Navigating the complex waters of new motherhood while maintaining a thriving business isn't for the faint of heart. Jess Ekstrom, founder of Headbands of Hope and Mic Drop Workshop, opens up about her entrepreneurial journey, from selling childhood toys on eBay to crafting a global movement that brings joy to children in hospitals. Alongside Jess, we share our personal experiences with the identity shifts that come with becoming a parent, offering an honest and vulnerable look at the challenges and triumphs that often go unspoken. Plus, who knew a quest for the ultimate breakfast burrito could lead to such profound reflections?
From an internship at Disney World to creating a business that addresses the needs of children undergoing chemotherapy, Jess's story is nothing short of inspiring. We explore how she leveraged her public speaking skills to scale her business and empower other women to find their voice through Mic Drop Workshop. Learn practical tips on mastering public speaking, including the "lighthouse mentality" and perfecting a signature keynote. This episode is a goldmine of insights on balancing personal growth, entrepreneurial endeavors, and becoming a professional speaker. Don't miss out on these valuable lessons and heartfelt conversations.
Key Takeaways:
About our Guest:
Jess Ekstrom is the founder of Headbands of Hope and Mic Drop Workshop, investor in women, 2x best selling author, Forbes Top Rated Speaker and new mom.
Her first brush with success was selling all of her toys on eBay when she was twelve. Since then, Jess and her companies have been featured on Today and Good Morning America and in Seventeen, Vanity Fair, Forbes, and People. More importantly, they've helped millions of women and girls around the world.
She’s the bestselling author of Chasing the Bright Side and Create Your Bright Ideas. Her hobbies include writing, hiking, board games with her husband, playing peekaboo with her baby, and searching for the best breakfast burrito in America.
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What is the worst thing that could happen? What would you do? Because you are like far more agile than you think. And so actually thinking about well, what is the worst thing that could happen? What would I do about it can actually be really calming?
Welcome to the ReLaunch podcast. And you guys, those stories that inspire me, that light me up. I know, when I hear them, I'm like, I gotta bring this to you. I gotta share this with you because it's just too good to pass up. Those people that are making such a huge difference in the world. And today I have Jess Eckstrom. She is the inspiring founder of headbands of hope and mic drop workshop, a dedicated investor in women, all things women, we gotta love that. A two time best selling author, a Forbes top rated speaker. Her entrepreneurial spirit was clear early on, and I love this one at just 12 She sold her entire toy collection on eBay. So not so great. headbands of Hope was inspired by juses internship at Disney, where she photographed children on Make A Wish trips. Seeing these brave kids, she wanted to boost their confidence post treatment. And so for every item sold a headband is donated to a child with cancer today, headbands of hope, have donated to children's hospitals in every US state and over 22 countries spreading hope and joy worldwide. And I think I even read that over 1 million headbands have been donated. Well since then, Jess and her businesses have been featured on today, Good Morning America and have appeared in 17. Vanity Fair Forbes people, most importantly, they have made a positive impact on millions of women and girls around the world. She is the very famous author of the best selling books chasing the bright side and create your bright ideas. And we're going to dive deep into that. But I love this. This fun fact about her is that she is on a quest for the best breakfast burrito in America. Jess, welcome to the show. And I know you are literally about to pop with your second baby. So thank you so much for being on the relaunch podcast and I gotta say I love little facts like that. And so before we dive into anything, where is so far in your quest, where is the best burrito? breakfast burrito?
breakfast burrito? Right? Yes, that is make sure we are huge fan of breakfast burritos. And my husband and I we actually went on an Airstream trailer travel tour. What was supposed to be only six months in 2019 than the pandemic for the book tour of chasing the bright side. But then the pandemic hit, we were like let's stay outside in our travel trailer and went around the country and turned into three years. So we have a lot of breakfast burritos. But there was this one outside of Glacier National Park in this like little shack along the highway. And I wish that I had pinpointed it or have the name of it. But I remember being in the car and eating it and saying oh my gosh, this is one of the best. I need to find it but so far. That's it right outside of it.
