We caught up with the brilliant and insightful Darren Gleeman a few weeks ago and have shared our conversation below.

Hi Darren , thanks for joining us today. We’d love to hear the backstory behind a risk you’ve taken – whether big or small, walk us through what it was like and how it ultimately turned out.

A risk I took that stands out was deciding to shift my focus entirely to ESOPs within the cannabis sector. I had been working across a broader set of industries, but the cannabis space was both challenging and full of untapped potential due to its complicated regulatory environment and the unique issues business owners face, like 280E tax exposure. At the time, many saw the cannabis industry as a volatile space with high barriers to entry, and I could have stayed in safer industries. But after recognizing the potential to help these businesses transition to tax-efficient structures while helping employees become owners, I made the leap. It required me to become an expert in both cannabis law and ESOPs, essentially carving out a niche where there was little existing competition. The outcome was successful; I structured the first few deals and began establishing myself as a leading expert in cannabis ESOPs. Over time, this risk paid off significantly as the market matured, and my reputation in the industry grew.

Darren , love having you share your insights with us. Before we ask you more questions, maybe you can take a moment to introduce yourself to our readers who might have missed our earlier conversations?

I specialize in structuring Employee Stock Ownership Plans (ESOPs), particularly in the cannabis sector. I entered this niche after realizing that many business owners in cannabis were facing severe tax burdens and limited exit strategies due to 280E. By focusing on ESOPs, I found a solution that allowed these owners to defer capital gains taxes, maximize their exit value, and create a tax-free environment for the business itself. What sets me apart is my deep knowledge of both ESOPs and the cannabis industry, as well as my ability to simplify complex structures for business owners. I’m most proud of the fact that I’ve structured every cannabis ESOP in the U.S., which positions me as an industry leader. The key thing potential clients should know is that I don’t just help businesses sell; I help them transition to structures that allow them to grow, thrive, and involve their employees in ownership, creating long-term value.

Any stories or insights that might help us understand how you’ve built such a strong reputation?

Building my reputation within the ESOP and cannabis industries has been a result of a few key factors: consistently delivering value, positioning myself as a subject matter expert, and fostering trust with clients. By being the first to specialize in cannabis ESOPs, I was able to carve out a niche and become the go-to resource for business owners in this space. My reputation has been built through successful case studies and by offering tailored solutions that combine my financial expertise and understanding of cannabis regulation. Additionally, my involvement in educational content, webinars, and LinkedIn posts helped solidify my position as a thought leader in this unique area of the market.

Are there any books, videos, essays or other resources that have significantly impacted your management and entrepreneurial thinking and philosophy?

One of the most influential books on my management philosophy is Good to Great by Jim Collins. The core principles of that book, disciplined people, disciplined thought, and disciplined action, deeply align with how we approach ESOPs.

In Good to Great, Collins talks about getting the “right people on the bus” before deciding where to drive it. That’s exactly how we operate. We don’t try to force a generic solution onto every business. Instead, we surround ourselves with top legal, financial, and operational experts who understand the nuances of ESOPs, especially in complex industries like cannabis. We know this space better than anyone, and we make sure the right people are in the room from day one.

Another key concept is the “Hedgehog Concept” – the idea that great companies focus on what they can be best in the world at. For us, that’s ESOPs. We don’t dabble in it. We live and breathe it. We’ve structured every cannabis ESOP in the country and we understand the tax code, the compliance landscape, and the structuring mechanics at a level few others do.

Finally, Collins emphasizes confronting the brutal facts. That’s something we’re never afraid to do. ESOPs aren’t simple, and they aren’t right for everyone. But when they fit, and they’re done correctly, they unlock tax-free operations, capital gains deferral, and long-term alignment in a way that no other structure can.

Good to Great reinforces everything we believe: get the right people, focus on what you do best, and execute with discipline.

Contact Info:

• Website: https://mboventures.com/
• Linkedin: https://www.linkedin.com/in/darrengleeman
• Youtube: https://www.youtube.com/@MBOVentures