How This Woman Launched a Multi-Million Dollar Company in College - Entrepreneur

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Founder of Headbands of Hope and Mic Drop Workshop, Jess Ekstrom, talks about her new interactive book Create Your Bright Ideas.
Jess Ekstrom launched a multi-million dollar company out of her dorm room in college. Today, she runs both Headbands of Hope and Mic Drop Workshop. She sat down with Jessica Abo to share how it all started and her advice for kids and teens who want to launch their own big idea.
Jessica Abo: Take us back to the early days. How did you get Headbands of Hope off the ground?
I got the idea for Headbands of Hope when I was in college. I was interning at the Make-a-Wish Foundation and I was seeing a lot of kids that would lose their hair to chemotherapy, and the immediate reaction would be to offer them a wig or to give them a hat to cover up their heads. A lot of them weren’t really concerned with covering up their heads, they just wanted something to restore their self-confidence, and honestly just feel like a kid again. I would see so many of them wearing these headbands coming into the offices or going onto their wish and I thought it was the coolest gesture of confidence that they didn’t want to hide what they were going through — they were just looking to restore their self-confidence through a simple accessory. I remember going onto Google and typing in “headbands for kids with cancer” and realizing that that was a connection that hadn’t been made yet.
The true moment you become an entrepreneur is when you are looking for something that doesn’t exist.
I like to also call that “inspiration from frustration.” When you’re frustrated about something that should exist or be better, maybe you could be the one to create it. I realized that no one had made that connection between headbands and kids with cancer yet. I call it the dumbest, smartest moment of my life, being 18 or 19 years old and thinking, “Well, why not me? I could figure something out to give headbands to kids with cancer.” This was around 2011, 2012 when TOMS Shoes was really popping off in these one-for-one models, so I decided, let me adapt that with headbands.
So I started a company called Headbands of Hope, and for every headband sold, we donate one to a child with an illness. We launched on April 25th, 2012. I remember my first order was from my mom, my second order was from my grandpa after he called me to figure out how to work the website. But little by little, I kept going with it and I kept throwing darts. I would beg college professors to let me speak in front of their class for five minutes about Headbands of Hope. But I remember the one time that we actually got traction, it was around the time when blogging was super popular and there was an article in Fitness Magazine that was top five fitness bloggers to watch.
I reached out to each one of the bloggers and told them about what I was doing with Headbands of Hope. And out of the five bloggers, two of them responded back to me, and then one of them ended up posting, and I still remember the name of the blog. It was called Healthy Tipping Point. I remember the day that she posted about Headbands of Hope on her blog. We got $500 worth of orders that day, and I thought I could retire. I was like, “Oh my gosh, $500. This is the jackpot.”
But it was one of those big turning points for me as an entrepreneur. One, I taught myself that sometimes you’re going to get a lot of no’s and all it takes is that one yes. And two, how validating it was that up until that point, anyone who had purchased on headbandsofhope.com was my mom or my cousin or my grandma who was just there to support me. But once you get that first order from someone you don’t know, it is a feeling that you can’t even explain because it just means that someone out there believes in what you’re doing and is willing to put their dollars behind it in order to buy whatever it is that you created.
Headbands of Hope, even though we’ve donated millions of headbands today, we’re the official headband provider for the NB. We’re sold in all Kohl’s locations. From the outside, it looks insane what we’ve been able to build over the past 10 years. It was crickets in the beginning. It was not fire right out of the gate. But something I love to say, and I definitely say it in Create Your Bright Ideas, is just because you hear crickets — doesn’t mean no one’s listening.
Why at this stage of the game is it so important for you to be reaching kids and teens through your book?
Junior Achievement actually did a study this year and over 60% of teens want to start their own business versus working a regular 9 to 5 job. And I think that a lot of that has to do with even The Great Resignation and watching their moms or their parents come back and maybe freelance or consult or start their own side hustle. The reality is that we’re just in a new era of entrepreneurship and in a creator economy where we can build a following on social media or start gaining traction on our ideas without a huge marketing budget. So the barrier to start is less, but that also means the barrier to scale can be harder.