I live in Boulder, Colorado and there's a place called snooze. It's on pearls. Oh, okay. I haven't tried that one yet. It may have to be one of the top ones. Okay, but I digress here. Let's go back into why we're here right now on the show. Why people tune in is to hear how your greatest relaunch has impacted you in your journey in establishing where you are with your businesses, with your kids. And I'd like for you to take us down that path before we get into Hey, how you're all gonna rock it on stages, how you're all going to have the mic drop moments, we're gonna go there. But first, why don't you take us through just what you think has been that most significant, most impactful relaunch moment.
When I was thinking about this, I was battling between two ideas. One is more business and one is more personal. I'll start with the personal wine. I think one of my biggest relaunches was becoming a mother I'm about to have my second. But with my first, I'll be honest, I felt like everything I knew about myself changed. And in. In me a lot of the narrative of having, you know, a kid is the purpose in the heart and love that it brings, which is totally true. But I think what also goes not talked about a lot is the loss of who maybe you felt like you were before. And this identity shift, you know, so much of my self worth, I felt like, came from my productivity, my achievements, my body, my, you know, hard work ethic. And when you have a kid, all of those things are on pause. And so I really had a tough time, feeling worthy in my new role, and finding, I hate to even use the word balance, because I think it's just a daily, you know, what's it going to look like today. And so I definitely try to be more vocal about my experience becoming a mother, because it has been the best thing that has ever happened to me, but also, one of the things that I questioned myself the most. And
I gotta tell you, I am sure people out there are hearing this, and thank you for taking us there. Because you when you said that, I remember I was coming home from the hospital with my twins, and they were almost seven weeks premature. And I pull up to our house. And my I remember it was my, my mom and her best friend, come running out. And my husband is sitting next to me. And they immediately go, and I'd had a C section, they immediately go to the back, they pull the twins out. They're doing that and I'm literally just sitting in the car, and I remember the car getting warmer, it was September getting warmer and warmer. And I'm like, Oh my God. Like, I mean, nothing. Like, what just happened in that timeframe that there is no longer Hillary, like what happened now used to be, you know, they used to care about me. And I remember sitting there just thinking like overwhelming like, oh, my gosh, I think I just disappeared. Yeah, it's so interesting,
had a very similar feeling. And, you know, now with my second thinking about my maternity leave and being self employed, is, you know, I can be a little bit more DIY with it. And one of the things that I'm doing differently this time is I feel like last time I you know, I do a lot of speaking and I made sure that there was no speaking on my calendar for like, four or five months. Yeah. And I feel like I almost questioned whether or not I could still do it. Because I spent so long not getting back in the saddle that I was like, why would anyone pay for what I have to say why I will never have a single creative thought again. And so this time, although it might be controversial to some people, you know, I have a speaking engagement, a month and a half, you know, after I'm giving birth because I was on this other great podcast by Lindsey Epperly. And she calls it leaving bread crumbs of yourself. Like, I'm purposely leaving breadcrumbs of myself. After I give birth to remind myself, I can do this and be a mother and still be influential and the other ways that I have worked so hard to be so jazzed personally, that's been a relaunch.
So I'm excited for that opportunity for you. Because yes, it doesn't mean that you're, you know, picking work over your child, it doesn't mean that you know, you're, you're you're taking you back, you're saying hey, this is something that is important to you and you doing something important for yourself will only add to everything that you're doing with your family. I love it. Well, I
was gonna say one of the reasons why I love this podcast so much, and I love the the concept of relaunches, because I feel like especially as women, it's really hard to give ourselves permission to evolve and change. And we it's like this pressure of like, what's your thing? Are you a mom? Or are you uh, are you working? Are you this Are you that and you feel like you need to put yourself in this box. And I feel like one of the biggest struggles I've had over the years has been evolution not just from being a mother but also from business to business. You know, the thing that I started what has kind of led me to this path of thought leadership being headbands of hope. And then all the Sudden headbands of hope, you know, I didn't feel that. I didn't feel that spark and that passion, like eight years into running this business. And I had a spark and a passion to run a different business mic drop workshop. And it took me years to come to terms with the evolution that that is okay, that you can start something and evolve and move on. But there's not enough narratives around that. No.
And this is so interesting, because, tell us more. I love the idea that you first decided to do something like this, you were at Disney, it was an internship and then tell us how this grew into being a business.
