Guest: Jessica Billingsley has learned many leadership lessons from extreme rock climbing. Currently, as Chairman of the Board and CEO of Akerna (Nasdaq: KERN), a Software as a Service ag-tech company serving the cannabis, hemp, and CBD industry, Jessica has successfully taken the company public, completed multiple accretive acquisitions, and maintained market leadership for over a decade. Before Akerna, she founded and led Zoco, a technology services firm with a diverse nationwide client base.

She has been recognized with numerous awards, including the Titan 100 CEO, Outstanding Women in Business, Inc. Top 100 Female Founder, and Fortune’s Most Promising Woman Entrepreneur. Her thought leadership has been featured in prominent media outlets, including Business Insider, Bloomberg, CNN, Cheddar, Fortune, and Forbes, in addition to her contributions to Entrepreneur and Rolling Stone publications.

Episode in a Tweet: At the end of the day, climbing, like business, is a mental game. It’s all about creating mental resilience and being able to think about climbing, not falling. In other words, playing to win, not to lose.

Background: Jessica Billingsley is one of the most inspiring CEOs I’ve met. Not only did she take the company she founded public, but she also pioneered the cannabis software industry. I met Jessica through Young President’s Organization (YPO) and have grown to admire, respect and love her as a dear friend.

During the episode, Jessica and I discuss how to get and keep more women in tech and what was like to start a bleeding-edge company and then take it public. Jessica, an avid climber, shares the most difficult climb she’s adventured upon and what she learned about leadership and growing a business from climbing. I love her description of the “sharp end of the rope.” In rock climbing, the rope attached to the lead climber is called the “sharp end.” It is the risky end of the rope, where falls are possible. This is a fun and insightful interview and I know you’ll enjoy it!

How to find Jessica:

LinkedIn: https://www.linkedin.com/in/jessicabillingsley/

Instagram: jessicabillingsley

Twitter: jessbillingsley

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