Brains Meet Beauty Podcast with the Caldwells, ShearShare Cofounding Team

Listen to the 30 minute audio HERE

Courtney and Tye Caldwell started as partners in life and are now partners in ShearShare, the first mobile app that lets stylists rent space on demand. From marriage, parenthood and startup life, the pair share the key lessons they’ve learned on collaboration and partnership in the decades since they met. You’ll also hear how they’re responding to the changing needs of the hair industry, and why they both think you’re clicks away from making your dreams come true.

 

ANNOUNCERWelcome to WHERE BRAINS MEET BEAUTY™, hosted by Jodi Katz, founder and creative director of BASE BEAUTY CREATIVE AGENCY™.
JODI KATZHi there. Thanks for tuning in. My name is Jodi Katz. I am the host of WHERE BRAINS MEET BEAUTY™ podcast. I started this podcast over two years ago. 2019 marks my third season and I’m so excited to say that and kind of amazed at how fast time flies. I started this podcast as a side hustle. My day job is running BASE BEAUTY CREATIVE AGENCY™, which I founded 12 years ago. We’re an omnichannel creative agency, hyper-focused on beauty and wellness. Being in this business for so long, I felt the tremendous need to humanize the business more. I was really feeling disconnected from the industry, feeling like I didn’t belong, I didn’t fit in. What I’ve been able to do through the pod is incredibly therapeutic to hear what’s on the minds of the people that are my peers in the industry and learn about their career journey, their life work balance, understanding how they deal with struggles and how they celebrate wins. It’s been incredibly fruitful for me, and I hope our listeners as well.

We bring new episodes to you every single Wednesday. For updates about the show, please follow us on Instagram. That’s where we share most of our news. That’s @wherebrainsmeetbeautypodcast. If you want to see the incredible guests that we’ve had the past two years, head to wherebrainsmeetbeauty.com. You can listen to all of our episodes there. You can read transcripts if you prefer to read than listen. I’m just so excited that you’re on this journey with us, and I hope you enjoy the show.

Happy New Year. Welcome to 2019. I’m super excited to present our first episode of our third season of this podcast. I can’t even believe that this is starting our third year. Thank you for joining us and being on the journey. This episode features Courtney and Tye Caldwell. They’re the co-founders of ShearShare. If you missed last episode, which was our last episode of the previous year, it featured Gib Long. He’s the CEO of GIBS Grooming. I hope you enjoy the shows.

Hey, everybody. Welcome back to the show. I am so excited to be sitting next to two very stylish people. This is Courtney and Tye Caldwell. They are the co-founders of ShearShare. Welcome to WHERE BRAINS MEET BEAUTY™.

