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Tom Regan of Root & Bloom: 5 Things I Wish Someone Told Me Before I Started Leading a Cannabis or CBD Business

An Interview With Candice Georgiadis

As part of my series about “5 Things I Wish Someone Told Me Before I Started Leading a Cannabis Business” I had the pleasure of interviewing Tom Regan.

Tom Regan is CEO of Root & Bloom, a Massachusetts-based cultivator, extractor, and manufacturer of craft cannabis products. Beginning his career in tech startups and then Cisco Systems, Tom developed a passion for building teams and growing companies. This passion eventually led Tom to transition to the cannabis industry, where he learned the businesses inside and out.

A pioneer in his field, Tom took the Colorado cannabis company Mindful from growing and extracting to distributing and retailing. His knowledge and enthusiasm for the industry led him to become a consultant for aspiring growers. After selling Mindful to a large national cannabis company, Tom joined Root & Bloom, a Massachusetts-based cannabis startup. His strategic vision is positioning the newly-established company for success, and his passion for the industry, process, and people are helping Root & Bloom put its stamp on the market as the purveyor of the finest cannabis products available.

Thank you so much for doing this with us! Can you share with us the story about what brought you to this specific career path?

I have a background in high tech and spent the beginning of my career at high tech startups, then went on to become a director at Cisco. I traveled around the world and had a lot of responsibility, but I came to a point where I wanted to get out on my own. I left Cisco and started my own software company. As I worked as an entrepreneur, one of my former colleagues had invested in cannabis in Colorado, and that company was struggling operationally. He convinced me to visit the business, take a look and see what they were doing. I fell in love with the business model after visiting this company.

When you are at a big company like Cisco, it can be hard to leave the comfort of that. I had a great career in tech, thanks to the great people and companies I got to work with. Had I not left Cisco and tried something on my own with the software startup, I might not have been open to getting into the cannabis industry. I’m so grateful to have had all these opportunities.

Can you share the most interesting story that happened to you since you began leading your company? Can you tell us what lesson you learned from that?

The most interesting part of joining Root & Bloom is witnessing how many extremely talented people we have been able to attract to our organization. We’ve been able to convince cannabis industry veterans to leave Colorado and move to Massachusetts, and we’ve been able to get some Mass.-based business superstars to leave high paying jobs and take a chance on our startup. The quality and the passion of the people we’ve been able to bring into Root & Bloom is so exciting, and I’m wowed by their commitment at all levels.

The lesson I learned from this is that attracting the best people comes down to culture. If your business doesn’t have a great culture, you can’t get the best people. You can lure people in with money, but you won’t get the passion that way. If you create a culture of independent thinking and accountability, plus caring, you can’t go wrong!

Can you share a story about the funniest mistake you made when you were first starting? Can you tell us what lesson you learned from that?

I first dipped my toe into the world of cannabis in 2014, when my former colleague invited me into his Colorado-based business. I had certainly been exposed to cannabis in my life, but not extensively at that point. I had never been involved in a grow. Right after I started at Mindful, I volunteered to participate in a grow, because I really wanted to learn about the process. I understood the manufacturing piece, but I didn’t know as much about the farming aspect. So, I suited up, went out on the grow with William, one of our folks that worked there, and…well, I learned something important. I didn’t realize that you wouldn’t get high if you just touched the plant, so I spent that day clinging to the walls trying not to come in contact with the plants. I thought if I touched the crystals I would get high. I didn’t realize that you had to combust the material to activate it. The growers I know will still remind me of it to this day, chuckling about how I was creeping along the sidewalls, worried that I would get impaired at work.

From this experience, I learned the importance of humility. At Cisco, I managed big projects and lots of resources but at the Colorado cannabis startup, I was the dumbest person in that grove for a long time. I learned that when you don’t know what’s going on, and you are surrounded by people who know more than you, you are best off asking a lot of questions and listening to those people.

Are you working on any exciting projects now? How do you think that will help people?

