Ep #11 | Giving Back Isn't a Trend Anymore, It's an Expectation


Jess is the founder and CEO of Headbands of Hope, a company she started as a junior in college in 2012. For every headband sold, a headband is given to a child with cancer. The company has been featured on the TODAY Show, Vanity Fair, Seventeen, Good Morning America and more. But more importantly, they've donated over 100,000 headbands to every children's hospital in the United States and 6 countries. Jess is also a professional speaker, author, and writer for Entrepreneur and The Huffington Post.



Shantel: Hey, Jess. Welcome to the show.

Jess: Thanks for having me. Happy to be here.

Shantel: Yeah. Of course. I am so excited to dive into your adventure and your story. If you could kick us off with telling the listeners a little bit more about Headbands of Hope and your journey, that would be great.


Jess: Yeah. I started Headbands of Hope when I was actually a college student at North Carolina State University. I was interning for the Make a Wish Foundation. I saw a bunch of kids that were losing their hair to chemotherapy. They'd be given a wig or a hat, something that was basically telling them to coverup their heads. But I found a lot of them weren't actually concerned with covering up their heads after hair loss. They just wanted something that could restore their self-confidence. I saw so many of the kids wearing headbands and no one was providing that. When I was 19, the end of my junior year, I founded Headbands of Hope. For every item sold, we'd donate a headband to a child with cancer.

Shantel: That's amazing. Was that your first stab at entrepreneurship? Or, were there other ventures before that when you were growing up?

Jess: I had my eBay days for sure.

Shantel: Okay.

Jess: I remember when I first discovered eBay, I think I was middle school, high school. I was just finding anything I could around the house. I was selling my American Girl dolls. I was pulling things out of my sister's closet. She got really mad about it and shut down my business. But that was the first time I got a taste of it. Growing up, I saw my dad start a business. He was an entrepreneur. It was something that made me feel like that was possible for, which I'm really fortunate of because I don't think enough people are in that close a proximity to entrepreneurship.

Shantel: Absolutely. Was he a big cheerleader for you when you started the company?

Jess: Oh, yeah, for sure. I would say he never said I should start a business. It was more just about raising my sister and I to just want to solve problems in whatever way that meant. For me it meant starting a business. For my sister, she does wilderness therapy and leads trips and basically lives in the woods.

Shantel: That's amazing.


Jess: Yeah, which is really cool. Whatever way that made sense for us, it was just about leaving the world a little bit better than how we found it. That was more of what entrepreneurship was taught to me. Not so much in the business sense, but more in the creating what I wish existed.

Shantel: Neat. Okay. Well, I'd love to dive a little deeper into Headbands of Hope and the team dynamics. Over to 19 and you're still very young. But over the few years that it's been in business, how have things changed? What does the dynamic of the team look like now?

Jess: Yeah. It started out when I was just trying to get my footing. I had a bunch of friends at different universities, and I wanted them to help me get the word out. I slapped together a campus ambassador program just so I could recruit my friends to help me. Now it's actually called our Headband Hero Program, and we have over 600 heroes at not just campuses but in different communities throughout the world actually, which is pretty cool. But beyond that, one of first people I ever hired who's still with me today was my freshman year roommate. The next hire was a girl who was in my orientation. It was one of those things that because I was a college student, there was so much excitement and energy around me. I think that the structure of Headbands of Hope, the culture that we have, a lot of this, this was our first job. This was the first thing that we did. Even though we're not all coming in with different experiences and different things under our belt, we all had this one common thing that came after college, which was following this dream and this business.  Just trying to figure it out along the way, which sometimes works and sometimes doesn't.

Shantel: That you guys essentially are creating the culture that you want and what makes the most sense for your dreams and aspirations. I think that's great.

Jess: Yeah. Yeah, it's been great.

Shantel: Hiring-wise, I imagine you got just extremely lucky with having some close people around you that were interested in it, too. Have you hired anyone externally that you didn't know when you were growing up?

