How Headbands of Hope Founder Jess Ekstrom Stays Positive by ‘Chasing the Bright Side’

Welcome to another episode of The Female Founder with Bridget Fitzpatrick, Co-founder of ASBN and the CBT Automotive Network. The Female Founder is a show all about helping women grow their businesses and reach their full potential. Each episode will highlight inspiring stories and advice from female entrepreneurs to help you build and grow your business. This show is designed to inspire and motivate other female founders to be the best entrepreneurs they can be.

Today’s guest has been inspiring entrepreneurs all over the world with her message of optimism and resilience. Joining the show today, is Jess Ekstrom, best-selling author, speaker, and founder of Headbands of Hope, Mic Drop Workshop, and Prompted.

Jess EkstromTranscription: 

Bridget Fitzpatrick:
Jess, thank you so much for joining us today.

Jess Ekstrom:
Thanks for having me. It’s been a couple years. Glad to be back.

Bridget Fitzpatrick:
It has been a couple years, and there’s been a lot going on in your life since then, including your book, Chasing the Bright Side, which we’ll talk about a little bit later. But for those watching that aren’t familiar with your story, can you talk to us about how you started your business when you were still in college?

Jess Ekstrom:
When I was interning at Make-A-Wish, I was seeing a lot of kids losing their hair to chemotherapy, and they’d be offered a wig or they’d be given a hat. And a lot of them wanted to wear headbands. And so I was like, “Well, why not me? I could do that.” And not knowing at all what I was in for, and any founder listening knows that moment of a spark and you just have no idea what you’re in for, but I think that’s a good thing. So I started Headbands of Hope. For every headband sold, we donate one to a child with an illness. And 10 years later, we’ve donated over a million headbands, reaching every single hospital in America and in 22 countries. We’ll be rolling out with Kohls this fall. So if you’ll have to look for us at Kohls.

Jess Ekstrom:
And then, eventually, that led to a speaking and writing career where I found that not a lot of women are present on stages and on shelves. So I started Mic Drop Workshop, which is my online course in community to help women become paid thought leaders. And then, more after that, but I’ll stop there.

Bridget Fitzpatrick:
We can talk about that again later as well, but let’s change the topic a little bit. Now, I practice positivity in my personal life, as well as in my professional life, and it’s not always easy when you have forces that are trying to bring you down. And I know you’ve been through some challenging times in the past. How do you remain positive even on your darkest days?

Jess Ekstrom:
That was one of the reasons why I wrote Chasing the Bright Side was because if I could pick a common thread that really pushed and propelled me to start Headbands of Hope, to get Mic Drop Workshop off the ground, and all these other things, it wasn’t necessarily entrepreneurial skill sets or knowing what I was doing. It was optimism. And I think one of the misconceptions that we have about all things good is that it’s always just hearts and flowers, and you write the big fat check to the organization, and you’re giving back. But what optimism is about is bring the good when things are bad because hard times give us that choice. They can be the excuses to why we do less or they can be the reason as to why we do more. And so optimism is about training our minds to not avoid the bad, but create the good.

Bridget Fitzpatrick:
I love that because I know some people that it seems like drama surrounded in their life. And I’ve always said those people seem to chase the drama. So your book is so perfectly titled, Chasing the Bright Side, embrace optimism, activate your purpose and write your own story. What do you think is the biggest takeaway that you want your readers to get from the book?

Jess Ekstrom:
I would say one of the bigger takeaways is that we can train ourselves to be optimistic. I’m not a naturally optimistic person, which is, I think, why I wrote a book on it because it was something I had to work on. My husband on the other hand, wakes up every day, and the sun is shining, and the tank is clean, and nothing’s ever wrong. But I would say, a quick tool that you can put in your back pocket as you go throughout your day and your life that is one of my favorites from Chasing the Bright Side is what I like to call the purpose test. And it’s where, if you’re watching right now, you can actually do this, take the thing that you’re chasing right now, what it is that you want, whether it’s in your career or your life. Imagine that you got it, you got that thing that you’ve been chasing, but you had to remove your name from it. So no one knew it was. You couldn’t publish a LinkedIn post. You couldn’t share it at the Thanksgiving family dinner.

Jess Ekstrom:
If you still got that thing, but you’re you were anonymous, would you still do it? And I think that as such a debt check that I have to do so often for myself of, am I chasing something based on how it looks or am I chasing something based on the impact and how it’s going to feel? Because it’s so easy to condition ourselves to just go for likes and comments and shares. But at the end of the day, we have to be able to recalibrate our compass when we need to.

Bridget Fitzpatrick:
That’s right. The validation should definitely come from doing good as opposed to just the… I mean, the world today is, how many likes did you get? How many followers do you have? And it’s just a slippery slope, right?

Jess Ekstrom:
Yeah. It can be like, you just have a front row seat to everyone’s trophy shelf. And it’s like, you just feel like your success is only in comparison to someone else, whereas you miss the opportunity to realize what you actually want, what your individual success looks like, because it’s different for everyone. Not everyone wants the white picket fence. I lived in an Airstream for three years for the book tour, and it was like, that was my definition of success, was being able to sleep in the woods.