COURTNEY CALDWELLHey, y’all.
TYE CALDWELLHappy to be here. I’m so excited.
JODI KATZThank you. You’re visiting New York today?
COURTNEY CALDWELLYes, we are.
JODI KATZRight now it’s late in the afternoon. How have you spent your day today in New York?
TYE CALDWELLWe have actually been here for Business Insider’s IGNITION Conference. Steve Case is one of our investors. We were on Google Demo Day, so we spoke today on stage with him. It’s been a very, very eventful day. Jennifer Patrick was there.
COURTNEY CALDWELL50 Cent speaking, Mark Cuban’s gonna be on stage. We were able to share the virtual stage with amazing people.
TYE CALDWELLAbsolutely.
COURTNEY CALDWELLAmazing individuals.
JODI KATZAre you zonked right now?
COURTNEY CALDWELLNo!
TYE CALDWELLNo, not at all, we hyped!
COURTNEY CALDWELLThere are very few times when we’re zonked.
TYE CALDWELLYeah.
COURTNEY CALDWELLBut we knew we were coming here. We were good to go.
JODI KATZAre you caffeine drinkers?
COURTNEY CALDWELLNot really.
TYE CALDWELLThat stopped a while back.
COURTNEY CALDWELLYeah, we’re green juice people. We’re those kind of people.
JODI KATZDo you like getting a full night’s rest at night? Is sleep important to you?
COURTNEY CALDWELLYes. Oh yes.
TYE CALDWELLSleep is very important. If we can get through the night. Normally I wake up at this specific time between 2:30 and 3:30-
COURTNEY CALDWELLHis mind is always going.
TYE CALDWELLMy mind is always going. I tend to write what I’m thinking, so that I don’t have to figure it-
JODI KATZYeah.
TYE CALDWELLSo I started talking to older gentleman who were business owners and CEO’s for years and me being one now for the last two and half years now, and they said that’s normal. They gave me their number and said, “Anytime you wake up in the middle of the night, you can call us.”
JODI KATZAnd do you?
TYE CALDWELLI haven’t had the opportunity to call them, but [inaudible 00:03:55] 3:30 in the morning. It’s really late, or early. I’m not gonna call them.
COURTNEY CALDWELLMeanwhile, I’m on the other end of the bed sound asleep. There could be a train passing by our house and I would still be zonked.
TYE CALDWELLI’m gonna tell you a secret, when she wakes up, if it’s at 2:30-
COURTNEY CALDWELLOh no.
TYE CALDWELLOr 3:30-
COURTNEY CALDWELLDon’t tell all.
TYE CALDWELLShe’s not going back to bed.
COURTNEY CALDWELLOh that’s true.
JODI KATZThat’s me. That’s me. I will use that time to catch up on email.
COURTNEY CALDWELLI do.
JODI KATZI know I’m not going back to bed, and then I’ll bring my pillow downstairs to the couch and I’ll watch whatever Real Housewives I haven’t caught up on.
COURTNEY CALDWELLOh my God! Guilty pleasure! Guilty pleasure.
JODI KATZIt’s beyond a pleasure for me.
TYE CALDWELLSometimes the most interesting shows are on late in the morning though. Early in the morning.
COURTNEY CALDWELLEarly, yeah. Midnight.
JODI KATZSo I guess everyone’s figured out that you’re not just partners in business but you’re partners in life as well.
COURTNEY CALDWELLThat’s right. I sleep with my CEO and I’m proud of it. No shame.
JODI KATZThat’s awesome. Alright, so, you had a very eventful day. Thank you for joining us here this evening. Tell us, what is ShearShare?
COURTNEY CALDWELLShearShare is the first mobile app that lets stylists rent space to work by the day. Simple as that. Someone called us Hairbnb, a couple of weeks ago, and we thought that’s pretty much what we are. The salon owner, the barbershop owner who has an empty station, an open suite and it’s just collecting dust, we fill it with a stylist who wants to work by the day.
JODI KATZWe were actually just in the hallway, you met one of my guests who was leaving, Eloise, who’s a hairstylist and she’s a freelancer, so she does commercial work and editorial work so she never has a salon. You walked her through the app and I could see “Ding! Ding! Ding!” Going off in her head. This is so great, she doesn’t have to do someone’s hair in their apartment anymore.
COURTNEY CALDWELLI know!
TYE CALDWELLBut the great thing about that conversation, which was very brief, seconds to be exact, is that we asked her where she worked, and the first thing she said was, “I do work at home.” Well, the interesting thing about this industry is that it’s been so archaic and old is that’s how people think. They don’t think about, “Okay, I wish I could go to another salon and do the work where I was classically trained,” because salons won’t allow them to do that. You have to go through all the rigamarole of trying to vet them. Are they really licensed? Where are they from? Are they gonna come in and tear my salon up? All the things that we have already put together because we’re from the industry.
JODI KATZSo when we were going through it, it felt a little Airbnb to me, and a little Rent the Runway to me. Because I think the coolest thing about Rent the Runway is not that you can just get clothes, it’s that other people, size 10 like me, are giving you reviews on their experience. Whether it’s too tight in the arms or it’s too loose in the waist and that’s what you’re getting on your app too.
COURTNEY CALDWELLThat’s so important. You have to have that kind of 360 degree viewpoint. It’d be great for us to put out hosts that had open space and empty stations and the stylists come and rent them, but how would you know if one’s good or not? So it’s very important for us to always have that open line of communication with our hosts and the visiting stylists.
TYE CALDWELLAbsolutely.
JODI KATZRight, and I would think that if I’m a stylist or a colorist or anything that I would want a space that presents well. That presents in my personal style.
COURTNEY CALDWELLExactly. Exactly.
JODI KATZSo that I can tell my story through that.
COURTNEY CALDWELLThe interesting thing, and I don’t think we assumed this when we first started is that the stylists who use ShearShare, they are hyper focused on their clientele. Now they have the opportunity to say, “Oh, okay, well, Danika’s coming in on Monday, I know she’s a lady who lunches, so I’m gonna choose a very frou frou chandelier and champagne type of salon for her, and then Courtney’s coming in on Friday and she’s more of a squiggly eyebrow and a punk hair color, so I’m gonna choose that type of creative space to service her.”

They’re literally choosing spaces to work based on their clients.

