Sophomore Syndrome and that Successful Feeling, with Jess Ekstrom

Jess Ekstrom started Headbands of Hope back in college, and the demand was more than she could have ever imagined. With the success of her first business comes expectations for her follow-up chapters.  So how has she responded?  Plus, Jess talks about why everyone should create 100-year goals and why you should celebrate the parts of the business you dread.


Dana: Welcome everyone to Hustle and Gather, a podcast by inspiring the everyday entrepreneur to take the leap. I’m Dana 

Courtney: and I’m Courtney. 

Dana: And we are two sisters who love business. On this show, we talk about the ups and downs to the hustle and the reward at the end of the journey. 

Courtney: And we know all the challenges that come with starting a business. Between operating our wedding venue, doing speaking and consulting, and starting our luxury wedding planning company, we wake up and hustle every day 

Dana: But we love what we do. And today we’re talking with Jess Ekstrom, CEO of Headbands of Hope, author and speaker. Jess, welcome to Hustle and Gather. 

Jess: Thanks for having me. Okay. I’m an idiot. I did not know you guys were sisters, sisters. Wait, who’s older?

Courtney: It’s me. I know. I look younger. 

Jess: Are you taller? I’m the younger one, but the taller one, I love rubbing it in my older sister’s face. 

Courtney: Well, I was all fine. And like, when we were like 12, I knew one day I was going to get my comeuppance because my whole life growing up, they’re like, it’s this your older sister?

And I was like, no, height does not equate to age. That was like one day when we’re 40, they’re going to upping your older. And someone, one day, asked if she was my mother. And it was like the best day of my life. But then recently on my 40th birthday trip, someone asked me if she was my daughter and I was like, what the hell?

Dana: How old do you think I am? He goes 20. And I was like, oh, you’re my new best friend. Yeah, add 17 years. 

Jess: That’s awesome. 

Dana: And I feel like it’s negated. 

Yeah. I can’t say it anymore. 

Jess: Well, my sister and I are complete opposites, in the best way possible, but I don’t know if we could ever run a business together. She, her business is like it called Burning Daylight Expeditions that she takes people on like wilderness trips, like deep in the woods. And I’m like, let’s do headbands and fashion. 

Dana: That’s awesome. Well, thanks so much for being here. I was telling you earlier. I’m like watching you on Facebook and Instagram and 

Jess: Awesome. I’m so glad. Well, I admire what you guys do because I have tried doing events and stuff in the past, whether it’s for my business and they are like, that’s not my zone of genius. You know, there’s some people that are like, love the chaos and the coordination of it. . And I’m like, I could never, yeah.

Courtney: I definitely think it’s, it’s more of a lifestyle than a job. I think. So I definitely think it takes a certain, a certain personality for sure. I’m not even saying I have it and not get it for a long time it’s not my personality, really. 

Jess: I’m definitely like maybe I have trust issues or something because it’s hard, like sometimes working with people that are like, okay, you’re bringing the balloons, you know, and it’s like, you have to trust that they will bring the balloons and it’s, you know, been hard sometimes as an entrepreneur too and I find that the more that I rely on my team and believe in them, the better that they’ll do, but it’s definitely a muscle that you have to train.

Dana: Oh yeah, a hundred percent. I do think that that’s a really good point. I think that makes it easier while we could build our team much quicker because we were used to even when it was just us, we had to have a team to execute events, and you had to trust that person was going to follow through. 

Jess: You had to yeah, or else you couldn’t do your job well, yeah. 

Dana: That’s a very good point. Well, let’s dive into why you’re an entrepreneur. So let’s hear a little bit about your story because it is a pretty amazing one, like how and why did you start Headbands of Hope? 

Jess: So I started headbands of hope when I was in college. I was at NC state. and it was so funny. I literally walked in here and I was like, oh my gosh, I forgot my headband in the car. So usually I’m wearing one. If you’re watching live just imagine, you know, a beautiful headband on my head. And I was interning at Make-A-Wish, and when I was there, I was seeing a lot of kids that were losing their hair to chemotherapy and they’d be offered a wig or they’d be given a hat, something to cover up their heads.

Full Episode Transcript

Chasing the Bright Side, by Jess Ekstrom
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Hustle and Gather is hosted by Courtney Hopper and Dana Kadwell, and is produced by Earfluence.  Courtney and Dana’s hustles include C&D Events, Hustle and Gather, and The Bradford Wedding Venue.

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