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“Have a sane estimate of your capabilities” With Fotis Georgiadis & Jessica Billingsley

Have a sane estimate of your capabilities. I mean that in the nicest way. When I think about my success, it is easy for me to see moments where I put my ego aside and asked for help. I am great at many things, but I’m not great at everything. The trick is recognizing the […]

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Have a sane estimate of your capabilities. I mean that in the nicest way. When I think about my success, it is easy for me to see moments where I put my ego aside and asked for help. I am great at many things, but I’m not great at everything. The trick is recognizing the talents others can bring to the table that will round you out and giving them a safe place for their talents to flourish. As an entrepreneur who has built businesses from the ground up and done every job you can think of, I know how hard this can be, but in my experience surrounding yourself with great people leads to great success.


In this interview series, we are exploring the subject of resilience among successful business leaders. Resilience is one characteristic that many successful leaders share in common, and in many cases it is the most important trait necessary to survive and thrive in today’s complex market. I had the pleasure of interviewing Jessica Billingsley. Jessica is the Chief Executive Officer of Akerna — the first cannabis compliance technology company to be traded on Nasdaq — making her the first CEO from this market to bring a company to a major U.S. exchange. Jessica co-founded Akerna in 2010 (then known as MJ Freeway), introducing the first seed-to-sale tracking technology addressing the entire cannabis supply chain. A few years later, the company would introduce the first enterprise resource planning (ERP) technology for the cannabis industry, and the first global platform for cannabis businesses. Today, the cornerstones of Akerna’s service offerings are MJ Platform®, ERP for the cannabis industry, and Leaf Data Systems®, the government compliance tracking solution. Both products track regulated cannabis — from seed to product to shelf to customer — through the complete supply chain. Since establishment in 2010, the company has tracked approximately $16 billion in cannabis sales across 14 countries and has served clients in 29 states across the U.S. Jessica is the first from the cannabis industry to receive the prestigious Fortune’s “Most Promising Women Entrepreneur Award,” is also recognized as one of Inc.’s “Female Founders 100,” and was chosen for Entrepreneur Magazine’s inaugural 100 Powerful Women list. Jessica received a degree in Communications and Computer Science from the University of Georgia and lives with her daughter in Denver.


Thank you so much for joining us! Our readers would love to “get to know you” a bit better. Can you tell us a bit about your ‘backstory’?

From very early on, I was in the camp of “if you tell me not to do something, I’m going to figure out a way to do it.” I grew up in Georgia, before the launch of girls in STEM initiatives. At 16 years old, I received a full academic scholarship to attend the University of Georgia, where I received a degree in Communications and Computer Science. I was one of a handful of women in the University of Georgia’s computer science program. I excelled academically, but my physical pursuits, like rock climbing, taught me that most limitations are mental.

Looking at my industry choice with that insight, the path I’ve taken makes a lot of sense.

I owned my own tech firm when I was invited to invest in one of the initial Colorado cannabis licensees. I believed in cannabis as an alternative medicine. I have a personal connection who is battling MS, and cannabis has proven to be efficacious for that. I also met Montel Williams at a NORML event very early on, and his personal treatment story touched me. I feel strongly, people wanted to know what they are getting with their cannabis products, and tech could provide the backbone of the industry to enable tracking, compliance, and product safety through an understanding of the supply chain of custody. That was the invention of seed-to-sale tracking and the start of MJ Platform.

I’ve always loved a good challenge, so the opportunity to apply structure, driven by innovative technology, to an emerging industry that offers medical benefits, along with social justice and counter-culture roots, was a very appealing challenge.

Can you share with us the most interesting story from your career? Can you tell us what lessons or ‘takeaways’ you learned from that?

My story as a woman technology entrepreneur and cannabis innovator comes with footnotes of stigma. It just depends on which angle you want to examine. There’s the stigma of cannabis itself, which comes with antiquated stereotypes and inadequate understandings of its medical properties. There’s also the challenge of often being the only woman in the room; women only make up 20% of executives in tech and 27% in cannabis. I really thought things were changing for women in that regard. I held a true belief as a young professional that the tide had turned, but, as a professional with 20-year’s experience, I can objectively look back to say it hasn’t gotten any better. We have a lower percentage of women in tech today than 25 years ago, which means we are going in the wrong direction. We, as a society — not just women — need to be thoughtful about how we progress again.

What do you think makes your company stand out? Can you share a story?

Akerna is a stand out in many ways. We are the first compliance technology company in the cannabis space traded on Nasdaq, and that’s just the latest milestone accomplishment for us. We are the first company to bring an enterprise resource planning product specifically for cannabis, called MJ Platform, to support transparency and accountability at scale in a rapidly growing market. We were the first cannabis technology company to expand internationally. Most recently, we extended office locations to Colombia in addition to our offices in Denver, Vancouver, and Madrid. Our international portfolio includes 14 countries, and we’ve tracked $16 billion in worldwide client sales.

