00:14 Hey, welcome back to another show. We are so excited today to have Courtney on because she is going to blow your mind with what she's doing to the beauty industry. Courtney, will you please tell us who you are and what you do?

00:28 Hey there Todd, thank you so much for having me on. And hey everybody, my name is Courtney Caldwell. I am first a wife, mother, daughter, servant, and I just happen to be the CEO of a beauty tech startup called ShearShare as in a pair of cutting shears. So ShearShare is the first B2B mobile app that connects salon owners to individual stylists to fill their empty salon space by the day. Like think of us as hair B&B. And so we're doing that across 900 cities, helping to keep small businesses open and helping to bolster on local economies everywhere. So we're very proud of what we do every day.

01:04 I love it. I honestly, I love it. I think of the whole, cause I grew up with a sister that was a hairstylist and I remember her having to go down to downtown Seattle to work in this one particular salon. And it was like a crazy time. And then now, you're really bringing the modernizing this whole industry. And this is, it seems like there's an obvious problem to fix. Tell us how you like got into this. Yeah.

01:28 You would think. You would think, Todd. I mean, 40% of salon and barbershop space goes unused every single day. And it shouldn't be that way, nor does it have to be that way. And so as my husband and I are from the industry, my husband, by the way, is number one bestselling author for how to be successful in the industry. He's been a celebrity barber, hair stylist for 30 years. He earned his doctorate degree in professional barbering and cosmetology. He's actually the first African-American male member elect to the Professional Beauty Association. So we were busy running our own, right? Like clearly this man loves beauty and barbering more today than he did 30 years ago. But so we were busy running our own award-winning salon and barbershop in Plano, Texas, which we still have in the family today. And we were noticing that there was like this shift, like all of a sudden the long list of people who we had to say, hey, the next time that nail technician leaves or that barber leaves, call me first. I wanna work out of your location your relationship to the community, what you guys do for the city and the metropolitan area, like we want to work out of your establishment. No problem. So always had a way to go. All of a sudden though, Todd, that list dried up and we started to look around saying, what is going on? And as we're advisory board members at beauty schools and barber colleges, we're talking to the rising generation of stylists and they're telling us over and over and over again, like, look, I don't want to do what you guys, the old guard did. I don't want to work out of the same chair for 15, 20 years. I want more from them and I want flexibility. And I want to build my book of business on my own terms. So whatever that means for me, I'm going to go out there and find it. And we said, oh, okay. So maybe that random phone call that we got from a stylist who said, I just want to run out your empty suite on a Friday, Saturday, is that possible? Maybe there's something to it. And so fast forward, we ended up finding ourselves manually matching stylists to empty salon space for three years before we looked up and said, there's gotta be an app for this, like where is it? And we couldn't find it. And so that was the aha moment behind ShearShare.

03:27 And meanwhile, you're on vacation in an Airbnb and the thought comes, duh, look at all this empty space, why aren't we using it?

03:37 Right, there's something here, hair, skin, nails, it's everywhere. We're one of those rare evergreen industries and we're actually the second largest industry for freelancers and independent contractors, which not many people realize.

03:50 That doesn't surprise me and probably the most scrutinized for tax for taxes, right? Just kidding. No, I.

03:57 Oh, oh my gosh. Oh, that's a whole another podcast.

04:01 Well, I say that lovingly I have family in the industry and I've got a daughter who is in nails nail school right now and she is this is really exciting because I honestly I think of all the flexibility that a hairstylist or a nail, you know anyone in the beauty industry wants and Now they could be like, you know what? I am gonna go on a trip But I'm gonna do it for two weeks and I'm gonna work out of this salon in this city and just see if I can draw up some business. I mean, that's cool

04:31 Yeah. That's right. Kids these days are using, you know, TikTok and Instagram and whatever else, right? They don't need us anymore to help build their book of business. They're finding people to serve on their own. And so we have Bravo, Bravo.

04:47 I love it, now this is fascinating. So it's very clear who you serve, it's very clear what you do. And by the way, those listening, go check out the website at sheershare.com because on the website, it has a look and feel that's very familiar to you if you've ever Airbnb'd. And the Airbnb is just an awesome model. I love this, really cool, really cool. 

05:07 Thank you.