Because it’s easier than ever to start and harder than ever to scale, what I think is so important for kids and teens to understand is the best ideas will scratch an itch.
If you’ve ever had that itch in between your shoulder blades that drives you nuts that you can’t reach, that’s what your idea should feel like.
When I discovered that headbands would really boost confidence with kids with cancer, but no one was providing that, that was my itch. That was my problem. Headbands of Hope, which provides headbands to kids with cancer, that was my scratch, that was my solution. And why I wrote Create Your Bright Ideas. It’s important for me to help kids and teens understand that entrepreneurship isn’t just about making a buck or having your own freedom, which I hope you do, and I hope you make a lot of bucks, but it’s about looking at the world through a lens that you could fix it. And next time you see something that you wish existed or that could be done better, maybe you can be the one to create it.
What do you hope people take away from reading your book?
I know that every generation has its own set of challenges, but looking at the past few years with kids and teens — whether it be the pandemic, being taken out of school, their extracurriculars, missing graduation, the stress of the election, or even just social media always changing and leading to a mental health crisis among teens — it’s been tough.
And one of the things that I think is so important when it comes to entrepreneurship that we oftentimes forget is that a lot of the good ideas were born in the bad because hard times give us a choice: Hard times can be the excuse as to why we do less, or they can be the reason as to why we do more. Of course, I want kids and teens to read Create Your Bright Ideas and do all of the journaling and even coloring activities (there’s even a tear-out business plan in the back of the book that they can start creating their bright ideas). But more importantly, I want them to feel like they can be the problem solvers that the world needs, that they can be the ones to make things better and that they believe that it can be them.
In fact, in the first chapter of the book, I make them sign a contract that before they keep reading, they have to believe that it could be them. Of course, I want kids and teens to read this book and start their own businesses, but more importantly, I want them to read this book and adopt the mindset of an entrepreneur, which means they’re a problem solver, they’re a creator, they’re an advocate, they’re a philanthropist, they’re looking at the world through a lens that they could fix it, whether that means starting a business or not.
If you could give one piece of advice to people out there who want to start a business, what would it be?
A few years into starting Headbands of Hope, I really wanted us to get into stores. And I had learned about this trade show in Atlanta where you could set up a booth and stores from around the world, come in and pick what brands they want in their stores. I had drained my bank account to go to this trade show in Atlanta, and I didn’t realize that there was also a seniority to booth locations. Because it was the first time I was there, my booth was literally behind the bathrooms. I couldn’t even find my own booth when I got there. I was like, “How is any buyer going to be able to find my booth?” I remember it was day two of a three-day show. I hadn’t written a single order, and I was thinking about how the heck I was going to pay for this.
I had seen out of the corner of my eye, a woman coming down the escalator. They all had these name tags on with their name and the store that they represented. Her name tag said “Ulta makeup stores,” which was a slam dunk for headbands. And I had this moment where I was like, “Should I go run after her and chase after this Ulta makeup store buyer? But what if she says no?” So I ran a quick analysis of the outcomes. I thought, “If she does say no, then I’m going to be standing right here behind the bathrooms just like I was before.” I took off running after this Ulta makeup buyer. I chased her down a flight of stairs, (I’m surprised she didn’t call security on me). I finally got to her. I launched into my elevator pitch. I think I literally took the headband off my head and gave it to her and was like, “I’d love to explore Headbands of Hope in Ulta stores.”
I got nothing from her, no response. She took the information, but I didn’t really see any pizazz in her eye. But I remember going back to the booth and realizing, “I live to tell about it. It’s okay.” And I almost felt better because I knew what the end result would be, instead of wondering what could have been, what if I had chased her down those stairs.
But four years later, four years, so on track with the next Olympics, we launched in all 1,000 Ulta stores because of that one split-second decision. It taught me a life lesson that I share in all of my speeches (someone even got it tattooed on their arm after they heard me speak!)
Failure will always feel better than regret.
And I’ll take it a step further and tell you that the aftermath of a “no” will rarely be life-ruining, but the aftermath of a “yes” could be life-changing. My piece of advice is you might as well make the ask, you might as well shoot your shot because the odds will be in your favor.
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