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Entrepreneur Jess Ekstrom On Her Start-Up Success, Running A Business Remotely, and Spreading Hope

Headbands of Hope has donated more than one million handmade headbands to sick children in hospitals right across the United States.

At 10 years old, the North Carolina State graduate recalls the moment her dad, Richard Ekstrom, announced to the family he was leaving his day job to launch his own company.

“I had no idea what it really meant to start a business [at the time]. But I saw him pour everything he had into this idea. He renovated our upstairs bathroom into his office.

“And so I feel like I had a front-row seat to watching someone go for it,” Jess tells Canva.

Years later while studying communications as a junior in college, Jess spotted an opportunity to begin her own business journey. And she went for it.

“I was interning at a wish-granting organisation, and I saw a lot of kids that were losing their hair to chemotherapy and they’d be offered wigs or be given hats. And a lot of them just wanted to feel like kids again and wear headbands after losing their hair. But no one was providing that.”

Jess’s Business Idea Breakthrough

Jess’s company, Headbands of Hope, was created late one night on her dorm room floor.

For every headband sold, a headband is donated to a child with an illness. “I call it the dumbest-smartest moment of my life,” she recalls.

In true entrepreneurship style, Jess rallied her friends, family, and university to get behind her start-up idea.

“I remember my first order when I launched Headbands of Hope was from my mom, and my second after that was from my grandpa after he called me to figure out how to work the website,” Jess says.

Today, Jess, 30, is the CEO of Headbands of Hope that now employs over 10 staff, and has donated more than one million handmade headbands to sick children in hospitals right across the United States.

Starting Inspired With Canva

Starting out as an entrepreneur, Jess admits building a business from the ground up requires what she calls “hustle muscle”.

“To say I started Headbands of Hope from scratch would be an understatement. It was as scrappy as they come in the beginning. And being a one-woman show, when you have this idea, you have to wear all the hats, or all the headbands as I like to say, and I really didn’t have any design experience.”

Designing With Ease

Global visual communications platform Canva became an essential tool to empower Jess and her team to share the Headbands of Hope story by designing on-brand social media posts, videos, and presentation documents, and thank you cards, “spreading hope” to sick children and their families across the globe.

“Being a small business, every dollar we spent mattered. To have a tool like Canva to create high-quality designs without the high ticket price was a game-changer,” Jess says.

With her team spread out across the U.S, Jess also admits Canva’s real-time collaboration capabilities has made it faster to connect with her staff and approve designs in real-time.

“Before Canva, it would take weeks to go back and forth to create one design, and then one small tweak would be another few days. As a small business, we need to be able to move and pivot quickly. Canva allows us to do that.”

And Jess really is living the entrepreneurial dream. Today, she operates her business while working remotely from her Airstream, travelling across the U.S with her husband, Jake, and their poodle, Ollie.

She credits Canva for enabling her the flexibility and ease to run her company from the road.

“We’re able to collaborate, work from anywhere, and make these incredible designs from wherever we are, so we’re able to continue to tell our story at Headbands of Hope.”

Jess’s Main Mission

And while Jess’s primary goal is to spread hope and confidence to sick children with illnesses, one headband at a time, she’s also driven by another mission: inspiring the next generation of entrepreneurs.

Jess, who’s also an established keynote speaker and author, also mentors female business leaders through her online course, Mic Drop Workshop, coaching them to overcome their fears of public speaking.

“I equip women with the tools they need to be thought leaders in their space. Women deserve to be seen and valued as experts, and kids need to see representation in leadership to know what’s possible for them,” she says.

Jess’s top three tips for future entrepreneurs?

Start now. “You’re never going to be ready, so you might as well just start when you’re inspired. Because, when I think about my day one, and how little I knew compared to what I know now, I’m so glad that I just went for it,” she says.

Stay focused. “Don’t worry about winning the Super Bowl, just get the first down. Because when you run a business you can think of all the big things ahead that you want to do and it can really distract you from the things that are within your control that you can do today”.

Back yourself. “One of the biggest lessons I’ve learned is that nobody knows what they’re doing. In fact, every expert was once a beginner. So everyone that you know that is so good at something once had no idea what they are doing. So if it could be anyone, then why not you?”

Giving Back To Others

Reflecting on her company’s early days, Jess recalls a touching letter she received that gave her the confidence to see her mission to help others was set to succeed.

“I gave a headband to a young girl in hospital. She was kind of shy. And then I got a letter a few weeks later from her mom saying that [her daughter] was in remission but her hair still hadn’t grown back yet. And up until that point she didn’t want to go to kindergarten because she was afraid of how she looked.”

“After that meeting, she went home and laid out her school supplies, and she was like ‘Mom, when are we going to kindergarten?’. And so, at that moment, reading that letter I was like, this is gonna work.”

“I founded Headbands of Hope on this idea that I wanted to show people that one small thing can make such a big difference in someone’s life.”

“And I hope that, what my dad was for me as an example, I could be for other people who want to start a business.”

Jess Ekstrom is one of three Canva community members appearing in the company’s ‘With Canva, you can’ campaign.

Written by

Mel Cornford

Mel Cornford is Canva's Community Stories Editor


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