Introduction
Media Jel connects brands and retailers with cannabis consumers through our ad network of mainstream publishers, mobile apps, games, and TV. We help cannabis companies advertise on Google, support SEO, and activate data with display advertising to support e-commerce sales.
Guest Introduction
Guest: I’d like to introduce Dennis O’Malley. Dennis is a serial entrepreneur and founder of Caliva, one of the largest vertically integrated retailers in California that was acquired by Jay-Z’s parent company. Dennis has a breadth of experience in the cannabis industry, and I can’t wait to hear his insights today. Thank you for joining us, Dennis.
Dennis: Thanks so much for having me. Looking forward to this.
Jeremy: Likewise. Well, let’s start from the top. What does your career look like before entering the cannabis space?
Dennis’s Background
Dennis: I almost can’t remember [Music]. All the battle scars over the last five and a half, six years on it. But before cannabis, I was really focused on technology in different parts of tech. One area that I think was a good transition into cannabis was what we founded at Ready Pulse, around 2010-2011.
We wanted to drive authentic marketing. We believed that putting models front and center in marketing didn’t make sense, and that customers were the best form of marketing. We sought out technology solutions to do just that—people trust people, not ads.
We developed technology to track social media—Facebook, Twitter, Instagram—at a time when social was still emerging. We put those photos front and center, working with over 300 websites of brands like Red Bull, GoPro, Nike, Adidas, North Face, and others. We had amazing partnerships and sat with brand marketing teams that developed authentic, inspirational marketing campaigns.
In 2016, we sold that company to ExpertVoice, which had two million trusted experts—think of lifeguards, ski patrols, store associates at Dick’s Sporting Goods—who were the most knowledgeable in their categories. This social proof and authentic marketing translated extremely well into cannabis, where social proof and trusted experts are some of the only marketing avenues available.
In cannabis, there’s no CPC button like on Instagram or Facebook, so you need to be super creative to get your message out.
Building Caliva
Jeremy: How do you leverage this previous experience when building Caliva?
Dennis: When building anything, you always go back to the core. I came into Caliva in 2017, with a core team that had built it from 2015. We focused on developing a North Star—why do we exist? We defined it as serving the informed consumer—asking, “What am I putting into my body?”
Our brand values centered around consistency, transparency, and accessibility. Everything we did—from product development to customer service—reflected these pillars. We aimed to be the most trusted name in cannabis, building trust with our customers, many of whom, like me, care about what they put in their bodies.
This transparency and accessibility guided our campaigns, allowing customers to tell their stories, providing social proof, and training wellness consultants as trusted experts. This helped us build that trust in a competitive California market, especially in San Jose.
Jeremy: I remember following Caliva and its campaigns around accessibility in the San Francisco Bay Area—wide reach from San Francisco to Oakland, down the peninsula to San Jose. It takes a concerted effort. Kudos to Rosie Rothrock, the creative lead, who came up with most of those campaigns. Cannabis marketing is tough, but she did an amazing job creating evergreen campaigns with lasting impact.
Dennis: Absolutely. Rosie’s campaigns had legs, and they could be built upon over time. They were expensive and took time to pay off, but they created a foundation for direct response and brand awareness.
Challenges and Learnings
Jeremy: What problems did you identify when entering the cannabis space or when you launched Caliva?
Dennis: Learning from mistakes. One that stands out was thinking I could develop an app for samples. I believed wholesale reps could sign up, provide samples, and track reviews. The idea was great, but in 2017, dispensaries didn’t allow mobile phones in stores. We were a couple of years early.
It taught me that cannabis marketing requires creativity and understanding regulations. Partnering with experienced, battle-tested partners who understand cannabis regulations is crucial.
Jeremy: That makes sense. Building trust in retail stores is challenging, especially in new markets where stores might have metal frames or look unwelcoming. I suggested doing Google 360 views of stores early on, but there was hesitancy due to security concerns. Now, with phones allowed, user-generated content is valuable. Influencers and consumers posting pictures help market cannabis stores, especially since there are limited marketing channels.
Dennis: Exactly. For example, Planet 13 in Santa Ana has great Instagram moments, and their drone videos at their Vegas store are incredible. Progress is happening.
Vertical Integration and Market Trends
Jeremy: When Dennis joined Caliva in 2017, was the company already vertically integrated?
