Making It Without Losing It: How to Stay Motivated in a World Where We Are Never Done With Entrepreneurial Success Story, Jess Ekstrom + How Jess Ekstrom Scaled, HeadBandsOfHope.com Reached the World With Her Product
Thrivetime Show | Business School without the BS
- 33m
- Transcript
Summary
Written by a model from the transcript; not yet reviewed.
This episode features guest Jess Ekstrom discussing her entrepreneurial journey, founding Headbands of Hope, and writing her book Making It Without Losing It. The guest and the host explore the hidden dangers of chasing success, the arrival trap, and how early childhood experiences and family history shaped the guest's perspective on ambition and self-worth. Throughout the conversation, Ekstrom explains how to survive success after achieving rapid growth, manage perpetual rejection in business, and transition from a spotlight speaker seeking personal validation to a lighthouse speaker focused on audience needs.
- Run the purpose test on your goals by asking if you would still pursue them if you had to remain anonymous. 7:30
- Embrace failure rather than fear, as failure provides valuable data while regret gives you nothing. 19:55
- Separate your ego from your work so that rejection of your product is not felt as a personal rejection. 22:45
- Shift from being a spotlight speaker seeking approval to a lighthouse speaker focused on audience guidance. 29:52
Chapters
- 0:00Podcast Introduction and Hosts Overview
The hosts introduce the Thrive Time Show, explain its purpose, and set the stage for the episode.
- 1:50Guest Introduction: Jess Ekstrom and Headbands of Hope
The hosts welcome Jess Ekstrom, introduce her background, and explain her mission with Headbands of Hope.
- 2:54Jess’s Early Life and Inspiration for Headbands of Hope
Jess recounts her college internship, witnessing children with cancer, and the spark that led her to create Headbands of Hope.
- 4:21The Bernie Madoff Connection and Personal Reflection
Jess shares her family connection to Bernie Madoff, the impact of the scandal, and how it shaped her understanding of success and ambition.
- 7:51Purpose Test and Redefining Success
Jess explains her Purpose Test framework, how it helps evaluate true motivations, and the importance of aligning goals with intrinsic values.
- 12:16Post‑Achievement Letdown and the Arrival Trap
Jess discusses the psychological trap of chasing milestones, the concept of the arrival trap, and strategies to stay present and curious.
- 14:09Scaling Challenges and Demoting the CEO Role
Jess talks about the shift from founder to manager, the need to demote herself from CEO, and how delegating allows focus on passion projects.
- 14:50First Sales and Early Traction for Headbands of Hope
Jess describes how her first Shopify order came from her mom, the role of blogs and word‑of‑mouth, and the pivotal moment of seeing her product in the wild.
- 19:55Handling Rejection and Building Resilience
Jess shares her perspective on rejection, choosing failure over regret, and leveraging insecurity as a strength for growth.
- 23:38Mic Drop Workshop: Empowering Women Speakers
Jess explains the origins of Mic Drop, its mission to help women secure keynote spots, and the framework she uses to coach speakers.
- 25:12Lightning Round: Quick Tips for Entrepreneurs
Jess answers five rapid questions covering outreach habits, redefining success, avoiding regretful purchases, messaging, and call‑to‑action for listeners.
- 30:38Closing Remarks and Final Takeaways
The hosts wrap up the episode, thank Jess, and provide final encouragement for listeners to act on the insights shared.
Highlights
- 2:36
Starting Headbands of Hopestory
The guest explains how interning at Make-A-Wish and seeing kids with cancer want headbands inspired her to start Headbands of Hope, donating a headband for every one sold.
- 4:27
The guest discusses discovering that her great-uncle was Bernie Madoff and visiting him to understand the human side of his catastrophic choices.
- 7:30
The Purpose Test Strategystrategy
The guest shares a personal audit called the purpose test, which checks whether you would pursue an achievement even if you had to remain anonymous.
- 10:33
The Arrival Trap Insightinsight
The guest warns against the post-achievement letdown and arrival trap, where individuals falsely believe a single milestone will solve all their problems.
- 16:41
Quantity Over Quality Startstrategy
The guest details how she gained initial traction for her startup by focusing on high volume outreach, blogging, and direct sales.
- 24:14
Less Than 30 Percent Womendata
The guest cites data showing that less than 30 percent of keynote speaking spots go to women, which inspired her to launch Mic Drop Workshop.
- 29:52
Spotlight Versus Lighthouse Speakersinsight
The guest contrasts spotlight speakers who scan audiences for approval with lighthouse speakers who focus entirely on providing guidance to the audience.
Quotes
“I started a company called Headbands of Hope for every headband sold. We donate one to a child with an illness.”
Unnamed speaker · 3:26 “And I think that looking at that time, not to say I will ever, you know, be grateful for it, but I would say it's a turning point in my life and a lot of my family's lives look a lot differently because of it.”
Unnamed speaker · 8:33 “I would say if you can reach out to one person a week, can you make that a habit?”
Unnamed speaker · 25:35 “If we have the ability to worry about the future, it also means we have the same ability to imagine a better one.”
Unnamed speaker · 28:29
About this episode
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Transcript
6,285 words · 8 speakers
Topics
- Making It Without Losing It
- Headbands of Hope
- Mic Drop Workshop
- Raleigh
- US Small Business Administration
- MakeWish
- NBA
- WNBA
- Shopify
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