Voices of Athena

Sit down with the highly accomplished members of Athena Alliance, an executive learning community for women leaders, to hear the personal tales behind their professional success. We learn the real story behind their inspiring executive careers — their fears, their failures, and what song they’re singing at karaoke. You don’t get to the top without creating some memorable stories along the way.

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No Right Way to Do Life with Jessica Billingsley

Jessica Billingsley
We humans, mammals have a need for an altered state. I would say rock climbing being one of those that there’s no room when you’re up on the side of a cliff, to be thinking about, did I do the laundry? Did I email this person back at work? How might I think about solving this big problem? You’re truly present in the moment and completely switched from left brain to right brain and in that flow state. And for me, that’s been a necessary balance to the amount of left brain activity that I have going on in the rest of my life.

Music

Priscilla Brenenstuhl
Welcome to Voices of Athena a podcast highlighting the more personal side of the remarkable women that make up the Athena Alliance, a learning community for executive women. I’m your host, Priscilla Brenenstuhl, and today we are conversing with Jessica Billingsley. She is the Founder, CEO & Board Chair at Akerna Corp, the first company in the cannabis industry to list on NASDAQ. And as we’ll discover today, that’s not the only trail she is blazing…

Jessica Billingsley
Hello, good morning.

Priscilla Brenenstuhl
Good morning, Jessica. Please, will you start by telling me how would you describe yourself?

Jessica Billingsley
Oh, hmm. So I think especially as we think about through the professional lens, and what, how I want to, to work and interact and spend my productive time. I’ve always been a tech nerd. So I’ve just I’ve just been fascinated with technology and how it can change how we live, how we work, how we play. And that’s, that’s been a motivational career driver for me as well. It was part of my drive to enter the cannabis technology industry. I saw promising studies on the plants healing benefits for multiple, multiple illnesses, including one have a close family member. And, and I coupled that with a real interest in health and wellness. And that’s my are my, the company that I founded, and ultimately took public is a tech platform that creates transparency and accountability for what we put in and on our bodies. And it kind of brings together two great loves of mine this interest in health and wellness and how we live and our lifestyles with technology and how technology can change our world.

Priscilla Brenenstuhl
I love that. I think was it I think it’s you who when I looked at your LinkedIn CV, said, Called yourself a futurist. Is that true? Am I remembering that correctly? Yes. Okay, good. Yeah, I love that. And that’s a very futuristic

Jessica Billingsley
trying to sit way out in the future and say what’s gonna matter then? And especially from it through a tech lens, sometimes, sometimes you get that right. And you do know what, what is going to be different. And then there is also disruptive technology that comes along and changes everything about the way we interact with our world that we didn’t see necessarily out into the future. And so that, that to me, that’s so juicy. The what can I see? How do I be prepared for the things that I can’t see?

Priscilla Brenenstuhl
Are you equally as juiced when things like that happen in your personal life? Where you’re moving along and you think you’re understanding something or you have a belief, and you’re holding fast to that belief or idea and then suddenly it’s like, bam, just kidding.

Jessica Billingsley
It depends on what those things are. Right? And the truth about life is sometimes they’re really great things sometimes they’re not so great things. And and that’s just life. There’s no right way to do life and without those events, it would be boring. So it’s not to say that we like the hard things when they come out of the blue, but but it is the stuff of life and learning right Yeah,

Priscilla Brenenstuhl
absolutely. And I love that you said that there’s no right way of living. There’s no right way to do life, there’s no right way to do life, there’s no right way to do I think that’s the first time I’ve ever heard that. Definitely gonna keep that along for the ride for me, because I’m always thinking, I think I’m always like trying to believe that there is like a right way to do life.

Who or what inspires you and why?

Jessica Billingsley
So I think I’m gonna have to go with my mother here, she’s been such an inspiration to me. And it’s through the lens of the generational lens, and that there were only so many doors of opportunity that would open for her, but she walked through every single one that she could, and she built her own doors when needed, and really understanding that for any of us to have a career in business, we’re standing on the shoulders of our mothers and grandmothers who fought for our right for us to do that as women and seeing her demonstrate persistence, dedication, resilience, that has been foundational to my adoption of an innovative mindset. And just as we think about some, some of the challenges that our, our our ancestors faced, right, as they were trying to pave a new path forward. That helps to become a mindset for me around innovation and not taking no for an answer.

Priscilla Brenenstuhl
Okay, so picking up on just saying that the territory that you found yourself in professionally as being a futurist. Is that something that you saw for yourself when you were young?

