Headbands of Hope: Changing Lives One Task at a Time

Jess Ekstrom

Jessica Ekstrom founded Headbands of Hope when she was a senior in college in 2012.  She created the company to bring joy back to kids who have lost their hair and help fund childhood cancer research. For every headband they sell, a headband is donated to a child with cancer.

Jessica was inspired to found Headbands of Hope after a summer internship at a wish-granting organization for children with cancer.  “I knew I wanted to contribute in my own way and solve a problem that I had seen with girls losing their self-esteem while going through something as traumatic as cancer. That should be the last thing that they have to worry about,” she says.

Since 2012, Headbands of Hope has grown from a one-woman show to a team of nine. The company has given tens of thousands of dollars to childhood cancer research and has donated headbands to every children’s hospital in the United States.

We sat down with Jessica to talk about what it’s like to build a “for-purpose” company as a 20-year-old, the advice she gives to students who are trying to figure out what to do with their lives, and how she uses Todoist to manage her growing team and ever-expanding responsibilities as a founder and CEO.

Creating a cause-driven company

Headbands of Hope is part of a growing “for-purpose” movement of cause-driven companies. For example, the shoe company TOMS, gives a pair of shoes for every pair they sell while the popular online eyewear company Warby Parker does the same for every pair of glasses. It’s a new way of doing business that engages customers in a cause, not just a product.

“It’s been amazing to be part of this revolution of for-purpose companies and that the line between being a non-profit and a for-profit has become blurred. I think that’s a positive thing,” Jessica says.

Creating a for-profit, cause-driven company, rather than a non-profit, gave Jessica the freedom to focus all of her time and energy on growing the business. She was able to make ends meet while promoting a cause she felt deeply about at the same time. “I don’t think you should have to choose one or the other,” she says. “Our business model has helped us reach more children and have a bigger impact.”

Having a physical product also helps engage customers in Headband of Hope’s cause. After their purchase, they have a tangible symbol of their support and are able to share the story behind it with others.  

“We live in such a sharing connected world. As the Millennial generation we really want to say ‘oh I’m wearing a headband and it gives back to kids cancer’ or ‘I’m wearing these shoes and they give one to a child in need.’  I wanted to create a very visual and tangible giving experience.” Jessica says.

headbands of hope

Lessons learned as a young entrepreneur

Starting your own company at the age of 19 presents plenty of challenges. Lack of experience and knowledge that come with being so young can make starting a business extremely difficult.  However, Jessica credits her initial naïveté for guiding her to where she and the company are today.

It’s funny because I would almost say that I was naive to the point that it was beneficial. If I had known how hard it was going to be or how many issues I would run into or what percentage of startups fail – I maybe wouldn’t have done it. I’m happy there were so many surprises along the way, and that I didn’t put too much time or research into it because that could have been detrimental to my motivation.

Four years into her own cause-driven venture, Jessica spends much of her time speaking publicly about her experiences. She goes to campuses almost weekly to speak with students and share what it’s like to have an idea and bringing that idea to fruition. It’s a way to share her knowledge and advice with students as well as build brand awareness for Headbands of Hope.

Jessica’s biggest two biggest piece of advice for students? Define what success looks like to you, don’t let others do it for you. Then stop dreaming and start doing.

In college everything is so numbers driven with your GPA, finding jobs, salary, etc. It’s easy to really get lost in the achievements part of your career. I’m not downplaying things. They’re great things to have, but focusing on them can blur the line between achievements and success. You don’t have to start a business or work for something cause-related, but when you can build a connection between what you do every day and why you do it, it can make for a more fulfilled life.

Jessica says one of her most tweeted lines is, “It’s not about what we do when we dream it’s about what we do when we wake up.”

“So much of our lives we’ve been focused on the dreams we have and not as much on the implementation – the reality of actually putting it into effect,” she says. “It’s great to have visions and to dream, to learn theory and think that way in college, but I think that there is this hesitation a lot of times to actually implement it. I just want to break that down for people and show that if you fail you fail. You’ll get back up on two feet and be better for doing so.”

Confronting failure, big and small, is an inevitable part of starting a business at any age. Average start-up failure rates can be daunting, but it’s how you deal with and manage those challenges and failures that will shape the direction of a company.

One of my favorite quotes is from the book The Last Lecture: “Brick walls are made to show how bad you want something.” It’s uncomfortable when you’re challenging the status quo and really trying to reach and grow further in your business. If everything is comfortable then you’re not doing enough. All these brick walls and challenges that come our way are indications that we are doing good, and that we are reaching further. We take those as motivations rather than setbacks.

How Jessica uses Todoist to get organized, clear her mind, and collaborate with her team

Jessica has been using Todoist for almost a year now and has made it the central hub of organization for both her work and personal life.  

With my business, and then with my speaking and traveling all the time, there are so many moving parts in my life. I was using the notes in my phone and having to delete or change things. It was hard to organize. I had tasks next to each other that didn’t make any sense. I was like ‘Man I wish I could just categorize the lists the way they are in my head.’

Then one of my fellow speaker friends asked if I had ever tried Todoist. I was a little bit skeptical, mainly because you get so many recommendations for apps and sometimes using them just makes things more complicated, but I said ‘we’ll see, I’ll try it.’ I knew just from the layout and how simple it was to use that the app was going to have a huge effect on prioritizing my lists.

I will say that I’m not a very organized person. When you’re a business owner a lot of times you’re pretty scattered, I can one minute be thinking of new headband styles for the summer and the next minute be thinking what I need at the grocery store. To be able to have that access so easily and quickly, and to be able to have it sync to both my computer and phone is so huge for me.  When I finally got Todoist my team started noticing a little bit more rhyme and reason to my thoughts because I was better able to organize and categorize them. They’re happy I got Todoist for my own personal sake, and for theirs.

Screen Shot of Todoist

Jessica’s favorite Todoist feature…

Setting a date for things. I have some tasks that aren’t very time sensitive and then others that are needed to get done by tomorrow or the end of the week and I need that reminder of a hard date. So that was really helpful.

Preparing for every meeting…

Todoist is my biggest organizer in my life. Obviously it’s huge for my own work, but it’s also amazing for meeting prep.

If I have a meeting tomorrow to discuss the next fall designs, I’ll have so many things in my head I’ll want to ask the designer. I’ll create a project that like ‘Meeting with Caroline’ and add everything as tasks there. Then when I’m on the call my brain isn’t as scattered, trying to remember things I wanted to ask or bring up.

It’s been really helpful for meetings and making sure I get all my points down. I’ll sometimes think of something at the most inopportune times or while I’m laying in bed in the middle of the night and I’ll just be able to get it all in my phone and type it into Todoist.

Using Todoist with her team…

headbands of hope

I made everyone download it. We have specific lists that we use for meetings or things like trade shows. We have a trade show checklist to keep track of the million different things we need to bring with us – anything from pens, to flash drives, to remembering the headbands. We put it all into a Todoist list so we know we aren’t missing anything.


Want to learn more about Headbands of Hope or how Jessica organizes her work and team?  Check out the Headbands of Hope website, reach out in the comments below, or follow Jessica on Twitter @jess_ekstrom.

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