So, you know, I call it the dumbest, smartest moment of my life being 18 years old and totally naive to what starting a business meant. You know, I was interning at Disney World as a PhotoPass photographer, photographing a lot of kids on their wish through make a wish, and then interning at make a wish and seeing a lot of kids losing their hair to chemotherapy and being offered wigs and hats when a lot of them wanted to wear headbands. And I just thought that was such a cool gesture of confidence. And like, of course, you all should have headbands. But there was no one providing that. And you know, when I speak about entrepreneurship or write about it, I like to say that that's the moment you become an entrepreneur, when you decide to create something that you wish existed. There's like a lot of extra talk and fluff around entrepreneurship and ideas and aha moments, but it's really inspiration from frustration, where do you get frustrated about things? Where do you think something should be done differently or better. And that was a moment where I was like, we shouldn't be telling these kids to cover up their heads with wigs and hats, if they want to wear something that just restores their identity like a headband. It
is the it is the sweetest, like I saw the pictures of these kids wearing your headbands. And I mean, it was it a million a million kids, you've now provided these
over 2 million now when you update the numbers. Yes, gosh, that
it just you know, when you think about it, and I've had I had melanoma, you know, you hear about and I was on a board for children called Max cure who had cancer and helping their families. And I gotta say, I visited so many. And, you know, there were sometimes a little headbands on them. And they were decorated. And it gives them a little something right? I remember one little girl that had it was almost like a, a tiara that had been created into this. So she just she felt beautiful. And that's what it's all about. And I and you said that you've been doing this for seven years now. The
company has been we started in 2012. So what is that now? 12 years? Yeah, gosh,
yeah, I must be reading I read something because I had a million and you're like, Oh, I
know. We need to update. update our numbers.
You really shouldn't. Because this is really impressive. Oh, thanks. I appreciate you. How do you how do you get the message out on what you're doing? You
know, one of the ways I was able to scale headbands of hope to what it has become, which is also how I feel like I collided with this other business that I started with my drop workshop was through speaking and so it started. I mean, I had no marketing budget, I had no idea what marketing fund was. And I was a college student. So I would beg college professors for five minutes of time before class, I'm like, can I please stand up in front of people and tell them what I'm doing. And then I learned if I can stand up there and tell them what I'm doing, but also put it back on them as to like how they can start something that matters for them, or how they can, you know, have inspiration from frustration, then I can get 10 minutes as opposed to five and if I can get good at that. Then people actually pay speakers which was crazy to me. So I started telling the story and eventually got did a whole college tour, where you know, get paid a couple $1,000 per University, which I again, I thought I was could retire at that point. I was like This is amazing. But when invest it back into the business, and that's how I was able to scale it through marketing and through funding it myself through public speaking. And
so that ended up causing you then to turn on another light switch moment and you decided, hey, I'm really interested now in teaching more people how to do this stage thing where Right. Yeah. And but you're doing both at the same time still correct. At the
time I was, I'm sure you have been, you know, on a panel or at an event where you realize, wow, there's a lot more women, or there's a lot more men on this roster than than women. And so I had had a few events that started. I would always ask them after they booked me to speak, you know, what is it about me? Why did you bring me to speak? And I remember this one event said, I'm going to be honest, we just needed a woman. We haven't really got like, really bad reviews last time that we didn't have any women's speakers. I'm like, have I just been, you know, teleported to the 50s? Or what's going on?