Jessica Billingsley
I don’t know if I sought it. But I always lived out into the future of what was possible. And I mentioned Being a tech nerd and I mean, I watched Star Trek as a child. It was my entire family we get home on Friday nights watch Star Trek. And I thought I’m the future and every now and then something will come up where there’s some you know some theory that is not not collaborated that is that is just made up, if you will, that we are actually in contact with the outer worlds and every time it does, I joked my husband and like, obviously, if this were happening, they would have already come and asked me I would be the one going to other worlds.

Music

Priscilla Brenenstuhl
Jessica, what song are you singing at karaoke?

Jessica Billingsley
So I have a 15 year old daughter. And we have rehearsed Lizzo’s Good as hell

Priscilla Brenenstuhl
yeah, how fun.

Jessica Billingsley
do my hair. Check my nails. baby, how you feeling?

Priscilla Brenenstuhl
Good? Yeah, thank you. I love that. So are we going to find a video somewhere of you and your daughter getting up on stage at some point?

Jessica Billingsley
Oh, man, I hope not. But if someone ever captures it, I’ll probably put it out for the world. Because why not?

Priscilla Brenenstuhl
What is your biggest fear?

Jessica Billingsley
The obvious is, you know, something terrible happening to to my daughter or my husband, or family member in some way. But if we if we take that off the table and say that’s those are the obvious fears, then I am I’m far more afraid of failing to risk than risking and failing. Just innately I, I’m I’m afraid of not trying.

Priscilla Brenenstuhl
Can you walk me through that a little.

Jessica Billingsley
It’s so easy to want to feel safe, but nothing good happens in that safe zone. And and it’s uncomfortable and it’s challenging. But it’s that’s when you grow and you feel better afterward. And it’s a maybe a professional version of type two fun. Have you heard of type two fun. So type one fun when you’re doing something athletic, for instance, that’s fun, that’s fun when you’re in the moment when you’re doing it. Type two fun is fun after the fact. Maybe you’re not enjoying it in the moment. But the the feeling of having accomplished that, having done that, having been that scared and pushed through that feeling later the that’s, that’s what we call type two fun. It’s kind of a rock climbers term. type two fun. And I think that that exists in the professional world as well. That it’s, it’s easy to feel a little complacent. But the things that really move the needle are the things where you risk and you’re not sure if it’s going to work out and sometimes it doesn’t. But when it does after the fact that’s when you really feel that you’ve you’ve done something meaningful.

Priscilla Brenenstuhl
Is there a time in your life where you wished you would have taken a risk and you didn’t?

Jessica Billingsley
I’m a bit of an extreme risk taker. So that’s not so much on I’m sure I could think of something if I thought long enough of where maybe I didn’t take a risk most of the time. Even if I delay it, I end up taking the risk.

Priscilla Brenenstuhl
What is the most daring thing then? Being a risk taker and all that you’ve ever done?

Jessica Billingsley
Gosh, I feel that I need to tell this story just because you’re in Africa, one of the most life-changing experiences for me This is a big rock wall mountain that I climbed in Namibia with a couple of climbing partners. And it’s been a couple of decades ago. This this rock, volcanic plug just shoots out of the middle of the Namib desert. It’s called spitzkoppe. And it’s not seen very many ascents. And my two climbing partners and I went and wandered into the University of ventec. And found the professor that had established this route originally and, and got his advice on how, what we what kind of gear we might bring how we might go about climbing this and, and just to put this in perspective, it’s a 6000 feet, it’s generally would be a multi-day under undertaking to climb this, there’s a lot of risk involved. If you don’t succeed, you’re there’s no way to get back down. You once you commit to starting the climb, you must reach the summit. And my partners and I intended to do it in a a newer, light and fast style of climbing where we intended to summit within a day. We pulled that off just barely, it was a 24 hour window, we probably took 22 hours. A couple things were really interesting about this experience, I had climbed a lot of big things, I climbed a lot of really challenging things. It just to put in perspective, climbing a big piece of rock in the middle of the Namib desert. It’s not the same as climbing a big piece of rock, say in Yosemite, which is of course, famous worldwide for its climbing and its big wall climbing. You know, in new Yosemite, if you can’t get to the top, the search and rescue helicopters can just come pluck you off. When you’ve committed to that in the middle of the Namib Desert, there’s nobody coming to rescue you can either succeed or you’re not going to succeed. And we were, we were all originally from Georgia, in the United States and use to climbing and some heat. And this was in the summer in Africa. And it was, I would say even hotter than we had anticipated. In terms of the way it actually felt in heat. And I remember being in the middle of the day, the only ledge of the this entire route, six foot wide ledge and there’s one little bush on and we’re taking turns like crouching under this bush to to try to get a little bit of shade. And the hardest, the hardest pitch of the climb so pitches a rope length, and you kind of climb one rope length of time on your way up the mountain. The hardest couple 100 feet of climbing was right above this ledge. And one of our my climbing partners. Woody, it was his nickname, Tom Woodruff he was famous for having established rock climbs all throughout the southeastern United States. But by the time I knew him, he was a dad he had a little bit of a dad bod going on. And I hadn’t seen anything just super special or super impressive in our in our climbing from him. And we’re on this ledge. Our other younger climbing partner had been leading most of the the pit the the rest of the climb up until this point. And you could just see us all looking at each other asking who is going to take this next? Who’s going to do this we were all just tapped out of and and I learned then what had made what he’s so famous and it wasn’t his physical ability. It was it was that mental grit, that metal determination. He just started putting gear on his harness. And he looked at us and southern guy, big southern guy and he said y’all I’m gonna lead this next pitch and we’re gonna get to the top because there ain’t no other option I’m going to accept and what he did. He did and I and I’ve never before or since in an in a lifetime of hobby of rock climbing. I’ve never been more grateful for someone to take, we call it the sharp end of the rope. The person who goes first who takes most of the risks Placing the gear and securing the rope for the others to follow. And I, I learned a lot about what made him famous, what made him that have the position that he had? And, and if you think about it business can be a lot like that too. How are you leading the charge? And are you making sure that you’re securing the rope for others to follow? And I think about that with what my mom did lostness and I think about it with other women with my daughter, and how do we make sure that we make we make it even easier for them than it was for us?

