Jess Ekstrom is the founder and CEO of Headbands of Hope, a company that gives headbands to kids with cancer for every headband sold. The company has been featured on the TODAY Show, Vanity Fair, Seventeen, Good Morning America and more. But more importantly, they’ve donated over 200,000 headbands to every children’s hospital in the United States and 15 countries. Jess is also a professional speaker, founder of Mic Drop Workshop, and curator of her positivity email series called Weekly Wink.

Thank you so much for doing this with us! What is your “backstory”?

Growing up, my dad quit his day job when I was in middle school to start his business. At the time, I didn’t realize how lucky I was to see someone chase their dream right in front of me (and be successful at at), but that definitely influenced my entrepreneurial mindset without even knowing it.

During the economy crash when cash was tighter, I got a white sheet from the closet and hung it up in my room and borrowed my mom’s digital camera and started taking product photos to sell all my stuff on eBay. I also loved clothes so I found a website where I could swap clothes with other people without paying for them.

I wasn’t the smartest kid in school or the “over achiever” but I was always thinking how I could get around things to get what I want or do what I thought was right. Little by little, an entrepreneur was born!

Why did you found your company?

During the summer before my junior year in 2011, I was interning at the Make-A-Wish Foundation. I saw so many adorable kids losing their hair to chemotherapy and they’d be offered a wig or a hat. A lot of kids weren’t concerned with covering up their heads, they just wanted something to restore their self confidence after hair loss. Therefore, a lot of the kids ended up purchasing headbands to wear instead of using the donated wigs and hats.

I looked up organizations that provided headbands to kids with cancer and realized that no one was fulfilling that need. In 2012, I founded Headbands of Hope. For every headband sold, one is given to a child with cancer.

Since 2012, we’ve donated hundreds of thousands of headbands to kids with cancer reaching every children’s hospital in America and 15 countries.

What is it about the work you’re doing that’s disruptive?

I feel that my work is disruptive because I’m helping kids with cancer disrupt their social norms of covering up their heads with wigs and hats after hair loss. Headbands of Hope allows them to stop hiding behind their illness and embrace their beauty and confidence with simple accessories.

We all need a little help along the journey — who have been some of your mentors?

My dad has been a huge help since he’s an entrepreneur, and also my biggest cheerleader. In the beginning, he taught me a lot about the nuts and bolts of business like business plans, finances, and hiring. But now as my business has evolved, he’s really taught me a lot about the mindset of business and how to handle it emotionally, because I had no idea the emotional roller coaster I was signing up for.

How are you going to shake things up next?

As a result of being disruptive through my business, I started to get asked to speak at events when I was 20. Now at the age of 27, I speak professionally over 40 times a year at conferences and business events, but I’m tired of being surrounded by males in a speaker lineup.

Therefore, I started Mic Drop Workshop, a course designed to help women get their stories heard and get paid to tell it through keynote opportunities. I want to disrupt the norm of events by empowering women to become speakers and encourage conferences to balance their lineups.

Can you share 3 of the best words of advice you’ve gotten along your journey? Please give a story or example for each.

1- Protect your energy. As an entrepreneur, there are 20 different things you could be doing at any moment in the day. In the beginning, I tried to do them all. I would say yes to every coffee meeting, yes to every networking event, yes to every collaboration and I’d find myself burning out before my real day even began. Recently I’ve tried to put more boundaries on not just my time, but my energy. It may be just 30 minutes of my time coaching you through this project of yours, but how will I feel after? Will I still be just as eager to work on my own ideas? Right now, I’m choosing to be a bit more selfish with my energy and I’ve learned that’s okay.

2- You’re tall enough for this roller coaster. I used to equate the feeling of being an entrepreneur like not being tall enough to ride a roller coaster but you sneak on and hope that no one notices. But the whole time you’re just sitting there wondering if you’re qualified to be here or if you’re going to fall off! The more I got to know other entrepreneurs personally, no matter how “successful” they are, the more I realized that so many people feel this way. So many of us feel like we’ve never “made it” or are comparing ourselves to the person standing beside us who seems to have it all figured out (they probably don’t!). So sometimes I just remind myself that I’m supposed to be here, even if I don’t know exactly what I’m doing all the time.

3- Success is not what it looks like to others, it’s what it feels like to you. Too often I’d chase different ideas and opportunities just because I thought it would look great to the public or cool to tell my friends about. But what is it really serving? A lot of times the benefits didn’t outweigh the costs…but I chased them anyway because I thought it would make me look more successful. But my success is so clear when I go into a hospital room with a basket of headbands, but sometimes it takes a few wrong turns to realize that.

What’s a book/podcast/talk that’s had a deep impact on your thinking?

Most recently, I just finished the book “Spark Joy” by Marie Kondo. Not your typical business book, but it’s about the art of tidying up. It really taught me to open my eyes to the things that we possess and what actually brings joy to us. And that mindset spread into other parts of my life too and really asking myself what makes me happy and how I feel after I do something.

Some of the biggest names in Business, VC funding, Sports, and Entertainment read this column. Is there a person in the world, or in the US whom you would love to have a private breakfast or lunch with, and why? He or she might see this. 🙂

Marie Forleo is changing the game for women and I love following her. Watching her and the tools she creates for people to pursue their dreams was a big influence for me to start Mic Drop Workshop to help women speakers. I love how she can sell her product but still feel like she’s your friend. I have a lot to learn from her and I would love if she read this!

How can our readers follow you on social media?

Instagram @jess_ekstrom and my company @headbandsofhope.


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