How Successful People Handle Rejection with Jenn Drummond

24 Jun 2026 · 56 min
56:17

In this episode of the Earn Your Happy podcast, host Lori Harder interviews Jenn Drummond, a former finance cold‑caller turned serial entrepreneur and Seven‑Summits mountaineer. The conversation weaves through Jenn’s Midwestern upbringing, early leadership experiences (babysitter club, coaching siblings), her misguided pursuit of a medical career, and a brutal entry into sales where she survived rejection by turning each "no" into a numbers‑game and even lying to herself to stay motivated. A pivotal car accident sparked a purpose shift, leading her to pursue high‑altitude climbing as a metaphor for business and personal growth. Jenn describes her training regimen, the science of acclimatization, the mental tools she built (momentum, offensive‑defensive mindset, pre‑planned toolkits), and the importance of teams (Sherpas, family, colleagues). She shares concrete lessons from specific climbs—Ama Dablam, a volcano, Mount Logan, and Everest—linking them to entrepreneurship, leadership, and resilience. The episode ends with practical takeaways about embracing rejection, building supportive teams, and using mountain‑style perspective to navigate business challenges, plus resources for listeners to follow Jenn’s work.

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