JODI KATZRight, that’s so interesting. Okay, they’re really personalizing the experience.
COURTNEY CALDWELLExtremely.
TYE CALDWELLAbsolutely. And the industry has changed so much is that now the salon or the brick and mortar is not only the brand anymore. The brand is the individual, the licensed professional, and when a stylist or barber or makeup artist or licensed professional leave a salon, they’re leaving with their clients. They’re not leaving and regretting the fact that, “Oh, I’m leaving XYZ salon and I’m not gonna be able to be successful.” No, their clients are coming with them.
JODI KATZRight. I suppose 25 years ago, the salon owned the clients and it’s really shifted. I go to my stylist, I don’t really care-
COURTNEY CALDWELLWhere she does your hair, right? I will stalk my stylist until she retires.
TYE CALDWELLAbsolutely. Even commission-based salons, I think that they’re still stuck a little bit because in a quasi type of way, you are controlling how much money that individual licensed stylist is making because you’re charging them a percentage. Now, you do get accoutrements like products for a certain amount, you’re making money on percentage of products, you’re making money on percentage of clients, but what now, if that client wants to be your stylist, now they’re gonna continue to come to you, and you’re gonna be talking to them saying, “Okay, when I come in, I want Angela to do my hair. I want Courtney to do my hair.” Now you’re getting preferential treatment, not only from the client, but you’re giving that client that preferential treatment as well, so it’s reciprocal. At the end of the day, once that stylist decides to leave or if that client moves, they’re gonna ask for you.
JODI KATZRight, and so much so in the fact that I think lately, I just text my stylist. I don’t even wanna deal with being on hold-
COURTNEY CALDWELLThe receptionist, right. No.
TYE CALDWELLYou see what I’m saying?
JODI KATZYeah. Where they don’t call back when they say they are? Okay, I love this and you know we had so much fun on our call when we were getting to know each other. I wanna start with the most important thing, how did you meet?
COURTNEY CALDWELLOkay, so not many people ask that question and that was very smart of you to ask that, which I think is the craziest way for us to meet, but thinking back now, I never could’ve planned it. We actually met at his salon almost 20 years ago. How perfect is that? Now, today, to have married the man of my dreams and be doing this with him, my absolute best friend.
JODI KATZSo you were a client in the salon?
COURTNEY CALDWELLI was a client, yes. I did not get gifted with the ability to do hair. I pray to God everyday that I can and it is just not my wheelhouse.
JODI KATZSo you were a client in his chair?
COURTNEY CALDWELLNo, not in his chair. In someone else’s chair. But he was always sitting there, first chair, always said hello to me when I came in, and then I learned later on that he had been striking up conversation with my then stylist and decided to ask me out.
JODI KATZOkay, so do you remember this day?
TYE CALDWELLYeah.
COURTNEY CALDWELLOf course! Oh I hope he remembers this day!
TYE CALDWELLI remember it very well. I asked about her six months prior, saying, “When is she coming back in?” That person said, “Oh, I really don’t know.” I said, “Well, when she come back in let me know.” The day she came back in, I was like, “Okay, she’s here.” I only came by for a minute. I was getting ready to leave. I said, well, I had a client in my chair, I was gonna leave soon after that, and she was getting finished and was getting ready to pay for her service, and I kazoomed through my client.
COURTNEY CALDWELLHe sure did. He was right there at the door.
TYE CALDWELLMade them leave.
JODI KATZI hope it was an almost bald man.
TYE CALDWELLIt was a fade. I walked outside, so I knew that she would come outside and I stopped her.
COURTNEY CALDWELLSure did.
JODI KATZAnd what did you say?
TYE CALDWELLI said, “Hello. How are you doing?” I said, “I’ve noticed you a few times that you come by and I would love to take you out to dinner or bowling.”
COURTNEY CALDWELLMm-hmm (affirmative).
JODI KATZDinner or bowling?
TYE CALDWELLWe went bowling.
COURTNEY CALDWELLWe went bowling.
TYE CALDWELLYeah.
COURTNEY CALDWELLWe sure did.
JODI KATZAre you both good bowlers?
COURTNEY CALDWELLI think it was less about the activity and more about just getting to know each other.
TYE CALDWELLYeah. I think I won though.
COURTNEY CALDWELLI was gonna say, I think I won.
TYE CALDWELLWe played three games. She won one.
COURTNEY CALDWELLIt’s okay.
JODI KATZSo did you know he was the one?
COURTNEY CALDWELLI did. I knew he was the one. It wasn’t love at first sight, but it was, I knew something was different about him immediately when he approached me. As we started to get to know each other, I was like, this is easy. It was too easy. It was very easy, so I said, “That’s my friend for life.”
JODI KATZBut this is easy for me right now, so I feel like there’s something about the two of you.
COURTNEY CALDWELLOh, thank you.
JODI KATZThe energy is incredible.
COURTNEY CALDWELLOur team says that too so-
TYE CALDWELLEveryone says that. I have many people that I look up to as a mentor, and they say the same thing, so I ask them, “What is it?” I’m inquisitive, so I wanna know what is it? I’m gonna give it back to you. What is it?
JODI KATZWell, there’s such a smile on both of your faces which is, I think, part of it. There’s a lot of people who present themselves in a cold way and I don’t even know that they think they’re trying to be mean or rough around the edges. They just are maybe shy or uncomfortable, but you both seem very comfortable in your own skin, so I think that that’s something about the tone that just rolls off of you. Your energy level is incredible. You seem really joyful.
TYE CALDWELLYeah.
JODI KATZGrateful.
TYE CALDWELLYeah. Very grateful.
JODI KATZSo I think that’s what I connect with the most.
TYE CALDWELLThank you so much. You’re right on point. I don’t know if you are, what do we call them? A clairvoyant.
COURTNEY CALDWELLA clairvoyant, yeah.
TYE CALDWELLBut you’re right on point.
JODI KATZIt’s my job to listen.
COURTNEY CALDWELLMm-hmm (affirmative). There you go.
JODI KATZIt’s my job here, and in my day job as well, and as a mom.
COURTNEY CALDWELLYes, definitely, always as a mom.
TYE CALDWELLYeah, you’re learning. And you’re learning people so you get to learn how things are, the spirit of people, the attitude and everything so that’s good. She did a good job today.
COURTNEY CALDWELLMade us smile even bigger.
JODI KATZAlright, so now we know how you met. You both talked about mentoring quite a bit on our previous phone call. Tye, you said that that’s part of your career forever. Take me through the stages. How did you mentor someone when you were just a salon owner, even before ShearShare was a thought in your mind?
TYE CALDWELLThat’s great. I’ll never forget. I started mentoring right before I got out of high school. I started mentoring little kids, so I had the opportunity to continue to go back to my english teacher, who I give so much prop to, Miss Ruby Richardson, who helped me so much in English. I would go back every end of each semester and I would help her grade papers. In helping her grade papers I got a chance to get to know the students, they got a chance to get to know me, she would always talk about me and brag about me as one of her favorite students of all time, so that made me feel good.