Priscilla Brenenstuhl
Yeah, how do we understand their story, our story and the future story all at once in a way that compels us to work towards and within each other and gumption is the word I was thinking of was woody kind of that you know, leading the charge that the guttural the energy that comes from the gut, and what a powerful force that can be and the way that you’re talking about it is like you know, cinema action like I’m feeling the feels I’m there. I’m also asking myself why just a couple ever you there, what? What made you want to do that just because the crazy factor or

Jessica Billingsley
there’s a book called stealing fire has co authors, but one of the authors is Steven Kotler, and he writes a lot about flow, and the flow state. And sort of the premise of the book is that we, we, humans, mammals have a need for an altered state. And an old friend and acquaintance of mine, Dean Potter, who has since passed, he’s actually quoted in this book. And he, he talks about how some activities can put you in that flow state immediately. So you could spend a couple hours of yoga and meditation and, and and sometimes achieve that flow state. And then there are certain heightens types of activities. I would say rock climbing being one of those that there’s no room when you’re up on the side of a cliff, to be thinking about, did I do the laundry? Did I email this person back at work? How might I think about solving this big problem, you’re truly present in the moment and completely switched from left brain to right brain and in that flow state. And for me, that’s been a necessary balance to the amount of left brain activity that I have going on in the rest of my life that and need to find a way to force myself into the right brain also, and being able to live in that flow state and, and have those breaks from all of the left brain activity.and certainly climbing something like that was was and I think is the height of adventure in some ways. And as I’ve, as I’ve gotten older, I’ve tried to continue to be really thoughtful about risk and taking risks that are maybe not spitzkoppe, high, but high enough that they can be attained safely.

Priscilla Brenenstuhl
And that brings me back to the thought of what you said in altered states and even how that ties into I mean, the grounding work that you’re doing when you’re saying, okay, right foot here, left foot here, and just bringing yourself deep into presence. I don’t have a rock climbing background, but I have a very active a very strong yoga background yoga, meditation, it’s like my, my specialty. And my devote tea, I should say. And then birth work, which is all about transformation and being in the work and just like very grounding. And transformative. But that is really what I focused on to how do i breathwork and certain meditation tricks kind of taught me over time how I could summon the grounding, quicker. Like you were talking about not having to take as much time so that I could begin to incorporate the possible state those altered states in my day to day life, and in my day to day interactions, just to have the ability to slow down really even have a conversation like this where, you know, it almost is like a wrench in the system from the being on the computer in the meetings and the dit, dit, dit, dit, and then, you know, we transition, we pivot, right, if we’re using professional terms for throwing it around, pivot, pivot, pivot, I think is acting, asking you to be able to summon an altered state at a moment’s notice, in a way. And your ability to understand that and also to react and how many tools you have in your toolbox has a lot to do with like maybe how successful you’re going to be at that pivoting. So I really am. I think I’m recapping because I’m just so inspired by what you said and how it ties together. In both the professional and personal

Music
Priscilla Brenenstuhl
tell me about a life defining your life changing moment,

Jessica Billingsley
Gosh, well, maybe. Maybe I will share something a little differently. I took a risk a life defining moment, a daring moment and in a different way. By choosing to pursue a investing first into a federally illegal industry, after seeing promising studies about the medical properties and and how I thought it could help my family members condition and then I didn’t just invest. I then launched my own company to try to help ensure that those products are are safely produced and brought to market with transparency and accountability for the patients and consumers and there were a lot of other risks along the way. I took out personal bridge loans to To to find those first couple of years even though that would generally not be recommended. I just believed in what I was doing and and went on to lead Akerna to be the first cannabis technology company to list on NASDAQ.

