Off The Vine with Kaitlyn Bristowe - Grape Therapy: Jess Ekstrom

Episode Date: November 21, 2019

Today. Kaitlyn is joined by founder and CEO of Headbands of Hope and author of, "Chasing the Bright Side”, Jess Ekstrom! These efficacious entrepreneurs exhort encouragement for their fellow fearless females. Jess shares some of the lessons she’s learned so far including how Improv class helped her in business. And she even tells a story about how attending an All That concert helped teach her to shoot for her dreams! See Privacy Policy at https://art19.com/privacy and California Privacy Notice at https://art19.com/privacy#do-not-sell-my-info.

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don't know if you've heard of it. Forbes, not a big deal. She's an absolute powerhouse who turned what was once a dorm room startup into a seven-figure business to help kids fight cancer through headbands. She is an entrepreneur, speaker, and writer who's soon to be released book, Chasing the Bright Side, shares behind the scenes of how she created her empire. She's a huge inspiration so excited to learn more about who she is and what she does please welcome to the podcast jess extram thank you for having me of course excited to be here yeah i'm so excited to have you i first of all we have this like live stream here is this live i don't think this is live but we'll we'll post it but you do have a live in um airstream is that we yeah yeah you and

your husband and your dog and our dog i need to hear more about this ramen and allie need a play date for sure i can tell he's going to start barking by the yes see did you see that? I'm not even making eye contact. I'm not even making eye contact. Okay, I won't make eye contact. It'll keep barking. He is, I swear to God, he knows when I start podcasting and that the attention is not on him anymore. My dog does the same thing. Anytime we start on a podcast or I'm doing anything important, he's like, now's the time to interrupt. See, and I, if you just ignore him, then he lays down. Okay, good to know. Okay, what kind of dog do you have? So I have a standard poodle. Oh, I love poodle. But we cut him like a regular dogs. You almost can.

really tell. Yeah. My husband is always like, oh, he's not like the regular kind of poodle. He's a cool poodle. He's a cool poodle. That's black? It's called a party poodle, which makes it even better. A party poodle. It's when they have a mixed coat. And so when we figured out that he was called a party poodle, we were like, we have a party animal on our hands. This is amazing. So he's brown and white. Oh, that's cute. Yeah. Yeah. I found him on Craigslist one day. And I was like, this is my dog and so now with him wait you found him on craigslist i randomly found him on craigslist it was my husband and i got married and um i said okay i'm going to need like a kid or a dog soon and he was like what

breed of dog yeah yeah i heard dog yeah yeah dog sounds good and so uh just i grew up with a poodle and i just like typed in poodle in craigslist and i found him and reached out and i told him I was like, let's just go look. Of course, that's the first thing. Yeah. And then we came home with him. Yeah, of course. So he's like 70 pounds now.

Still thinks that he's a lap dog. But we travel around in the airstream. We've been traveling for like eight months now and going all around the country. Wow. It's been so fun. Wait, now I'm confused. What do you mean? You travel around the, with your poodle?

With the poodle. Yeah, the three of us. So we have a truck that we tow this airstream with. And we're mobile. So we started in North Carolina And now we are Yeah, yeah We're out west and just

And that's why you're in Nashville Yeah, so in Nashville for some of the book tour The airstream's actually parked in Las Vegas right now Oh my gosh, where are you originally from? North Carolina Okay, yeah, yeah So not too far from here But we've been having a really good time

I was on the road all the time anyway For Headpants of Hope stuff and speaking And my parents have actually been living in an RV. They're entrepreneurs as well. They sold their company, sold everything they owned. No way. Got in an RV. They've been living full time for five years in this RV and they just became park rangers, which I think is the cutest thing. That is adorable. Yeah. Yeah. They're living their best life and their little ranger outfits. So being entrepreneurial is like in your blood. Well, it wasn't even like entrepreneurial. It was a problem solver. I remember when we were kids, we went on this like

family camping trip we were always going camping our poodle growing up his name was camper that's how legit we were camping and i remember one day i was uh camping and i was going through my like rebellious like pretty teen years i was like i'm going to listen to my walkman you know not the outdoors yeah and i take out these headphones and they were like getting tangled in this knot yeah i was like this is stupid you know headphone cord should roll up like a slinky so they don't get tangled and i just said to my dad. I was like, I'm just going to invent that. And he sat me down and he looked me in the eyes and he's a pretty goofy guy. So when he was serious, I thought something terrible would happen. Like he forgot the marshmallows or something bad. But he looked at me and he was like, that's already been

invented. But I want you to keep thinking that way. Yeah. And it was, I remember that moment so distinctly as like that was when I really became an entrepreneur was when I thought about the world through a lens that I could fix it. didn't realize that that was entrepreneurship. It was just solving problems. Right. You're just a problem solver. Yeah. Yeah. Just I like to call it inspiration from frustration. I mean, we get so frustrated about so many things. It's like maybe in the next time we're frustrated, think about why and what if we were just inspired to make a change about it instead. I love that. Good. That's that. Wow. And what age were you? Oh, man. So that was around like 12 years old.

then that was when I started getting into eBay. Yeah, I was going to say you were auctioning off toys on eBay when you were 12. I can't believe that's public information, but yes, I do my research. Yes, thank you. I really, like, struck it big with selling my American girl dolls. I remember, like, when eBay hit, I was like, oh, I'm going to make some money. I'm going to be, like, the cool kid in school. And I ended up getting this, like, white sheet for my mom's linen closet, threw it in my

bedroom borrowed like a digital camera and took photos of these like american girl dolls like post product photos i was like oh this one's gonna be hot like get it well it lasts and uh that was like my first you know business and got shut down when i started selling my sister's toys but yep that was that's illegal that's business i know i've learned that now you learned at a young age yeah yeah i'm glad i got that out of the way early do you know when i was 12 i started my own doll hospital. Did you really? Yeah, in the crawl space of my basement and anytime somebody's doll was broken or something was wrong, I would have them into the doll hospital and I would help fix them and bring them back to normal. What was your remedy? I don't know. I remember putting them on like an ironing

board. That was like the operation table. That was the operation table. And I would like, I don't know if I pretended or actually tried to fix them. Yeah. But I just wanted to like run this hospital and help dolls. Yeah. I mean, it's a big problem in the world right now. Yeah. Yeah. We need more people like you saving dolls lives every day. Thank you. Yeah. Thanks for a hero. Yeah. I don't know if you guys are like me, but I like to give gifts for the holidays. I don't like overspending on all those gifts. Definitely not. So why spend more than you have to? Finding the lowest price is easy if you have honey. Honey is a free browser extension that automatically finds the best promo codes whenever you shop online. This means you always get the best deals without even trying on over 20.