After that, I started to go to different elementary schools and primary schools to just help around and volunteer my services, then I started speaking, so I started going to career days and then individual kids would come to me and say, “I don’t have a dad that I can talk to. My dad is in whatever situation it was,” so I started to become a mentor then as I started to go through beauty and barber school, because at the time I went to a dual school where you did cosmetology and barbering.

I became a student instructor. The teachers liked my attitude they liked the fact that I caught on quickly, and it just became one of those things where people always gravitate to leaders. I go back to when I was 15, my football coach told me, he said, “You’re a leader.” I was like, 12 years old. That goes back to what you said earlier, just something about the people or the person or the individuals that people see something in. Just mentoring, helping people, as I started going through business and being a business owner, writing a book or seeing people looking at success at whatever level they thought it was, they started to ask me, “How did you do this? How can I do that?” Whether it was about financial situations, whether it was about business, whether it was just about personal, being married you have a lot of married people come to you and say, “How are you making it happen?”

You hear so much stuff in chairs. You’re almost like a quasi-psychologist, so you begin to really understand people. Once I started realizing that I had a gift, I pretty much said, you know what? I accepted it. Because for so many times, I’ve wanted to be wrong more times than not, and I’m always right. I don’t say that to be arrogant, I say that because I didn’t wanna be right. I was like, “You let me be wrong.” Then, she’ll come back after we had a disagreement, she’ll be like, “You were right the whole time.”

COURTNEY CALDWELLThat makes it really easy to argue with my husband and it makes it a little difficult to have a disagreement, because I know that what he’s telling me is the absolute truth and he always has our best interest at heart, but I know if I turn around and come back, I’m like, dang it. He was right. Golly.
TYE CALDWELLI gotta say this, my book, Mentor by Failure was a book I wrote and it gives people five steps on how to maintain success in the beauty and style industry. I wrote the book because I didn’t have a mentor. I wish I woulda had someone that could tell me, give me some quick little exits and cues on what it’s gonna take to become successful, how long it’s gonna take for this to happen, let me be prepared for it. Being a mentor to me is super important because it helps people see the forest for the trees.

So many times you don’t know, and it’s good to not know, but when you have people that can help you they can lead the way.

JODI KATZIt’s interesting you just said that. Maybe that’s one of the reasons the podcast has been so valuable for me therapeutically, because I didn’t have a mentor. I didn’t even know you could, honestly. I didn’t know you could ask for help. I did this all by myself, so I know that I’m giving people a gift of, for free, just listening to the lessons of other people who have before them because I was alone, and I was lonely. I just didn’t know. I really didn’t think that … I thought you were birthed into it, or you went to college with someone whose parents were this, or you just had it. I didn’t know that you could find it yourself.
TYE CALDWELLI think that’s why the industry now, and the world, is changing. Because what we once thought from the Baby Boomers and the ones before them is not real. You were chosen. You were gifted in a position and you made it work. You had so many family members because it was family businesses back then.
JODI KATZRight, right.
TYE CALDWELLThey helped you. They made you go to school because you they knew you were coming back. They said, “If you don’t go to school, you’re not gonna be successful.” So many people back then went to school and are working, doing the things they wanna do, now people are going to school and they’re not doing what they wanna do, so they end up getting college degrees but they’re not working in their field, or going to college like I did and saying, “You know what? This is just not happening the way I want it to happen. There are things I wanna do. Let me do it.”

When I started school for cosmetology and beauty, to me, to me, it was a flunkie industry. It was a flunkie profession to get into.