05:09 So now you've had a journey because you were based in Texas, and you are now part of a program, I mean obviously you want to grow and scale this thing, tell us about what you've done to grow and scale this thing because it's kind of a fascinating journey.

05:23 Yeah, it's crazy. I never thought that we would have left the state of Texas, but we moved from Dallas to Buffalo, New York, by way of the 43 North Startup Program. And so if they choose to invest in you, they ask you to relocate to the area for 12 months. We've been here for a little bit longer than that. And we are loving the, not only the capital that came with the startup win, but also the relationships and the advice relates to hiring and being able to get additional PR. And the expansion opportunities here because we're so close to Canada means that ShearShare will be international pretty soon.

06:02 Woo, that's awesome, that's awesome. 

06:05 I know. Yeah.

06:06 So with that, I mean, that comes a lot of stuff with that. I mean, you just unpacked a lot of stuff. So let's talk about this for a minute. So first of all, you knew you needed to raise some money, you wanted to raise some money. What drove you to that need and what were you thinking? What was the initial ambition for wanting to raise some money?

06:25 Oh, Todd. Well, first of all, we started out bootstrapping Shearshare for like three years. Honestly, when I was working at Oracle, like I was my husband is the entrepreneur. I was having fun working in corporate America for 25 years. Last gig before starting Shearshare was at Oracle, where I was responsible for digital demand generation and innovation across five continents. So I thought, OK, if anyone knows, you know, tech marketing is probably me. However, I had no idea about the startup world, which was crazy, because I was literally flying from Dallas into, what was I going, into Redwood City every single month when I was going back to the headquarters at Oracle. And so I'm literally landing in Silicon Valley, but these worlds never, never connected, never crossed wires until there was a lady on LinkedIn who said, hey, somebody, somebody told me to get in touch with you and hey, the next time you're in California, let me know. So we connected and ended up going out for coffee. She is so engrossed in the startup ecosystem to where she can't even walk from her car to the grocery store without being pitched a startup idea. And so I remember my husband, we were having this issue and talking about, okay, now we've, you know drain the savings account. Now we're draining the 401k. And I still clutch my pearls thinking about that. He's like, I think what we're building is that word startup that lady used when you went to go meet her for coffee. Like call her up and see what advice she has for us. And thank goodness we did because she ended up helping us to like navigate through this whole new world. We started going to pitch competitions, which I had no idea even existed.The very first one that we entered, we actually won. That ended up taking us to one of the startup accelerators, 500 startups, or now 500 global. Y Combinator Fellowship, and then after that, those couple of programs we officially launched and started raising money. Because we saw what we were able to do as a team of two back in the day, for Shearshare, now being a team of 10, and we knew that we needed capital in order to run this race really, really quickly and to truly own the market. We didn't feel like anybody else was going to have the type of considered care that we do for this industry. And we knew what we need to do to be successful, not just for ourselves, but all these other small businesses or small businesses of one that we were then supporting. And so thank goodness, you know, we have some amazing investors like Mark Cuban behind us and Steve Case, AOL, and Arlen Hamilton, of course 43 North. The list goes on, but it's been a wild ride. And I'm very grateful actually that we bootstrapped first before we started fundraising.

09:01 Yeah, yeah, no that's so cool. So you were revenue positive before you started raising money? 

09:06 Yes, it would work because it's just the two of us.

09:08 Awesome. Dude, hey listen, I just had to ask because I tell you what, I don't know what the deal is nowadays but I feel like everybody's trying to idea, raise money. Before they even have a single client, you know what I mean? And I love that you bootstrapped, I love that you got some client onboarding first, I love you got that experience and then you went to raise money, which is awesome but I think that's the way everyone should be doing it. And for those listening who are thinking about raising money, raise some clients and then raise some money first. Next, after.

09:39 Yes, make sure people are voting with their dollars for what it is that you're putting out there first and then you can easily travel like that in a conversation with an investor.

11:22 100%, 100%. So tell us about that though. I mean, becoming part of the whole network inside of Silicon Valley and then moving into New York, how is it different by the way, the East Coast, West Coast vibe, right? And tell us what you prefer about either one or the other.