Because I did read this, that you said less than 30% of paid public speakers are women. Yes,
exactly. And the numbers are abysmal, especially when it comes to how much they're getting paid to. And so I decided, you know, just to help some women out, let me just rent the bottom floor of this restaurant here where I live in Raleigh, and I put up in Eventbrite, and said, you know, any woman that wants to learn the ropes of paid public speaking, come here Thursday night, I'll have wine and cheese all she'll tell you everything I know. And the room was packed. And women were like, can you record this? Can you put it online? Oh, I don't live here. How do I attend? And so in 2018, you know, I decided to just put it together in a course online just to reach more people. And then that eventually became mic drop workshop, and we've trained 1000s of women to become professional speakers. But yeah, there was a time you know, in the spirit of this podcast, Hillary that where it was like, I didn't know, it was there was an overlap. And there's almost a guilt that you feel of being excited about someone or something or someone else. It's like a relationship where you're like, you're with someone, but you're like, oh, that seems attractive. And but I feel guilty, because there's nothing wrong with this one. And so giving yourself permission to evolve. And I was actually talking to another entrepreneur about this the other day, who's, you know, looking to relaunch and evolve out of a business that she started for no other reason other than she just wants to. And it's I think there's sometimes comes a point where you overstay your welcome at your own business. And that's how I've started to feel
well, and I also think when you think about the relaunch of a business, you have the ability to relaunch into something totally different, something totally new, you need energetically to have something that you're now back to being inspired and fire in the belly. And then there's the, hey, I really still have a passion for what I'm doing. I just need, I need to relaunch part of it, I need to relaunch a certain direction of it a product line. And then there's that you know what, I think I am ready to 100% take what I've done, have give it to somebody else, have somebody else run it. And let me simultaneously do something new infusion. I just talked to a gal who has four companies now and running them even more successfully now. Then, when she was just running one company. Hmm. And so where are you right now in how? You know, you're you've got you've got two passions? Are you completely out of the headband? Are you still working with that? Are you what, how do you spend your time?
Yeah, I am out of headbands. Pope I have an amazing team. And that was the other part too is like, you know, I think a lot of time, people might have founders syndrome where they think because they started it, that they're the only one that can run it or have great ideas. And I think I'd be doing a disservice. And that'll probably happen with Mike drop to what I'm doing right now. Where if I feel like I'm the only one with the ideas, and the company can become stagnant. So I have, you know, evolved out of headbands of hope. And I'm now in my drop workshop. But I think you're so right as to there is a time where you can almost relaunch and find other avenues within your own company. Like we, you know, we started by helping women become professional speakers, which we are doing, but then we had a lot of requests from women at work, who were like, look, I don't want to give a TED talk. I don't want to get paid to speak. I just want to be able to give a presentation at my job and do it really well. Or I want to be able to lead a meeting with confidence. I want to be able to handle q&a, and all of these things that involve public speaking at work and So we were launching a new program this year called mic drop workforce that helps women, you know, become better speakers at work. And again, it's like, you get to put that relaunch hat on. But within the bounds of a company that you already created, which I think is unnecessary, and so fun to do, and there's probably an argument that's like, well, you could get a lot further and a lot faster if you just did one thing. But I also believe that this should be fun. And it's not fun for me to do just one thing. So I've come to the fact that I, we are all multifaceted human beings that can do multiple things at once.
So just how, okay, if you're sitting here, and you're hearing from somebody that okay, whether you are somebody who just wants to do a better presentation in front, whether you want to go do a TEDx, whether you want to get on a huge stage, small stage, as you're saying, you know, there's so many different varieties, what's the first thing that you start to really focus on when they come in those initial tips and strategies that you say this is what we need to focus on?
So a lot of times people come of like, what do I say? Or, you know, what do I how do I stand? What do I do? And a lot of times that fear of public speaking, and the reality is, is like most people fear public speaking more than they fear sharks, is the fear around how you'll be perceived. What will people think of me? What if I mess up? What if I forget what I'm saying up there. And so the first thing I like to do, no matter if you're speaking professionally, or speaking at work, is learn the difference between what we call being a spotlight speaker, and being a lighthouse speaker. So a spotlight speaker, you're up there and the light is shining on you all attention is on you. You want to be liked, you want a standing ovation, you want everyone to adore you and you want to be perfect. It is all about how can I be perceived. But a lighthouse speaker shifts the light from themselves to the audience. And a lighthouse is more of a guide. They're not worried about the light being on them. And they're like, How can I help people get to where they want to go? How can I further them in their journey. And I'm just the I'm just the guide doing that. And so when you have the the mentality of a lighthouse versus a spotlight, it helps ease your nerves because it's not about you, it's about them this and it also creates so much better content, and so much better value for your audience, because it is all about getting them to where they want to go. So no matter what the first thing that you need to do is just most of us start with a spotlight mentality. Because that's what we've been trained that speaking is. And I want you to kick that to the curb and become a lighthouse. So that's step one. That is
so great. I love everything about that, because it's not about you. It's it's about what your story is that's going to impact somebody else.