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then you probably know someone who is so do them a solid and tell them about honey honey honey can help make sure that you're getting the best price for whatever you're buying it's free to use and installs in just two clicks get honey for free at joinhoney.com slash vine that's joinhoney.com slash vine so tell me how you first became involved in working with kids who have life-threatening illnesses, like what was your path from first starting to work with kids to starting your business headbands of hope? So, believe it or not, it starts in Disney World. Okay.

I was a freshman year of college. I was actually like going through a breakup and, you know, those like high school boyfriends where you're like, oh, we're going to be together forever and, you know, like, what are we going to name our kids? And then you get to college and you're like, oh, never mind. Yeah, JK, JK. Yeah, exactly. but so it was one of those like I need to get away and like go find myself kind of things and then there was this flyer for this Disney college program and I was like Disney sounds like the happiest place on earth and so I go to Disney World I'm a photopass photographer which was so fun I got to take pictures of people from all over the world but my favorite thing that I got to do there was photograph kids that were there on their wish through the make a wish foundation that's great yeah so then I got back to school and

turned for make wish. And that was when I was really starting to discover kids that would lose their hair to chemotherapy would be offered a wig or they'd be given a hat. Yeah. And a lot of them really didn't care about covering up their heads. That wasn't the goal. They just wanted something where they could feel good about themselves and feel like just a kid again. So I would see them coming to the office or would see pictures on their wish where they're wearing headbands. And no one was providing that. I was seeing, you know, if there was any companies or organizations out there where I could get some headbands which is crazy yeah i and that was really the moment you know i think that a lot of times we like to overcomplicate entrepreneurship but it's just about creating what you wish

existed and that was something that i wish existed for the kids and so without a lot of thought which i think was to my benefit i just went for it yeah yeah wow good for you and explain to everybody listening how headbands of hope works so for every headbands sold we donate one to a child with cancer. So to date, we've donated over half a million headbands to kids with cancer and reached every children's hospital in America in 15 countries now. Wow. Good for you. But I also like, I mean, one of the things I love about your podcast, Caitlin, is that you're just so real and authentic. And one of the things I loved about your season. And one of my pet peeves with entrepreneurship or like any success story is like it's like the A to B and the snap of a finger.

right one day I had this idea and the next day like Oprah just keeps calling me yeah she won't stop calling I just need some space yeah and I feel like that was the narrative I kept hearing when I was starting had bands of hope and I was running into these like really massive mistakes which I'm happy to get into but yeah I never heard any um story that kind of normalized like the messiness of a startup or just going after something yeah it was always just the, I had an idea and I just did. Here I am. Like, parked, you know, my yacht is in the harbor. And so I really want, you know, my story of Headbands of Hope and what I speak and what I share in the book to be real, including mistakes. Of course. So what kind of mistakes do you think

I mean, not just you personally, but like what kind of like roadblocks did you run into along the way. So in the beginning, I, you know, I was a college student. I had this idea to give headbands of kids with cancer. I was studying communications. I mean, I couldn't even spell entrepreneur. I had no idea what I was doing. I don't know if I can. I was going to say, I'm still questionable. Don't test me on that. I can't spell restaurant. I'll tell you that. Yeah, so you can't spell restaurant. I can't spell entrepreneur. But I just started kind of using what I had in college. I paid this girl to build my website who was a computer design student and I paid her in Chipotle Burritos and that was how I made my website. I needed a logo. I walked into

this like graphic design class and that I wasn't in and I went up to the teacher and I was like, you know, it would be a great idea as if for your next class assignment, everyone had to make me a logo and I picked the best one. And that was how I got my first logo. And that was how I got my first logo. And so little by little, like, things started to come together by not focusing on what I didn't have, but things that were right in front of me. And that's one thing that I like to tell people who have an idea is just like, don't look over the fence. Someone's going to have more money than you. Someone's going to have, you know, more contacts than you, but what's within your control. But then I needed to create the actual product. I needed the headbands, you know, small

detail. And so I started working on this list of U.S. manufacturers that I found in this database and going down the list, just hoping that one of these factories would just take a chance on me. And I was like, look, I know that I'm coming at you from like a dot edu email address with like don't judge. Yeah, comic sans font probably in a 12 line email signature about how I'm present at the ping pong club or something stupid but just like hoping that someone would see the good and the potential in what I'm doing and go for it yeah and two months of radio silence no one got back to me finally this factory in Kansas got back to me and they wanted to get on a call and I was so excited I get on this call with them I tell them about my idea and they love it they're like we're going to be here for

you in this and so they send me some headbands some samples to give them feedback I send them back So for about two more months, we're, like, sampling the product. So finally, they shipped me a headband that I'm good to go with. I'm like, let's do it. Let's make this headband. You know, had this moment. I'm like, here we go. So they sent me over the invoice.

And it was for $10,000. And I was like, you know, I probably should have asked this before. Right. But I... Learning lesson. Exactly. But I also want to be honest in, like, this mindset that I had at the time. was anyone who was working with me was like doing me a favor you know and sometimes I think especially

as women we can get this hierarchy in our head yeah where we think we deserve like the scraps in the kitchen when really we have a seat at the table just like everyone else but in my head I was thinking I'm not good enough I'm not at this I'm who am I to be doing this anyone who's working with me is just doing me a favor so I wasn't speaking up or asking questions um but at the time I didn't have that kind of clarity. And I was just thought, where am I going to get this money? Right. So I started to do some research. I started thinking, okay, can I get a loan from the bank? Could I get an investor and give away some equity? And I was talking to my dad about these options who, as I mentioned, is also an entrepreneur. And he was like, look, I've seen your business plan. You know, I really think

that this is going to be something big. This is a great idea. It's going to help a lot of kids. one of the mistakes I made starting my company was I gave away too much equity too early and I don't want you to have to do the same thing. So I will front you the loan for $10,000 and you can pay me back as the business starts to make money. And that was like hearing my dog speak English. I was like, what is happening? I just, and I recognize this immense privilege.

of course, financially, but even emotionally of having like a family support of just going for it. And so I just was so excited that he believed so much in this idea. And you, because I think a lot of times people and kids feel so much pressure from families to like go to school and get this career. Right. You know, so that's fine with me taking this other path, which was awesome. Yeah. So I ran to the bank. It was a Friday afternoon.