Priscilla Brenenstuhl
Yeah. And the first female CEO. Right. Is that right is that

Jessica Billingsley
we were the first period. So then the fact that I’m female gets to be incidental, which I love.

Priscilla Brenenstuhl
Well, that is Yeah, I mean, I think that that all together, you’re like, wait, it doesn’t even matter that it’s for the first period. Exactly. Yeah, exactly. I hear that. It’s, I think it’s because like, I come back to that story I said about it being such a male LED industry, but so the fact that you were female facing, I guess for me, and being an Athena, I can’t help but notice, but like, yes, let’s get it correct. You’re the first in the whole industry, like did it first doing it? Like that’s remarkable and takes a lot of gumption? What is it like to what is it like to push forward with a belief. And so publicly, that is controversial?

Jessica Billingsley
Certainly, that has gotten a lot easier. Over the years, as cannabis has gained more acceptance. I will share that it was hardest in the early years, when my daughter was little, and other parents. Sometimes I would try not to share what I did for that I work in a niche ERP, we got to do software, which was all true. But the minute they heard cannabis, sometimes they would just assume you know that. It’s over here. smoking joints. Parenting well,

Priscilla Brenenstuhl
your children.

Jessica Billingsley
Right, right. So that was more it presented more of a challenge in my personal life than my professional life. Although certainly, still, today, sometimes professionally, I get that look of, oh, I don’t know how I feel about a vise industry. And I don’t think of it as a vise industry. I think of it as an especially the role that we play. I think I think of it as health and wellness and medical benefits and safe regulations, supply chain technology in some ways that all of that could be considered boring. It’s never been boring to me, because I thought they were compelling problems to solve. Yeah, let’s

Priscilla Brenenstuhl
take away what the product is. And talk about the process. And actually, yeah, and I love that because I mean, I definitely had that even in my experience with, you know, they call it an up trim scene. But for me, it was really, again, it helps when you you believe in it, and you have a different perspective, and you’re guided by a different perspective. I was like, you know, before it was late, I mean, legal. And I’m like, Yeah, but I’m fascinated with in general, the use of psychedelics in health care. I’m fascinated with traditional medicine. I’m fascinated with our biology, I’m fascinated with understanding the way that our bodies connect to our environment, including like the plants growing around us. And for me, it was freedom and being in a tent in the middle of nowhere for a long time, and then being able to save my money so I could travel and it was all of those things, you know. So yeah, I like I said, it’s helpful to, to have a perspective to guide you through when you’re going against the grain. I think

Jessica Billingsley
it’s true reminds me of I had lunch with a colleague this week, and he described it to me is lifestyle design. He said, I been trying to be very thoughtful in my life, about lifestyle design. And it almost brings us full circle a little bit to where we started the conversation with there’s no right way to do life and how do you want to live and changing that mindset? To not maybe necessarily being these certain goals or these certain things, but to think about how you want to design I in your life?

Priscilla Brenenstuhl
Yeah. And that it can change and pivot and grow at every moment. Like, that doesn’t mean that you are designing maybe a blueprint, even for the next 10 years, you’re saying, you’re assessing like, where am I right now? Like, right? Even right? In this moment, you notice this feel good? Like, wait, stop the track. And let me make sure that, like, what I’m laying down is actually what I want to be laying down. Maybe I’ve never even done that, like, and then what I’m seeing the track? Could be, could it be even more than that? Like, have I, you know, have I allowed myself to envision what a more scenic route or a slower route would look like, or whatever. And then it’s not a moral an indication of loss of morality or vision, or, I don’t know, all of the judgments that kind of shape how we plan our lives are live accordingly.

Jessica Billingsley
So true, so true.

Priscilla Brenenstuhl
If you weren’t doing this, what would you be doing?