Bridget Fitzpatrick:
So I own another platform, just like ASBN, called CBT News, which caters to the automotive industry. It’s a very heavily dominated male industry as you know. And you’ve been killing it on the speaking scene over the last few years. Can you share with us some of the challenges that you face being a female in such a male-dominated industry and how you overcome them?

Jess Ekstrom:
Yeah. I was actually just talking to someone about this and how some of the stories that we’ve shared behind the scenes. And I just remember one time being at an event and being backstage, and one of the man keynotes asked me for a cup of coffee, thinking that I worked at the event or was someone’s assistant. At that moment, I was faced with a left or right. I could either be like, “Whoa, how dare you? I’m a speaker,” or I saw the coffee 10 feet away from me. I was like, “Okay, I’ll get you cup coffee. Cream and sugar?” And handed it to him, miked up, went on stage. And he was like, “Oh my gosh, had no idea.” But it was one story that so accurately depicts the climate right now of if you were a woman backstage, then you were either working there.

Jess Ekstrom:
And so that’s when I started to realize, I’m like, this needs to change. And did some research and realized only 30% of speakers are women. And so that’s what led me to start Mic Drop Workshop, was to just try to change the industry. But I think women coming together in male-dominated industries is more important than ever because we have to be able to refer someone for the promotion or say, “Hey, Bridget’s doing a great job,” and be able to pass the baton and keep supporting women.

Bridget Fitzpatrick:
Yeah. Can you talk to us a little bit more about Mic Drop Workshop and how you’re helping females and thought leaders in that department?

Jess Ekstrom:
Yeah. I think one of the things that changes as you go about your career, at least for me, is for so long, I thought my success was, how many stages can I speak on? How many books can I write? How many businesses can I start? And what can I do? And then once you reach something, you realize that you’re in such an amazing position. If you’re a rock climber, to throw the rope down to people who are also climbing that same mountain. And so that was when I started to think, “Well the amount of stages that I can be on is limiting. And so what if I just used what I’ve learned and helped a ton of other women get onto stages.” And so Mic Drop Workshop is the way that we do that. There’s online courses, live events, and a closed community of over 1,500 women speakers who are all out there getting on stages and getting paid to speak, which is the goal, and making an impact and income at the same time.

Bridget Fitzpatrick:
That’s great. Good work there for sure.

Jess Ekstrom:
Thank you.

Bridget Fitzpatrick:
Now, you have a huge social media presence where you offer little nuggets of advice to help entrepreneurs every day. If you could choose just one piece of advice to tell your younger self when you were just starting Headbands of Hope, what would that be?

Jess Ekstrom:
It’s so funny. I was talking to someone the other day, and I said, “If I could talk to my middle school self, I would tell her, no one knows what they’re doing. And everyone is just as insecure as you are.” And then the moment it came out of my mouth, I was like, “Oh my gosh. That’s exactly what I need to hear as an adult as well.” And so I feel like if I could tell my middle school self that, but it’s also a reminder to myself that no one knows what they’re doing. Everyone’s just as insecure as you are. And everyone’s just figuring it out along the way. And that’s such a relief to know that people aren’t thinking about you as much as you think they are. And to some people, that might be a disappointment, but to me, it’s such a relief.

Bridget Fitzpatrick:
It is. It is. No, that’s great advice. I think there’s so many times that people are in a room and they think, “Oh my gosh, what do I have to offer? Why would someone listen to me when everybody else feels the same way?” So when you you start thinking that way, you probably speak up a little bit more, or try new things, or really get out there and do what you got to do.

Jess Ekstrom:
Yeah, exactly. I think it’s almost like, what do they call, sophomore syndrome, when you reach a little bit of success, then you get worried that the next thing has to be really good. And I definitely experienced a little bit of that after… Not after Headbands of Hope, but during Headbands of Hopes success. And I had other ideas and things I wanted to create, but I’m like, “But what if it doesn’t surpass, or what if it’s not as good as the first thing that I created before?” And I think that’s where I discovered there’s like two different types of ambition that we operate from. There’s this anxious ambition, where we act and we do things because we feel like we’re behind. And then there’s inspired ambition, where we act and we do things because we feel like we’re making something better. Yeah.

Jess Ekstrom:
And so this analysis paralysis and sophomore syndrome comes from this anxious ambition, but that’s where that purpose test comes into play, where, how can we operate from a place of inspired ambition where no matter how it does, no matter if like our moms, our only customer, you feel like you’re contributing to the betterment of something?

Bridget Fitzpatrick:
I love that. A lot of people listen to you for inspiration and motivation. Is there someone that inspires and motivates you that you listen to?