I was like, I want them to get the money before the weekend because I'm a businesswoman, clearly. And I wired them $10,000 and I never heard from them again. You're joking. No. Oh, shit balls. No way. Yeah. I had.

Oh, I was like waiting for this like great. I did not see that curveball coming. Neither did I, clearly. Oh, no. Yeah. It was, I still, like my heart is racing. And this was like eight years ago or so I'm still, I get so upset. wait I'm so confused so this company you found them online and they seemed legit and you had gone back and forth right oh it was months of conversations months of conversation so what happened after did you huh yeah I know so we ended up going to court and like I was like 18 years old like being deposed about stuff and it ended up the money was gone we were just spending more and more and like legal fees like and so

We had to come to this point where we were like just cut our losses and move on. But then I went online and was like, I'm going to make sure that no one else works with these people. And then I found all these forums that they had done the same thing. And so they got shut down and everything. But I remember, you know, after this happened, going to bed. And, you know, when you go to bed and you just like run through all your life's mistakes. Everything. Every night.

You're like, why did I do that in 1997? Yeah. Of course. So I'm closing my eyes, and I was like, you know, I could stomach being embarrassed, the embarrassment of failure. But this idea, Headbands of Hope, was started because of a problem. It was started because these kids weren't feeling confident when they were losing their hair to chemotherapy. Right. And I like to think of the best companies, organizations, anything that's created, start because someone has an itch, like a need. and then companies provide a scratch a solution so kids not feeling good about themselves after losing their hair was my itch headbands of hope which provides headbands to kids with hair loss was my scratch right and so i remember just laying there in bed and thinking like this isn't really about embarrassment of failure it's about this itch not being scratched and you know like i just couldn't sit with that feeling and so i got up and the next day i went to my school they

were giving away these $300 grants to students who were starting companies. Mind you, I lost $10,000. $300 was a starting point. I bought two different types of headbands from some supplier in Bismarck, North Dakota, who let me buy really low minimums and threw them up on my website, April 25th, 2012, and I never took outside money again. Holy crap. Hey, question for you, Black Friday, Small Business Saturday, Cyber Monday,

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I would have given up after that, or how do you trust after that? Or how do you believe in, like, humanity after that? Like, you're trying to do such a beautiful thing with children suffering and here some asshole is scamming you out of $10,000 for it. That's sick. Like, how do you keep going? I think that moment to happen so early really taught me how bad I wanted it. And it was like this this fork in the road of like either I'm committing to this and going all in or this is a really great excuse to turn around.

Yeah. And something that I feel like I've learned over the past seven, eight years, starting this business is that hard times give us a choice. It's either the excuse to do less or the reason to do more. And so this one single time. Oh, good. Go on. Like this one experience can trigger like two completely different reactions. It could be the excuse as to why we hide and don't want to put ourselves in that way again. Or it could be the reason as to why we do something more.

I mean, similarly with you, when you were having a tough time with your season, it's like you could have easily used that as an excuse to like, I don't want to ever be in the public eye. I don't want to do anything. But you use it as a reason to be an advocate. And so it's one single experience that can trigger two completely different reactions. And one of my favorite analogies for it is that boiling water can soften a potato, but harden an egg. So it's not as much about the circumstance as it is about the subject and who we are. So it's... You are inspirational. This is like motivating me right now. I've been going through a bit of a hard time with a lot of things like online or what people are saying. And you would think after all the time on, you know, going on the show and going through things and coming out of it where I am now,

you'd think I'd be like tough and have thick skin, which I do. And I am tough. And but I'm like going through this weird rut in life where I feel like I'm kind of going into this place where I'm like, should I just go away and hide for a bit? Because people are mean. But you're right. No, that's not who I am. It's not who you are. And I think that that's what, makes the people who love you, love you so much, is because you've chosen that one experience or all those experiences, not as the excuse to do less, but the reason to do more. And when you think about like any great movement that's ever happened, whether that's the Me Too movement or civil rights or whatever it might be, none of those things began when times were good. Right.

And so sometimes when we think about like doing good and optimism and charity or like we think about like the hearts and flowers around it but sometimes what we have to remember is that like the darkness is where we move because when everything is good why change right but when we're faced with a tough time when something isn't right when something you know is unfair that's when activists are born that's when philanthropists are born that's when people raise their hand and so sometimes we have to be able to like see that light at the end of the tunnel going through tough times like sometimes we do and thank god you did because look how much you're changing you know you're helping people and you believed in yourself and what you have to offer and you just kept going even though

somebody absolutely robbed you yeah and such a beautiful idea but you just kept going and now you have this successful company that does this and like first of all where can people get these headbands yeah you can go to headbands of hope.com yeah and purchase them and uh that we have so many different products that you can choose from i know you're a fan of the knotted you wear there's a lot that looks so good on you oh my gosh you can time around dogs next ramen can wear one yeah because i got i still have a bunch of headbands from you guys and you brought me more so i'm so excited um but i remember how i mean was that two years ago i think it was yeah yeah um my my my team had kind of reached out and said what you were about and that i could get headbands and i was like hell yeah like what we were

so so excited my whole headbands of hope team is such a fan Oh, well, I'm, I am a fan of just, I mean, obviously what you're doing and who you guys are as people and just what a, what a movement and what a great thing that you've done for everything and everyone. I'm just, I was so excited to get some and not only to get some for my hair, just to like spread the word. Yeah. And now to be able to have you on my podcasts, it's like one of my favorite things in life is to use my platform to bring awareness. It's your reason to do more. Yeah, it really is. I love it.

and it selfishly brings me joy. Good. But, I mean, at the same time, it's for a good cause. We'll be right back with more Austin Vine, Grape Therapy. This is Austin Vine, Grape Therapy. Can you tell us how you come up with the designs for the headband? Yeah, it's actually a running joke with the team whenever I have any input on design or let's do this pattern or, oh, this will be super cute. like those are the products that don't move.

