What we talked about
Damon Lembi is the CEO of Learnit, a 3x bestselling author, former Division 1 baseball player at Arizona State, and host of The Learn-It-All Podcast. In this conversation with Federico Ramallo, Damon shares how his “all-in” mindset helped him reach 200+ podcast episodes in under two years:because for him, podcasting feels like getting a personalized MBA through deep conversations with great people.
Show notes
Damon Lembi was drafted by the Atlanta Braves out of high school, chose college instead, hit a home run in the College World Series at Arizona State, and then wasn’t drafted again at 22. The identity crisis that followed, ending a baseball career he’d built his entire life around, turned out to be the entry point into a leadership career spanning 30 years. He joined his father’s company, Learnit, as a receptionist, deliberately refusing to be placed in a senior role he hadn’t earned.
What we covered
- Lembi spent his first five years at Learnit working in essentially every position, setting up servers in classrooms, teaching classes, making cold calls, not because he was technically inclined but because he wanted to build empathy for what each team member actually did; when the CEO role opened up, he successfully argued he knew the business better than any outside candidate.
- The “athletic education” he carried from Division One baseball translates directly into leadership: in baseball, failing seven out of ten times makes you a superstar, which builds the kind of tolerance for failure and persistence that most professional environments never teach; athletes also learn to absorb feedback and implement it 30 minutes later, which is the pace of real organizational improvement.
- His framework for the Learn-It-All leader centers on four qualities he calls the four Cs, character (doing what you say and maintaining consistency, including keeping scheduled one-on-ones), curiosity (the drive to question current processes and explore how AI might improve them), courage (because learning requires stepping out of comfort zones, and learning without doing is, in his words, “treason”), and confidence (which builds incrementally as you take risks and act).
- The know-it-all failure mode he most frequently encounters in organizations is leaders who become the bottleneck: when everyone brings every decision to the founder or manager, growth stalls, strong talent leaves, and the organization stops generating new ideas, the fix is setting clear outcome-based goals and boundaries, then genuinely letting people execute.
- His children’s book, The Learn-It-All Leader for Kids, tells the story of a baseball team where the Pandas face the Oaks and a young know-it-all kid who steps into a coaching role learns that he can’t figure everything out alone; his eight-year-old daughter Lucy appears in the book as the catcher who reads books and asks questions, and his four-year-old son Wally is the relief pitcher.
- On imposter syndrome, Lembi offers a four-step framework: label your fear and think through the worst-case scenario to see if you can survive it, take the leap anyway, engage in deliberate practice focused specifically on the weakest areas (not comfortable repetition), and then in the moment of performance, let go of technique and trust your preparation.
About Damon
Damon Lembi is the CEO of Learnit, a corporate learning and development company his father founded, which he has led for 30 years after starting there as a receptionist. He is a three-time bestselling author and hosts The Learn-It-All Podcast, which reached 250 episodes within its first two years.
- LinkedIn: https://www.linkedin.com/in/damonlembi
- Website: http://www.learnit.com
Episode 88 of the PreVetted Podcast.