be part of of the structure of the company, right? Whether you're in trucking or you know canning you know people are hungry for for stories and video content these days and you know media just needs to be part of

7:23 your business ecosystem or that's the that's the world we live in. Everyone's content addicted and they're hungry for you know informational avenues. That's that's actually very uh important that what you mentioned there because something I noticed looking through your career generally is that you seem to

7:42 have moved increasingly towards people and stories and you started as a filmmaker went heavily into digital strategy and brand building with 420 interactive and now a lot of your high times work you know profiles the actual people and culture behind cannabis.

8:01 it. What what I want to know here is was that a deliberate shift or did working in this industry eventually convince you that the human story is more powerful than the marketing strategy? Um, you know, just seeing all the different characters and again business

8:20 outlets, you know, again working at 420 Interactive as an incubator accelerator, you know, we we really worked with a lot of startups and, you know, some big established brands in the cannabis space, but seeing the spectrum of, you know, people who are solopreneurs to a big corporate machine and how they function and again the the the weave

8:40 that penetrates them all is is storytelling and, you know, personal stories and being able to commun communicate that to keep a customer, you know, retention in, right? A customer and building a community is what's key to a successful business. There needs to be a reason people keep coming back. That's why Josh at RAW so successful in

8:58 my opinion. He puts himself out there publicly. He's truly the face of his brand and people resonate with that. You know, there's lines out the door to meet him at every convention that that he pops up at. You know, you don't see that for a lot of other companies and brands. people still don't know who the CEO of some of these other cannabis conglomerates are and so you know why

9:18 why should they be invested in your company if they don't even know who who's there? Yeah. Do you feel like it's it's when when speaking about that, do you feel like there is a relevance and importance towards that personality sort of and I'm using probably a word that might sound

9:36 crazy, but like a personality cult when it comes to people representing their own companies or do you feel like it's, you know, it it's a good addition, not extremely relevant, or do you feel like it should go that way? It's, you know, again, people really push, you know, everyone's a LinkedIn influencer these days. I just feel like

9:54 for job security, you need to kind of have that personal branding these days and kind of build your own community that that follows you wherever you go cuz, you know, people are job hopping a lot these days. You know, they don't know where the next mission is going to be or who they're going to be with. So, hence the key on on the education around building a personal brand and you being,

10:13 you know, your own product and and you know, being part of the market that way. So, you know, there's layers. There's some people who want to remain behind the scenes. Hey, I've got a successful business here and you know our systems are working and I don't need to put my face out there, you know. Gotcha. Okay. And so also switching back

10:32 now a little bit to High Times as well is so you've described joining High Times the first time as giving you a front row seat to the culture and the people behind cannabis. Now, you're responsible for partnerships at a brand

10:51 that helped define that culture before legal cannabis even existed. How do you and and I want you to give me like your sort of uh thought trail here as well. How do you personally decide which partnerships move high times forward without turning uh

11:10 counterculture institution into just another corporate cannabis media brand? Absolutely. And I mean cannabis has kind of penetrated the mainstream these days in my opinion and that's why we need to be doing more outside the box things that are not your traditional cannabis community events. For example, we just did an amazing high times partnership,

11:29 the submersion festival here in South Jersey. It's an EDM music festival. This was their biggest year yet. You know, you I'm sure you look like you enjoy music festivals. Might have been to a few. You know, Bonaroo, Coachella, all these type of things. Alcohol is everywhere, but these people are bringing in a variety of substances and

11:48 plant medicines, cannabis being, you know, one of them. So, I don't understand why these companies don't, you know, cannabis is mainstream now. These are giant multi-state corporations that out operate, you know, just like some of these alcohol businesses. So, why wouldn't they be included in the conversation as part of these mainstream music events? So, what we did at the

12:06 high times hub is I part was able to reach out and negotiate a partnership with submersion festival. again, one of the uh south, you know, northeast's biggest EDM music fests. They had about 4,000 people there. And we built out the High Times hub and I partnered with six local New Jersey brands and a dispensary

12:24 partner to be able to sample out cannabis, have a huge cannabis presence at this fest. You know, honestly, there was only one little alcohol booth there, which you don't normally see, you know, a lot of festival goers. and the population in general I feel is moving away from alcohol and and cannabis is going to be that replacement for them.