Jessica Billingsley
He could have to come back to, to the the tech nerd piece. I, I’m certain I’d be involved in technology in some way. And I separately, I’ve been very interested in what I can do to address the dropout rates of women in tech. And there’s there’s actually a lower percentage of women in technology today than 25 years ago. And it’s, it’s been we there’s a lot of programs to get women into tech, but but not so many to keep them in and the statistic is 56% Drop out in the first, the first 10 years of their tech careers. And so how can we, how can we help not just encourage women to get into tech with more STEM programs, etc. But also, what does it take to keep women in tech because these are the if we think about technology is the lens that literally defines the ways in which we interact with each other in our world today. And then we need, we need 50% of the population to be working on that also. And that, to me is really important. I actually launched a corporate social responsibility campaign around this four or five years ago called The One woman challenge, with the idea being that we can and it’s it’s been steadily running, I mentor, three to four women a month I’ve a number of people have joined me in this. And the idea being that you don’t have to go start a big huge new program, start by helping one woman and one introduction, one email one mentoring session, how can we how can we provide a hand up and drop a rope down for those who are going to come next and help with the next step and I I, I love that idea. I like to think that I would somehow in taking the next step in tech be able to continue that work maybe in a in a bigger and more meaningful way. And the theory behind it being that all those little acts of helping one woman in some way which is not, by the way limited at all to women helping other women. My my male co workers have joined me in the challenge and helping helping Women Helping Women in Tech. And the idea being that all those little acts might seem like drops in a bucket but they can become the swell of real change

Priscilla Brenenstuhl
like you said technology touches every part of our lives. And if women aren’t part of the leadership for creating it and reviewing it, and it’s like our voices lost even in the in the creation of community. Our voices lost in the creation of community. And that’s so powerful. And so I think even this small bit, I mean, I would agree that the small, you say it small, but the the mentorship part, I think that it’s a small but steady actually solution. You know, just to, to help increase the interactions and the support of women who are already there surely will lead to a better environment for the women that are coming up, and more opportunities. So that’s part of, you know, why I’m enthusiastic about Athena, actually, is the mentorship in the community around keeping women in leadership and also keeping women as part of the creators of, of what story is being told for sure. Is there anything else that you poured at

Jessica Billingsley
It’s important work that Athena is doing. I agree, it’s really important work.
Priscilla Brenenstuhl
Thank you.

Is there is there anything else kind of on your mind, before we wrap up, I don’t know something that just kind of came or something that comes now a whim that you’d like to share before we close?

Jessica Billingsley
Gosh, I think that’s, we’ve had the really fun. It’s been a really fun conversation for me in a, a bit of a break from the normal work day. And I think what occurs to me at this moment in time, there, there have been some really big challenges in our world geopolitical conflict and pandemic and economic recession. And it’s, it’s a time of change, and that change is uncomfortable. And one of the things that I’ve been thinking about a lot lately for just for myself, and as I interact with my group of friends and family, etc, how do we use this opportunity, this time to build to create so that when there is a, the coming time of expansion, and opportunity, that there’s something important to to build upon to expand with to come out of that, not just to there’s no shame and hiding, hiding on the couch a little bit too but but I’ve been spending a lot of time thinking what can we be be building and preparing during during this time for for the future coming wave of expansion?

Priscilla Brenenstuhl
Yeah, I think that the sentiment that you’ve expressed so well throughout this is again, now a reframe it pivoting and transformation, and it’s always happening. And so we always get a chance and another opportunity and to be able to even know that and live with the anticipation instead of just the bog down because transformation is tough work. It’s exhausting. It can be disheartening. You can question your sanity, your lifestyle choices, you can question your neighbors you know, just all that comes up during it but to be able to hold fast and and recognize what’s possible at the other end and that that that you’re in that time right now like oh wow, I’m in these like murky waters and I get to clear a new path for myself and that might might actually be kind have cool or necessary, it’s clearly necessary at the moment because it’s happening. But it also could be a good thing. It could be cool. It’s an opportunity create something marvelous.

Jessica Billingsley
Exactly, exactly.

Priscilla Brenenstuhl
I love that. Jessica, I think you’re super cool. First of all. I just was excited. You know, professionally, I’ll say I was excited because I could tell that you were a risk taker. And we’d have a different perspective to share. And yeah, I’ve just really, I’ve had fun too. I’ve had a really I’ve really enjoyed my conversation. I really appreciate hearing your perspective. And thank you so much for sharing your time with me today.

Jessica Billingsley
Thank you for having me.

Music

Priscilla Brenenstuhl
Thank you for sharing your time with me today. Please tune in to our next episode with Chief Marketing Officer, Startup Leader, Investor and Advisor, Kirsten Newbold-Knipp.

If you are a member of Athena and would like to be featured on an episode, please reach out to me at [email protected] Your story matters.

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