Jess: That's a good question. I have before and it didn't work out so great. But I'll also say that about hiring someone that I know. Sometimes you just don't really know how someone acts in certain situations, and how they can think on their feet. An interview or a LinkedIn profile or a resume is really just skimming the surface of a person and not really getting into the core. One of things that we really do now is we use our Headband Hero program almost as a vetting or scouting process if you will for talent. People who are a Headband Hero and really standing out amongst the crowd who are working with influencers, arranging a bunch of donations, maybe securing some media and really standing out, we discuss what that might look like in a bigger capacity with them.

Shantel: That's a great recruitment tool for future teammates.

Jess: Yeah. It's great to see someone in real scenarios and how they respond and not just what they say they're gonna do.

Shantel: Definitely. At the beginning when you were figuring out the designs of the headbands, was it you crafting them? Or, would love to talk about that first. Did you have to figure out how to source them? What did that journey look like?


Jess: Yeah. When I was getting the idea, I started making them myself and realized no one would buy these. These look absolutely awful. I'm not a crafty person or anything. That was another moment where I was like, "You know what? My goal is just to do what I'm good at and what I love, and find people who are good at other things to fill in the blanks." Once I realized that I would not be manufacturing these headbands myself, actually, my first step was Etsy. I found some really talented people on Etsy to help me source a first run. As we grew, our production has grown to accommodate higher volume and new styles. But it really did start with me gluing flowers to a band in my dorm room, which is funny to look back on.

Shantel: Well, how has that shifted today? What are your day-to-day responsibilities? Or, what do you take a lot of ownership on for the business and the direction it's going in?

Jess: Yeah. My role, it's been really interesting the past year, year and a half to figure out how it's shifted. Because when you're a one-woman show for a while and just trying to wear all the hats and do whatever you can to make these meet, sometimes it's hard to step back and let people that you know are better than you at certain things do what they do best. Because it's something that you've cradled and done since its existence. That was hard, but once I started to learn how I can be a better leader and where I can best utilize my strengths, that reflected in the company's growth. I spend most of my time doing a lot of the external work, marketing, PR, strategy ideas. Then I do a lot of public speaking on different campuses, conferences, businesses, just about how to keep that innovation for good.

Shantel: That's great. How did you get into the speaking piece?

Jess: Well, first, I really like to talk as you can tell. But it really started on accident. I gave the commencement address at my graduation for 20,000 people, so that was my first speaking engagement. It was like going down the black diamond before the bunny hill or anything. But I was hooked. It was one of those things where I get nervous when I speak, but it's also the most energizing nerves I've ever felt. It's one of those kinds of nerves that makes me just really want to do a good job and rise to the occasion. Not only was I hooked on the energy that it gave me, but I was also just really motivated by the response and how I can be someone who humanizes this path of entrepreneurship. It doesn't have to mean you went to some Ivy League school or had all this money or had a ton of experience. It really can just be as simple as seeing a problem and creating a solution through a business. That, after I gave the commencement speech, it was uploaded to YouTube. Then I got a call from an agency called CAMPUSPEAK that connects colleges with speakers. I really didn't even know that was a thing to be honest. I was like, "Yeah, that sounds great," thinking I'll maybe do two or three a year, which has turned into sometimes between 30 and 50 a year, which is great. Also, now as I've grown as a person coming out of college, I think I now have different messages for a wider range of audiences like corporate America and maybe people who are now transitioning back into the workplace and seeing where else I can spread some influence through my story.

Shantel: I love that. I'm glad also and relieved to hear that you still get a little nervous. Because I think that I'll have to chat with you offline. I have a speaking engagement for my university that I'm going back for.

Jess: Oh, great.

Shantel: It's like 600 people, but I could start sweating just thinking about it right now.

Jess: Yeah. No, nerves are a good thing. They mean you care. But whoever said, "Pretend everyone's in their underwear," that was not a good idea. You shouldn't do that.

Shantel: No, that would be uncomfortable.

Jess: There are other things that I can teach you. Yeah.

Shantel: Yeah. Okay. Thanks. Well, you talked about how you got to a point in your business where you realized you wanted to be doing the things that you loved and not necessarily wasn't building the headbands. What do you see as your true strength and that thing that gets you up every day that you're most excited about?

