73: Learnit’s Origins: Damon Lembi on Family, Sports, and Building a Learning Legacy

Release Date:

Oct 9

What do you do when your big dream falls apart? Can you rebuild and come back stronger?

In this special rebroadcasted episode, “The Learn-It-All Podcast” host Damon Lembi takes the guest seat on Jeff Struecker’s Unbeatable Podcast for his “most candid conversation ever.”

Jeff Struecker is a retired U.S. Army Ranger and a true American hero, having served seventeen military tours over five wars. He played a critical role in Black Hawk Down and was named U.S. Army Ranger of the Year in 1996. In preparing for this episode, Damon wanted to be as transparent and vulnerable as possible, and the result is a powerful conversation you won’t want to miss.

In this exceptionally candid and personal interview, Damon opens up about his journey from aspiring baseball player to corporate leader and discusses how he overcame imposter syndrome, navigated the collapse of his family’s business, and copes with an ongoing life-changing health challenge. Damon’s story offers leaders valuable lessons on resilience, transparency, vulnerability and how to turn setbacks into fuel for future success. If you’re a fan of “The Learn-It-All Podcast” and want to learn more about Damon, his background, and the story behind Learnit, this is the episode for you.

What You’ll Learn:

Damon’s baseball career and the tough lessons he learned from his athletic journey
Overcoming imposter syndrome and building confidence through hard work
Navigating the collapse of a family business and finding new purpose
How to face personal health challenges with strength and optimism
The importance of leadership, transparency, and resilience in both life and business

In This Episode:

(00:00) Introduction – “The Learn-It-All Podcast” host Damon Lembi introduces this special episode, where he appears as a guest on The Unbeatable Podcast with Jeff Struecker.
(02:00) Baseball Dreams and Setbacks – Damon reflects on his journey as a high school baseball star and how he dealt with the disappointment of not making it to the major leagues.
(05:30) Imposter Syndrome in College Sports – Damon discusses his struggles with self-doubt at Pepperdine University and how his coach helped him overcome imposter syndrome.
(09:00) From Baseball to Business – Damon shares how his athletic experience shaped his approach to leadership and how he transitioned into his family’s business, Learnit.
(12:33) Navigating Business Challenges – Damon recounts the impact of the 2009 recession on his family’s real estate empire and how he led Learnit through difficult times.
(17:00) Facing Personal Health Challenges – Damon opens up about his diagnosis with a progressive eye condition and how he remains optimistic and resilient despite the challenges.
(21:30) Lessons in Leadership and Transparency – Damon explains the importance of transparency and resilience as a leader, and how he applies those principles at Learnit.
(33:18) Advice for Aspiring Leaders – Damon offers final thoughts on leadership, resilience, and how to thrive in the face of adversity.

About Our Guest:

Damon Lembi is a 2x bestselling author, the host of “The Learn-It-All Podcast,” and CEO of Learnit – a live learning platform that has upskilled over 2 million people. Drawing from his prior baseball career, Damon brings an athlete’s perspective to leadership. Through his journey, he has gained invaluable insights into what helps organizations grow, how great leaders learn, and why learn-it-all companies outpace their competitors every time.

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