Ep. 99 - Failing Epically & Pivoting Toward Progress: Pioneering an Emerging Industry - with Larisa Bolivar

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Larisa Bolivar is a long-time social justice advocate and a pioneer in the cannabis industry. Policy changes over the last few years have brought in a lot of new players looking to get a slice of the market while it’s still in its infancy, but Larisa has been in this space for two decades — and she sees an opportunity to do a lot of good in the world and create social equity after decades of targeted inequity in the communities most impacted by the U.S. drug war.

Being the first to do something is always difficult. But to forge a new path for yourself and a new industry while simultaneously trying to nurture understanding, change people’s perceptions, and guide the creation of more equitable policies — that’s a lot for anyone.

When I first met Larisa, I was head of marketing for an energy management software company and I didn’t know much about her: she worked at the front desk, was going back to school for her master's degree, and was restarting her life. She was smart, driven, and eager to learn, as evidenced by her interest and commitment in working with me and my team. 

I had no idea she was this trailblazer in the cannabis industry — or the crazy twists and turns that her life had taken up to that point.

We reconnected over the last year and I started learning more about her past and her career journey... and I was just blown away.

I wanted to interview Larisa because she’s created something totally unique — but she leveraged strategic planning principles that anyone can use to do so, often without even realizing it, and she charted this path with incredible fortitude and integrity.

Larisa is also working on a book right now, an autobiography and murder mystery to correct the historical narrative of cannabis legalization. Our interview focuses on her unique career mashup and what it took to get her there, as well as insights into the cannabis business, but I wanted to give you an idea of the Netflix Original-level drama that she’s persevered through:

The mysterious death of a mentor. The infiltration of a social movement by corporate interests. A clandestine meeting with an undercover agent who is organizing her escape.

I want to let Larisa tell this story on her own terms, and I’ll definitely let you all know when the book releases, but I also wanted you to understand just how much she has managed to overcome without sacrificing her mission or integrity.

A Non-Linear Path Driven by Unexpected Pivots Towards Progress

Larisa has quite a career mashup — one that encompasses leading multiple businesses and organizations to create change in an emerging industry.

As a consultant, hemp lifestyle business owner, and executive director of a consumer advocacy group and non-profit board, she has chosen to pursue all of these paths in parallel. But why?

Larisa says it’s the demand. “That's what's being demanded of me... I am being stretched thin and pulled in a bunch of different directions. And so what I did is I started enrolling other people. And so I have teams in each of those areas that helped me... We're just all building it as we go.”

But when you dive deeper into her story, it’s really because of her  desire to make a social impact on the world coupled with her breadth and depth of skills built over time that’s enabled her to do so. 

However, getting into the cannabis industry wasn’t a planned path. In fact, she’ll tell you that 

“initially, it was kind of like gumping my way through it. I had always been an advocate for cannabis and I've actually always been pretty anti-drug war. I myself found personal benefit from medical marijuana early on. I had a traumatic childhood because of, you know, growing up in an immigrant working class family barely out of poverty.”

She was also passionate about social equity given she grew up in a civil rights family, part Latina and part Indigenous. All of that ultimately laid the foundation for her beliefs, which eventually drew her deep into the cannabis movement. 

Yet she started her career as a recruiter staffing government contracts during the dot com boom of the mid- to late-90s. Then 9/11 happened and her situation changed.

She moved out to Colorado to follow her soon-to-be husband after he chose to start a cannabis growing business. This unexpected change in the world forced her to make that leap into the cannabis space full-time when the recruiting work dried up.

It was also a serendipitous meeting with a groundbreaking marijuana rights activist that helped her learn about the potential of cannabis to do good. He tapped into her latent desire for social justice and ultimately set her down the path she is on today. 

Failing Epically, Having a Growth Mindset, & Finding Fit 

Throughout Larisa’s career journey, she’s had to overcome some harrowing experiences, even losing almost everything she had at one point. 

“My failures were losing everything and starting my life over with $500 and half a basket full of clothes. Like literally I drove back from Colorado to Virginia with a laundry basket full of ... not clothes that you would wear in corporate America but like what you would wear growing marijuana.”

Yet she started over, went back to school (graduated with honors and got a master’s degree), and climbed her way back up to the top even though fear often got in the way. It was her perseverance and network that helped her create the traction and momentum necessary to progress. 

And Larisa will tell you that failing epically helped her curb that fear of failure. 

“I think that it has completely curbed my fear of failure, because... that fear is what gets in the way of anything. And so failing epically removed that fear. And when I say failed epically, like I failed everything, my marriage, my business. You know, everything. I lost everything and started over.

“And so, if I can do it, anybody can. I know that sounds so cliche, but seriously, it's so true. And you know, it cured that fear.”

She’ll also tell you that when she started as a young leader in the cannabis industry, she didn’t have much training or any role models to turn to. But she did have an innate understanding that she needed to grow, mature, and expand to tackle this new challenge; she had to possess a growth mindset while continuously acquiring new skills.

“I've been doing workforce development my whole career in cannabis. My whole career period, when you think about it. And so it's just such an easy fit. And then, the skills that I was missing, I sought.”

In the end, this convergence of her passions, interests, experiences, and skills ultimately enabled her to achieve this alignment and fit. She didn’t realize what the end goal was when she started the journey, but every pivot took her a little closer.

Mashup of Identities - Our Greatest Strengths, Our Greatest Challenges 

Larisa’s ethnicity, gender, upbringing, educational background, and work experiences have all shaped who she is and has given her a lot of strength.

