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Headbands of Hope with Jess Ekstrom (ep. 212)

Jess Ekstrom

John O’Leary welcomes Jess Ekstrom to the Live Inspired Podcast to share about Headbands of Hope and how you can start a ripple, too.

Jess Ekstrom, founder + CEO of Headbands of Hopes, has had a front-row seat in finding inspiration in frustration.

As Bernie Madoff’s great-niece, Jess channeled the embarrassment of that highly-publicized scandal into the reason she’s changing the world, one headband to a child fighting life-threatening illness at a time.

Today’s episode will warm your heart, spark motivation, and have you asking yourself, “what more can I do?”

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  • For every headband sold, Headbands of Hope donates one to a child with cancer. Since launching in 2012, they’ve donated over a half-million headbands to every children’s hospital in America and 15 countries!
  • Front-row seat to watching ambition: Jess’ mother + father inspired her in business + life.
  • Make the ask: Jess’ grandfather reminds her it’s okay to throw out the plan and ask for what you want.
  • Entrepreneur at heart: Jess got her start in business by selling American Girl Dolls on eBay.
  • “We can’t always control what happens but we can control the meaning we give to it + how we respond.”
  • The Bernie Madoff investment scandal personally affected Jess + her family, yet it taught her incredible lessons.
  • “Optimism is not about staying in your happy place. Sometimes it’s about sitting in the dark, absorbing it, and then fully coming to an understanding of what you can do about it.”
  • Inspiration from frustration. Hard times give us a choice. They can be an excuse to do less or the reason to do more.
  • “Failure will always feel better than regret”
  • “I’m not living a life. I’m building a legacy.”
  • “Every expert was once a beginner.”
  • Stay connected with Jess Ekstrom on her websiteInstagram or through Headbands of Hope.
  • Get Jess Ekstrom’s latest book Chasing the Bright Side here.

Jess + I chat about my friend and past Live Inspired Podcast guest Travis Thomas. On ep. 20, Travis shares how living “yes, and…” has shaped his life + how it can shape yours. Listen to our conversation on ep. 20.


1. What is the best book you’ve ever read? That Will Never Work by Marc Randolph.

2. What is a characteristic or trait that you possessed as a child that you wish you still exhibited today? Having no shame.

3. Your house is on fire, all living things and people are out. You have the opportunity to run in and grab one item. What would it be? A photograph of my family from a photo booth when I was a kid. It’s on my refrigerator.

4. You are sitting on a bench overlooking a gorgeous beach. You have the opportunity to have a long conversation with anyone living or dead. Who would it be? Sara Blakely, the founder of Spanx.

5. What is the best advice you’ve ever received? Say yes and figure it out.

6. What advice would you give your 20-year-old self? Just because you hear crickets doesn’t mean no one is listening. Keep putting your truth out there, keep going after what you believe in, and eventually, people will find you.

7. It’s been said that all great people can have their lives summed up in one sentence. How do you want yours to read? The girl who went for it.


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