12:42 So was a cool mainstream way for these brands to interact directly with consumers, local buyers who would who would obviously become loyal to them and you know what better way than under the High Times storytelling umbrella. So I'll be producing a documentary about our time there as well that'll live on the High Times YouTube channel. Again,

13:01 I've been finding when I talk to, you know, a lot of these media brands as the dire director of partnership, you know, these cannabis brands, they get excited when I'm pitching video content. Sure, you know, some of the traditional digital media things like running meta ads or, hey, I want to hit your email list or do sponsored articles and cool

13:20 and all, but that's not moving the needle these days versus, you know, video production and having, you know, a permanent presence on the High Times YouTube channel, for example. there's a case study you could show off over and over that grows year after year, more people discovering the story you wanted to tell or the experience you were part of.

13:38 Tell me about the documentary uh that you just mentioned. Uh what can you share about that one? Uh, you know, I just wanted to kind of recap our our our time at Submersion, what it meant for the brands to be there, why, you know, music festivals are involved are evolving to feature cannabis, why

13:57 alcohol is down, and kind of tell that story. I've recently produced a number of other documentaries and shows as part of the relaunched high times. One of them being a documentary about the Woodstock cannabis brand and the cultural impact of the famous Woodstock music festival and now how again that has rebranded and relaunched itself as

14:16 part of the cannabis conversation. Another show we recently produced that was super successful again bridging the cultural gap between cannabis and mainstream. Uh as high times we produced a show for the World Cup that came to the US called kicking back. We had our host Ethan Zohn. He visited uh a handful

14:34 of cities around the US who were hosting the World Cup game, meeting the fans. He's an ex-professional soccer player, playing some pickup soccer games, um and you know, exploring the local cannabis scene as part of the World Cup. You know, all these all these Europeans visiting the US for the first time. And you know, they could buy from legal

14:53 dispensaries. It was weird for a lot of them. So, you know, again, telling cool stories, weaving in brands in an organic way as part of that. and you know having a a cultural piece there that lives forever. Yeah, that um that is absolutely an interesting thing

15:11 to keep an eye on. But um let me really quickly go back to the documentary about alcohol and cannabis. And this is a very interesting subject to me because I've recently done an episode on that as well where I I believe and I please um I might be mistaken about the actual

15:29 numbers. I feel like there is roughly around 40% forecast of alcohol usage decrease in the upcoming generations and I wanted to ask you what do you feel like without spoiling the the documentary obviously but what do you feel like is the reason for that?

15:50 You know, I think the younger generation is just more wellness conscious, let's call it. A lot more information out there about what we're putting in our bodies and how substances make it make make us act. You know, cannab, you know, alcohol, I feel, has lost that that millennial and younger generation right now. And and cannabis is that

16:08 replacement. You know, you're not hung over the next day. You're feeling good about yourself. You're getting into a vibe. And I just think people, more and more people are realizing who didn't grow up with alcohol advertisements, you know, in their face like uh some of these older generations are, you know, not even aware of it.

16:27 Yeah, I agree. I feel like that's probably the reason especially when it comes to the availability of information that maybe um previous generations can really grab easily and uh process quickly when in fact today we have AI, we have um the search engines and all

16:45 the other stuff and it sort of gives you a better um better base for you know conclusions. Um so one last question that I have for you which is specifically um talking about that you spent close to

17:05 a decade moving between film making agency work cannabis brands and high times and you've seen the industry during both the enormous optimism of the late 2010s and the much harder reality that followed. What do you understand about cannabis as a business today that

17:26 the Kyle who first walked into high times would have completely misunderstood? Um, you know, fundraising is always super important, but you got to be lean and mean, you know, to survive long term and have systems in place. I think in 2018, everybody was super excited. California