And so they're like, you have no, you need to move away from the room for right now. Because I'm like, oh, something shiny. Let's do it. And so I have a product development team. And so one of the things that we've been really excited about doing, though, we actually just did it right before this at Monroe Carroll Children's. One of the things we noticed when we go into the hospitals is that the kids don't have a lot to do when they're there. You know, to think they're being pulled out of school or like, you know, all the things that. kind of are helping them in this developmental process just go on pause. So we're like,

how can we still fulfill our mission, but also give them something to do? And so we started doing these DIY headbands. So we have these make your own flower crown kits where the kids can actually design and create their own flower crowns. But what we just launched was are these coloring book headbands. So there are these bandanas. And then Sharpie has given us like a ton of like these custom sharpies where the kids can actually color in these bandanas and wear them. So it's really cool. So they get to like create their own. So that's what gets me really excited on the product development side, not just like

the consumer facing side, but how can we do fun products for the kids and the hospitals that they can like get their hands dirty? Gosh, what a great idea too that, you know, like you said, I think there's so much around kids going through what they're going through if they're going through cancer and chemo that you don't even think about the fact that they're missing out on like certain things that they would just be doing simple at home school crafts that kind of thing you know right to the simplicity the simplicity and i think a lot of times when we think about giving we think about the like ellen degenerous style of like oh i'm gonna you know fund a rainforest or like something like you know i created a library and it's like millions of dollars and then when we don't when we can't do that we feel like we can't give at all yeah And when I think about headbands of hope, one of the things I love about it so much is because a headband is so small. It's so simple. But it's like one small thing that can make such a big impact for people.

Especially kids. Like the big things don't really matter to them. Like the money, you know, the dollar signs behind things of a funding a library or all these things. It's the little things that they can do to like coloring a headband that they can wear means so much to a child. Oh, for sure. But I think, like, a lot of times we take ourselves out of the game if we can't afford the, you know, big, big style of giving, then we don't do anything at all.

And chasing the bright side, I say, like, if you can't give a whole chicken, just give a chicken nugget. Like, it's still such a great gesture and the small things add up. Absolutely. And forget Caitlin Bristow. Celebrities like the Kardashians were your headbands. I don't know. I think that you were one of the top of our list.

Get out of town. That's, I mean, just to have someone like Chloe Kardashian with the platform that she does, wearing them is just, again, like another small gesture that's a headband, but that can reach so many people and make such a big difference. Yeah, yeah. It's been really cool to see the celebrities and people that have come on board with it. But I'll admit, I got really caught up in that for a while. I think, you know, when I was first starting, Handpans of Hope, it was like, I feel. felt like I had it all figured out. I was like, oh, I'm doing what I love. I'm making a difference. Like, I discovered the meaning of life. But then as I, the company started getting bigger and you

have more employees and then you have like warehouses and then all these things. And I started really like getting caught up in how it looks and not how it feels. And those are like two completely different things but I think especially with social media now and social media is great but sometimes we do things based on how it will look you know instead of like what does it feel like to me and so all the celebrities with Headbands of Hope has been great but like one of the things I've been trying to work on is like not get so caught up in like the accolades and the achievements of this business and focus more on like is this aligned with what I want to be Well, I get what you're saying, but that can bring so much more awareness to what you're doing.

You know, like forget who they are and like what they have. It's the fact that they can reach so many other people that can know about what you're doing and help. Yeah, exactly. I mean, I think that the ripple effect of it all is super helpful. But I think like sometimes I would get in my head of like that is what success is. Of course. of being on this show or being in this magazine

and it was kind of like I'm looking at ramen right now with a dog and you're like a dog getting conditioned with a treat like every time you get something it's like here's a treat and so you become like oh I need to get more more in these lists and then it kind of gets blurry as to like why am I really doing this

well I mean first of all it's good that you even just have that awareness to think about what the bigger picture is a lot of people don't and so good for you for knowing like you did get caught up and that you don't want to lose the you know purpose or yeah or how it makes you feel but i mean don't be too hard on your yeah yeah because it's i mean part of what success can look like is is you know the exposure yeah the exposure because especially when you're doing something like what you're doing like if we're just trying to you know it's what you are you're not selling something you know you're like you are but it's for such a good cause yeah that it is exposure is a big part of

that it is it is and so it's hard uh sometimes like to adjust your focus but one of the things i started doing i have a um file on my computer like any picture that we get from the children's hospitals any like letter from a parent like nurse i throw it in this file and whenever i'm feeling that kind of like off you know or something doesn't go my way i open up that full and just look at that but one of the eerie thoughts that I have that like gives me chill sometimes when I open up that file is like what if this file didn't exist because what if that like one failure in the beginning of like wiring that money was the reason like no never mind and so I look at like the hundreds of thousands of kids that we've impacted yeah and it's like

to think that like one person could have controlled my fate and hundreds of thousands of other people's fate by one failure is just what a great lesson like I'm just so excited for everybody who listens to this to just hear that thing that you just said oh good yeah because that's what a what a true statement yeah I think for a while it was like I connected these like wounds to my worth I was like if I mess up therefore you know that's on me and who I am as a person I hear that yeah and you think that like if I failed then I'm a failure and now And it's honestly, I mean, it's people being transparent like you who have made something of themselves but are transparent about the process that goes to show that like failures aren't

reflections of our worth. They're just reflections of growth. It's just a part of the process. I'm trying to be more cognizant of that and thinking that way because I hear stories like yours or what you're doing. And I'm like, that is, you know, a testament to that. And when I think about mind. I'm like, oh my gosh, sometimes I can't believe I let something bother me, you know, when it's, as much as it did, when it's like there's no, nothing to it. Yeah. But how do you come to that clarity, like when you feel off? Jason helps a lot because he's just so level-headed about everything can really just see the other side of it. Yeah. You're good at that. Yeah. And so it's, it's nice to have a little

reminders around, you know, I'm living with this person. So it's nice. But I think just, again like you said you go and look at this folder of everyone you've helped and I think I can do that too just by going into your DMs yeah like you know there's so many great people out there listening to this podcast too have so much love and and I just I mean it's very two very different things for what we're talking about but same thing like everybody in their life can look at a negative and have the you know pity party or try and give up but you can look at it and you can look at it and as an opportunity to grow and look at other things in your life that are great and and keep powering through. And I totally agree. And one of the things that really helps me is just this like rooted belief that failure will always feel better than regret. Oh, always. And so sometimes when you've like messed up or something doesn't go your way, you're like, I'd rather be like, I'd rather have a story than wonder what if. Yeah. And so you can always kind of feel. And so you can always kind of rooted in that fact. It was so funny. Did you ever watch a show all that growing up on the

