Jess Ekstrom

April 25th will be the five year anniversary of my college startup, Headbands of Hope. For every headband sold, one is given to a child with cancer.

I was inspired to start Headbands of Hope after an internship with a wish-granting organization. I discovered kids losing their hair to chemotherapy and wanting to wear headbands instead of wigs or hats.

To date, Headbands of Hope has been featured on Good Morning America (we’ll be on again in May!), Vanity Fair, The TODAY Show, Seventeen Magazine (three times), Cosmopolitan and worn by countless celebrities. But the biggest milestone I’m most proud of donating over 100k headbands to every children’s hospital in America and six countries.

Jess Ekstrom

Sometimes when you have a business or goals in life, you’re always looking forward, and it’s hard to realize how far you’ve come. Now five years later, I look back to my junior year in college when I founded the company, and I realize I’ve learned so much. I continue to learn every day (usually by making mistakes…but we’ll get to that later) but here are five key things I’ve learned the past five years since the start of Headbands of Hope…

1) Use your resources

I started Headbands of Hope 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 even 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, 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 my college had to offer.

It’s easy to have an idea and think about what you need. You can always come up with a list of things you wish you had, but you’d be wasting your 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 supposed to be really smart and hardworking and that’s what makes them successful. That could still be true, but there’s a key element that is even more important than hard work and brains: your team. Headbands of Hope would not be what it is today without the people around it. 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, and also ensure that they feel valued and important (because they are).

Steve Jobs most likely didn’t come up with the iPod, but he built a team of people who believe in innovation and were trained to think outside the box. I’ve learned that being a leader isn’t being the smartest or having the best ideas; it’s creating a team that cultivates innovative ideas and passionate work.

3) Show up

When I look back on turning points in Headbands of Hope, I can usually pinpoint it to 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 is going to be there, what can I get out of it, what’s the expense, etc. Now I try to not look at things so transactionally and just understand that any time I have the opportunity to meet new people and learn from them, it’s worth getting up and going to.

One time I was asked to speak 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. It turns out the other speaker was Jeff Hoffman, the co-founder of We hit it off, and now he serves on my board of advisors, and we talk regularly. He’s been an amazing mentor and wonderful friend to have in my life.

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

I’m sure you can visualize what I’m referring to. 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 put a mark on their perfect path. Because of that, they usually stay right where they are or play it safe (which isn’t where growth happens).

One time I was in a business competition at Under Armour and 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 using their extra materials and repurposing them into headbands to donate to John’s 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 anything can be really really hard. There, I said it. Headbands of Hope 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.

Want to bring Jess to your campus? Learn more about her program offerings. Visit