Jess: Yeah. That's a great question. That's something that has been some serious internal reflection. As we're making these hires and bringing people on, it's thinking, "Okay, well where does this leave more room for me to do? What is that that I want to do?" When I think about what really excites me, it's definitely the mission of why I started this. Just seeing the impact that a simple accessory can have. Definitely being involved in that and how can we better share that story with our followers, with influencers and really showing what that can do. But also it's opened my mind to maybe I have some other ideas. Headbands of Hope is the first real company I've ever started. I've learned so much about the industry, about social enterprise that maybe I can take what I've learned and apply it to something else that I think deserves some attention. That's been on my mind as well, which is exciting to me.

Shantel: Absolutely. Yeah. It's exciting as a business shifts to redirect focus and your energy and offload some of the stuff on your plate but then have time to explore other projects. I think it's exciting, but that's a big change after you've been doing something for so long. I totally relate to that.

Jess: Yeah. Like what you're doing now with this. I was so thrilled to see that. I think this is just perfect for you and it really compliments Imagine Media. But I can see that this is definitely something that you were meant to do.

Shantel: Well, thank you. We're still working through the kinks, everyone listening. I appreciated that. Yeah. I've heard so often about just staying outside of your comfort zone. That has become a personal mantra of mine. But this is certainly something very outside of it, so we're pushing the boundaries there a little bit.

Jess: Yeah. Well, I'm proud of you.

Shantel: Thank you. I appreciate that. You talked about wanting to learn to be a better leader. Where do you pick up this information? Or, how do you continue to learn and grow?


Jess: A lot of the leadership qualities, I can simplify it to just trying to think, "Okay, well how would I want to be treated in this situation?" Or, "What would make me motivated to do this?" Being in such a small company where everyone's role is so important, everyone wears so many different hats, sometimes I feel like I am, I don't want to say, "Not the leader." But I don't have to be the one with all the ideas. I want to create an environment that inspires them to have ideas. By making my team feel like they are such an integral part of this mission and this solution that we're working towards, to me I think that's the most effective leadership. Because I can wrack my brain all day for what to do next or what's gonna be our next move or next campaign and this and that. But I've learned that I can exhaust myself quickly by doing that. How can I instill an environment with my team of creativity and innovation where not only are they coming up with ideas, but because they come up with the ideas they're more empowered to execute them.

Shantel: I love that. It certainly empowers the entire team to have this ownership over the company that ultimately makes them want to be there more I'd imagine.

Jess: Yeah. I've found that sometimes CEOs or leaders of companies try to shield their employees from down month. Or, if things aren't going so well. I've found that whenever I have brought the team together and exposed that and said, "Okay, this is down this month." Or, "We didn't do as well as I thought we would." Just put it out there and see what their thoughts are and what we could do differently. They usually have a lot better ideas and better solutions than if I were to just sat in a room by myself thinking about it.

Shantel: Yep. Yeah.

Jess: Yeah. I think being transparent, too.

Shantel: I think that creates a level of vulnerability that shows that you're a real person. Entrepreneurship I think can be glamorous sometimes into, "Wow, you have it so great. You have your own company." It's humbling to bring in other people. It's great to hear that you're doing that because it makes it very real. It's like, "We're doing this together and I don't have all the answers." I think that's an awesome way to approach a problem.

Jess: Yeah. Showing that I'm human, too, and I need your help.

Shantel: Yeah. Speaking of culture, you touched on ... Actually, you didn't touch on this yet. But the for good for-profit methodology. I think that so many companies are wanting to find a way to do something good in the organization every day. Has that at all ... Maybe not been a problem in recruiting ... but been something that you've had to fight for everyday in keeping that top of mind for the team because it's now so widely accepted and common to have that for good piece?