But even with 20 years in the cannabis industry and being one of the original trailblazers, she still needs to fight to get a seat at the table. It’s what she describes as a Glass Box.

“I feel like the things that make me so dynamic and unique can also work against me,” Larisa says. “Because if I'm too loud about something, then I don't get the support I need. If I'm not loud enough, it's just very challenging because discrimination is real. And then when you're dealing with competition, you can feel the discrimination even more.

“It's not just myself. It's other women and other women of color that I see are constantly trying to make their mark and keep their mark in the space based on the things that make them themselves, and then get overwhelmed by people maybe with more capital and more media reach.”

Being a minority female, you realize that there is a higher mountain to climb. And you inevitably feel the pressure to over-perform because you innately understand the odds are stacked against you, particularly being a woman in business.

For Larisa, she continues to persevere despite the challenges, and it’s those hard as well as soft skills that she’s worked so hard to acquire that help her stay ahead.

What it Takes to Make it in the Cannabis Industry

There are a lot of myths and misconceptions when it comes to starting a business in the cannabis space, despite it being such an emerging hot industry.

Many believe it’s easy to start because of demand; ‘build it and they will come.’ But there is a lack of understanding around the policies, the product, and the process that results in many businesses failing. 

Most want the big win as fast as possible by getting out to market quickly and focusing on quantity over quality. Larisa tells us that it truly takes time and attention to build any business right, with a clear purpose and reason for being to do good from the start. It’s that long game we’ve been talking about all season.

To really make it in this industry, it comes down to having a solid sense of self, not being ego driven, and having a good strategy along the way. That means being methodical and having a plan. And for Larisa, integrity is key: “Without integrity, there’s nothing.” 

The Fluid Career System

Without even realizing it at the time, the way Larisa moved through her career, leveraging all of the skills she developed along the way, reflects the five components of the fluid career system outlined in “Building the Business of You.”

  1. Spotting the trends (internally and externally). Because you have to get a lay of the land before you can chart a course. So this includes taking stock of what’s happening in the marketplace in addition to taking stock of yourself. What are the environments you like to work in? What are the roles, skills, and interests that you have? Where do these things intersect?

  2. Creating your compass. This is really identifying the goal you want to work toward and then figuring out the approach (or approaches) to help you realize it. 

  3. Preparing for change. And that's all about dealing with that fear we all commonly have in starting something new or different, and really embracing that fear as part of the process. What is a small thing that you could just do and try to help you build that courage and confidence along the way? Hearing stories from people like Larisa is a huge help for me, personally, when it comes to preparing for change.

  4. Building your network. The relationships you nurture will have a profound impact on what paths are available to you and help you get clarity on what to be aware of or even what to do along that journey.

  5. Building your skills (hard and soft). This is continual skill development, being a lifelong learner, and Larisa reflected this during every stage of the journey that she shares in this episode. 

All together, her lived experience gave her necessary perspective on how to shape policy that promotes positive change and social equity. And when you mash that up, what you get is someone with the ability to identify and solve problems in this specific space better, faster, and more effectively than just about anyone else.

This is just a strategic planning framework. None of us are taught strategic planning and strategic thinking in school, but in today’s world of work, it’s critical because we all need to look at ourselves as a business.

Redefining Career Success - Happiness and Fulfillment

For Larisa, the satisfaction of being able to carve your own path, using her skill sets and not having to work for people has been worth all the risks. Her definition of career success since her early working years has evolved from being about the acquisition of material things to now focusing on “having the flexibility to do what I want to do and when I do it, period.”

It’s this desire to pursue happiness without obstacles — because, for Larisa, success is about working in your passion and feeling fulfilled in what you do. 

But we should all remember that having a foundational strategic plan is valuable to helping us get there.

Career Advice

  • Work where you have the most passion because that’s where you’ll be most success

Key Takeaways: 

  • We all fail and we have to because there’s no other way to learn anything. 

  • It’s critical to have clarity about who you are and what your mission or purpose is and having that integrity to stick to that regardless of the situation or potential outcome. This clarity and confidence can help you calibrate your compass so that you’re always progressing toward your goal.

  • The Fluid Career System is a strategic planning framework that you can leverage to start getting more strategic about the Business of You.

    • Spotting the trends (internally and externally). What are the environments you like to work in? What are the roles, skills, and interests that you have? Where do these things intersect?

    • Creating your compass. Identify the goal you want to work toward and then figuring out the approach (or approaches) to help you realize it. 

    • Preparing for change. Fear is part of the process whenever we do something new. What is a small thing that you could just do and try to help you build that courage and confidence along the way? Hearing stories from people like Larisa is a huge help for me, personally.

    • Building your network. The relationships you nurture will have a profound impact on what paths are available to you and help you get clarity on what to be aware of or even what to do along that journey. As Larisa mentioned, you network is your net worth.

    • Building your skills (hard and soft). This is continual skill development, being a lifelong learner.

  • To make it in the cannabis industry and any new emerging industry it takes having a solid sense of self and having a good strategy and approach to what you want to do in it. 

  • In the end, all you really have is your integrity, your work and who you are because in the end you are banking everything on that.


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Ep. 100 - Leveling Up Your Leadership From Founder to CEO - with Alisa Cohn

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Ep. 98 - Creating a Side Hustle to Build Momentum & Progress - with Nick Loper