Empowering Women To Write Their Own Story

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Marketing Podcast with Jess Ekstrom

In this episode of the Duct Tape Marketing Podcast, I interview Jess Ekstrom. Jess is on a mission to help women tell and sell stories through writing and speaking. She’s also the creator of an organization called Headbands of Hope. Jess has also written a book called — Chasing the Bright Side: Embrace Optimism, Activate Your Purpose, and Write Your Own Story.

Key Takeaway:

Jess Ekstrom is on a mission to empower women from all over to share their message and their stories through writing and speaking. Jumping into entrepreneurship during college, she started a for-profit, for-cause company called Headbands of Hope that has recently reached 1 million headbands donated. In this episode, I talk with Jess Ekstrom about her journey as an entrepreneur and how she’s overcome the many challenges she faced along the way.

Questions I ask Jess Ekstrom:

  • [1:28] How would you package up your entrepreneurial journey in a short story?
  • [3:37] Where does your e-commerce brand Headbands of Hope stand today?
  • [4:42] There seems to be now an entire industry of women helping women – what would you say is unique about your point of view that you’re trying to bring to it?
  • [6:44] What’s the difference between a woman storyteller, a woman speaker, and a male speaker or a man who’s trying to go out there and tell stories?
  • [10:14] What’s been the hardest for you in your entrepreneurial journey?
  • [12:05]  You started at a very young age – have you ever felt like that has held you back or have you felt that it’s actually been a positive strength for you?
  • [14:36] Going from shipping headbands to developing software is a bit of a leap – what was your process for doing that?
  • [16:35] Do you have contributors that are contributing to the prompt pathways in Bright Pages?
  • [18:01] Where can people find out more about you and your various ventures?

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John Jantsch (00:00): This episode of the duct tape marketing podcast is brought to you by the MarTech podcast, hosted by Benjamin Shapiro, brought to you by the HubSpot podcast network. Ben's episodes are so awesome. They're under 30 minutes. They share stories with world-class marketers who use technology to generate growth and achieve business and career success. Ben is a great host. I've been on his show. He's been on my show. He always really digs down and gives you actionable stuff that you can take away and do. And he's always bringing up new stuff. The science of advertising, how to figure out what to automate, just things that marketers are wrestling with today. Check it out. It's the MarTech podcast. Find it wherever you listen to your podcasts.

John Jantsch (00:51): Hello, and welcome to another episode of the duct tape marketing podcast. This is John Jantsch. My guest today is Jess Ekstrom. She's on a mission to help women tell and sell stories through writing and speaking. She's also the creator of an organization called headbands of hope, and she's also written a book called chasing the bright side, embrace optimism, activate your purpose and write your own story. And let's just throw on top of it. She's also got some software called bright pages. So Jess, welcome to the show.

Jess Ekstrom (01:22): Thanks for having me excited to be here.

John Jantsch (01:25): A lot of ground that we can cover here in your intro stuff. I want to start with, tell me just, I love just hearing entrepreneurial journeys. So how do you, how can you package yours up in a couple minutes story since

Jess Ekstrom (01:39): I got you? So I first started when I was in college. Um, I was interning at Make-A-Wish and seeing a lot of kids that would lose their hair to chemotherapy and they'd immediately be offered awake, or they'd be given a hat. And a lot of the kids weren't really concerned with color with covering up their heads. They just wanted something to feel good after hair loss. And so I would see a lot of them wearing headbands and I just thought it was such a cool gesture of confidence that they would, you know, just wear a headband. And so I went on to Google and I think I literally typed in like headbands for kids with cancer and nothing came up and I call it like the dumbest, smartest moment of my life, where, you know, being 19 years old, I was like, oh, I could tackle that.

Jess Ekstrom (02:23): And so I started headbands of hope for every headband sold. We donate one to a child with an illness. And the funny part that I haven't really shared a lot before is that the founder of Tom shoes, who's named Blake, not Tom surprising was spoke at my school about a week prior. So after hearing him speak and hearing his story of starting his one for one model, I have that fresh on my mind and thought that maybe that could be me. And so unknowingly, I realized in that moment, the impact that storytelling and speakers can have on audiences as well. So I grew headbands of hope and then eventually realized that the story of how headbands of hope started and the scrappy beginnings going to a million headbands donated was a really impactful product in itself. So I started speaking and writing and got book deals and all these amazing things. And to realize that there was not a lot of women out there doing the same thing, I would be the token woman on a panel or not a lot of women on the shelves that I wanted to see. So that's when I started my Trump workshop, which is my online course and community to help women tell and seller story. So there it is. That's my, my, I don't know if it was two minutes, but I tried

John Jantsch (03:37): No. So tell me where it just had headbands of hope stand today. Are you, is that still an active, you know, e-commerce business that then has the one for one model?