11:48 Oh, I like both to be honest with you, but they definitely have their differences. So every conversation that's dealt with an investor out in Silicon Valley was all about what can we do to own the market? Like I don't care if you're spending $100,000 a month, I want to make sure that you're adding more chess pieces to the board than you had the month prior. And then when you go to the East Coast, most New York investors want to see your financial projections for the next three to five years. And they're really in tune with making sure that you're a capital efficient business. They want you to own the market, obviously, every investor does, they want you to be able to 10X their investment. However, they're more about the nitty gritty numbers and the basic blocking and tackling within your organization. California is like, let's go big or go home. Yeah.

12:35 I love it. That's a really funny mix. And I think it's even better coming from someone from Texas because you're right in the middle of the two worlds and it's like, huh, somewhere in the middle, there's a good solution there. That's awesome. Well, this is awesome. So a lot of people out there are scared. A lot of people are nervous to raise money. A lot of people get, you know, kind of self-conscious about, well, I don't have all the answers right now. What was kind of the thing that you had to get over in order to make this jump and make these moves of these investors?

13:09 Oh, that's so good. You know, to be honest with you, it's really about personal time. I think I struggled the most as a founder with time blocking, like trying to figure out how to, yeah, and it really ties back into, you have a finite amount of time, you have a finite amount of energy, you have a finite amount of money, resources, team members, et cetera, et cetera. How can you choose the best decision out of all the great decisions that come at you? And so if you took the time to time block and figure out how can I box my time and my energy so that I am focused on being super efficient and super productive according to topic A, and then I can now change my brain waves and start thinking about topic B, that has been really, really helpful. But even then, it really ties back into making sure that you are the healthiest you can be. Because honestly, like your business is only gonna be as healthy as you are. And so if I'm walking around in Snicker bars every day and drinking a bottle of wine at night and trying to subsist off of like two hours of sleep, first of all, none of that is attractive. And that is not at all going to get you across the finish line faster. It's all of those daily non-sexy disciplines that you have to have in order to figure out, one, what's the best way for me to time box my time? But then also, how can I make sure, I'm giving myself like a brain hack so that I have this unfair advantage when it comes to making decisions and making the best decisions for the company. And so you got to make sure you're eating well, you got to make sure you're hydrating well, you have to make sure you're moving well, even if that for me is like pushing back from the computer and taking the dog for a walk sometimes. Like it doesn't mean that I'm in the gym for two hours a day, it just means I am not staring at a screen or on a phone call with someone. I also need to sleep well. And I tried the whole sleeping two hours a day, like just to get me an extra edge across the competition, but that doesn't really help. I found out that working with my therapist for sure, I need eight hours of sleep a night and that delivers back into the world the best Courtney that I can be. And then you also need to socialize well. Like you gotta find time to say, I'm gonna go hang out with the kids. I'm gonna go on a date night with my husband. I'm going to go meet a new person at the comedy club down the street. You have to have those five things that you're doing every day. And I promise you, it doesn't sound glorious at all, but those are the things that will help you wake up every day and you are able to put one foot in front of the other and eventually you're gonna turn a corner at every challenge you run into.

15:42 Love it. Ah, I love that advice. That right there is a podcast in and of itself. I truly believe that what you said is the gospel truth. Like when you think about what it takes to be an entrepreneur, what it takes to grow a business, you've gotta be sharp, you gotta be rounded, you've gotta be like, you've gotta have that balance between family and work, otherwise you just burn out. And people say that all the time, you know, but until you burn out, you really don't understand what that even means. And, It's horrible! Burning out is horrible!

16:22 It is. It's so horrible. I burn out in corporate America, you know, and I was that person who would stay up, you know, literally working like 20 hours a day, Todd. And it got me pretty far. You know, I was able to add teams to my plate who were in Tokyo and in Bangalore and in Australia, whatever else. So it was wonderful, but I was dying literally like on the inside. And so thankfully I was able to take those learnings, the things that I didn't want to copy and paste into the startup world and said, no, I know how I am as a better person, a better leader, a sharper leader, a more emotionally present leader. And I wanna be that for this team called ShearShare. Yeah.

17:01 Love it, love it. So with that, I mean, with that being said, taking a step out of the Oracle life and taking a step from corporate into this new kind of lifestyle, how is that, what did you, was there any big surprises? Like, was it like, holy crap, this is really cool or holy crap, this is like so much harder than I thought? Like, but tell us, can you share with us any of those kind of things that kind of came to mind?