And I think that that's true for so many careers and industries. And just, we're in a world that is so focused on perception, you know, social media, and how will I be perceived? And what will it look like? That we kind of forget that like, the real value is helping people and being a guide? And who cares? If you have I've learned that some of my best performing stories on stage are the ones where I look the worst. And so it's not about how you look. It's about how you're furthering them.
So when you're working with somebody, and you're talking about, you know, getting up there, it's not about being the spotlight. You're the lighthouse, what's that second step that you let people know, this is kind of where you need to go from here.
I would say decide what you want to be known for. And I know we've talked about, you know, not being shoved in a box, but I think with speaking specifically learning, what is the thing that you want people to come to you for? Because we call it you know, when you're someone who's like I can do anything I could speak about leadership. I could speak about confidence. I could speak about this. We call it being a cheesecake factory speaker, which if you liked the Cheesecake Factory, no, no hate to you. But I would rather go to a restaurant that has four menu items than 40 menu items. I want to know what you're good at
400 they have? Yes, right. There's no difference. Sometimes they do have that good breakfast burrito. Yes,
exactly. But you know, the goal is to find like, well, what's my chef's special? And so I asked people, you know, what do people come to you for advice for? Or what's the thing that you could talk about totally unprompted? Or what's the thing that you know, when you think about how you want to leave your mark, or a lesson that you've learned, that could be your motto? What would it be? So we create what's called a speaker statement, which is a super clear, concise, Hi, my name is Hillary, and I help audiences blank, we're Hi, my name is Jess, and I help audiences blank. And so it really gives people a North Star, instead of feeling like they have to be everything to everyone. Because otherwise, no one knows what to come to you for. And so I like to help people find what's the one thing that you want to be known for? And this
suggests, does this mean that you have a keynote? Or you have your go to stage president and you just keep doing that same one every single time? And you perfect that? Or do you have like a handful of these?
It is I have a signature talk. And that is the other thing that people think it they get wrong about speaking is that they think that in order to be a high quality, valuable speaker, that they need to start from scratch, and oh, I'm speaking to a financial company, well, then I need to create a talk around finances. No, the financial company wants you to give a talk that you have perfected that you've done before that you've proven, and maybe tailor five to 10% of it to their industry. And so I say our method is build that signature keynote talk, get good at that. And then maybe once you have enough reps in it, and you know that there's another talk you want to give, you can add that. But I think that's one of the biggest mistakes I see speakers make is they list 11 different topics on their website that they can speak on. And instead, I want you to have one signature talk
and how many times you have to deliver it before you think all right, you perfected it, it's now good enough to go big time.
You know, I would say we see in my drop workshop, women kind of give a trial run for free, maybe one to three times and then start charging for it. And so I would not say that you need to have a long runway, which is one of the things I love about speaking is like, the path to making money with it is pretty short versus some other industries where it takes a long time, even like writing a book, which I think writing a book is great. And we teach how to do that too. But the path to actually seeing a financial return is a lot longer. And so but I would say the one thing that I would caution people is, you know, get 70% There 70% there with your keynote with your website, or whatever it is that you're working on. Because you'll never feel 100% on anything. It's just never going to happen. And so feel good enough and take good because you're good enough. Is someone else's, like mind blowing.
So we have to remember that. And how long do you think a signature talk should be?
One hour is the typical length for a keynote talk. And then that can fluctuate anywhere 3045 minutes to an hour, but have the hour talk. That's what we teach and mic drop workshop is like building the our signature keynote. And then we like to build it in basically five smaller talks that make a one hour talk. So then if you're asked to speak for 45 minutes or 30 minutes, then you just remove one of those talks. Instead of rewriting and reworking the whole
story saying it would be a steak take five sections for the one hour and then if you're not going if you're going to be on for 45 you could potentially take one of the stories away
you're that's Yeah, yeah.
And so with your program, I What is the normal like, you know, I Okay, hey, I've never spoken before or I just want to get better at it. Like a lot of times when I'm coaching people I'll say, you know, go go take one of those improv classes because you gotta get you know, you got to get a little bit more on your feet being able to talk you're asked to speak it's time versus I'm not ready. I'm not ready I'm not ready. What do you what do you suggest? As you know people hearing this right now that that want to get involved in a program like yours? What's the first thing they can do?