Jess Ekstrom:
Oh my gosh. A lot of people. I would say, the ones that are in my ear the most, I listen to Morgan Harper Nichols, her podcast, almost every day. She has a great, short, daily podcast. And then Sara Blakely, and I know she’s in Atlanta. So this is my shout out. She has been such an inspiration to me, that you can have fun and do business at the same time. I think sometimes, as women, especially, you almost have to put your tough girl. You feel like you have to put your boxing gloves on every time you walk into a boardroom. And I was worried that people would confuse my kindness for weakness in business. And she just showed that that’s so not the case. You can be a total baller business woman, and also make pancakes in different shapes on the weekends, and just ski naked down a hill and just have fun.

Bridget Fitzpatrick:
She is very inspirational. And I know she has said in the past that in order for a female to be successful, you don’t have to act like a man. And that resonated with me. I love that because, for so long, I thought, “Okay, you got to be suited and booted and ready to go like a man,” but you really don’t. You can be yourself, be as feminine and silly, and like you said, making the pancakes, and ski naked down a hill. And look at her, one of the most successful women in the world. Right?

Jess Ekstrom:
Yeah. And so I have just looked up to the way that she operates so much in that I don’t have to lose myself in order to win.

Bridget Fitzpatrick:
Yeah, for sure. So for you, running two companies, writing a book, and speaking all over the country wasn’t enough. You also started a company called Prompted that helps people reach their goals. Can you talk to us about that?

Jess Ekstrom:
I, to be honest, was tired of the traditional self-help space of constant answers. Do this before you wake up in the morning, and this is what millionaires do before you’ve done anything. And I just felt like, in order to get something that was made for me, it’s like, well, you have to hire a coach or you have to invest in a conference. And so there really wasn’t anything out there that I felt like instead of giving answers was asking questions. And so I decided to do this little test with my Mic Drop Workshop, my course. And instead of telling them what a keynote was, I created 21 prompts. And I said, “Okay, after the end of these 21 prompts, when you fill these out, you’ll have your keynote talk. And so it guided them to an outcome. Instead of telling them what to do, I prompted them with questions. And they loved it.

Jess Ekstrom:
And so I called it a keynote pathway. And then that’s where Prompted came to play. It’s like, what if we tapped into experts and thought leaders all over the world to create a series of prompts in their areas of expertise to help people achieve their goals? And so that’s what Prompted is. You can log in. You can browse from hundreds of different pathways. You can take the co-founder of Netflix has a pathway about making your ideas work. We even have someone who specializes in breakups, if you want to take her breakup pathway. And so it’s a way to get accessible self-help with coaching like results at a fraction of the cost.

Bridget Fitzpatrick:
That’s great. So many people have a great story to tell. Everybody really has a story to tell, but they might not know exactly how to get started to tell the story or what the most interesting part that they should share. So that’s fantastic. I love that.

Jess Ekstrom:
Thank you. Yeah. It’s been really cool to see also what questions can do for the brain instead of answers. Studies show that questions actually allow us to focus. When we’re thinking about the answer of a question, we can’t do anything else, but think about that answer. And then it actually influences behavior more than sometimes reading an article does. And so I really am excited about how Prompted can change some of the self-help prescriptive answers. And instead, start asking people the right questions.

Bridget Fitzpatrick:
Now, in your opinion, what qualities does it take to be an entrepreneur?

Jess Ekstrom:
I think that in order to be an entrepreneur, you don’t have to know where you’re going, but you have to know that you can. And I think that entrepreneurship is such a foggy path where you can maybe see maybe two, three steps in front of you. And if you’re someone who really likes a lot of structure, I find that, for me, in my entrepreneurial experience, structure is thrown out the window. And so to be able to adapt and know that problems are an absolute normal part of the process. I used to think I could get to the bottom of the problem pile. If I just kept working hard enough, all of a sudden the problems will be at zero. And I learned that it’s like every single day, you’re going to have new problems. And so it’s about not trying to solve every problem, but learn to almost enjoy the problems as a science experiment. So when you can start enjoying the process, I think that’s where the results will be better for it.

Bridget Fitzpatrick:
Yes, honor the struggle, right?

Jess Ekstrom:
Yeah, absolutely. Well said.

Bridget Fitzpatrick:
Now, you have a lot of runway left, so what is next for Jess Ekstrom?

Jess Ekstrom:
Oh my goodness. Well, I am working on some stuff for kids right now. I think one of the big blessings that I had, not knowing as a kid, was being able to watch my dad transform our upstairs bathroom into his home office when he had his business idea. And I think that was really transformative for me, that I was seeing what was possible at a young age. And I think that not many kids have that front row seat to entrepreneurship. So working on some different projects and books that’ll help reach kids, more specifically, young girls, about how they can start looking at the world through a lens that they can fix it and they can be the one to pursue their own ideas. So that’s what’s getting me excited right now, and hopefully, we’ll have something by the end of this year.

Bridget Fitzpatrick:
Awesome. Well, I can’t wait. Congratulations on all your success, and we look forward to watching you as you continue on in your journey. So thank you so much for joining us today. It’s been great.

Jess Ekstrom:
Thanks for having me. Thanks for your support over the years. You guys have been OG fans, and I appreciate it

Bridget Fitzpatrick:
Of course. Yes we are. All right. Thanks Jess.


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