Some entrepreneurs are shaped by opportunity; others are forged through setbacks. Caleb Counts, co-founder of Connected Cannabis, embodies the latter. In this episode of Keep Going, Counts shared his journey from navigating the gray areas of cannabis sales as a teenager to leading a multi-state cannabis operation. His story is one of perseverance, reinvention, and a refusal to quit, even when faced with extraordinary challenges.
Setbacks as Starting Points
Counts’s journey began long before the legal cannabis market took form. Selling cannabis illegally as a teenager and young adult helped him fund his college education. But by 2003, he shifted gears, stepping into real estate, only to be pushed out during the 2008 financial crisis.
The collapse of the housing market might have ended the story for many, but for Counts, it was a call to pivot. He returned to cannabis, this time aiming for legitimacy during a period when California’s cannabis laws were evolving. With retail as his entry point, he founded one of the early dispensaries in Sacramento, participating in regulatory efforts to legalize and standardize the industry.
“I thought having a permit meant safety and legitimacy,” Counts reflected. “But I didn’t expect the federal government to issue what we called the ‘landlord letter,’ effectively shutting us down.”
Why Keep Going?
After federal enforcement action shuttered his dispensary, many would have walked away. Not Counts. His drive came from a deep desire to operate without fear, combined with a belief in the potential of cannabis to transform lives and industries.
“The opportunity to do what I loved without looking over my shoulder was extremely exciting,” he said. “I had many sleepless nights during my illegal selling days. Going legitimate felt like a chance to leave that behind.”
But going legitimate came with its own challenges. Regulatory hurdles, federal interference, and market commoditization pushed Counts to continuously adapt. “Every promise made to this industry—whether from politicians or the market—has either been broken or delayed,” he explained. “But I wake up every day asking, ‘What’s next? How can we overcome it?’”
Lessons for Entrepreneurs
Counts’s experience is a blueprint for resilience. For those looking to enter any challenging industry, he offers a sobering perspective:
Understand the Risks: “This isn’t a get-rich-quick opportunity,” he warned. Building a cannabis business—or any business—requires significant funding, careful planning, and the ability to weather long periods of uncertainty.
Have a Unique Offering: With cannabis becoming increasingly commoditized, innovation is key. “Whether it’s small-batch quality, unique marketing, or better technology, you need to stand out,” he said.
Be Ready to Face Resistance: Whether from regulators, competitors, or market forces, challenges are constant. “No one wants us to win,” Counts admitted. “But that’s what makes overcoming those challenges so rewarding.”
The Drive to Build a Legacy
For Counts, the cannabis industry isn’t just a business—it’s history in the making. “This transition from illegal to legal hasn’t happened since alcohol prohibition,” he explained. “Being part of this moment is legacy work. It’s something I’m proud to wake up and fight for every day.”
Looking Ahead
Today, Connected Cannabis operates across California, Arizona, and Florida, with products in over 500 stores and a thriving retail presence. But the journey is far from over. As market prices drop and regulations evolve, Counts remains focused on innovation and efficiency.
“It’s brutal out there,” he said. “But it’s also exciting. Every day presents a new challenge, and I’m here to meet it.”
For entrepreneurs and dreamers alike, Caleb Counts’s story is a powerful reminder: setbacks don’t have to be the end. For those willing to adapt, innovate, and keep going, they can be the beginning of something remarkable.
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