The Costly Expansion Mistake That Made Damon Lembi a Better CEO

My guest for Episode #320 of the My Favorite Mistake podcast is Damon Lembi, CEO of Learnit, a live learning and development platform that has helped upskill over 2 million professionals.

Episode page with video, transcript, and more

A former college baseball player and now a two-time bestselling author, Damon shares the story of how youthful ambition and overconfidence led him to push Learnit into a rapid, unsustainable expansion during the dot-com boom. Despite his father’s cautious advice, Damon got his way—and then faced the harsh reality of a collapsing market and near bankruptcy.

In our conversation, Damon reflects on the hard-earned lessons from that pivotal mistake, including the dangers of comparing yourself to others, the importance of thinking through worst-case scenarios (what he now calls “purposeful awfulizing”), and the humility required to be a “Learn It All” leader. His resilience and willingness to grow through adversity helped him guide Learnit not only through the early 2000s tech crash, but also through the 2008 recession and beyond.

“If you’re always right, you’re not listening hard enough.”

Damon shares how his background as a competitive athlete shaped his mindset around failure, feedback, and agility—traits that now inform how he builds his team and company culture. We also talk about his podcast, The Learn It All Podcast, where he continues learning from top authors, leaders, and changemakers. Damon’s story is a powerful reminder that mistakes can be an expensive—but invaluable—education.

“Make new mistakes, learn from them, and move forward.”

Questions and Topics:

• What’s your favorite mistake?
• How did you go from playing baseball to becoming CEO of Learnit?
• What lessons did you take from your baseball career into business?
• Did you ever regret turning down the chance to play minor league baseball?
• Was anyone cautioning you against overexpanding Learnit?
• What did you learn from that experience as a young CEO?
• How did you apply those lessons during the 2008 recession?
• How has your leadership style evolved since then?
• What does “being a Learn It All” mean to you?
• What kind of people do you look to hire and why?
• How do you balance vulnerability and confidence as a leader?
• What did you learn about receiving feedback from your time in sports?
• How do you avoid letting one failure affect your next decision or meeting?
• What’s the difference between failure and a mistake?
• Can you share more about your Learn It All podcast and what you’ve gained from it?