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A 28-year-old founder lost $10,000 but grew a $2 million company


  • Jess Ekstrom’s family lost almost all of their life savings to her uncle, Bernie Madoff. Then, after launching her business, Headbands of Hope, she lost $10,000 to a fraudulent manufacturer.
  • She started to build Headbands of Hope — which gives a headband to a child with cancer for every item it sells — while she was in college. She leveraged school assignments to focus on her business. 
  • After her $10,000 loss, she got back in the saddle. She received a grant from her school, did door-to-door outreach, and — most importantly — reaching out to fitness bloggers for marketing help. She later started an ambassador program.
  • Today, the sum annual revenue of the company — combined with Ekstrom’s earnings from public speaking and an online course she created — is over $2 million.
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Jess Ekstrom has had two distinct experiences in her life that might have quashed anyone’s dreams of business success. 

In December 2008, when she was 17, Ekstrom — who is Bernie Madoff’s niece — awoke one morning to the news that her family had lost nearly all of their life savings through the now notorious Bernie Madoff Ponzi scheme, the largest scam in history that robbed billions of dollars from victims worldwide. 

For years, she said, “I tried to hide it as a completely separate part of my life. I didn’t want to be associated with someone who could do something like this.” 

Jess Ekstrom

Jess Ekstrom.
Jess Ekstrom

But just this month, Ekstrom has started talking about the experience for the first time with the November release of her new book, “Chasing the Bright Side: Embrace Optimism, Activate Your Purpose, and Write Your Own Story,” which devotes a chapter to her story.

“After seeing my family lose everything to my uncle Bernie Madoff, I unknowingly redefined what the American Dream means to me. I chose purpose over stability and felt this burning desire to be able to point my work to something bigger than just dollars: meaning,” she said.

The second life- and career-altering moment happened in 2012. Soon after launching her business, Headbands of Hope, which gives a headband to a child with cancer for every item the company sells, Ekstrom realized she had been ripped off by a fraudulent manufacturer — to the tune of $10,000.

The now 28-year-old shared with Business Insider how she ultimately overcame both devastations to emerge as the CEO and founder of a multimillion-dollar company that has donated over half a million headbands to kids with cancer, and according to Ekstrom has reached every children’s hospital in the US.

An internship sparks the idea for Headbands of Hope

While Ekstrom maintained that she never really thought about becoming an entrepreneur, she was still “always tinkering with something” when she was growing up. 

After discovering eBay in middle school, the then-preteen hung a white sheet in her room as a backdrop and photographed her toys with her mom’s digital camera to upload them to eBay. 

“I ended up selling my American Girl dolls for about 100 bucks and thought I had made it in life,” she said.

Around this same time, Ekstrom also benefited from seeing a family example of entrepreneurship in her dad, who quit his day job to start an email technology company for fitness clubs. 

“I saw him transform a bathroom in our house into an office and spend 10 years of his life creating a business he felt was solving a problem,” she stated.

By the time Ekstrom was in college at North Carolina State University, while she admitted that she didn’t have stellar grades, she did have a sense of confidence that she too could be a problem solver. 

She found an opportunity to put this belief into action after seeing many children losing their hair to chemotherapy during an internship at The Make-A-Wish Foundation. 

Jess Ekstrom

Jess Ekstrom.
Jess Ekstrom

“Immediately, the kids would be offered wigs or hats to cover up their heads,” said Ekstrom. “But they weren’t concerned with covering up their heads, they just wanted to restore their self-confidence after hair loss, so I saw so many of the kids wearing headbands, but yet no one was offering that.” 

With a quick Google search, she saw that there were no companies giving headbands to kids with cancer and decided to create one herself. So she spent her junior year juggling her studies with building Headbands of Hope, and officially launched the company in April 2012, at the end of her junior year. 

Utilizing school resources to launch a business

Ekstrom’s first order was from her mom, and because of her initial budget limitations the then-college student built her website by paying a computer design student in Chipotle burritos.

“It wasn’t fire right out of the gate,” she confessed. “I love to be transparent about that because so many narratives we hear today paint this facade of overnight success.” 

She described the role that college played in her startup as “more of a springboard for my business, not a barrier.”

“Whenever I had a question about something I didn’t know —how to create a business plan, how to create a logo, how to build a website — I reached out to different professors in those departments,” Ekstrom said. “The guidance I received from professors helped me build a strong foundation for my company without having to do hours of research.”

During her senior year, she began requesting from her professors that her assignments and projects relate to her business. The appeal worked, and Ekstrom was able to do double duty working toward her bachelor’s degree in communication and media studies while learning more about her company. For example, when she was given an assignment to create a media kit, she designed one for Headbands of Hope. 

“Not only did it help me to create a media kit, I was also graded and critiqued on it with professional feedback,” said Ekstrom.