COURTNEY CALDWELLThat’s how they-
TYE CALDWELLThat’s how they made it seem.
COURTNEY CALDWELLThat’s how they wanted you to perceive it.
JODI KATZRight. I had a friend say to me, “If you didn’t want to be a doctor or a lawyer or whatever, then you just go to beauty school.”
TYE CALDWELLExactly.
JODI KATZWhich is so the opposite of the way the business is.
TYE CALDWELLExactly. I wouldn’t have done it any different. I think that this is the best industry. I love people. There’s unlimited amount of resources that you can-
COURTNEY CALDWELLAnd opportunities.
TYE CALDWELLAnd opportunities that you can make in this industry.
JODI KATZLet’s go back to the disagreements between partners. Whether you’re married partners or working partners. There’s this saying, it goes something like, “You can be right or you can be happy.” Have you heard something like that?
TYE CALDWELLOh yeah.
COURTNEY CALDWELLDefinitely, sure.
JODI KATZI think I’ve adopted that. Does it really matter if I win the argument?
TYE CALDWELLI don’t think it matters. It depends how aggressive you are. I’m a Gemini, so I can play both sides of the fence as a individual. Geminis are the only humans in the zodiac sign. Everything else is a animal or insect or whatever it may be, so we tend to have a difference in the way that we think. I think that the reason that I’m so strong about my opinions is because I’m very perceptive of the things that I’m saying. I’m not just say anything.
COURTNEY CALDWELLYeah, he chooses his words very carefully.
TYE CALDWELLVery carefully. So I’m saying things that are beneficial not just for me, but for both sides, because you don’t wanna have the last word where some people want to have the last word. You don’t wanna make it argumentive, but is it gonna matter two to five years down the line? If it’s not gonna matter, let’s not make an argument. Let’s have a conversation, and let’s disagree.
COURTNEY CALDWELLYeah.
TYE CALDWELLBecause we’re two individuals. Getting married, having a partner doesn’t mean you’re one person. You’re still two individuals with two different mindsets. Let’s see how we can make it work. My wife has been right so many times, I’m like, “That’s the way we’re gonna say it. That’s the way we’re gonna do it.” It’s fine, because at the end of the day, if she sees something different, coming from her background, corporate, me coming from entrepreneurship, that’s different. Then we bring it out together and then we have a entrepreneur/corporate business. It makes everything work.
COURTNEY CALDWELLI think it’s funny too, that when people always ask us, “How do you guys make it work? You guys work together, you live together, you eat together, you work out together. You do everything together. Do you ever get tired of this guy?” First answer, no, I don’t get tired of him. Secondly, I think it’s funny because the marriage was really our first startup, if that makes sense. Then we’re parents, so I guess parenting is our second startup, and so when ShearShare came along, it was just another thing to do together.
JODI KATZHow old are your children?
COURTNEY CALDWELLOne. One child, it’s a son, and 17. He’ll be graduating high school this year.
JODI KATZOh, a young man.
COURTNEY CALDWELLYes. Yes.
JODI KATZCongratulations.
COURTNEY CALDWELLThank you. We’re so proud of him. He’s such a good kid. Such a good kid.
JODI KATZIs it crazy to be the parent of someone who’s not a child anymore?
TYE CALDWELLWell we went through every phase, so yeah-
COURTNEY CALDWELLYeah, we’ve been through every phase. I would say, no, it’s more rewarding now, sitting on this side of it. Seeing what people say about him as a gentleman, what his girlfriend says about him, his girlfriend’s parents say about him, his employer, when he’s working and it’s not football season. The way his coaches talk about him and his teachers, it just feels so good to say, all of those hard years of sometimes saying the same thing about a million times, it feels really good to be on this end of it.
TYE CALDWELLBecause when they’re young, you just wanna get them to make good decisions. Once they get past that threshold of 15, you just want them to be productive in society.
JODI KATZRight.
TYE CALDWELLSo, I tell him all the time, I’m gonna repeat myself over and over again, but I’m preparing you for the world.
COURTNEY CALDWELLThat’s right.
JODI KATZThis is a conversation I had with my son yesterday, which is, my job is to teach you how to be an independent thinker, to do things for yourself, not to rely on other people, and kindness.
COURTNEY CALDWELLKindness.
JODI KATZThis is my job.
COURTNEY CALDWELLSimple.
JODI KATZRight?
COURTNEY CALDWELLBut sometimes parents don’t get that right. It sounds so simple, but it’s really not, at the end of the day. I can point to a lot of different students I’ve seen over the years who’ve grown up with our son, I’m like, “Gosh, I wish that the mom or the day had caught him at age eight or something.” Yeah, it sounds simple, but it’s really not.
TYE CALDWELLThere’s definitely chapters in this growth thing.
COURTNEY CALDWELLOh yeah.
TYE CALDWELLYou gotta be consistent.
JODI KATZYes. Well I say the same thing over and over again.
TYE CALDWELLThere it is.
JODI KATZWhich is, “Get your hands off your sister.”
COURTNEY CALDWELLYou’re already winning.
JODI KATZ“Stop touching her.”
COURTNEY CALDWELLYeah, you’re already winning then. You’re good.
JODI KATZ“Just stop.” Why do they have to be magnets to each other. I don’t understand what’s going on.
COURTNEY CALDWELLWell Tye has seven other siblings, so the whole magnet thing, yeah, they totally get that.
TYE CALDWELLWe’re a clan within ourselves. We can be around 2000 people and we probably won’t talk to any of them. We’ll be talking to each other like we’ve never seen each other.
COURTNEY CALDWELLLike you’ve never even met. I know. It’s a crazy thing.
JODI KATZSo you live in the Dallas area?
COURTNEY CALDWELLYes.
JODI KATZAnd are all the siblings in that area too?
TYE CALDWELLAll but one.
COURTNEY CALDWELLEvery one except one. Isn’t that crazy?
JODI KATZThat’s nice.
COURTNEY CALDWELLYes, and whenever we have family get togethers and we’re cooking for people, you have to cook for 40 people just to feed the family. If they bring plus ones you’re like, oh my gosh, I gotta order in.
JODI KATZDo you have a home sized for entertaining that number of people?
COURTNEY CALDWELLWe do, yes.
JODI KATZWe have a tiny house. We live in a town where all the houses are 100 years old-
COURTNEY CALDWELLWow, that’s beautiful.
JODI KATZIt felt like a mansion when we moved in.
TYE CALDWELLWhat’s the square footage?
JODI KATZLess than 2000.
TYE CALDWELLThat’s a good size.
COURTNEY CALDWELLOh, that’s not bad. That’s all good. You could fit a lot of people in there.
JODI KATZThey’re not all in my bedroom, you know? I actually am in this process now, because they’re a little older, this doesn’t have to be a playroom anymore. This could be another sitting room.
COURTNEY CALDWELLExactly.
TYE CALDWELLExactly.
JODI KATZI’m ready for change.
COURTNEY CALDWELLYeah, turn the page.
JODI KATZWe just got off track. Okay, so we were talking about mentoring. Let’s talk about why hair? Why are you in the hair business?
COURTNEY CALDWELLYes. That’s what we know, for one. Beauty has fed our family for years.
TYE CALDWELL25
COURTNEY CALDWELLYeah, and it’s-
JODI KATZThat’s such a sweet thing. Beauty has fed my family. I never thought of it that way.
COURTNEY CALDWELLYeah, and it’s true. It’s so true. It’s what we know. Everyone in the family understands what it is that we’re trying to do, and so they totally get it. This man right here loves the industry more today, is this accurate? More today than when you started 25 years ago.
TYE CALDWELLYup. I love it a whole lot more.
COURTNEY CALDWELLNot a lot of people can say that.
TYE CALDWELLI’m able to go to so many different shows, able to speak on so many different platforms and when I’m doing these classes, we have a partnership with L’Oreal, and we also go to premier shows, so SalonCntric is there. They turned my classes into CE courses. You have people coming in that need to get this teaching, so when you’re sharing some valuable information, valuable lessons and you’re sharing your story, people get it. There’s no group of people that I can’t talk to.

