5 Things I Wish I Knew Before I Started: “You will have to prove your professionalism” with Jessica Billingsley

You’ll get marked with a scarlet “C.” I can be called many things — a businesswoman, entrepreneur, mom, daughter, mentor. When I joined the industry, I was instantly tarred with the cannabis brush. People in my daily life make assumptions about my use of the cannabis, instantly assuming I’m a pothead. I have to prove my professionalism.

I had the pleasure of interviewing Jessica Billingsley. Jessica is an early investor in one of the first legal cannabis businesses in 2009, Jessica co-founded MJ Freeway to fill a need to track and manage inventory in what is now the fastest growing industry in the U.S. Billingsley created a new technology category with the launch of MJ Freeway’s first seed-to-sale software solution in 2010. Since then, seed-to-sale cannabis technology has grown to a multi-billion-dollar global business. MJ Freeway is a market-share leader serving clients in 11 countries with commercial and government technology products, as well as data and consulting services. MJ freeway has processed more than $10B in legal cannabis sales. Jessica is the first woman ever from the cannabis industry to receive the prestigious 2015 Fortune Most Promising Women Entrepreneur Award. Jessica was featured in Cannabis Now’s Eight Cannabis Entrepreneurs to Watch, included in Entrepreneur Magazine’s Annual List of 100 Brilliant Companies, and was listed in Inc. 5000’s list of fastest growing companies in America for three consecutive years. Billingsley’s respected reputation has won her a board member seat for six consecutive years on the National Cannabis Industry Association. Jessica is recognized nationally as an industry expert and has been a frequent guest speaker at many industry events. She has been interviewed and quoted in many local and national media outlets including CNN Money, Fortune, Wall Street Journal, USA Today, WIRED, CNBC, and Forbes.


Thank you so much for doing this with us! Can you share with the ‘backstory” about what brought you to the cannabis space?

There are two chief reasons why people dive into this industry. They are either passionate true believers of the efficacy of cannabis or adventure seekers, excited to claim new territory. I consider myself an adventure seeker, although I rapidly became a true believer as well. I was one of three women in my college computer science program. I later saw an opportunity and invested in one of the initial license holders here in Colorado which was the first state to license and regulate cannabis businesses. It was in that business venture where the linkage between my computer expertise and the adventure in the emerging cannabis market came together. The industry had a need to monitor, manage, and report effectively and accurately on this unique product. Seed to sale technology is the solution, and MJ Freeway was born in January 2010, inventing the category.

Can you share the most interesting story that happened to you since you began leading your company

I find new frontiers and evolution of the industry to be most interesting, particularly when I can see the writing on the wall for the future before others are able to read it. In December, I shared my 2019 predictions for the cannabis industry, one of which focused on the importance of Latin America. My instincts were validated during my recent trip to Colombia. I stood at the edge of our client, Pharmacielo’s, large production facility in the mountains above Medellin and looked out on a sea of green. The beds and fields extended as far as the eye could see, being fed by natural and electrical lights — generated onsite — that enhance the flowering phase. The result is the highest quality, greenhouse cultivated marijuana being produced at 15% — 25% of what it costs to produce in a high-volume greenhouse facility in Colorado or California. While I was in Colombia, it was also announced that another of our clients, Clever Leaves, was approved to be the first Colombian company authorized to export cannabis into Canada. This is an area of unlimited growth on an international scale that produces a high quality product. That’s an interesting combination.

Can you share a story about the funniest mistake you made when you were first starting? What lesson did you learned from that?

Let’s set the scene — it’s my first investment event. There’s fifty people in the room, all of whom are men. I wore a professional businesswoman’s attire, complete with a skirt and three-inch heels. I approach the presentation stage… look around… and there’s no stairs. I had to swiftly navigate how to get on stage with some semblance of grace and professionalism. Now, I’m well aware the world is not designed for women, and I always consider the presentation environment, including if I’m seated or standing.

Are you working on any exciting projects now?

Innovating solutions that solve our clients’ problems better than anyone else is one of my key drivers, so delivering advanced tech infrastructure creates undeniable excitement. We recently released MJ Platform’s 2.0 — OG Kush release, which is a major release of our flagship product. There’s no other technology solution that’s fully compliant across the entire supply chain with the scale to keep up with the industry’s growth. So, I am incredibly proud to be creating a blue ocean in terms of innovation, especially when it directly provides effective solutions.

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?