Nickelodeon channel? It sounds familiar, but I can't picture what it is. It was like Amanda Bynes, you know? Oh, yeah, yeah, yeah. Okay. So I went to the all that, the all that concert was my first concert. I'm like, thanks, mom. And when I got there, there was this tent that they had, we were hosting auditions. Yeah. To be on all that. And there was like this three hour line. And I was like, mom, I am waiting in this line. No way. This is my moment. And I had no like singing, dancing, acting, nothing like you experience. But I was like, I love this show. But you had the heart. I had the heart. I missed the entire concert. I waited in this line. You make it to this tent. And it's just like a camera on a tripod. Like no one even operating it. I don't even know if the camera was on.

Yeah. And you go in there and you like read this like script. And yeah. And I'm still waiting on my callback. But I remember. Yeah. And I just remember. watching that show like moving forward and just having a little sense of pride of like I went for it you know and just being a kid and having that realization when I was like this feels better than wondering what if totally um I think was like a big quality that I didn't realize was going to carry on so far and I think once you do that once in your life you kind of learn from that a lot of people could live their lives not even going for that one opportunity but as soon as you do you kind of get empowered to be like I can do another one or I can do something else and I yeah you know because to do

do something scary or like it's something that you're not comfortable with always will benefit you in some way even if you quote unquote fail and you get better at hearing no it's like all a sudden the nose become like less like a bee sting and just like I'm okay moving on yeah and so you just you just get better at like making your comeback stronger than your setback you're just like I can just keep getting back up and you just get better and better at it each time that's a good Great life lesson. I like that. Hey, are you guys looking for a thoughtful, unique gift this holiday season?

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something that I decided I was doing a lot of public speaking and I was like, you know, maybe I could be more loose on stage and some of one of my friends suggested improv comedy which is terrifying. I live for improv comedy and I am too scared to go to any kind of. Oh, I feel like you would crush it.

Really? No, I'm like, that terrifies me to think about it. I could like. Could you do stand up like a scripted? Yeah. I could definitely do that. But to go into an improv class and be put in a situation where you just have to like. Yeah. That is terrifying. And you did that. Yeah. But I mean, it was like a very small, small level. But I mean, I was always really interested in comedy. It's like my dream to have a Netflix standup special. But I was like, I'm like, I'm going to get there. I'm going to do. one day. You still can. Yeah, I feel like I'm going to get there. Absolutely. So I took these improv classes and thinking that it would just be helpful on like the public speaking side. Yeah. But this principle that they teach you is called yes and where you have your partner and let's say you're like, hey Jess, like let's go to the moon. And I was like, no, thanks. Then the scene would end. Right. But if I was like, yes, Caitlin, let's go to the moon. I like hear what you say. And then, you know, we could discover life on other planets yeah and so it's about like saying yes to an opportunity and then like building something on top of it yeah and so many of us live in like the yes but like oh that

would be great but yeah and so improv really taught me like what if we just focused on like the expansiveness of what could happen like all the possibilities that are out there like we could pick up a guitar in this recording studio today and be on tour with cold play in a year like what that could happen right and but we have to be willing to say yes to opportunities when they present themselves because otherwise we kind of sit where we are we stay in that same room so improv i don't know if it made me funnier but i think it gave me a better outlook on life you're pretty funny actually thank you i appreciate that so are you well when we're like sitting here there's certain things that you say you're quick like oh good yeah you said a couple

of funny things wrong yeah that's my life goal is just where katelyn bristow i think i'm funny Well, I do. I think you're smart and you're funny and you're making a difference in the world. And I love it. We'll be right back with more off the vine, grape therapy. Hey, everyone, if you like my show, then you're going to love adulting like a mother-father. Join parents and new parents, Danielle Monet and Andrew Gardner, every week as the duo navigates all things adulting. Health and fitness to finances and romance, all while balancing their careers and new baby. Listen along as they chat with experts, celebrities, and friends.

Be sure to subscribe so you don't miss adulting like a mother father every week on Apple Podcasts and Podcasts 1. You're listening to Off the Vine Race Therapy. A lot of people listening, I think, have that desire to be an entrepreneur, start a business, but people just never know what to start. And I just had a couple of questions. What do you think are some of the biggest misconceptions about starting a business or being an entrepreneur? that you have to have it all figured out it's i like to think of like our paths as foggy and like that's okay yeah sometimes when we're driving and it's foggy we're like oh we can't see you know the end of the road but we can see like what's right in front of us and that's a lot like being

an entrepreneur is we might not be able to see exactly where we're going but we can see those like few steps and i think that you know something i used to do was like i would have these set outcomes that I wanted. I was like, this is what I want to do. This is what I want to be. And I would like grip this outcome. Like it has to be this. And so then when you aim like when you land slightly to the left or slightly to the right of this outcome that you were like so sure of, it feels like a failure. But instead as we're kind of like figuring it out, hold these outcomes instead of with like a clenched fist with an open palm and be like, you know, it could land here. but I'm also open to the different directions that might take me.