One of the things I love about it is that the industry is changing in products. I’ve had to learn how to restructure my thought process on using tools, color, different other things that are changing, so it makes me like the industry more, because I’ve adapted to the change.

COURTNEY CALDWELLMm-hmm (affirmative). And great ideas, honestly? They start on the inside. What is your problem that you have? ShearShare to us was an accident, to be honest. We had expanded our salon, we had rebranded, and we weren’t getting people coming in saying, “I want to do booth rental, I want to work by commission.” Instead, he came home one day and he was like, “Babe, I got this strange phone call. There’s this stylist who moved an hour away. She’s afraid she’s gonna lose all of her clients who live in this area. She just wants to rent our suite on a Friday/Saturday. What do you think?”
COURTNEY CALDWELLI was like, “What? That’s the craziest phone call! Who would ever do that?”
TYE CALDWELLI was like, “It’s collecting dust, but it might as well collect dollars though.” The opportunity was there, had a great experience and three years in, we were manually matching stylists.
COURTNEY CALDWELLYes, for three years.
JODI KATZThat’s awesome.
COURTNEY CALDWELLIt’s crazy.
JODI KATZIt’s awesome that you were able to see the value of that phone call.
TYE CALDWELLExactly.
JODI KATZ‘Cause I’m sure, she might’ve called a few other places too.
COURTNEY CALDWELLShe had.
TYE CALDWELLShe had. Everybody said no.
JODI KATZRight. So you saw opportunity in [inaudible 00:25:26], but I think that’s the genius of having to be a retailer right now and be successful at it, because if you were, let’s say, a retailer where your business is only really busy at night, well you have to [inaudible 00:25:35] to bring in money during the day. You have to be clever. Otherwise you can’t make money. You can’t pay your people.
COURTNEY CALDWELLThat’s right.
JODI KATZYou can’t feed your family. I love that you listened to this phone call. Did she ultimately rent space in the salon?
TYE CALDWELLYeah.
COURTNEY CALDWELLNot full time.
JODI KATZBut for that-
COURTNEY CALDWELLOh yeah, yeah. That’s what really was the catapult for ShearShare, because she came back and said, “Gosh, I really enjoyed it. How did you like it?” Tye was like, “Yeah, that was random but I enjoyed it.” She said, “Well now I have to go to San Antonio and Houston and Austin. Do you mind doing for me there what you did for me in Dallas?” We were like, “Okay, sure, you’re a fellow stylist, we can help how ever we can.” Then she started telling her friends about us. People had our personal cell phones and they would call us and say, “Hey, such and such told me about you guys. I have to go to L.A. for the ESPY awards. I’m doing a destination wedding in Florida. I need this amount of space and these types of amenities.”

They were literally calling us to find them space.

TYE CALDWELLSo we were helping them just in different ways. Some people were in Cali calling us because we had one stylist that was a Dallas stylist and a L.A. stylist so she was like, okay, can they help me? They just wanted to, I guess, take upon me to call the salon owner and say, “Can you talk to them for me? You understand both sides of the industry.”
JODI KATZ‘Cause you’re saying, “Yes this is an incredible person, she’ll take care of your stuff, she won’t get in the way of your-
TYE CALDWELLYup. I vetted them for her.
COURTNEY CALDWELLYeah, and the beautiful thing about that, doing it for three years manually, when it came time and finally the a-ha light bulb moment came on for us and we were like, we have to create an app for this, it doesn’t exist, we had all those three years of data to inform what needed to be on the app. We already knew what the salon owner was expecting. We knew what the barbers would ask for. We knew what kinda pictures they wanted to see, what kind of amenities they expected, and so all of that, it was just a beautiful ending.
JODI KATZSo how many years has ShearShare, actually the app, been around?
COURTNEY CALDWELLSince 2016. End of 2016.
JODI KATZIs this self funded?
COURTNEY CALDWELLIt was in the beginning. And it was only bootstrap, because we didn’t know that people were out there wanting to give their money.
JODI KATZHave you since started to-
COURTNEY CALDWELLFundraise?
JODI KATZYeah.
COURTNEY CALDWELLYes, we have. Steve Case, the founder of AOL, is one of our investors. We have some early investors in Uber because they totally understand the sharing economy, Kim Kimble, celebrity hairstylist to Beyonce, Oprah Winfrey, she’s an advisor for ShearShare. We have some phenomenal investors and advisors.
JODI KATZThis is really cool.
COURTNEY CALDWELLI know.
TYE CALDWELLWe’re excited.
COURTNEY CALDWELLYou can not imagine this.
JODI KATZAre you in the dreams come true phase of your business?
COURTNEY CALDWELLI think everyday you work as hard as you really can, because you’re always thinking, the phone calls that we hate to get are when a salon owner calls us and says, “Thank you guys for everything you’ve done, but I have to close my salon.” We just cringe when we hear that. We got tired of seeing our friends close down their barbershops.