Jess Ekstrom (03:46): Yes. More, more than active. So headbands of hope is going extremely well. We just reached 1 million headbands donated, which is awesome, but it was something that was like not fire right out of the gate. I was a one woman show teaching myself everything. And so it was like just trying to use all the resources that I had. I would literally like hire college students to help me build my website and pay them in Chipotle burritos. And that was like how I got started. And then using tools like Canva, where I have no graphic design experience. I couldn't, I didn't have the money to hire designers, helping me create social media posts or banners for the website. It was really small beginnings that has come quite a long way.

John Jantsch (04:32): You mentioned that the, your token woman on a panel, and I certainly see that it play out in large conferences and things of that nature, but I will say that there seems to be now an entire industry of women helping women maybe take that to the next level. So what would you say is unique about your point of view? I saw Marie Forleo. Blurbed your book. She's obviously been doing similar model of having courses and teaching women, not exclusively women, but primarily women to, to, to start and run businesses. What would you say is unique about kind of your point of view that you're trying to bring to it?

Jess Ekstrom (05:08): Yeah. I would say that with my workshop, it's really about helping figure out how your story can help people in their story. A lot of speaking courses out there, first of all, are not focused on women and ours is exclusively for women or people who identify as that. And they forced you to be an expert. What's that thing that if they would, they have a library after you or something crazy, and the story that the course starts with storytelling, and then we do something called the moment to meaning where, what are the moments in your life? How can you pull the meaning at them out of them to teach to others? And I would say the other part of it too, is that speaking is one of the industries that can be highly collaborative and beneficial in that collaboration, if you let it be. And so, you know, sometimes as thought leaders or entrepreneurs, you really want to compete. But with speaking so much of my growth as a speaker has come from people referring me to gigs, other women saying, Hey, I just spoke. Jess would be a great speaker. So in my drop workshop, we have a closed community for all the students who refer gigs, um, after they've done them and create that referrals.

John Jantsch (06:16): Yeah, no, I've experienced that over the years as well. And if you think about it, if somebody has me speak at their conference, you know, probably going to be a couple of years for, they want me back. So, uh, tee it up. And I also, quite frankly, it's that whole reciprocation

Jess Ekstrom (06:31): And what goes around, comes around is like so true and speaking.

John Jantsch (06:35): So let me push, I just want to hear a clear answer on this. I'm not debating it, but I want to push back a little bit on this idea of your workshops or for women. What's the difference between a woman storyteller, a woman speaker, and a man speaker or a man who's trying to go out there and tell stories.

Jess Ekstrom (06:52): Yeah, no, I think that was a great question. And I think that what we're trying to do with my Trump workshop, making it exclusive for women is one, you know, I hate when people say safe space, but it really is. It gives women the opportunity to go out there, share feedback, you know, test their keynote in a really safe environment where they don't feel like they might get, you know, pushed to the side or spoken over, or they just feel like everyone in here is on that same page. But the other thing that I've noticed too, is I I've done some research around it with like, why aren't women getting the big keynote spots? Like what, what is that? And yes, there are like opportunities for war, more women to be on the selection committees. But I think the other part of it is I was at this event once and they were talking about, you know, diversifying lineups and this woman who's like the meeting planner for a huge corporation said, look, I want to book more women speakers.

Jess Ekstrom (07:50): They're just not applying for like, I'm not just seeing them in the application. So I think a part of my drop workshop that I want to teach is not just obviously the business side of speaking and telling your story, but how do you put your name in the hat even before you feel ready? Sometimes there are so many studies that show that women won't apply for jobs unless they hit a hundred percent of the qualifications and men will, and it's the same for speaking. And so there's a confidence factor to it that we're also tackling at the same time.