So you might start a business and you think that you have everything that you want in the next five years. But instead of like gripping that outcome, just see where it takes you and just kind of begin where you are, even if you don't have it all figured out. Yeah. Yeah, that's and what I mean, I just know, I think from reading into the Facebook group that I'm in and that off the vine people, I think people are always asking questions about what the first steps. they should take would be I ask one of the things that I love to ask people is what feels light to you right now because sometimes we can take ourselves out of the game before we even begin because we put this pressure on ourselves to like start the next Spotify or start the next Airbnb so it's like well if that's the scale then I have a long way to go but when I first

started Headbands of Hope my goal was like oh it'd be really cool to give a headband to a child with cancer. Okay, I did that. Oh, it would be really cool to be able to give an entire hospital headbands. Okay, I did that. And what if I did an entire state, you know, hospitals got headbands? And so each time I would just set the bar a little bit, a little bit higher, a little bit higher, instead of saying like, I'm going to revolutionize the headband industry. And so I think like focusing on what feels like, what are the small things. Maybe that's doodling a logo. Maybe that's buying a domain. Maybe that's getting coffee or wine with someone who's been there and give yourself permission to do the small things because the small actions gives us the confidence then go do the

bigger actions. But if we just set the bar like so unattainably high in the beginning, then everything we do, every time we don't make it, it'll feel like we're less when we're not. That's, I mean, just simple, like I always try to do small goals for myself, like instead of. like what you're saying even if it's as little as I'm going to go to the gym today I might not go tomorrow and I might not have the body that I'm like looking for in three weeks but I'm going to go today and I'm going to feel good about it yeah and I think just having that mindset in anything you know like obviously you want to dream big and and have ambitions and like an end goal but to just think about day to day things that you can do to reach your goals to make them bigger

every time like people people just kind of set like you said set the bar too high and then just feel disappointed in themselves instead of just giving themselves small goals to work through to grow and get bigger and aim higher as you go on. Yeah. I kind of feel like it's like cleaning my house or right now my earstream that I'm in. But like when we say, oh, spring cleaning, I'm going to scrub the entire place like, you know, floor to ceiling. Then sometimes we're like, oh, I don't really want to do that. But instead if you're like, you know, I'm just going to like clean the bathroom. And then you're like, well, while I'm here, I could do this. And so same thing with our like goals and dreams. Like what feels like to you right now?

And once you get started, you gain that momentum. It's like breaking the seal. All of a sudden, once you just take that first step, it feels a little easier to take the next one. Yeah, absolutely. And you created, which I love, Mike Drop Workshop, which is an online course and community for women who want to make an impact through public speaking. Yes. And without giving all your secrets away. Yeah.

What are some of the biggest mistakes you see people make when speaking in public? Yeah. I mean, one of the things I had noticed, I was speaking a lot, and I was like the token woman in a lineup. It would be like, I'd show up to an event, especially anything like business or tech related. And it was like, oh, good. You know, we have a woman. And there would always be like all male panels, like, called manals. You can find like a really funny Tumblr that's called Mantles.

So I said, you know, we should, there needs to be more women out there telling their story. And I think one of the reasons why I created Mike Drop Workshop was to solve. this problem of women have amazing stories. They have incredible things to say, but sometimes they feel like they have to reach a certain platform in order to feel qualified to say it. Like, oh, my company needs to make this much money before I can start speaking. Or I need to have such and such accolade or a doctor in front of my name in order to become a speaker. And being a speaker isn't about being an expert actually. I mean, maybe it used to.

It's definitely not anymore. I've spoken to universities or something and I'm like, who the hell would have thought Caitlin would be a speaker? You know, I'm not there, but I am because it's about what you have to speak about. Yeah, you have something to say. And I think that if mic drop workshop can help women like giving them the contracts,

giving them negotiations. Oh, thank you. Oh, thank you. Yeah. Okay, go on. Anyways. And just like, let's get get rid of all the questions that you have around public speaking and just help you focus on your story and facing it outward so people can learn from it because it's not about lecturing it's just about inspirational storytelling yeah people don't want you to stand up there with like and my next exhibit is like this research that i found and da da right they want you to talk about you know

your time on the bacheloret and how that affected you and how that you know is a lesson that they can learn in their lives because that's also how they know you and yes they want to hear something that they understand like what they watched and what they know and hear you speak to it. Yeah. Rather than just like a PowerPoint done like, you know, that's something Jason's trying to do. And I think he'd be really good at motivational speaking. Oh, yeah. And talking to different colleges or universities because he has so much to offer and he's gone through so much and he knows that world so well.

And he's so good and passionate about what he's, I'm like, you need to go do that. Yeah. Like he is just, he has so much to say. and so knowledgeable about it and that's I find that that's what people want to hear you know like he's he's very different from other people that went on the bachelor and the bachelorette right that's what he has to like find his way in that side of things because he could be so great yeah and offer so much to people one of the things and you can share this with jason if he's listening that i like is yeah busted um is i call it the sandwich method yeah so how we can deliver information through our stories is like the bread is the message that we're trying to share and the meat is a story that supports it. So start with your message. What is it that you want people to know? And then use a story that you have that supports that message and then hit him again with that message. And so a lot of speaking, you know, isn't about having this like perfect talk where you're so polished. It's just about

creating messages and sharing stories that support that message. Especially now. Exactly. That's why I love Bray Brown so much. Like just when she speaks, I'm like, she is so relatable and she's funny and she leads with her flaws. Absolutely. Yeah. People aren't looking for perfect. So like, let's stop wasting our time trying to be. Nobody wants perfection anymore.

No one's like, man, they were perfect. Yeah. Like lifelong fan. Yeah. It's like, no, oh my gosh. She talked about, you know, this time that was really hard for her. And one of the things I've learned about speaking is like the audience will match the depth that you go. And so it's a lot about reciprocity. So if you're just going up there talking about

more the surface of your life or like, and then I figured it all out, like no one's going to really go in that depth. But if you really get deep in yourself and things that you've experienced, they'll go there with their own stories as well. Absolutely. Yeah. And it's the same with podcast listeners. Yeah. I'm like, you need to start a podcast. All right, guys, it's time for us to rethink the way we period. I am always looking for new ways to be as comfortable as I can possibly be because I like to move around, get a little crazy, I don't want anything to stop me, pads can be sticky and bunchy, tampons can be uncomfortable. Why haven't things changed for us? There is a better way, meet things. Things is period-proof underwear that absorbs your flow up to four tampons worth.

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Tell us about when it comes out and how people can get it. Yeah. So my book is called Chasing the Bright Side. It comes out November 5th. And it's really about how we can use optimism, not just like a mood or like a be happy all the time thing, but more as a strategy to create the better world that we want to live in. So I talk about the story of Headbands of Hope, but also just other life events that, I'll admit, were kind of hard to share in this book. My family was in a very public scandal when I was in high school. And it was something that I, like, kept in this, like, closet for so many years.