We’ve successfully innovated for almost ten years by casting vision for the future. We hone in and truly understand the problems the future holds so we can build tomorrow’s solutions today. It’s a deliberate approach that enables us to rise above the mire of consuming issues and stay focused on opportunity, which supports our growth and the industry’s success.

Akerna is unique in its technology mission in that we are building technology that through robust data tracking and accountability across the entire supply chain, brings an unprecedented level of transparency and visibility to businesses and consumers. The kind of transparency and visibility consumers are demanding more and more from the products they consume. And the kind of accountability and visibility that drives better compliance and public safety for governments. We — Akerna and MJ Platform — are inventing technology that will, ultimately, be repurposed from cannabis to other industries like agriculture.

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?

My parents are entrepreneurs who have led by example in so many ways. My mother supported our family of 5 as a professor of nursing while my father started their business nearly 40 years ago. When the business became more successful, she left her promising career path to join him as an equal partner (both in equity and responsibility) in building their business. Growing up with entrepreneur parents always shone a light on an alternate path where you can create your own destiny and build the company at which you want to work every day.

Ok thank you for all that. Now let’s shift to the main focus of this interview. We would like to explore and flesh out the trait of resilience. How would you define resilience? What do you believe are the characteristics or traits of resilient people?

That’s an interesting question. Being first takes a real commitment to lead where there is no path to follow and certainly no guarantee of success. And for a woman CEO in tech, in cannabis, and now publicly-traded, I’m out at the bleeding edge of the leading edge. What I’ve learned about leading on the bleeding edge speaks to resilience. I’ve learned these lessons from rock climbing where it comes down to Mental Grit, Problem-Solving, and Determination.

For those who aren’t familiar with rock climbing, the person leading the climb is said to be taking the sharp end of the rope. The “sharp-end” refers to leading the climb, where most of the risk lies, often climbing many feet above your gear and risking big falls. Rock climbing is primarily a mental challenge. Yes, it takes physical strength, but what great climbers really have is the mental grit to go vertical up thousands of feet with very little in the way of a safety net. Falls have the potential to result in a bad injury — think broken back or cracked skull type bad — or worse, death. As leaders, many of us are out there, at the bleeding edge, and what can separate success from failure is the Mental Grit to block out the noise and trust yourself.

Now, I rock climbed primarily for several years after college and considered making a professional career of it. I led many climbs at the sharp end of the rope where I learned, if you focus on what is wrong, you’ll fall. Period. You must focus on the climb, on progressing by solving the problem. You must read the route correctly and make the right moves. You can only do that if you are always thinking in solutions. You CANNOT make those moves if you’re thinking about the consequences. You can only make forward progress if you’re focused on the positive result and outcome. There’s no space to hold any anxiety or to consider what happens if you fail. As we say in climbing, “Don’t think about falling; think about climbing.”

Finally, never underestimate the importance of determination. I’ve seen it, dangling off the side of a cliff, arms pumped out and still a quarter of the way to go before you reach the top. Some people quit, they just give up, but to reach the top, to be the first in business, you have to push away the doubt, push away the detractors and be determined to get to the top. If it were easy, someone would have done it already. It’s unlikely you thought of the idea first. But being the first to execute is where the magic lies. You will encounter a lot of challenges in your quest to be first. Being resilient means being determined. Failure will never overtake you if your will to succeed is strong enough. Shake out your arms. Focus on your goal. Climb on.

When you think of resilience, which person comes to mind? Can you explain why you chose that person?

I mentioned my parents’ general contracting business previously. There was a time when I was in high school when we were “losing our shirts” on a big job just outside of town, and the business’s future was in jeopardy with default and bankruptcy looming on the horizon. My dad was heading to visit that job site after a day at the office on Friday afternoon. As he was driving out of town toward the more rural job site, traffic was completely stopped on the two-lane highway for an overturned Mack truck in a ditch on the side of the road. All my dad could think was, “At least that’s not our truck in the ditch.” Unfortunately, as traffic crept closer and he could make out the decal on the side of the truck, he realized it was his truck in the ditch. It was a low point for their business, and I focused hard on looking only at colleges where I could win a full academic scholarship. Watching my parents somehow separate work from home life and rise strong from that year to thrive in business again was a lesson for me in patience, perseverance, and grit.

Has there ever been a time that someone told you something was impossible, but you did it anyway? Can you share the story with us?