We’ve got a couple of really exciting things going on at Root & Bloom right now. We are on the cusp of bringing our own flower to market. Also, we are working on bringing a bunch of interesting brands to the Massachusetts market. These brands have unique products and nothing comparable is available to consumers in the Commonwealth right now. We’re very excited about the products we are bringing to the public.

As for how this will help people, I learned early on that the cannabis plant is medicine. The more variants and permutations of that plant that you can present to people, the better opportunities they have to take advantage of the plant’s benefits. Many people use cannabis to manage pain, anxiety, or other issues, and it makes a real difference in their lives. The new flower that we are about to bring to the market is among the best available in Massachusetts, and we will deliver it at a fair price. We are going to bring a differentiated product to Massachusetts consumers that is high quality, but not high priced.

None of us are able to achieve success without some help along the way. Is there a particular person who you are grateful towards who helped get you to where you are? Can you share a story?

So many people have helped me along the way that it would be hard to name them all. I’ve been very fortunate that I haven’t had to update my resume in more than 20 years. The reason for that is there has always been someone who helped me take the next step in my career. I’ve had so many great mentors in my professional life and I’m extremely grateful for that.

Early in my career, I worked with a wonderful gentleman, and he really helped me lay the foundation for my professional growth. He not only taught me how to be a leader, but he showed me the importance of being a compassionate leader, while also demanding results and getting the best from people. I modeled my leadership style after him, and I certainly think about his advice regularly.

This industry is young, dynamic and creative. Does your company use any clever and innovative marketing strategies that you think large legacy companies should consider adopting?

Something really important for the cannabis industry is to acknowledge and pay homage to the people who paved the way for this industry. The people who went to jail, the people who gave up everything to get this industry to the point of being accepted and normalized deserve to be remembered. I’m proud that our marketing team doesn’t shy away from the history of cannabis. It’s important to understand the word, “legacy.” The Root & Bloom marketing staff has made it a point of acknowledging the role of the others who came before us in today’s cannabis industry. I see a lot of the big cannabis companies ignoring that history and trying to sterilize the industry a bit. Companies positioning themselves as “the Apple store of the cannabis industry,” really ignore the very recent past. I don’t like that. Today’s cannabis industry needs to acknowledge the legacy of what the industry has been for the last 100 years, as well as where we are today, and where we are going.

Can you share 3 things that most excite you about the Cannabis industry? Can you share 3 things that most concern you?

There’s so much to be excited about in the cannabis industry. First, I love the technology and the transformation. It’s amazing and thrilling to see people taking the plant and using IP to make it more than just a bud. Human ingenuity, chemistry, and physics can transform the plant. There are thousands of business models within cannabis that haven’t even been tapped yet. There’s so much potential.

The second thing that excites me about the cannabis industry is the people. Root & Bloom, and many others in the business, have attracted a lot of people to this industry who have been marginalized by society. Brilliant people who weren’t given a shot, but are getting an opportunity in the cannabis industry. The expertise these folks bring to the industry is going to take us to places that we can’t imagine.

The third exciting thing about being in the cannabis industry is that we are really experiencing the cutting edge of a dynamically emerging and evolving business. I love it. I enjoy being a part of something that hasn’t been done before. Technology and systems for the industry are still evolving. The industry is ahead of the support structure and a lot of the peripherals, and it’s exciting to see those elements developing. It reminds me of the early microelectronics business in the 1970s and 80s before microchips came out. People started by making their own boards and sharing them with each other until eventually, that evolved. Seeing that kind of innovation happening in the cannabis industry is thrilling and feels like watching history unfold.

In terms of my concerns, the industry is still emerging and the public narrative hasn’t fully evolved. I think operators like us must be open, honest, and work to change public perception. It’s a huge opportunity, but it does concern me. Across the nation, there are pockets of understanding, but we still have a ways to go. It’s our responsibility to educate the public about what the opportunities are for this business but also what some of the challenges for society might be.

Another concern is that a lot of the peripheral industries are funding and banking. For example, we don’t have a federal construct to do banking and it really creates challenges for businesses to grow and access capital.