The shame box. Exactly. Oh, yeah. I like that term, the shame box. It literally just came to me right now because I was like, I have a box in my closet. And in my head, I'm like, it's the shame box. Yeah, that's exactly what it is. And you feel like, okay, I'm going to keep it safe.

Lock it up. And if it's out of sight, then it's out of mind. But it's been kind of like now it's been over just around 10 years since this has happened. And I realize I can connect the dots, you know, from this one experience as to like how I've written my story now. And I think that as we were saying sometimes, like, the best things can come out of our worst moments and so if I can share that and again match that that depth and that vulnerability that I hope the readers will get yeah then then I think it's it's time to share it and not only can that benefit the people reading it's probably therapeutic for you oh my gosh it was this just

relief to say you know this isn't something I'm hiding anymore that I don't want to associate with it's a part of me yeah and it's and I'm proud and it's probably a big part of where you're at today. I don't think that I would have started Headbands of Hope had it not been for this like, like, rattle, you know, of just like, whoa, what do I want to do with my life, you know, after this? I just want so many people to take away from podcasts that I do. And anyway, not just podcasts. I do anything they listen to or look into. I just, the whole thing that we talked about earlier with failure being a learning lesson instead of a, like, reason to stop. Like, it's just such a good, any failure you have ever gone through, a breakup, a hard, like,

like bad things happening to you no matter what scale it's on it will shape you yes and it's such a big part of your journey and where you're going to end up yeah i used to think like people who had a really smooth path people who like got there no hiccups those were the people who were successful but now i know that people who have the smooth path it's not success it's safety that they were striving for and when you think about like how many people have we read about in history books that were like well I played it safe that's where I got to where I am today yeah and so you have to realize like that the bumps the hiccups the like you know the things that we experience are just a normal part of the process but which is why I think like your podcast is so important and hopefully chasing the bright side will do the same where let's just like humanize the hustle let's like we're all in this together no one knows what they're doing so let's stop pretending I mean we can We don't know what we're doing, but we're going to get to where we want to be if we are passionate about it and accept the failures as opportunities. Yeah.

And let's just be in this together. I think, like, you know, relationships are stronger when we can just be, like, transparent about it. Oh, don't I know it? I feel like you might know a thing or two about that. It is nice to. Yeah. It's, I mean, just communication, no matter what relationship you're in business, you know, like that's just key. talking about things and being open and sharing your what does my therapist call it it's like

your your dark closet or something like open that dark closet and share the and you realize it's not so scary when you do that and that and that probably and that every single person I was going to say probably no every single person has a dark closet yeah so was being on the bachelorette did that make you more transparent or did it send you the other way for a little bit no it I've always been pretty transparent in life, I think, through even if, yeah, even if I was trying to be somebody I wasn't, I was kind of like I would own it afterwards or I'd like figure it out and I'd always want to talk to people and be open. But going on the show, I just opened up that door with a lot. More people. More scale. Yeah. And I realized that I was helping more than I was hurting.

Like, I was helping people more than I was hurting them. Yeah. And I had people, so many people reach out and just say, like, it was so nice to see that. I've been through this. And I was like, oh, now I'm at a point where I'm like, do I share too much? No. I think that that's, like, how you built your tribe is by the level in which you share. And when you see is what you get.

And do I ever make mistakes. And, you know, like I do open up my world and my life to so many people. and I don't want to try and be perfect and I do get a lot of slack when I'm not, but that's the right people are there supporting me, you know? But sometimes it's so hard because if sometimes like the three people who aren't on board, we hear them louder than the 3,000 people who are. I said that today. I was talking to one of my girlfriends and she had said something. Something was on a website that involved her because of me and I felt guilty because I'm like, I don't know how you got dragged into that. I'm so sorry.

And she was like, I just felt such a small portion of what you go through every day and like opening up that, you know, like just having one person. And I said, yeah, it's just so weird to me that sometimes the hate and the trolls are so much louder than the love. Like the love's there. But people are like, oh, I love you and you change this. But they don't, they're not going to reiterate that every day where the haters will. Right. Well, let me tell you something. When I was talking to my mom yesterday and she was asking me some of the things I was doing in national.

And I was telling her about you and I said she was the Bachelorette, but one of the things that I love most about her was something that you did after your season and there was some troll that said something really awful and instead of engaging in something negative back, you ask people to send love this person's way. Yeah. And like this person really needs some positivity today. Let's support them. Yeah. And I just was so blown away by. that. It was brilliant. And people did too. Yes. I saw. And I just think that that's so, like, what an example to set when you're in those situations. Because how many times do we say, well, I'm going to be the one with the last word, you know? And thank you for saying that because I have gone the other way to where I want to have the last word. And I am pretty sassy sometimes. And I always learn a lesson through that, too, because I never feel good after that. Yeah. That's a good. That's a good realization. Yeah. And I still make that, I just did the other day. I took a screenshot and I put

it up and I didn't even think to block out this person's name because I'm like well clearly she wanted me to see that and I felt really terrible after and and it hurt her and I know she hurt me too but that's not a reason to like get her back yeah and I just wasn't thinking I was thinking emotionally and I did it and then I'm like that didn't feel good you know yeah and sometimes we think like yeah play to win you know and then when you quote unquote win you're like how does is this winning yeah you know because I mean I'm all about a sassy comeback but when you're like when two wrongs don't make a right at the end of the day you know that old saying so it's like well she got me but I got her back and that doesn't feel good where it did feel good to like some

I'm like this person's clearly hurting for them to say something so nasty to me let's actually send her positivity and said and that's what I want to continue to do but again well do you have any advice for me in this because I am kind of new to like putting my all this stuff out there and it's it's great that you know to see people coming back with the positive notes but of course when you reach the masses there's going to be someone or something out there yeah that doesn't have like the best things to say so how do you how do you go about that i don't even know what my advice would be it's more just like um like if you see someone clearly just throwing shade to hurt you I hope that doesn't happen for you and I can't see that happening.

But like, you know that they're just looking for attention. And I think you can tell the times where people want attention or where they don't know how to deliver a message and it comes off a little snarky or when they're just like giving you constructive criticism. Right. So I think it's compartmentalizing like who is an asshole troll who just wants attention. Who's actually like doesn't know how to deliver a message and just wants to help. and then who's actually being constructive yeah yeah who's actually just giving you like some feedback yeah without feeling like um defensive yeah those are good like categories to think about and again going back to brine brown thing is like does it serve the work what this person is saying

is it anything that i can take and serve what i want to do and sometimes the people that are you know so aggressive you're like i can't even take any of this and use it at all yeah yeah well i just adore you. Oh, the feeling is mutual. And I'm just like, you are such an inspiration. You're such a go-getter and you have such a good heart and you're funny. Thank you. Netflix special coming soon.