When I was doing the coursework for my computer science degree, we were assigned to write a computer software program that would play virtual 4 square, which is just a touch easier than writing a program to play say chess or checkers. The students’ programs would be played against each other and would be graded on a perfect bell curve based on how often your program won. The program was a specific assignment to write a recursive algorithm; however, I thought there was a much cleaner, logic-driven approach to solving the problem. I asked our professor if I could write the program without using recursion, and although he told me it was impossible, he said we would only be graded on results. I wrote that program in less than an hour while classmates spent weeks writing theirs, and I got an A, winning the most against other programs. It’s important to remember that creativity, diversity, and different points of view are critical to solving our most important business problems as well.

Did you have a time in your life where you had one of your greatest setbacks, but you bounced back from it stronger than ever? Can you share that story with us?

In 2011, after experiencing 800% YOY growth in revenue between launching our seed to sale software and its second year of sales, we were turned down for equity financing. And I mean turned down by EVERYONE. We had several very promising term sheets, but when we got further into definitive documents, someone’s attorney or accountant would shut the investment down. I was left with few options. I had already foregone a salary for 1.5 years. I decided I truly believed in the company’s mission and growth prospects, and I took out loans that I signed for personally to continue the company’s operations. I managed to turn the company profitable by 2012, in record time, and pay back all loans in full by 2013.

Did you have any experiences growing up that have contributed to building your resiliency? Can you share a story?

There’s nothing that hits as close to home as when someone has a serious illness. Supporting someone with a longterm, chronic illness puts most of life’s other challenges into perspective and builds the muscle of resilience for everything else. Having a mission for what you do every day helps you to rise strong from setbacks as well. In my case, my mission is related to providing healing benefits to millions of patients, product and supply chain transparency, and accountability that supports research and data that prove outcomes that change lives every day. Early in Akerna’s life, I met an MS patient at one of our clients. When I met him, after just six months of cannabis, he had gone from being wheelchair-bound to having run a 5K. Having a mission that compelling helps me continue through the tough times. For me, the mental shift that works is to think that I am not doing this for myself but to think of all the other people’s lives that are impacted.

Resilience is like a muscle that can be strengthened. In your opinion, what are 5 steps that someone can take to become more resilient? Please share a story or an example for each.

Five steps. First, and this is going to sound totally Colorado, I think you need to take time to be quiet, focus your attention and meditate. I’ve practiced Yoga for many years, and through my practice, I can quite my mind, center my energy and gain clarity. I recommend mediation.

Second, I am fortunate to be part of the Young Presidents Organization. YPO is a global leadership community of chief executives driven by our belief that the world needs better leaders. I understand not everyone can be part of an organization like YPO, but every leader can make a conscious effort to surround themselves with people who can make them better. I’m talking about mentors, teachers, advisors who can help us grow stronger, and we, in turn, can help.

Third, define your mission and never lose sight of your vision. I think so often we can get distracted by all the noise and the naysayers that we can forget, the idea we started with was amazing. I encourage the idea of getting clear about what you want to do and why. Write it down, carry it around with you, and when in doubt, pull it out to remind yourself of your purpose and to motivate you to keep moving forward.

Fourth, have a sane estimate of your capabilities. I mean that in the nicest way. When I think about my success, it is easy for me to see moments where I put my ego aside and asked for help. I am great at many things, but I’m not great at everything. The trick is recognizing the talents others can bring to the table that will round you out and giving them a safe place for their talents to flourish. As an entrepreneur who has built businesses from the ground up and done every job you can think of, I know how hard this can be, but in my experience surrounding yourself with great people leads to great success.

Fifth, take time to celebrate. It may seem obvious, but far too often in the drive to succeed, we can forget to stop and celebrate the little wins. I have a member of my team that closes staff meetings by asking each person, “What’s the one thing you’re proud of?” The idea is to stop and think and for one-moment share gratitude, share joy, and recognize something good.

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. 🙂

Thank you. As a person of great influence, the movement I hope I am inspiring is #StoptheDrop. I want to reverse the growing decline of women in tech. It’s appalling to learn there’s a smaller percentage of women working in tech today than 25 years ago. At Akerna, we launched the #OneWomanChallenge to empower women in their careers and to keep more women in Tech. Please learn more about the #OneWomanChallenge on our website and social pages and get involved.

We are blessed that some very prominent leaders read this column. Is there a person in the world, or in the US with whom you would love to have a private breakfast or lunch with, and why? He or she might just see this, especially if we tag them 🙂

Two come to mind, Safra Catz, Oracle co-CEO, she has helped to lead Oracle’s acquisition strategy and Amy Hood, CFO, who has done so at Microsoft.

How can our readers follow you on social media?

You can follow Akerna on Twitter @AkernaCorp, you can follow me at @JessBillingsley. We are also on Facebook and Instagram.

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

Thank you!

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