17:28 I want to say, and I know for sure, not even I want to say, I know for sure that I say on a daily basis, wow, this is really cool, more so than I say, oh crap, that's really hard. And I remember like the first thing that we started at ShearShare, you know, you start thinking about things that you didn't have to think about when I was at Oracle. Like when I got to Oracle, my new job, somebody would hand me a laptop, they would remind me of the pay schedule and how much PTO I was able to negotiate and remind me all my benefits. And ShareShare, like you have to, when you're starting a company, you have to create all of those things. So you are legal, you are HR, you are having to figure out employment tax benefits, state to state. Yes, you're having to hire, you're having to vet vendors, you're having to, all the things from buying a laptop to creating a website, to setting your legal structure for your business, determining what's best for you. And so I think Those are things that kind of surprised me.

18:30 So this is really cool because I love your story. I love where you've come from. I love what you've been able to do. And I will have to say, you know, when I speak to people who are new into entrepreneurship or newer business leaders. The most common thing I hear is exactly what you just described of I had no idea the burden of knowing that I have to carry the, like my decisions mean whether these people that work for me are going to get paid this month or not. Right?

18:58 Yeah, these are whole families that depend on this paycheck, you know, at Share Share. And so that's so important. Like that, that in itself is a weight, right? But then you have this bigger vision that you have for the company and the people that you get to serve every day, and that's a weight. And so if you're a person who is not comfortable with carrying really heavy weights, this is probably not the best place for you, to be honest. 

19:20 It's not for the faint of heart. Yeah, for sure.

19:23 No.

19:24  Well, and it's different what you're doing than what a lot of people do. You know, I, the thing I love about your model is that even with just 10 people right now on your team, you've been able to branch in a 900 cities, right? With your software. And that is a huge congratulate. I mean, that is just so cool. Like way to go, right? And so when you get into 900 cities and you're managing all these different properties and managing different stylists and different people, you're really targeting two different brands, right? You're targeting the operator and you're targeting the real estate part of the whole equation. Which side is harder to market to and what are you seeing in terms of messaging-wise? What is it that you're trying to do to catch both targets?

20:13 Yeah, that's a great question. So I would say it depends on the day of which one is more difficult, the supply side, which is the brick and mortar or the demand side, which is the independent professional. We just listen intently, to be honest with you. We listen intently to our customer advisory board and to how people are choosing to maneuver on the app. So much so to where we eventually called up Lloyds of London, and this was through a cold email. We called up the world's largest insurance company and said, Hey, you know what? It's really hard out here for independent stylists to get professional liability insurance. What can you do to help? And we courted them for two years, Todd, but all in all ended up being a great relationship because they helped us pioneer daily liability insurance. So for five bucks a day on the ShareShare platform, I know, I know, for five bucks a day on the ShareShare platform, your daughter, who's about to graduate from Cosmetology School is in Neltech, she can get up to a million dollars in coverage in professional liability insurance and it doesn't exist anywhere else. I know, so we did faith as a service and now we do liability insurance as a service. But then again, we're listening intently and people are saying, you know, I got into this industry because I'm super creative. I wasn't thinking about what happens if I get sick or I get COVID or I break my arm, you know, playing pickleball on the weekend. And so now we have portable healthcare benefits. So where if you live in the state of Texas, but you're doing a destination wedding in Tennessee and you hurt yourself, no issue. You are covered no matter where you are, where you go, whether you work for salon A, B, C, D or yourself. I know it's just important. I mean, this gig economy, or I don't even wanna say gig economy, this hybrid economy, it doesn't just stop at technology workers coming to every industry, even Main Street. And so we're making sure that whatever it is that these people need in order to be successful in their career, that we provide it on a pay as you go basis and meet them where they are, which is typically on their mobile device.

22:12 Wow, wow. I absolutely love, I love what you're doing. I love the model, I love the people you're helping, especially knowing people that you're helping. Like it just, that is really, really cool. So gosh, I, seriously. So as you look out, as you look out and as you've made this move, you know, obviously your husband has been in the industry his whole career, you're jumping into this industry. Is it what you thought it would be? Is it different?

