My Favorite Mistake — 243: Moving Mountains: How Jenn Drummond Conquered Entrepreneurship and World Peaks

My guest for Episode #243 of the My Favorite Mistake podcast is Jenn Drummond.

Episode page with video, transcript, and more

She is a Mom of seven, a successful business owner, and a World Record holder.  As the first woman to climb the second highest summits on each of the seven continents, she now spends her time inspiring others to create a thriving business and lasting legacy of their own. 

She shares her story and strategies for success through her upcoming book, Break Proof: 7 Strategies to Build Resilience and Achieve Your Life Goals, and her “Seek Your Summit” podcast, programs, and signature talks.

Great successes are often built on the foundations of past mistakes and lessons learned from them. Jenn Drummond walks us through her transformative journey, a beautiful tapestry of perseverance and the wisdom gained from failed attempts. Drummond’s story is one of relentless pursuit and thoughtful adaptation, as she has made waves as a mountaineering record-holder, a mother to seven, and a successful businesswoman.

What’s her favorite mistake? In the early steps of her business journey, Drummond confesses to falling into the typical trap of prioritizing aesthetics over function—a common mistake in the entrepreneurial world. She sheds light on how this misstep shaped her understanding of business essentials and offers a case study on the importance of prioritizing core business aspects over superficial elements. Expounding on the essence of flexibility in business, Drummond narrates how recognizing her initial plan’s inefficiency and implementing drastic changes became a turning point for her financial services company. Her story is a testament to the power of adaptability in the face of challenges, and an inspiration to hopeful entrepreneurs.

Questions and Topics:

  • When you go independent — allowed to bring your clients?
  • How did that business work out?
  • A pattern of being willing to listen to advice or new ideas
  • Later, putting life on hold until kids got into college…
  • 2018, a horrific car crash 
  • Setting a world record… climbing — tell us more about what inspired that…
  • Is Antarctica the hardest to get to?
  • Climbing mistakes? Bigger risk of physical mistakes or mental mistakes? Keep going or turn back?
  • Balancing advice vs. your own gut??
  • How was the process compared to what you expected? Did you have a “book sherpa”??
  • Tell us about your podcast, “Seek Your Summit.”
  • How do you elevate entrepreneurs to go beyond a life of success to a life of significance?