John Jantsch (08:23): Yes, men will definitely fake their way through it a lot sooner. I'll give you that. So you don't do any men bashing in your communities?

Jess Ekstrom (08:31): No, not at all. And it's not like, you know, I think when you do women focused work, but some people might construe it as like anti men and that's not the case at all. It's just like, how can we use a community of women who aren't getting these gigs, who haven't been selected and come together and do that. But it's definitely not, not anti men at any cost. I

John Jantsch (08:56): Have four daughters. I, you know, I, I joke, I joke all the time.

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Jess Ekstrom (10:18): I would say, I mean, during the pandemic, there was a lot of pivoting. Like a lot of businesses had to do sure. But to add another layer on it, my husband and I had recently moved into an Airstream trailer and had been traveling around the country, what started as book tour, and then we just stayed in it. And so being able to be connected with my team, who's all over the country was a struggle. And so using things that are collaborative, different softwares, again, like Canva, when we were working on a new lookbook for fall, for all the stores are working on different social media posts have being able to have those collaborative features where we're not in an office has been really helpful. But additionally, I would say, and I touched on this before. One of the blessings and the curse of being an entrepreneur is you really have this, uh, something in your brain that tells you it's not enough.

Jess Ekstrom (11:16): And no matter what you do, and no matter how many podcasts downloads you have, no matter how many headbands you sell or books you sell, you always feel like there's more in you, which can be great because that's a field of your hustle, but it can also be really detrimental to just like your mental health and like how you feel about yourself. Yeah, yeah, exactly. And so I think that that's, you know, additionally, a struggle that's, that's tough for me is I like having my hustle muscle on and always wanting to do better. But then it's like, when, when is the time where you say good job, you know, that stumps me. It's sometimes hard to do yourself. Nope,

John Jantsch (11:53): Nope, no question entrepreneurs tend to, uh, always be looking at the horizon rather than looking at back behind them and seeing how far they've come.

Jess Ekstrom (12:01): Exactly. Yeah. So

John Jantsch (12:03): Let me ask you an age question. How has you started at a very young age? Has that been, have you felt ever that that's held you back or if you felt that that's actually been a real positive sort of strength for you?

Jess Ekstrom (12:17): That's that's a good question. Um, I would say in the beginning I was naive to the point of a benefit. I was like, oh, no problem. I can start a headband company. I had no idea what, you know, a P and L was, I didn't, couldn't even spell entrepreneur. And I think not

John Jantsch (12:34): Having the data, people actually can't spell it.

Jess Ekstrom (12:37): I still can't really spell it. I'm not gonna lie to you, John. But, um, I would say not having like, the data was really great for my fearless leaping and just saying, yeah, like I can do it. Yeah. And then, um, also just your energy level, like, I don't know what I was on, but I, the amount of things that I could get done in a day was, um, you know, limitless. And then now, um, you know, having the data and real, and having these life experiences that you can pull from and saying, you know, this might not work because of this, um, can be harder because you're leaning more on strategy then than gut instinct. Um, so I definitely like, anytime I speak at schools or colleges, I'm like, you're in the biggest do over period of your life. Like even if you start a business and it utterly fails, um, you have more information than you did before. Um, and you're more qualified to go after a job or whatever it is you want to do next after having done that. So there's definitely pros and cons to both, but I'm definitely pro start young just for the learning experience.

John Jantsch (13:45): That's right. Absolutely. Uh, because, um, um, you know, I hate to say, but those books don't contain the lessons that you learn when you start trying to do it, do they? Exactly. So it's funny you had a, I want to highlight something that you kind of said was that if you had known how hard it was, you might not have done it. I'm

Jess Ekstrom (14:04): Pretty sure. I think

John Jantsch (14:05): That's a real benefit. Yeah.

Jess Ekstrom (14:07): Do you, do you ever feel like that if you had known what you were in for?