17:44 just went recreational. a lot of VC and you know private money was flowing in and these guys thought you know the the funding would would never end, right? They were blowing money on giant parties and and uh you know some of these giant trade shows and you know not really putting the right people and systems in place to truly be build you know

18:04 something for the long term. Um, so not to say there aren't still people who are enthusiastic or excited. You know, I think cannabis is is the perfect opportunity to bring back small business in America. You know, we really need to let these mom and pop dispensaries thrive and and, you know, give people the opportunity to create a living for

18:22 themselves, which is what cannabis should should always be about. Um, something, you know, again, you know, I was very naive, I feel, coming into the cannabis industry. At the end of the day, you know, again, some of these guys who say their legacy were potentially nefarious characters, right? You know, they were there a lot of lot of drug

18:40 dealers who who, you know, which is what this was. You had to be a risk taker to want to be involved in cannabis. So, you know, there's always uh walking a fine line seeing who's real, who's claiming to be real, and and you know, who's built. That's why I think building publicly is so important. So, you know, you can show who you are and what you've

18:59 accomplished and and show you're a real person. Got it. Do you feel like there is a little bit of um um you know, missing that cannabis spirit from what it was before to what it is right now or do you feel like it's sort of going towards a right direction? No, it's going towards a right right

19:17 direction. A lot of those people again who maybe were nefarious actors have now fallen out of the industry or people have gotten wise and there's still a lot of enthusiasm as new states come online like Virginia you know and even New Jersey and New York where I'm based. Um lot of excitement. They're excited to have it here. A lot of cultural movement

19:36 happening. Um you know again one of the most surprising things I learned during our Kicking Back documentary. Who would have thought Missouri and Kansas City is one of the largest cannabis markets in in the country? Um, so you know, it's super cool to explore kind of states you wouldn't think would be, you know, cannabis popular and seeing a thriving

19:54 cultural community there. Uh, [clears throat] you know, a bunch of small business owners all trying to make it and do it and have fun together. Yeah. No, 100%. Okay, Kyle, thank you so much. Really do appreciate what you've shared with us today. This is really really important stuff and um obviously

20:14 coming from someone who's who's got such an experience is extremely helpful for whoever is going to be watching this episode. Um very quick, where can people find you? Tell me your socials. What are your plans on future events? Sure. Yeah. And you know, my name is Kyle Rosner. You can find me on LinkedIn. I'm GoodKyleSmokes on

20:34 Instagram. You can get more of my uh let's call it cannabis cultural side there. check out some of our submersion footage. You'll see my face popping up on the High Times channels. You know, again, check out the YouTube and and stuff like that at High Times. Um, and you know, before we go, I want to just say thank you to Headquarters. Your CEO

20:52 has been an amazing mentor uh towards me. Met him at my first iteration at High Times in 2018, you know, and 420 Interactive has worked closely with headquarters over the years. I can't vouch enough for the systems that you help companies build and integrate yourself into. and, you know, being a key resource if you want to be a

21:10 successful cannabis business. Thank you, Kyle. I really do appreciate that. And what about events? We we're missing that one. Uh, next event, we've got the Massachusetts Cannabis Cup coming up with High Times. If you're a Massachusetts based cannabis company, you know, hit me up to get involved. That party is going to be December 11th.

21:28 You can catch me at a Hall of Flowers coming up here at the end of October. I also do a monthly event in New York City called Legacy to Legal where I highlight a lot of the legacy cannabis operators who've been able to successfully transition to the legal New York market. We've got an awesome venue and and you

21:46 know, it's invite only. We invite the who's who of the New York cannabis scene. So, if you want to, you know, inject yourself into the best of the best, I' i'd highly recommend coming out. Awesome. Thank you so much once again. I really do appreciate your time. I feel like we're going to do probably a part

22:04 two sometimes in the future. Maybe after uh the documentary and after a couple of these events as well, so we can go through those too. But again, thank you so much for your time. Really do appreciate it. Um have a great rest of the day and uh we will definitely chat soon. Amazing. Appreciate you.