Jess: Yeah. This is right up my ally. You chose the right question. I think that giving back in your company is not enough to make you unique anymore. I think there was a time when you were a for-profit business and you had some CSR initiative or an element that really set you apart from the rest. I think it's wonderful that that's not unique anymore because so may companies are doing it. I do think that giving back with your company is not going to be a trend as much as it's going to be an expectation of for-profit businesses. It's not if you're giving back, but how are you giving back? How can we still maintain that edge of social enterprise even though everyone else is doing it? Some of the things that we've thought about for that is we are the only headband company that gives headbands to kids with cancer. That is something that is very specific to us. It creates a unique giving experience for the product that you're getting to also be the product that you're giving. We also work with our stores across the world that carry out products. That their purchase and their store actually benefits a kid at that local children's hospital closest to that store. Then when they buy online, they'll get a donation confirmation email within about two to three weeks of receiving their order with the exact hospital that their purchase benefited. For us, we don't think that just giving back is enough for us to ride that wave or as a marketing crutch. We want to show that we're transparent about it. We're also doing the best that we can.

Shantel: That's great. I love the piece on which hospital it went to. I think that there's, unfortunately, a little bit of fear sometimes now. If I donate, does it actually even go anywhere?

Jess: Where does it go? Yeah.

Shantel: Mm-hmm. That transparency I certainly see the whole non-profit but also for a good for-profit space moving in that direction. Because people want that now.

Jess: Yeah. Then also, I think from a marketing perspective, not only are we being transparent and hopefully gaining our customers' trust by sharing that information. But it's also giving us another opportunity to get in front of them and to get in their inbox and to remind them of this impact that they had. Hopefully, they'll forward it to a friend or see what else they can buy.

Shantel: Yeah. Definitely. Touching back on that speaking piece. I'm just imagining your week-to-week with all the travel. What do you do? Yeah.

Jess: I had a flight at 5:00 AM this morning so-

Shantel: Oh jeez. Well, thank you for spending some time with me.

Jess: Oh, no. Of course.

Shantel: Not going to bed. Well, what do you do to recharge when you're feeling drained?


Jess: Yeah. I would say I'm probably not the best example as we speak with a cup of coffee at 3:30, but let's pretend like it was a good day. I really try to make working out in the morning as important as this call is with you and me. It's in my calendar. It's something that you have to block off that time for yourself. For me, that's in the morning. I know some people like working out at night. I think it's almost an adjustment at the start of the day where it can clear my mind and just get me in that right mentality. Because I find that sometimes when I feel I'm so swamped and so busy that I say, "Well, I don't have enough time for that," and I skip it. I'm not as sharp. I'm more irritated. I don't do as good of a job throughout the day than if I had taken an hour in the morning to go to yoga or to go for a run or do something like that. Really trying to stay on top of my personal health. Then also just things that make me happy. That's something that's new for me. I think I was trying to be so regimented with the routine that works and that I can work out and cook. You'll appreciate this. I got a dog about a month and a half ago. This dog is the light of my life. Don't tell my husband. But this dog is the best thing that's ever happened to me. That's a stretch. But it's just having something that makes you just playful and gets you outside and interrupts your day in the best way possible has also helped with my energy and just positivity towards the day.

Shantel: Mm-hmm. I love that. We'll have to share some pictures.

Jess: I know. I'm not gonna lie. I stalked your dog and want to meet him.

Shantel: We can have a play date next time we're both in the same place.

Jess: Definitely.

Shantel: No, but I totally relate to that. Sometimes when Gunner, the big fur ball, rolls in the mud. Before I had him ... I didn't physically birth him ... but before he came into my life, I would have been very stressed that that interrupted the day. But now it's like, "This is the good things that are supposed to happen in life," that, yeah. I'm glad to hear that.

Jess: Yeah. Exactly. Yeah. No, I think that sometimes there's something, even there's a hiccup at work or something that can throw you off track. Then there's just something there that's just so happy and so positive that can just remind you that this is not the most important thing. Life will go on. It's okay. It's good to have that reminder.

Shantel: That's great. Are you, with the exception of the 5:00 AM flight today, are you an early, early riser? Or, pretty normal?

Jess: I would say I get up at 6:00, 6:15 every day. I know people that get up way earlier than that. I think in the world of entrepreneurship, that might be a late riser.