John Jantsch (14:13): I never, I never really do, but that's, I've been doing this for 30 years and I, I, I love it still. So I, you know, I don't know that I don't know that I wasn't, I mean, I'm kinda the same with you. I never feel like I know no one and it'll be done or I'll be done. You know, I'm always, there's gotta be better, more ways to do stuff, but, um, I'm having too much fun to really worry about it. That's awesome. You've developed some software. Um, that's, you know, that's going from shipping headbands to developing software is a bit of a leap. How, uh, how, what was your process for doing that? I'm assuming you aren't a programmer yourself and you had to go, I wish the had X and

Jess Ekstrom (14:52): Got it done. Yeah. I think if there's one policy that I live by, it's create what you wish existed. And I think that's the most simple way that we can approach entrepreneurship. So during the pandemic, you know, like I said, everything was upside down and, uh, I found the thing that was really helpful for me was writing. And when I was writing, chasing the bright side and I had a manuscript deadline, I had, I had to write every day. Like I had a certain amount of words and it was probably the healthiest Headspace I've ever been in and also clearest on what my priorities were, what I wanted to do and realize that there's like a lot of science behind journaling. I mean, your head can only hold seven pieces of information at a time. And so it really gives away to download and digest what's going on and also set goals and what you want to do.

Jess Ekstrom (15:42): Um, but I found that the journals out there, whether it was online or tangible, like physical journals were very like gratitude driven and very, um, introspective, which, you know, I can appreciate, but that's not what I need every day. I wanted a journal that helped me pursue the things that I wanted to create. And so, um, again, you know, same thing, typing headbands for kids with cancer and to Google, it's something that I couldn't find. And so I started bright pages, but we're actually gonna, um, be rebranding to prompted. Um, and we're the first and only journal to create what we call prompt pathways. So you can select a topic, um, a goal, whatever it is you're interested in and get prompts based on that. So if some, one of your listeners wanted to start a pathway, they could take John's pathway of how to start a podcast and get journaling questions, guiding them through that.

John Jantsch (16:35): Yeah. So do you have contributors that are contributing those, uh, those pathways, so to speak,

Jess Ekstrom (16:40): They're all created by guides. It's really cool. We have anyone from, we have like an NBA coach on there. We have someone who has their own like Netflix show. We have podcasters thought leaders from all over, um, creating these pathways and they're anywhere from like seven to 21 prompts. Oh, that's

John Jantsch (16:56): Awesome. That's awesome. So what's the future, hold them for you.

Jess Ekstrom (17:00): That's a good question, John. Um, ask myself that every morning, but you know, I think I want to do things and you, you hit on this, which I love and not a lot of people talk this way, but like, I want to do things that are fun to me. You know, I think life is too short to not enjoy what you do. And I've definitely gotten involved in some things in the past where, you know, the, the price tag that I would get from, it looked really good and it looked good on paper, but it just wasn't fun for me. And so I think I'm really grateful to be at a point in my career, pretty early on where I have the privilege and the luxury of choice as to what I do next. And the things that I know I love doing are writing and speaking and helping women do the same or just really unheard voices. There's so much, so much stats out there with like women of color, not getting gigs. And so I really want to figure out how can I use what I've created and help change the who holds the microphone. Okay.

John Jantsch (18:01): So tell people how they can find out more about any of your various ventures. I know they can start at your namesake homepage, but to go ahead and invite people to connect with you any way you wish and tell us the name of your dog too, but

Jess Ekstrom (18:13): It's going to say the, the, I was like, of course the mailman came by right then my dog's name is Ali, a 70 pound standard poodle. But if my husband was on the call, he would say, oh, he's like a man's poodle though. I can't just say standard poodle. Um, so yeah, I would love to hear from you. You can head to my Instagram at Jess underscore Ekstrom and, uh, same with my website, Jess ekstrom.com. If you want to learn more about Mike drop, you can go to mic drop workshop.com and brightpages.com. I think that's it

John Jantsch (18:46): Just thanks for stopping by the duct tape marketing podcast, and hopefully we'll run into you and your Airstream someday out there on the road.

Jess Ekstrom (18:53): I would love that. Thanks, John.

John Jantsch (18:55): All right. That wraps up another episode of the duct tape marketing podcast. I want to thank you so much for tuning in, feel free to share this show. Feel free to give us reviews. You know, we love those things. Also, did you know that we had created training, marketing training for your team? If you've got employees, if you've got a staff member that wants to learn a marketing system, how to install that marketing system in your business, check it out. It's called the certified marketing manager program from duct tape marketing. You can find it at duct tape, marketing.com and just scroll down a little and find that tab that says training for your team.

This episode of the Duct Tape Marketing Podcast is brought to you by the HubSpot Podcast Network.


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