To us, we have to fill the chairs. We have to get the stylists in, making the money, working at a place where they can. I’m sorry, go ahead.

TYE CALDWELLBut it is a dream come true, simply because, and just to answer your question, we looked at the opportunity, we didn’t shy away from it, we weren’t the type of people who were engineers and knew how to build a tech app. We asked questions. We called up a friend of ours in the Valley and said, “This is what we have an idea about.” This was when she was working at Oracle. She had met a young lady named [Tia Lo 00:38:34] who was an advisor with NAPA ventures, and she told us, you guys have a beginning of an idea.

We didn’t know what to do, so the dream come true is jumping and doing it. Most people will say, “It’s gonna take so much to do that. I don’t know if I want to sacrifice that.” We sacrificed. I’m used to doing it, I’ve been doing it since I was 19. I had to get her on board, coming from the corporate industry and say, “Hey, you know what? We gotta do it. Trust me, it’s gonna feel real bad at first.”

COURTNEY CALDWELLEvery day, this man grabs my hand and says, “Let’s run and jump off this cliff.” I’m like, “Okay, let’s do it!” That’s how life with Tye Caldwell is everyday.
JODI KATZI liken the entrepreneurial experience to being on a roller coaster and when it’s not good, you’re hanging upside down on that loop.
COURTNEY CALDWELLOh yeah.
JODI KATZThe car is not moving. You’re just hanging all skewed.
COURTNEY CALDWELLYeah.
TYE CALDWELLAbsolutely. I would agree with you totally.
COURTNEY CALDWELLBut he always brings me back to reality, because I’m the, it’s gotta be this, we have to always run at 100 miles an hour no matter what. He’s like, “Babe. First of all, we need to shut it down and turn everything off. It needs to just be me and you time for a minute.” I’m like, okay, gotta come back to reality.

Then he reminds me, just because we had a not so good day, we’re about to turn the corner and it’s gonna be a good day. I’m just looking for the corners at every turn. Whenever there’s a not so good day, I’m like, where is the corner?

TYE CALDWELLI say, it doesn’t matter how many investors we talk to, it doesn’t matter how many people that think about what we do. You can’t make people do anything. The market, the industry is gonna happen. But, at the end of the day, what you have to realize is are you doing the things so when the masses take over, to get ready for the shift? Because once that shift happens, it’s gonna take off.
JODI KATZSo you have to keep your side of the street clean, you have to keep moving forward, you can’t expect anyone to sign on the dotted line when you want them to, it’s not gonna happen that way. You just need to keep going.
COURTNEY CALDWELLThat’s right. Gotta be consistent. Just be consistent every day. He doesn’t share this story a lot, but the first day he went to work at the shop, he cut one head for 10 dollars from a 12 hour day. Who would’ve said, I’m gonna get up and go do that again tomorrow? And he did, but just having that modeled in our household was like, okay, you just put one foot in front of the other. When we thought about ShearShare, it was like, okay, we’ve already been through not so good stuff, how hard can this be? You just figure stuff out.
TYE CALDWELLI tell people failure is not scary. The scary thing is success. What are you gonna do, because most people think failure first, what do you do if you hit the bullseye?
JODI KATZRight.
TYE CALDWELLBecause every time you’re doing something, you’re aiming for it. What if you hit it? You’re gonna be happy, right? We play the lottery. What if we win? What are we gonna do? Why be afraid to lose? You oughta be afraid when it hits and it happens. What am I gonna do? Nobody is prepared for success.
JODI KATZRight. I reference this scene in the movie Tangled. Did you ever see that? There’s a scene where Rapunzel is sitting there across from Flynn Rider in a boat and she’s about to have her dream come true, which is, if you didn’t see the movie was to see the lanterns. Very symbolic for her. But, she’s terrified of, if I make that dream come true, what happens next? She’s been thinking for 16 years about this one thing, and it is very scary. Reaching your goal, I get very emotional when I … ’cause I’m in a dreams come true kind of phase right now in my business and it’s more about me and my heart than actually the business, where I’ve gotten to, and now I get to actually sit and think about what I want to do now.
TYE CALDWELLYeah.
JODI KATZIt’s overwhelming and can be scary but now I have people to talk to ’cause I know I don’t have to do it all.
COURTNEY CALDWELLDefinitely.
TYE CALDWELLThe good thing about this because I know we’re coming to a close soon, I wanna say this to you, and to our listeners. This is probably one of the best podcasts, and I’m gonna tell you why. Because you’re genuine, you really have a heart for the people you’re talking to, but not only that, we’re comfortable. You make us feel comfortable and we can see you. We’ve had some awesome podcast interviews over the phone and I can name a couple, but to be in person and to have this interview is amazing. There’s so much that God wants to give you. You’re close to getting where you wanna be, and then there’s another level.

You’re getting to where you wanna be, but that next level is where you’re gonna start learning. Right now, you’re just going through the preliminaries.