Shantel: Oh, yeah. I'm still pretty late. I'm like a 7:00 or 7:30. I'm trying my best to get up earlier. I've spoken to a few people and it's 4:00 or 5:00 and I'm like, "Not happening." Not yet.

Jess: Oh, yeah. This other entrepreneur I know, he's like, "Yeah, my goal is to have zero inbox by 6:30 in the morning. I'm like, "What?" But yeah. I actually saw the other day on the Scan there was an alarm clock that literally sets off something like flying in the air. You have to get up and get it and connect it back for the alarm to stop. I'm like, "That sounds brutal, but might work."

Shantel: I'll have to look into that. I'll be sure to link that in the show notes.

Jess: Yeah.

Shantel: I've just got a couple of more questions for you, Jess. Actually, I'll finally talk to you a little bit about a book.

Jess: Oh, yes.

Shantel: Can you tell the listeners a little bit about that?


Jess: Yeah. No, actually, I'm so glad you brought this up. It's so funny. Sometimes when I talk about my company, it's so easy to have everything that you usually talk about. It's really exciting to share new projects. One of the things that I learned starting my business, I would reach out to other entrepreneurs or other people that are trying to do something big and start a relationship, try to get some inspiration. I would hear the same response of, "Well, where they got their idea and where they're at now." For me, it wasn't very inspiring to just hear the spark and basically their highlight reel. I wasn't very moved or motivated by that. But then, I saw an article of the Airbnb founder who leaked all of his rejection emails that he got from investors. People saying his idea, the liability, and that they don't think people would stay in other people's houses. Just very polite noes to his idea, which we all know is pretty successful now. He really didn't have much to say around it other than that like, "Life goes on. If you really believe in your idea, you'll figure out a way to make it work." The transparency in that really inspired me. I am writing a book called Fill in the Blank, where you're filling in the blank between that initial spark and where you're at now, and those times that really make it real. Because I think if we can all share that and share those kinds of hiccups, or pivots or moments where you maybe had to rethink things or kick the hustle into high gear. I think if we can share those, it might normalize pivots, speed bumps, and hurdles just as a regular part of a successful journey. I think if you're just trying to do anything big, you're bound to run into something. Maybe that won't be so scary if you know other people do that, too.

Shantel: I love that. Again, the word transparency keeps coming up with all the stories and experience shares that you're talking through. People don't do that in my opinion. People, they're not that deep that fast and that's, I think, what everyone needs and wants to really hear. I think that's awesome. I cannot wait to read it.

Jess: Well, even when in your world, I'm sure you're seeing this on social media. The posts that are now being shared the most and going viral are those posts where a girl is standing a certain way that makes her look really skinny. Then she shows the picture right beside her is she's actually just a really normal, beautiful girl. It shows how the camera can be deceptive. Everyone's just being more transparent on social media. I think that it shows in the numbers that that's what people are responding to now.

Shantel: Mm-hmm. Definitely. Are there any other new adventures for you outside of the book? Things you're really excited about.

Jess: Yeah. We, actually next week, are rolling out into all Ulta stores in the country.

Shantel: Whoa.

Jess: You can find is in every single Ulta, which I am super excited about.

Shantel: That's huge. Congratulations.

Jess: Thank you. It's our first huge retailer. We're excited about the amount we'll be able to donate from this and the kind of exposure we'll be to get and the new people we'll be exposed to. We're really excited for that. Then we have some really fun donations coming up for the holidays where we're having the patients make their own headbands to gift to friends and family. That'll be really fun, too.

Shantel: Nice. Well, congrats again. That's huge.

Jess: Thank you. We're really pumped.

Shantel: Just how can people get in touch with you if they want to learn more about your story or your book or learn more about Headbands of Hope?

Jess: Yeah. Well, in the spirit of Imagine More social media-

Shantel: Nice.

Jess: ... yeah, you can follow us at Headbands of Hope, Instagram, Facebook. You can also find my personal handle at Jess_Ekstrom.

Shantel: Great.

Jess: I'm happy to talk to anyone and everyone.

Shantel: Thanks, Jess. Thanks so much for being on the show.

Jess: Yeah. Thanks for having me.

Shantel: Of course. All right.