S1 E.3 Jess Ekstrom: CEO of Headbands of Hope
In this EpisodeOn this episode, we welcome Jess Ekstrom, the founder and CEO of Headbands of Hope. As two young business owners - and especially with so many similarities between their companies’ missions - Adriana and Jess have crossed paths time and time again, so it was about time that we welcomed her onto the show.
Before getting into the thick of the episode, let’s first touch on the incredible company that is Headbands of Hope. Jess started Headbands of Hope in her college dorm room in 2012. After interning with Make a Wish, Jess realized that kids who were losing their hair often wanted headbands, but nobody was providing them. It became Jess’s mission to make children going through chemo feel beautiful during treatment, and Headbands of Hope was born. She was also inspired by TOMS Shoes to build her business on a 1:1 giveback ratio – for every headband sold, one would be donated to a child with cancer.
Throughout the years, Headbands of Hope has grown immensely, and in 2020 alone, over 600,000 headbands were donated. Even more inspiring, during the COVID-19 pandemic, Jess and the company were able to manufacture and donate masks to those who needed them.
However, the point of this episode was not to point out all of the great things that Headbands of Hope has accomplished from its inception, but rather to talk about Jess’s journey as the founder and CEO of a company, and where her life has led her since then.
Jess talks a lot about stepping back in her role as CEO of Headbands of Hope in order to make more space in her life for the things that are important to her. Aside from starting the company, she’s also taken on a variety of other career paths such as public speaking, writing, and creating workshops, all while still playing an important role with Headbands of Hope. Jess started to realize that just because she was the founder of the company didn’t mean that she had to maintain control over it; she knew that there were other paths that she would be interested in aside from the company. Jess talks a lot about taking a step back from what you once thought deserved your full attention in order to learn more about yourself and where your interests lie. Through it all, Jess recognized the importance of having a team behind you that will allow you to discover these new passions about yourself, and more importantly that will allow you to follow those passions without fear of failure.
Jess still serves as CEO of Headbands of Hope, but sees the company on a much broader scale than she did when she first started. Although it wasn’t easy for her to take a step back, she told us about something that a life coach taught her which we immediately wrote down in the notes app on our phone – she talked about finding your one personal mission. What makes Jess, Jess? What makes Adriana, Adriana? And what makes Mariah, Mariah?
For Jess, it was a central belief in helping people believe in better, and then setting out to do it. Once Jess figured out her purpose, she started to drop the balls that she was juggling which didn’t serve that mission, and started focusing more on the ones that did. That’s why she started to focus more on speaking and writing. While at one point she felt that she couldn’t juggle those passions without dropping the ball on Headbands of Hope, once she learned to trust in the team she had built behind her, and once she realized that speaking and writing were means to her passion, she was able to let go of some control of the company and focus more on what mattered a lot to her.
We also touched on navigating comparison, especially on social media, in this episode. Jess actually unfollowed Adriana on Instagram at one point. Of course, it wasn’t out of spite, but when it happened and Adriana brought it up to her, Jess told her the truth – she was comparing herself to Adriana, and she needed to unfollow her to work on herself and not focus on that comparison. What came out of this realization that she was focusing too much on what others were saying, doing, or posting, was that in the realm of social media, we only see the successes. People don’t often post about the failures of their lives, or the trials and tribulations of their business. The points of comparison that we see online are always the peaks, and never the valleys. But, Jess used this as a new way to look at how she personally wanted to present herself on social media, and how she wanted to lead her team. She wanted to start focusing on leading with flaws, because if she was going to start giving advice to others, she wanted to be coming from a place of transparency. To come from an authentic place would mean shedding light on the flaws, because that’s where we really learn, anyway. The unfortunate truth about social media is that we may always feel like we are farther behind someone else, but it’s more important to look for genuine people on platforms to look up to, rather than the picture perfect ones who we find ourselves comparing to.
Jess has been a friend to Adriana, Mariah, and Little Words Project for a long time. Adriana and Mariah always felt that they could go to Jess for business advice since their companies’ missions were so aligned, and because they knew that Jess and Headbands of Hope subscribe to the same narrative in life that the rising tide raises all ships. LWP and Headbands of Hope are special in that they aim to not focus on competition, but rather on collaboration. Once we learn to help each other out, we’re both better for it. We’re able to lift each other up, and we are so lucky to have talked to Jess on this episode. She is someone who we consider a great friend, and who we are grateful to have in our lives.
Important Times0:47 - Welcome back!
1:51 - Introducing Jess Ekstrom, CEO of Headbands of Hope
5:18 - Jess is on the line!
7:02 - A little more about Jess and Headbands of Hope
10:43 - When Adriana first came across Headbands of Hope
11:53 - Jess unfollowed Adriana?!
17:27 - From Mariah’s perspective
18:45 - Did Jess’s goal for Headbands of Hope ever change?
24:30 - How did Jess keep her fire lit for everything she’s done?
26:49 - The importance of being able to pivot & the role of the pandemic
29:37 - Making sense of your purpose
31:55 - Jess’s worst speaking story
38:37 - Adriana’s piece of advice
42:40 - Loosening the grip on outcomes
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Welcome bestie.
We’re so glad you’re here.
We’re Adriana and Mariah. Co-hosts, entrepreneurs, BFFs, and girls just like you trying to figure it out as we go.