Parents wear a lot of hats, and mine were also my mentors. They led by example as owners of a successful, mid-size, contracting firm, so the entrepreneurial spirit is woven into our family. I had living models of what it takes to run a business, an example of the commitment and drive to be successful, as well as the associated required high level of risk tolerance. I also picked up amazing insights by osmosis and being in the car or living room during discussions. Now as a business owner, they continue to provide mentoring, especially from a people perspective.

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

As in many things, the blessings are also the concerns. For the cannabis industry, my three areas are international expansion, consolidation, and accelerated growth. Creating an international marketplace has the potential to generate expansive opportunities. However, it is all dependent on how it evolves. How do we build in labor considerations to protect workers? How does America stay competitive if cannabis isn’t legalized on the Federal-level unlike our Canadian neighbors and other trail-blazing countries? In looking at consolidation, elevating to the enterprise level supports delivery of better products with stronger consistency, but do we lose the cottage industry and craft products in the process? How do we consolidate and protect our small farmers and innovators of the industry? Last, the accelerated growth rate is exhilarating. Nearly every day this March there was a piece of legislation that moved forward at either the state or Federal level. Each state passage is a step towards ending prohibition and expanding growth. However, we need to ensure our industry grows in a way that supports representation. We must ensure those marginalized most by the drug war can pursue opportunities in the market. The challenge is the market is growing so fast they are being excluded.

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

My advice to other leaders is to invest in and solidify your culture upfront. The culture and values you define will serve as your foundation and will be the bedrock upon which every aspect of your business will be built. It gives you a place to guide your employees in times of growth and/or decision, and it is measured or tested when you provide a feedback loop. I would also offer that clear accountability and metrics are important to the employee relationship. None of us can feel comfortable and ready to achieve without knowing how the time and effort will be measured. I’ve found that checking in on metrics closer to real-time is a particular need for millennials, so I’ve looked hard to find a balance between the immediate need to help them succeed while also keeping a larger perspective on the radar.

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. :-)

I am fiercely committed to stopping the drop of talented women in tech. Right now, our female tech talent pool leaks like a sieve and requires immediate attention. We’ve seen the campaigns to get girls engaged in tech. However, more than half — 56 percent — of women who enter the industry drop out of the workforce midway into their careers. Right now, there’s a smaller percentage of women in tech than 25 years ago, and almost exclusively men design the technologies on which we spend our time. This Women’s History Month, I launched the One Woman Challenge to ignite the discussion of parity for women in tech and to generate career supportive actions for women in business. The ask is simple — commit to one supportive career act for one woman. While the campaign launched in March, the effort lives on, and we will continue to look for answers to keep our talented women engaged and thriving in their careers. We know parity contributes to innovation, productivity, and profitability, making this is a cross-gender issue which affects us all.

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.

1) You’re going to have problems with your bank accounts, credit cards and insurance even if you’re an ancillary company.

This was particularly true in the early days of cannabis. We had issues securing bank accounts, obtaining merchant processing, and getting insurance. All these industries are heavily tied with the Federal government, so there was an inherent conflict in having us as customers. Keep in mind this is not all past-tense. There was a recent wave of merchant accounts canceled for some hemp or CBD proprietors. The oddity there is hemp was legalized under the Farm Bill signed in December.

2) There will be challenges in raising capital.

From the beginning of MJ Freeway, we saw an encouraging environment for raising capital. There was positive early growth, and we assumed equity investment would follow suit. We learned through hard work that our assumptions were wrong, so we had to pivot to securing bridge loans while continuing to work on equity investment. While there’s constantly news of the investment community interest in cannabis, the pipeline is still more limited than it is for traditional businesses.

3) Buckle up! This industry is moving fast.

The industry’s growth rate is at Autobahn speed with states changing legislation, as well as regulations, with great frequency. You have to be prepared to move at this rapid pace and provide your team with human and financial resources to accelerate pace.

4) You’ll get marked with a scarlet “C.”

I can be called many things — a businesswoman, entrepreneur, mom, daughter, mentor. When I joined the industry, I was instantly tarred with the cannabis brush. People in my daily life make assumptions about my use of the cannabis, instantly assuming I’m a pothead. I have to prove my professionalism.

5) Politics will have a direct impact on your income.

My livelihood is now based on the rate of glacial government change. Never in my life did I imagine I would become a single issue voter, but that one vote can mean new opportunities or protected banking options. Now, I fervently and intently invest my time in the election cycles, particularly at the state and Federal levels in addition to donating my time as a board member of the National Cannabis Industry Association to lobby for change and fair treatment at the federal level

Thank you so much for joining us!