My last concern is something that I think about all the time, and is extremely important to me: How do we attract more talent? How do we get a woman who is working at Oracle to come in and share her talents in the cannabis industry? Or someone from Kraft Foods? Or someone who has worked at a really small business that might have expertise and ideas that could help us grow? I’d like to see wider participation in cannabis across all kinds of people in society. That will only make us stronger.

Can you share your “5 Things I Wish Someone Told Me Before I Started Leading a Cannabis Business”? Please share a story or example for each.

I’ve learned so much along the way, it’s been a great experience. Here are the top five things I’ve learned:

Number one: Growing cultivation is incredibly hard. When you jump into the cannabis industry, you are a farmer now. People might not think of what they are doing as farming because they might be indoors, and might be using hydroponics, but it’s still farming. If our plants get sick or don’t grow as expected, that’s a farming issue. I had to shift my mindset to understand the different challenges and opportunities involved when a business is built around farming.

Number two: Planning is important, but as soon as that plan is done, you should be thinking about the next plan. In cannabis, I learned demand creation is important, but it’s more important to pay attention to supply. Supply is an even greater challenge. You have to pay more attention to planning with regard to supply because there is more potential for challenges there.

Number three: The regulatory component of the cannabis business is way more complex and dynamic than you would expect. The industry is new and developing. For example in Colorado, they created a great model for regulating the industry, and it was the first in the nation this had taken place. Massachusetts and many other states copied the blueprint and tried to learn from Colorado’s experience. That being said, in Colorado you could come into work on Monday and find that the regulatory body changed a regulation on Sunday, and you had 24 hours to comply. They’d be closing a loophole that someone was exploiting. The challenge was that fixing it often meant that our business had to scramble to comply. Compliance could be costly or disruptive to the business, and it was hard to anticipate when these challenges might arise.

Number four: There is room at the table for people from different aspects of society in the cannabis industry. Diversity of thought and experience is extremely important. I learned this very quickly while working in the industry. We’ve had people who weren’t from cannabis-based businesses who have incredibly valuable skills and insights. We found amazing people who were in the restaurant business, liquor industry, high-tech, etc. These folks brought ideas and knowledge that really helped us succeed.

Number five: If you build the right team, you are going to be fine. You are only as good as the people on your team. You can talk about business models or money when it comes to what determines success, but, really, it’s the people. One of my big lessons was when you build a team, a little conflict is good. It’s OK to bring together divergent viewpoints. It has to be managed, but understandably, it can’t be chaos. If the team understands what their common interests are, and everyone treats each other with respect, a little conflict can be productive.

What advice would you give to other CEOs or founders to help their employees to thrive?

That’s a great question. The first thing is to understand that it’s OK to fail. Failing is not the problem. If you want to try something innovative or unconventional, you should take a risk! Bring new ideas, start small, and if it works, double down on it.

Another really important piece of advice for CEOs is to have humility. If you think you are infallible, or if you think the best ideas have to come from you, you are cooked. The greatest ideas come from every area of the company, and listening is a big part of being a CEO. You won’t succeed if everything is top-down only. I understand the urge to be the center of everything, but you’ll be missing out on untapped resources if you are the only person contributing new ideas.

You are a person of great influence. If you could inspire a movement that would bring the most amount of good to the most amount of people, what would that be? You never know what your idea can trigger. :-)

Act locally. A lot of us, and I’m guilty of it, think someone else will organize a movement locally. Ben Franklin, as a young man, created these societies, and they would problem solve different issues impacting the community. For example, they invented the first fire department and they formed a library. They listened to concerns to address local needs and found ways to solve problems. Now we have all these big organizations, NGOs, etc. But people don’t act locally as much as they should. It doesn’t take a conference in Aspen to solve all our problems. I’d love to see a movement that encourages people to act locally and problem solve with their fellow citizens at a local level.

This was very inspiring. Thank you so much for joining us!



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Candice Georgiadis

Candice Georgiadis is an active mother of three as well as a designer, founder, social media expert, and philanthropist.