Yeah, I'm like, well, and I would love to do something like we have with the do scrunchy brand. Yes, I love it. We're coming out with, you know, new stuff all the time and we want to do headbands and I would love to work with you in some way. That would be amazing. Yeah, we would absolutely love that. And I know that the kids in the hospitals, I'm sure, like having them would

be amazing. Maybe they can help design. I would absolutely love nothing more than that. Yeah. And is there like with the like the Nashville, don't they have a children's hospital? I've been to it. The Children's Hospital here. Yeah. Like I. They love, they would love it. We were just at Seacrest Studios there. Yeah. Yeah. I've been there. Which was so cool. It's really cool. But they will absolutely love doing Headbands of Hope projects there. So we should definitely do something together. It really changed my life actually going in there when I did for the Seacrest show because these kids just have the best attitude. Oh, best attitude. So we were just there at the Seacrest Studios and this kid comes in to be in the interview with me and he's sitting there in his like dinosaur costume for Halloween and talking and we're playing like this never have I ever.

And it was so funny, the host was like, so have either of you played never have I ever? I was like, probably not the questions I were asking. here but it was like this Halloween edition yeah and um at the end of the at the end of the show the host asked a kela oh do you have any questions for jess this kid's like seven he's like so where can we find your book i'm like you're are you my child like you're hired you're coming with me like just i look around and like publicist i'm like did you tell him to say that and they're like no so these kids are where can we find you how can people and where can we support you Yeah. Please tell me. I'll put my lunch money towards this. What a sweetie. So sweet. So they just have, I mean, so much of what you'll see in chasing the bright side has been lessons learned from these kids.

Yeah. Just this rooted optimism that they have during some of the toughest times. What a great book, too, to just have that. And people to, well, I feel like it would be a day changer. Like you just read the book and you just feel, you know, inspired or. But I'll say like it's, you know, with chasing the bright side, one of the. the things I wanted to make sure when I was writing it is that it's not this like positivity pledge. Happy go lucky, rainbows and yeah. Because I feel almost like this guilt sometimes when you're not happy all the time. Like I'm not living life at the highest volume every day. Some days I just feel like crap. Yeah.

It's okay. And so optimism with chasing the bright side, it's not about being happy all the time. In fact, it's using the times when we think there could be better and like being the one that creates it. but a lot of times that means like sitting and absorbing some of the things that we're not happy with. Yeah. So I hope people get a lot out of it. That's great. Good for you. I say that too. I'm like sometimes you just got to sit in the uncomfortable. Yeah. Yeah. Be uncomfortable. I think like sometimes when we try to just push ourselves to our happy place and like that's the worst. It's the way. You're not

processing anything. No. Yeah. You got to process. You got to feel the feels. Yeah. Feel all the feels. I think, you know, one of my friends Amber Ray, um, she said like our feelings aren't the problem. It's our relationship to them and so that's I think about that a lot like when I'm feeling sad or upset there's this guilt like why am I sad why I'm upset I have a great family I have that I do that all the time and you feel that so then it gets more because you're like why am I not grateful I should be happy right now but and so instead of guilting ourselves to feeling that like let's just sit with it and see if maybe there's something here that could bring something better yeah and if you just practice you know practice what you preach and do those things.

It's crazy how much of a difference it can make without you even realizing if you just have that awareness every day to just practice those little things. Yeah. Little things. Exactly. And I think like that's what I wanted chasing the bright side to be is sometimes I read a book where I feel like I have a long to do list afterwards of like, oh, well, I need to be more ambitious and I need to like be creative.

And I want chasing the bright side to feel light and manageable for people. It's like little shifts. I call them simple revelations. Like what are these like simple things that we can do every day that it's just like we don't have to revolutionize who we are, but maybe just like a one or two percent better than we were yesterday. Well, even who can't relate to like if you're feeling like you can't get out of bed, but then you do and you just clean your room. Oh, yeah. Think of how much better you feel after doing that or going to the gym and then think of that on a bigger scale and just like how, you know. Small decisions.

Small shifts. I like that. Yeah. So where can we find your foot? so just i mean that is how i usually usually like to wrap things up as how people can find you yeah um so you can go to chasing the bright side dot com and that is where i would love to hear from you i'm on instagram at jess underscore extram and yes jes s underscore e k s t r o m yes and then you can find us at headbands of hope dot com and hopefully something between us will happen no i'm we're going to do it that's a no brainer for me i would love to love to love to do something with you yeah let's do it okay awesome and you need to start a podcast

i'm i'm down you've inspired me i mean this hasn't even felt like a podcast it's like i mean obviously we're sitting here having wine but i'm like i could talk to you all day this is great well we can do part two yeah i always say that to people when i have great conversation i'm always like so part two yeah yeah i'm sold well once we do the headband launch and we do something with you guys we can do another podcast oh i would love that thank you katelyn again i really appreciate that you doing this podcast and using this as your reason to do more no thank you We just go back. Thank you.

No, thank you. No, seriously. Thank you. But seriously, thank you. Thank you. Your session is going to be. Thanks for listening to Off the Vine, grape therapy. Tune in to hear new mini-sodes every Thursday

and check out new full-length episodes every Tuesday exclusively on Podcast 1.com, the Podcast 1 app, and subscribe on Apple Podcasts. Who's that with OTV? This week's grape therapy is sponsored by Honey. If you're buying gifts this holiday season, then you need honey. Get honey for free at join honey.com slash buying. Mercari, finally an app that makes you money.

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$10 off your first pair. All right, I hope you guys enjoyed listening to this great therapy with Jess. I have some really exciting news I wanted to share with you guys before I end the episode. So Headbands of Hope has donated over a half a million headbands reaching every children's hospital in America and 15 countries. So I decided to partner with Jess to help my Vino's headband together to support her important cause. So for every fur keeps headbands sold, three special coloring book headbands will be donated to children battling cancer.

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