A $10,000 mistake

While still in college, Ekstrom began working with a manufacturer to make the headbands that were to become the core product of Headbands of Hope. 

“I needed $10,000 to start the first round of production,” she explained. “This was a problem because I had about $500 in my bank account at the time and was still on the college ramen noodle diet.” 

After considering whether she should try to get a loan from the bank or get investors, Ekstrom’s dad stepped up to be her first investor. 

“He wrote me a check for $10,000 and I shook his hand with a commitment to pay him back as the business started to make money,” she said. 

Ekstrom walked to the bank that afternoon, wired the factory the money … and then crickets.

“I never heard from them again,” she said. “When I realized the money was gone, I remember laying in bed that night trying to close my eyes and thinking to myself: ‘How could I let this happen? I’m clearly not cut out for this. Let me just apply for a job and start to pay my dad back,'” she said.

But the almost-entrepreneur kept hitting a snag in that plan. 

“Headbands of Hope was inspired by a problem: Kids losing their hair loved to wear headbands after hair loss to boost their confidence,” she said. “So it wasn’t really about the embarrassment of failure for me, it was about this problem not being solved. That was what I couldn’t sit with.”

So Ekstrom resolved not to give up. 

“When you feel like your business is more than just a business but a vehicle to solve a problem, that’s when your resilience and grit kicks in,” she said.

Getting back on the horse to generate $2 million in annual revenue

Ekstrom began to dig herself out of the $10,000 loss by applying for a $300 grant offered by her school, and with the money bought two different types of headbands from a supplier she found on Etsy that let her buy “really low minimum quantities.” 

Once those started selling, she had a little cash to buy more headbands. 

“You have to be willing to start small and work with what’s right in front of you,” Ekstrom explained. “Ask for what you want. A ‘no’ is not life-ruining, but a ‘yes’ could be life-changing.”  

In addition to building her website by paying a computer design student in burritos, she also got her company logo by asking a graphic design teacher to have her logo creation as a class assignment, convinced the school newspaper to do an article about the business to get some traction after launch, asked sororities and campus groups if she could come in to speak and sell headbands, and went door-to-door to local stores with a box of headbands.

She identified a turning point for the company’s ultimate financial success as a simple outreach effort she made after seeing an article in Fitness Magazine in August 2012, while still in college. 

“The article had ‘5 Fitness Bloggers To Watch’ with their pictures and blog sites listed,” recounted Ekstrom. “I went to each website and found their email and reached out. I told them about Headbands of Hope and how I would love to send them some product to wear. Two of the bloggers got back to me and one posted.” 

The blogger who posted helped Ekstrom generate $500 in sales that day, which was more money than she had made in the first few months of her business. 

“Five hundred dollars doesn’t seem like a lot, but it was the first feather in my cap (or headband, if you will) that reassured me that people aren’t just buying my product because they’re friends or family, there are people out there that believe in it who don’t even know me,” she said.

After college, Ekstrom credits speaking engagements for really accelerating business growth.

“The more I spoke, the more people learned about Headbands of Hope and then would go purchase them and follow us,” she said. “We did a survey last year to see how people discovered us, and the number-two result (next to social media) was hearing me speak.”

She also launched an ambassador program. “I used social media to recruit what we now call ‘Headband Heroes,’ which are our brand ambassadors,” said Ekstrom. These people, she explained, would be given a list of tasks such as set up events, pitch to the local media, arrange hospital donations, or reach out to influencers. Each task gave them points that they could cash in for products. “It was a great way to get word-of-mouth marketing going on a low budget,” she explained.

User-generated content is one marketing tactic that Ekstrom still relies on to this day. “In the early stages, we would put a note in each order asking [the customer] to post a photo and tag us,” she said. “We asked them to share why they wear Headbands of Hope, and it turned out to be a great social media campaign that not only spread the word about us through people sharing personal experiences, but it also got us user-generated content we could share on our platforms so we didn’t have to pay for professional photos.”

Little by little, revenues climbed. “Baby steps are still steps,” said Ekstrom. “And the baby steps add up. One day you’ll look back and all the small things you did will accumulate to something really big.” 

Jess Ekstrom

Jess Ekstrom speaking.
Jess Ekstrom

Today, the sum annual revenues of Headbands of Hope — combined with her earnings as a professional speaker and from an online course she developed called Mic Drop Workshop that empowers women to share their message as speakers — are over $2 million, according to the company. 

Ekstrom now employs seven staffers, and the company offers over 200 different products — not only baby- to adult-sized headbands but also branded apparel like shirts, sweatshirts, and beanies. With all of this growth, she was able to pay her dad back for his initial loan and then some.

“I joke that I threw in an extra dollar for interest,” she said.

The Headbands for Hope founder reported that while she used to think a clear path meant you were successful, she now realizes that a clear path isn’t success; it’s safety. 

“Success is not about the absence of resistance; it’s just the navigation of it,” she concluded.


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