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“Take care of your people.” With Jess Ekstrom

Take Care of Your People. I used to think great entrepreneurs and business owners were successful because they were all really smart and hardworking. That may still be true, but there’s a key element even more important than hard work and brains: your team. My company would not be what it is today without the people […]

Take Care of Your People. I used to think great entrepreneurs and business owners were successful because they were all really smart and hardworking. That may still be true, but there’s a key element even more important than hard work and brains: your team. My company would not be what it is today without the people around it, and I find the most important element of my job is making sure my team has everything they need to do the best job they can — whether that’s tech tools or simply my support and trust.


I had the pleasure of interviewing Jess Ekstrom. Jess is the founder and CEO of Headbands of Hope, which 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. She’s the author of the book, Chasing the Bright Side: Embrace Optimism, Activate Your Purpose and Write Your Own Story (November 5, 2019, W Publishing), and has been featured in major media outlets such as The Today Show, Good Morning America, The View, Vanity Fair, Seventeen magazine, Huffington Post and Forbes. Jess is also a professional speaker and the founder of Mic Drop Workshop, an online course with the mission of empowering more women to share their message as speakers.


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

Mybackstory begins selling my American Girl Dolls on eBay when I was 12. That’s when my entrepreneurial spirit started to kick in… until I started selling my sister’s toys and my operation got shut down.

Then when I was in college, I was interning for a wish-granting organization and I saw that kids loved to wear headbands after losing their hair to chemotherapy. So my junior year of college, I launched Headbands of Hope. For every headband sold, one is given to a child with cancer.

Can you share the funniest or most interesting story that happened to you since you started your company?

I met a girl named Embree when I first started Headbands of Hope in the hospital. She was being treated for leukemia and we immediately hit it off. Almost six years later, she was the flower girl at my wedding!

What do you think makes your company stand out? Can you share a story?

When I first started Headbands of Hope, I barely made any sales. I was still a college student, I had no money and no idea what I was doing. But I started delivering headbands to hospitals anyway (even when I didn’t have the sales to match).

One day I got a letter from a mom whose daughter was being treated in the hospital. She said her daughter was supposed to start kindergarten but she didn’t want to. She was afraid everyone would think she was a boy because her hair hadn’t grown back yet. However, once she got her headband in the hospital, it gave her the self-confidence she needed. Her mom said she laid out her kindergarten outfit and all her school supplies and asked her when kindergarten would start!

That’s when I knew this company had to work.

None of us are able to achieve success without some help along the way. Is there a particular person who you are grateful towards who helped get you to where you are? Can you share a story?

My dad. As you’ll read in my book Chasing the Bright Side, he took a huge gamble on me and gave me a loan for my first round of production. The manufacturer I was working with was fraudulent and ran with the money. Nevertheless, he still believed in me and I’m proud to say I’ve paid him back… with $1 interest!

Are you working on any exciting projects now?

We just started creating these coloring book headbands in hospitals where kids can actually color-in these fun, patterned bandanas. It’s a great way to make the headbands interactive and tap into their creativity.

How have you used your success to bring goodness to the world?

Beyond the nature of Headbands of Hope bringing headbands to kids with cancer, I believe I’ve used the story of Headbands of Hope to bring goodness to the world. Through speaking and writing Chasing the Bright Side I’m able to show that you don’t have to know exactly what you’re doing to know that you can do it.

Do you have a favorite book that made a deep impact on your life? Can you share a story?

Marc Randolph’s That Will Never Work is the birth story of Netflix. It really goes to show that success is within all of us and you just have to be scrappy and adaptive to figure it out. I actually did a Q&A with Marc that you can see when you order both of our books here.

Can you share 5 of the most difficult and most rewarding parts of being a “TwentySomething founder”? Please share an example or story for each.

1. Use Your Resources

I started my business with a small account of funds I had saved up from my Disney World internship the year before. I never sought out investors or thought about the funding I didn’t have; I looked at what was on the table for me right then and there. Beyond money, the biggest resource I had was being a college student. As a communications major, I knew very little about entrepreneurship (it took me forever to learn how to spell it!). So, in between classes, I set up meetings and appointments with students and professors at the business school to share my idea and get their input. I started to tap every department I felt could help me: design school, textiles school, the marketing department, and the list goes on. Little by little, Headbands of Hope evolved into a strong startup because I used all the different areas of expertise that my college had to offer.

You can always come up with a list of things you wish you had, but that’s not an efficient use of time. Instead, identify what’s right in front of you and start there. You’d be surprised what you can accomplish when you’re resourceful.

2. Take Care of Your People

I used to think great entrepreneurs and business owners were successful because they were all really smart and hardworking. That may still be true, but there’s a key element even more important than hard work and brains: your team. My company would not be what it is today without the people around it, and I find the most important element of my job is making sure my team has everything they need to do the best job they can — whether that’s tech tools or simply my support and trust.

3. Show Up

When I look back on the turning points in my business, I can usually pinpoint a time where I chose to just show up. It may sound silly or simple, but opportunities won’t happen to you if you’re not there for them. It’s easy to stay at home and work from your computer, but that’s not where life happens. I used to weigh opportunities by who else was going to be there, what could I get out of it, what the expense was, etc. Now, I try to not look at things with a lens of a transaction and instead understand that it’s always worth meeting new people.

One time, I was asked to speak the last minute at a conference in Raleigh. I was busy that day but decided to show up to give a quick talk and then get back to work. Turns out, the other speaker was Marc Randolph, the co-founder of Netflix. We hit it off. Now (many years later), he serves on my board of advisors. We talk regularly. He’s been an amazing mentor and a wonderful friend.

Don’t have an agenda or a list of people you want to meet, just come as yourself and be open to opportunity. You never know what will happen.

4. When You Fall, Make it a Part of Your Dance

When you slip up, just weave it into your story. Failures don’t have to be a red light or a brick wall in front of you; consider them a pivot or an extra step.

I’ve found that people who have perfect track records usually become a prisoner of their own success. They’re afraid to take risks for fear it might mar that perfection. Because of that, they usually stay right where they are or play it safe. Safe places aren’t where growth happens.

Once, when I was in a business competition at Under Armour, I made it to the final round and lost. But when I was there, I developed a great relationship with Under Armour and we ended up repurposing their extra materials to make donated headbands for Johns Hopkins Children’s Hospital. It wasn’t the outcome of the competition I was hoping for, but it still developed into an incredible experience.

You might not always get what you want, but always look for value in the experience.

5. Remember Why You Started

Starting a company can be really, really hard. There, I said it. Starting and building my business has been the most challenging thing I’ve ever done, but it has also been the most rewarding. I’ve learned that meaningful work doesn’t mean it’s easy — it means it’s going to be worth it. Whenever times get tough, I pull up a file on my computer of all the pictures and letters we’ve received from hospitals (thousands of them) and remember why I started this in the first place. At the end of the day, success is not what it looks like to others, it’s what it feels like to you.

What are the main takeaways that you would advise a twenty year old who is looking to found a business?

Begin where you are. Don’t wait until you feel like you’ve “arrived” at a certain level of knowledge or success. Success comes to people who start.

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.

My answer to this question will always be Sara Blakely. She’s my entrepreneur idol. She makes entrepreneurship relatable, fun and empowering.

What is the best way our readers can follow you on social media?

www.instagram.com/jess_ekstrom

www.facebook.com/jessekstrom

www.twitter.com/jess_ekstrom

https://www.linkedin.com/in/jess-ekstrom-59160342/

This was very inspiring. Thank you so much for joining us!

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