22:48 It's, you know, so I was not blessed to be a licensed cosmetologist. So you don't want my hands in your head or on your skin or on your nails, but I do have experience as a salon owner, right? So I would help in hiring, vendor relations and marketing, all that good stuff. And so yeah, it's exactly what I thought it'd be. I mean, I would spend my weekends and evenings, you know, at the salon and barbershop that we own and talking to, you know, our peers. And so I think it made it easier to start going door to door, which was how she or she got started. We literally started going door to door to our fellow salon and barbershop owners and saying, hey, we can help you feel that empty seat that you have. And this is how I know this works because I am you and you are me. And so the trust factor was super important. And that immediately helped us to rocket ship into the 900 cities that we're in now because they feel like they're talking to their peers and they are.

23:40 Courtney, I love it. For those of you listening, honestly, this is such a breakthrough for so many of you, I hope, because you're hearing someone who's been in an industry that's a little bit old, a little bit stale, a little bit out of date, and taking modernized models and just literally bootstrapping that into an industry that needed it so badly. There's so many opportunities out there, and there's so many opportunities to grow and scale, and I love that you're raising the right kind of money, you're getting strategic partners. And what a beautiful thing. It sounds like you're making all the right steps, Courtney.

24:16 Yeah, hope so. It feels like it. I mean, again, we just, every month, people vote with their dollars. And so, so far they're telling us, keep going, you're doing the right thing.

24:31 Fantastic. Well, before I let you go, I gotta get a shout out because we love giving the credit to those who deserve it. And is there someone that has been there as a mentor or someone that's, it sounds like you have this person in California who's a great mentor, but who is it you'd like to give a shout out to that's gonna help to get where you're at?

24:34 Yeah, there are actually three women that I think of, I mean, besides my mom, and you talk to my mom for five minutes and she would make you think that you can grow wings and fly. She is that kind of optimistic person. And you have to have that person in your corner because I firmly believe that optimism is a competitive advantage, right? But when I think about just like.

25:02 Mom, check. Yes.

25:03 Definitely. So, when I think about the women who have helped me every step of the way, because this is a brand new territory, like I've never run a tech startup before, right? And so first one would be Ms. Titi Lowe, the lady who I mentioned before, who I was like, you said the word startup, is that what we're doing? She's been with us every corner, every up and down within the organization. And I'm so very grateful for her. But then also Mary Grove of Bread and Butter Ventures. Mary Grove started at Google. Pretty much created Google for startups. She's been a wealth of knowledge and just like, you can do it, go get them, and being able to connect us to different people. And then I have to say, third is Shashi from Hearst Corporation. She helps to run level up ventures out of the Hearst strategic BC arm. And these women, I tell you, like, if there's a bad day, I can text any one of them at midnight and any one of them would come back with some kind of words of wisdom or like a pointing in the right direction and it's always been super helpful. So, yeah.

26:05 I love it. I love it. Now, I'm not gonna point fingers, but it sounds like all these are West Coast.

26:10 Let's see. No, Sashi is East Coast. She's New York. 

26:14 Oh! Oh, okay, yeah. The Hearst family can be either side.

26:17 And Mary was actually... And actually, Mary Grove is Minneapolis. And TD is the only one without the valley. So I got the whole country covered every time zone.

26:28 Bless your heart, bless your heart. Well, listen, Courtney, I am so pleased that you came on the show with us today. I'm really, really honored that you came. And thanks for sharing your story. Thanks for doing what you're doing. And for those listening, you gotta follow up with what she's up to. Go check out her site, Shearshare. And honestly, it's like an inspiration for any of you who are thinking of disruption, of going into an industry that needs solutions. It's not that far to reach. So thank you, Courtney, for sharing your experience with all of us.

26:57  Thank you so much, Todd. And if you people who are listening in want to just have see a quick commercial about ShearShare, we were actually on the Today Show last Monday. So go to the Today Show Twitter and you'll see ShearShare there sharing our story. Yeah.

27:14 Nice, nice. And now you've moved up to the Growth and Scaling podcast. This is like, I don't know what your next step's gonna be. This is amazing.

27:19 The next step is Michelle Obama. That's the next step for me.

27:23 Get Oprah out of retirement! This is so cool, Courtney. Thank you.

27:32 I love it. Appreciate it Todd.