An Interview with Jess Ekstrom

CEO & Founder of Headbands of Hope

jess ekstrom

Jess Ekstrom is the founder and CEO of Headbands of Hope, a company that gives headbands to kids with cancer and funding to research with every purchase. Jess founded her company at the age of 20 and has been featured on the TODAY Show, Seventeen Magazine, Vanity Fair, Forbes and much more. But more importantly, she’s been able to donate headbands to every children’s hospital in the United States.

As a frequent public speaker, Jess travels to universities and companies across the US. She’s spoken at companies like Citrix and to tens of thousands of college students. She’s also given a TEDx talk at the University of Akron. Her book, The Freshman Fabulous: The Girl’s Guide to College, is a humorous, helpful and honest interactive guide written by a recent grad, for the future grad. It has been featured in Justine Magazine and dozens of college blogs.

Jess is passionate about the millennial generation, in particular, young entrepreneurs. She’s a regular contributor for and (Source: Jess Ekstrom’s Linkedin)

In this interview with Startup Savant, Jess shares her very inspiring entrepreneurial story and purpose. She also tells us how to overcome challenges as business owner and how to crush any fear in your way.

Jess’ advice to entrepreneurs starting a business:

My biggest piece of advice to other entrepreneurs is to not just find your ‘why’, but also keep it in clear sight. Put it in a frame, wear it on a bracelet, post it on your fridge. When things get hard, your why can get blurry. Always keep it in clear focus to help you through it.

Be sure to keep a close eye on Headbands of Hope by following Jess on Twitter! She’s making some seriously cool moves and making other millennial entrepreneurs (like me) proud.


What ignited the spark in you to start a business? Where did the idea for Headbands of Hope come from?

During the summer of 2011 when I was in college, I interned at a wish-granting organization for kids with life-threatening illnesses. I saw so many girls migrating towards headbands instead of wigs after hair-loss. Headbands gave them the opportunity to regain their confidence without hiding what they’re going through with a wig.

I started searching for organizations that provided headbands to girls undergoing chemotherapy but couldn’t find any. Therefore, I founded in April 2012 during my junior year of college. For every headband sold, one is given to a child with cancer.


What is your favorite aspect of being an entrepreneur?

I love solving problems. I once read in a book called Rework that starting a business is like having an itch. You find an “itch” that bothers you or is an issue and you create a “scratch.” Kids losing their confidence after hair-loss is my itch. Headbands of Hope, providing headbands to restore confidence, is my scratch.

When you find a social issue or a problem that needs help and you create a solution, you also understand the value of what you do a lot more than if you just pulled a business idea off the internet.

And because of that, I know that every minute I spend on my company is connected to something I believe in. Not every day is glamorous, but I can always remember my purpose and why I started.


How do you generate new ideas for Headbands of Hope to keep growing? Is there a secret that you have figured out over the years?

I think listening to your customers is key to growth. It’s important to grow as a company as your following grows. This could be developing new styles to keep up with the trends, or creating a Headband Heroes Ambassador Program to help expand our reach through story telling.

It’s easy to run your business the way you’ve ‘always done it.’ But then your followers might grow beyond you if you don’t keep things fresh.


In your experience, what is the best way to build a successful customer base? Are there any mistakes that our readers can learn from?

The great thing about Headbands of Hope is the stories behind every purchase. Social media, especially Facebook and Instagram, have both been instrumental platforms for sharing our cause and what we do. We don’t want people to just purchase a headband and get a receipt. We want them to feel connected to the impact they just made with their purchase.

We can share these stories through the individual pictures we get from the hospitals or from the families of the kids and the YouTube video we created. On our website, we have a Giving Gallery of pictures of the kids wearing our headbands.

Another important way we get our name out there is making our product shareable. People want to tell other people about their headband and where they got it. Our packaging makes it easy for our customers to plug us on social media and tell their friends and family about their purchase.


As a business owner, what is your greatest fear and how do you keep it under control or harness it?

My biggest fear is taking care of others. When you grow enough to hire people, your business is not just a part of your life, it’s a part of your team’s. The decisions you make have a direct impact on everyone, which is why it’s also important to make everyone’s voice heard at all times to stay on the same page.


Who has been your greatest influencer along your entrepreneurial journey? How did they shape Headbands of Hope?

My dad started a business when I was around 7 years old. Therefore, I was taught to think like an entrepreneur early in life and saw what it was like to pour your energy into one idea you’re passionate about.


What do you feel is the major difference between you and other entrepreneurs? Is there something that has guided you along the way?

On top of running my business, I do a lot of public speaking on college campuses about taking action and standing up for the millennial generation. Because of this, I feel a responsibility to be a role model for my generation.

When things get tough, I have a file of the hundreds of letters and messages I’ve received from students saying my story inspired them to live a life of purpose. Of course, I’m motivated by my cause and the kids we benefit, but also knowing that my story has helped inspire the younger generation to take action and responsibility on social issues really keeps me motivated to keep moving forward.


Have you faced any failures with Headbands of Hope? How did you overcome it?

Not exactly a failure, but sometimes it’s hard always being “on the clock.” As an entrepreneur, your company is 100% your responsibility. There’s no room to point fingers at anyone; everything is on you. Therefore, I feel compelled to always be connected. And in this day and age with technology, it’s easy to always be plugged in.

But always having your earphones in and email up isn’t healthy. I think sometimes we’re programmed to see people who are always working as hard workers. That may be the case, but constant work doesn’t mean constant quality. Instead, pick and choose your times when you work and put in the best quality.

One of my New Year’s resolutions was to not check email after 8 pm! I’ve also grown to a point where I could hire a team of staff so I can focus on growing the company instead of just continuing to maintain it.

I realized just running myself into the ground with work and responsibility wasn’t helping Headbands of Hope grow. Instead, I needed to focus on quality of work versus quantity and hire when it hurts. When our wholesale partnerships with stores started significantly increasing, I hired a Director of Wholesale.

However, I still do all the graphics and social media myself because that’s something I feel that I can manage and that I excel in. Don’t just hire because you can. Hire only when it hurts.


What was the best piece of advice you have ever gotten from another business owner? The worst?

Never stop learning. No matter how many successful businesses you’ve started or how seasoned of an entrepreneur you are, everyone has room to learn from each other. We also cannot keep looking to the top for guidance, we can learn from everyone we come in contact with, no matter his or her status.


What advice would you give to aspiring entrepreneurs in North Carolina who have a business idea but don’t know where to get started?

In the book Start With Why by Simon Sinek, he defines the difference between success and achievement. Achievement comes when you attain WHAT you want. Success comes when you’re in clear pursuit of WHY you want it.

It helped me realize that we need to stop seeing tangible achievements as our final destination. We can attain a new car and expensive vacations, but we can only feel success deep in our hearts, where it’s difficult to put those feelings into words.

The moment I open the door to a girl’s hospital room with a basket of headbands and see her smile, that’s when I feel my success. There’s no other way to explain it. There’s no numerical number I hit or competitor I beat. It’s just that feeling that I get where I know that all my hard work is making an impact and changing a life.

When you have a clear vision of your “why,” work doesn’t have to feel like work. My biggest piece of advice to other entrepreneurs is to not just find your ‘why’, but also keep it in clear sight. Put it in a frame, wear it on a bracelet, post it on your fridge.

When things get hard, your ‘why’ can get blurry. Always keep it in clear focus to help you through it.


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About Ryan James

Half hardworking hermit, half avid adventurer, Ryan founded Startup Savant to simplify entrepreneurship and pay it forward by donating a portion of all revenue to support children's education via