Jess Ekstrom, whose grandmother is the sister of Bernie Madoff's wife Ruth, tells PEOPLE how the experience reshaped her path

By Diane Herbst
November 06, 2019 04:20 PM

Jess Ekstrom will never forget waking up one morning in December of 2008 to hear her father say the family had lost most of their life savings.

Later that day, Ekstrom, then a high school senior, discovered the family were victims of her great uncle Bernie Madoff, the mastermind of the biggest Ponzi scheme in history, an $82.3 billion global scam. “It was just one of the most outer-body experiences I’ve ever had,” Ekstrom tells PEOPLE. “It was tough to see my family experience that.”

It was especially hard on her retired maternal grandfather and grandmother — the sister of Madoff’s wife, Ruth Madoff — who were in their 70s at the time and left with nothing. Their entire nest egg, what they needed to live on, was gone.

“It was just crazy to think [Bernie] knew that this was going on,” says Ekstrom, “to have all of us and so many other innocent people invested, it was just just mind blowing.”

But for Ekstrom, now 28, the pain of Madoff’s deception turned into a unique learning experience as she watched her elderly grandparents overcome their bad fortune and start an airport ride service cab in their Florida town in order to survive.

That entrepreneurial spirit and sense of optimism was imbued in Ekstrom as she went on to college at North Carolina State. “Seeing my family go through this,” she says, “really made me start to think about what do I want to work towards.”

Jess Ekstrom and cancer patient
| Credit: Courtesy Pena Rose Studios

She quickly found her answer during an internship with the Make-A-Wish Foundation. There, she saw children with cancer losing their hair after chemotherapy treatments, and wearing headbands rather than a wig to cover up.

“I thought it would be really cool,” she says, “if someone would provide headbands to kids with cancer.”

So, at age 19, in her dorm room, Ekstrom launched a company called Headbands of Hope, which for every headband sold would donate one to a kid with cancer.

Credit: Courtesy Jess Ekstrom

As of today, Headbands of Hope has sold more than 500,000 headbands and donated another 500,000 to patients at every children’s hospital in the United States as well as in 16 other countries, according to the organization. Khloé Kardashian’s daughter True, Lea Michele and Lauren Conrad have all worn one of the beautiful styles. Sales now top several million annually through her website, over 2,000 retail stores and on QVC.

“Making that happen has been some of the most rewarding, impactful work I could have imagined,” writes Ekstrom in her inspiring new book Chasing the Bright Side.

The book includes a chapter on Bernie’s effect on her family, as well as the ups and downs of starting a business. Throughout, Ekstrom writes, she always looks for the positive — no matter what the situation.

“This was the book I needed to read when I was starting out,” she tells PEOPLE. “I was exhausted over the same success narrative that we hear all the time — this ‘one day I had this idea and the next day, my brand is in Macy’s.'”

Ekstrom reveals her “messy parts” on the path to success, including her first foray into manufacturing when she sent $10,000 borrowed from her dad to a factory to make the headbands, only to never hear from them again.

“That was devastating on all fronts, especially because my dad had been working so hard after Madoff to get back on his feet,” says Ekstrom, whose parents owned a marketing service for fitness clubs. “After that happened, I remember being like, ‘Who did I think that I was that I could do something like this?'”

But Ekstrom picked herself up and found reputable factories for production. “I think that we feel we have to fill out this checklist in order to be qualified to do something,” Ekstrom says. “But really when I got the idea for Headbands of Hope, I had no idea what I was doing. I just believed that there could be better and why not me?”

Ekstrom, whose home base is in Raleigh, North Carolina, has travelled the country since March in an Airstream with her husband, Jake Kahut, and their poodle, Ollie. Ekstrom is also a motivational speaker and creator of Mic Drop, an online motivational speaker course for women.

Jess Ekstrom with husband Jake Kahut and their Airstream
| Credit: Courtesy Jess Ekstrom

Thinking back over the 11 years since her great uncle Bernie — who at 81 is now serving a 150-year prison sentence at the Butner Federal Correctional Complex in North Carolina — Ekstrom says she “can see how the experience wrote so many different stories for my family.”

“I learned that success really is not what something looks like to others,” Ekstrom adds, “but what something feels like to you.”