Dennis: Yes. We implemented vertical integration because of regulations. San Jose required all 16 license holders to be vertically integrated—having both cultivation and retail licenses. We focused on products, compliance, child-proof packaging, and being ready for regulation enforcement in 2018. During COVID, we ramped up delivery, electronic payments, and other innovations.
Jeremy: How is the San Jose market now?
Dennis: It’s evolving. The city will issue more licenses, but zoning restrictions mean new stores will be in more attractive retail areas, not industrial zones. San Jose is the 10th largest city in the U.S., with a higher population than San Francisco. Increased competition will be balanced by better retail locations and convenience for consumers.
Jeremy: Do you think San Jose did it right by limiting licenses compared to places like Santa Rosa?
Dennis: Yes. San Jose funded enforcement and compliance well, collaborating with police and local agencies. They required vertical integration and managed micro markets effectively. Competition is tough, but the legal market offers a better experience than illegal operators.
Retail, Delivery, and Omnichannel
Jeremy: How do you see the future of retail and delivery in California?
Dennis: The delivery expectations accelerated post-COVID. It’s challenging but essential. Retailers need to focus on service, electronic payments, accurate product info, and reliable delivery. Scheduled deliveries, with a focus on service over speed, can build loyalty.
Jeremy: How long did it take to develop a true omnichannel strategy at Caliva?
Dennis: No one is ever fully satisfied, but managing inventory across multiple locations and micro markets is key. Understanding local preferences and micro-market needs is crucial. The goal is to have the right products in the right markets, backed by consistent messaging.
Jeremy: Where should businesses start when building their omnichannel strategy?
Dennis: Start with brands. They do a good job telling their story, engaging consumers via email, videos, and social media. They should provide consistent content and activate their audience through texts and updates.
For retailers, focus on the in-store experience—budtenders are the frontline. A good website with pickup options is critical. Delivery is complex but important long-term. Use tools like Google Analytics and third-party tracking to measure ROI.
Jeremy: Agreed. Mobile-first websites are essential, as over 80% of visitors are on mobile. Accessibility, quick ordering, and seamless in-store and online experiences are vital.
Dennis: Absolutely. The retail landscape is shifting. Brands are relying less on billboards and more on digital channels like programmatic ads, influencer marketing, and content-driven campaigns. Building community and redirecting traffic to retailers is the future.
Marketing, Reviews, and In-Store Strategy
Jeremy: With economic challenges, ROI tracking is more important than ever. Investing in SEO, reviews, and local discovery platforms like Google and Weedmaps is crucial.
Dennis: Yes. For example, Caliva’s strong SEO and product info helped customers find us during consideration. Reviews, especially on Google, are king—over 93% of searches happen there. Simple tactics like QR codes for reviews and automated post-visit messages boost reputation.
Jeremy: How do you connect online experiences with in-store interactions?
Dennis: Use trusted experts—wellness consultants—to review products and provide recommendations. Social proof, reviews, and accurate product info help build trust. Training budtenders to be knowledgeable and current is essential.
Jeremy: And how about syndicating product reviews across platforms?
Dennis: That’s a future opportunity. Currently, no unified voice exists for product reviews across all channels, but it’s coming. Consumers mainly search locally, so brands need to be discoverable where they shop.
Delivery Services and Final Thoughts
Jeremy: What about delivery services? How do you ensure a seamless customer experience?
Dennis: Delivery is a separate service requiring a unique value proposition—reliability, good service, electronic payments, and flexible options like scheduled delivery. Starting small, expanding gradually, and focusing on service quality are key.
Jeremy: Did you do scheduled deliveries or more spontaneous ones?
Dennis: We started with scheduled deliveries in 2017—narrow windows, small areas. Over time, expanded geographically and added minimum order amounts. The focus was on service, not speed. Customers appreciated reliable, friendly drivers.
Jeremy: How long did it take to achieve a true omnichannel approach?
Dennis: No one is ever fully satisfied. Managing inventory across multiple locations and micro markets is complex. Local preferences vary, so understanding micro markets and tailoring product selection is vital.
Jeremy: Where should businesses begin with their omnichannel strategy?
Dennis: Focus on content, storytelling, and consistent engagement. Build a strong digital presence—website, social media, email. For retail, optimize the in-store experience and pickup options. For delivery, ensure reliability and service quality.
Wrap-Up
Jeremy: Thanks, Dennis. I appreciate your insights and wish you continued success.
Dennis: Thanks, Guillermo. Looking forward to the future of cannabis marketing. It keeps us on our toes!
Jeremy: Thank you, Dennis.