Cultivating Trust and Boldness: A Journey from NYC Media to Cannabis Leadership

This sounds like the setup to a dad joke: Jane Pratt, Christina Kelly, Annemarie Conte and Johan Svensson walk into a dispensary. But this reunion of Jane Magazine alumni was an actual event I helped co-plan this past summer, and it was an invaluable reminder of why community building is baked into my DNA.

Before I began a career in the cannabis industry when I joined Grasslands as Chief of Staff almost six years ago, I spent over two decades in New York City media at companies like Conde Nast and Rodale. 

As my career has evolved, what I’ve learned is this: Whether you work in a traditional, established industry like publishing or an emerging one like cannabis, the rules are always being rewritten. When you work closely with people in the trenches through that change, through those highs and lows, it builds trust. And that trust allows you to be a little bit bold.

The memories were flying as much as the samples from Grasslands clients and partners GALYNA, Banyan Botanicals, Fable, Puffco, Made in Xiaolin during our gathering at Culture House, which hosted the Jane Magazine reunion. Later that week, the same was true with the conversations over drinks at The Madison Lounge, where my former colleagues from Men’s Health convened from as far away as Michigan, Minnesota and California. 

Our careers have gone in all different directions in the decade since we worked shoulder to shoulder. I'm now in Denver building and scaling a cannabis PR & Marketing agency where I’m cultivating and nurturing a team of 25 marketing professionals. Others have landed at The Wall Street Journal, The New York Times, Target and Hermes.

When I met Grasslands Founder Ricardo Baca in 2018, I recognized someone equally committed to building community. Ricardo has always found creative ways to bring people together, whether it was co-founding and organizing the Underground Music Showcase (UMS) in Denver or throwing The Grasslands Party in Las Vegas each year. 

Indeed, one of the key qualities the Grasslands leadership team shares is a dedication to building not only community but also cultures of care. This is fully baked into both our individual and institutional DNA. 

That is why we take such pride in our earned ideas program, working with clients like Housing Works, Illegal Pete’s and O.pen to create strategic partnerships with like-minded brands. That’s also why we continue to invest so much time and money into bringing our signature take on over-the-top hospitality to The Grasslands Party and Supper Clubs, Nightcaps and Daybreakers throughout the year. 

You really can’t put a price on meaningful connection. That’s what I learned first as a Managing Editor and have continued to learn as a Chief of Staff. Rugged individualism is so common in American culture and in entrepreneurial circles, and as someone who is fiercely independent, competitive and driven to figure it out—I get it. But rugged individualism can only get bold people so far. Ultimately to go the distance, you need the continuity that comes from relationships.

Whether I’m talking to a prospective hire or a prospective client, a few of the things I’m asking myself are, “Will they be a good partner?” “Will they be accountable and be authentic communicators?” Bold moves get a lot of attention. But smaller actions can make a lasting impression—like holding yourself accountable, sharing the win with your teammates and partners, and staying curious and open even in the face of adversity.

Because cannabis is such a new industry, many of us came to this industry through other passions and professional directories. Many of my colleagues at Grasslands arrived from the music industry, academia, journalism or natural products PR. I came from an industry that hinges on both hard work and storytelling—where forging a compelling network is key to success and personal growth.

I’ll be honest, reconnecting with my fellow Jane and Men’s Health alumni was probably as close as I’ll ever get to attending my own funeral. “Debbie, because of your coaching I went on that first date and met my husband.” “I will be forever grateful that you took a chance on me and hired me.” Humbling. On some level we all want a glimpse of how we’re regarded and the difference we’ve made in others’ lives.

These reunions were a chance to really feel not only the power of these communities but my place in them. It was deeply satisfying to know that 10 years from now, my colleagues at Grasslands and our broader cannabis community might attend a similar reunion and look back on this moment in the industry, and see how it transformed us and made us a little more innovative, a little more brave, a little sharper and bolder.

We need to surround ourselves with the people who motivate and inspire us—but we also need to motivate and inspire ourselves to show up in a way that helps other people feel like they have the freedom, resources and care to succeed. 

‍Want to grow your community? Let’s talk.