Chasing the Bright Side

“We feel like we have a tug of war between passion and profit, but what if we found a lane where we could do both.”

-Jess Ekstrom

Her Story of Success…

Jess Ekstrom , Founder & CEO of Headbands of Hope. For every item sold, one headband is given to a child with cancer, and to date has donated half a million headbands to children’s hospitals in 16 countries around the world, including every children’s hospital in the United States.

Jess has been featured in major media outlets such as Entrepreneur, Forbes, the Today Show, Good Morning America, Vanity Fair, and Huffington Post. Jess is also a professional speaker and the founder of Mic Drop Workshop, which is an online course with the⁠ mission of empowering more women to share their message as speakers. She currently is living in an Airstream, traveling America with her husband and their 70-pound poodle, Ollie. Otherwise, they call Raleigh, North Carolina home.⁠

Jess joins Leah in the Nashville studio for a fun conversation about the humble of Headbands of Hope, why she started a social enterprise instead of a nonprofit, and some of the lessons learned from her book Chasing the Bright Side

They discuss some of the challenges Jess faced growing Headbands of Hope, how she redefines what entrepreneurship means, and how she is passionate about humanizing the hustle of success and normalizing the mess in the middle. 

Jess tells the story of hearing Blake Mycoskie from Tom’s Shoes speak and how he inspired her to believe that we don’t have to choose between making a living and making a difference.  

She shares how taking improve classes helped her look at life in the expansiveness of possibilities instead of just making strategies and plans, and that some of the turning points in her life happened because she said yes and showed up. 

Jess also shares how the process of writing her book Chasing the Bright Side was a humbling experience of receiving that kind of feedback. She said the rough draft of your book isn’t supposed to be perfect,and that message helped her realize it is true in life too. 

Through Chasing the Bright Side, teaches us how to “Believe in Better” and then go create it. We hope you enjoy this conversation! 

Sponsored By

Today’s episode is sponsored by Givful,philanthropy company that provides employers the ability to engage their workforce through volunteering and giving, helps nonprofits raise funds and awareness, and makes individual giving simple and fun though their technology platform. If you are looking to enhance your corporate giving or community involvement strategy, you can find more information at

Nonprofit spotlight

Girls Inc.- Inspiring all girls to be strong, smart, and bold. 

Their programming focuses on the development of the whole girl. A combination of research-based programming, long-lasting mentoring relationships, and a pro-girl environment that equips girls to lead fulfilling and productive lives, break the cycle of poverty, and become role models in their community. You can find more information at