Well, I love you saying taking improv classes because so much of like getting over your fear Speaking is just about getting reps in. So wherever I mean, I feel like my speaking career really started when I was giving tours on campus as a campus tour guide, and then teaching spin class, you know, on Thursday mornings of just like getting in front of people. And so anytime you have those kinds of opportunities, just getting your reps in is always a good thing. But when it comes to the nerves side of it, and just like, Okay, it's time, I think, you know, there's physiological things you can do right before you're supposed to speak. I mean, there's box breathing, there's sniffing, peppermint, all of these things that are proven to help your nervous system, which are more like in the moment, but if you have there were there was actually, we just did a podcast with this woman named Britt Frank who talks about your like nervous system and gave some tips and it was really interesting. But there's, there's in the moment tips, but I much prefer working with people that are like three or four months out from when they have to talk and really getting in the right mindset of, I'm there to help people. It's not about me, and also thinking, What is the worst thing that could happen, which is usually a question that invokes nerves, but I think it actually is a sense of calm, because what is the worst thing that could happen? Okay, you get up there. One time I broke a heel, so I took my shoes off, or I know that one time, I
think, you know, ice breaker right there. Now Yeah, like my only I like
my Spanx were coming through, you know, like my short, the Spanx shorts I was wearing. And, you know, I just called it out. And so what is the worst thing that could happen? What would you do? Because you are like, far more agile than you think. And so actually thinking about well, what is the worst thing that could happen? What would I do about it can actually be really calming?
So I had a speaking coach one time, I can't remember if I was interviewing them, I think I was. And I said, best tip you could ever give. And it was all around the idea of a lemon and pretend to cut a lemon and place a lemon in your mouth and your mouth. Everyone out there right now Your mouth is starting to water. It just happens that does Yeah. And I think that the stat was like 60 to 70% immediately go to that dry mouth thing. So that was something and I actually use that one. I was on a big stage about a month ago. And normally I'm good. Like I love it. I think exactly. I'm like, Oh, I get to deliver tune in and have people like learn this incredible two minute or less process. I got up there. And I just, you know now Grant who was in Las Vegas, it was a little dry. It was a little bit I mean, I had I was like lemon lemon lemon. I'm
like, my mouth. That's a great tip. I never heard that before. Yeah, I
was like, Oh my gosh, I've got Lemonade Factory going on here. Okay, so as we're wrapping up, what is that message that you really want to convey to people, especially women, when you hear that 30% of paid speakers are women? What message do you want to give them?
I think if I could create a headline of, you know, the past, what 1213 years of starting things, whether it be headbands of hope, or my drop workshop or becoming a speaker or an author myself. And if I could show everyone the piles and piles and piles of rejection letters, whether they're from events or literary agents when I was trying to get my book published, or retailers that were trying to get in. And it because you can just it's so easy to see the winds. And I think if there's one thing I have learned it is that the failure will always feel better than the regret. And so the powerful failures of the things feel almost like research now, because they happen so often, where we have more information from trying, then we were sitting on our couch wondering what could have been. And so that failure will always feel better than the regret and so just have peace in that if you try something and it doesn't work. Now you have the information to go do something else
and you're one step closer. So just how can people find you? How can they follow you? How can they get involved in your workshops?
Well, you can go to Mike drop workshop.com If you would like to learn more about our programs, but my favorite way that people can follow me every Monday, I sent out a hypertext of like a quote or a thought or a prompt for your week. And so you can join that text you can text the word hype to 704-228-9495. And you'll hear from me every Monday at 11am. Eastern.
Okay, that's 704-228-9495 Yes. And we will definitely put this in the show notes. Thank you again. Now go have that second baby. And I can hardly wait to hear how you do in six weeks after you're going to crush it. And that will be a great podcast in itself right there. Sure. Yes.
Hillary appreciate you.
Ah, thank you again and again, we always talk about live now love now relaunch now relaunch into that remarkable you because it is all within you. And if you're looking to be a speaker, if you're looking to make an impact in what you're trying to put out there, definitely get in touch with Jess and make it happen. No time like the present ReLaunch now and we will see you again next week.