JODI KATZThank you. Thank you. Well, this podcast is so important to me because of this. Because we get to humanize this business. Number one, I never would have met you, well, maybe in 10 years. I’m not in the hair business, I wouldn’t have come into direct contact with you, so the fact that we’re connected together now is amazing to me. Doing it face to face, it wasn’t my original intent. When I started the podcast, I just wanted to make it easy so I did it over the phone, but then I had my first pod when I was interviewing two people and I’m like, I can’t do two people over the phone, it’s too complicated. I can’t see the eye contact, we can’t figure out who’s talking next, so I did it face to face and I’m never going back.

This is what it’s about, the podcast is about connecting. That’s what it is for me.

COURTNEY CALDWELLEnergy.
TYE CALDWELLThat’s what we say about ShearShare, it’s about connecting. So many times we would learn to do the Uber, we would learn to do the [inaudible 00:33:59], we would learn to do the Airbnb. The reason it works is because people want a humanized understanding of the people that they’re seeing. Don’t trust in the homeowner, don’t trust in the salon owner. Trust in the company. We’re doing this for you. We’re taking out the hard work, the brunt work that you gotta go through and we’re making it easy. You’re clicks away from having your dream come true.
JODI KATZTell me again how many states and countries ShearShare operates in?
COURTNEY CALDWELL433 cities and 11 countries as of this morning.
JODI KATZThat’s amazing.
COURTNEY CALDWELLWe had a list of about 250 cities that people have said, “Please ShearShare, I need you in this city.”
TYE CALDWELLWe’re never gonna not say that they’re important, but we definitely want to make sure that we’re building the concept up right and so those adoptive cities, we’re definitely taking care of home base which is Texas and Dallas. California and New York are very technology adoptive, so they get it. When something like this comes out, they jump on it really quick. Now you still have your other cities, maybe smaller markets, you still have Florida-
COURTNEY CALDWELLGeorgia.
TYE CALDWELL-and you have Tennessee that are really doing well, but people like Chicago, all those cities right there, they have the mass amount of salons and stylists, but they may not be as adoptive as the East and West Coast.
JODI KATZRight, but think about what you are giving someone who maybe lives and works in a city that they’re clientele is not adoptive as, but she wants to move. She doesn’t have to move and-
COURTNEY CALDWELLNot have a place to start.
JODI KATZRight. If she has one client in this city, she can have a business.
TYE CALDWELLYes she can.
JODI KATZShe doesn’t have to just hope that people don’t wanna come to her apartment because it’s not big enough or bright enough or whatever. She can have a real, legitimate place to work for not even a lot of money, at that point.
COURTNEY CALDWELLThat’s right. The least expensive price per day on the ShearShare app is 25 bucks. And even, there’s one here in New York that’s 40, and that’s a steal for the city of New York, right?
JODI KATZYes.
COURTNEY CALDWELLNot only hairstylists and barbers can use ShearShare. Every licensed specialty within cosmo, so anything related to hair, skin, and nails. We have a lot of microbladers now who are using ShearShare.
JODI KATZOh my God, I know lots of microbladers.
COURTNEY CALDWELLYes.
TYE CALDWELLThat’s blowing up.
JODI KATZWhat I love about this, and it ties back to what we talked about, the energy I felt between the two of you, is that you’re doing this to help other people grow this businesses. This isn’t satisfying your own personal needs. You’re helping other people be entrepreneurs or build their business, or stay in business and pay the bills.
COURTNEY CALDWELLOr launch out, like a student who graduates and gets licensed next week, they can immediately go rent a salon space on the ShearShare app.
JODI KATZRight. I so enjoyed talking with you. Let’s close with telling me what your vision is, beyond what you’ve already accomplished. Where does this go now?
TYE CALDWELLI would definitely like to say first, and I’ll let you close it, Courtney, definitely to the people whether you’re coming out of school or you’ve been in the industry for 20 years, I wrote a bestselling book called Mentor by Failure, and I would love for people to get that bestselling book off Amazon. It’s something that people need to understand is that you have people out there that really wanna help. We don’t look at the beauty industry as competition, we look at it as community. So, I try to give five nuggets of wisdom on how to be successful.
COURTNEY CALDWELLI would say, big picture scheme, just to be broad, is that ShearShare wants to be that bee to bee ecosystem, so whatever kinda bee to bee tools you as a stylist need in your life, we wanna make sure that we provide them to you to be successful. We’re thinking, today we are space to work by the day, but we’re thinking, liability insurance by the day, we’re thinking where you can get taxes done and you get your pay stubs, weekly pay stubs for free. Products and tools, anything in the industry that’s gonna help you maximize your earnings potential, that is why we are here.
JODI KATZI love it. And I told you this on the phone, once you figure out that final aspect of it which is all the annoying administrative aspects of being in business for yourself, there is application for this beyond beauty. We are a big economy now and this is really what you’re servicing, and you have all the learning at your fingertips now, so kudos to both of you. Congratulations on what you’ve built together, and thank you for your smiles.
TYE CALDWELLThank you.
COURTNEY CALDWELLWe appreciate you having us here today.
JODI KATZOh, I’m so grateful.
TYE CALDWELLAwesome podcast. Awesome.
JODI KATZThank you. I am so grateful. For our listeners, I hope you enjoyed this interview with Courtney and Tye. Please subscribe to our series on iTunes, and for updates about the show, follow us on Instagram @wherebrainsmeetbeauty.com
ANNOUNCERThanks for listening to WHERE BRAINS MEET BEAUTY™ with Jodi Katz. Tune in again for more authentic conversations with beauty leaders.
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