ShearShare: On Becoming Startup of the Year, Solving Problems, and Bootstrapping

Each day we applaud startups for their latest round of funding no doubt a challenging accomplishment, but it can mean we often overlook those who bootstrap. These startups tirelessly plan, scrape, save, and sacrifice their way of life in order to achieve something great. Bootstrappers are an entirely different breed of entrepreneurs. ShearShare, Tech. Co’s Startup of the Year 2016, is one such company, and its rise to recent success is only just beginning.

ShearShare is essentially a “hairbnb,” or a way for licensed beauty professionals to rent salon and barbershop space by the day.. The sharing economy is already a proven concept by way of AirBnB, but for the two founders, ShearShare is the offspring of personal problem solving, not just an uberizing of an industry. Launched in February of this year, the app is already in use by salons, spas, and barbershops in 250 cities and 11 countries around the world.

However, their story starts well beyond this short window of time, back to when they were doodling on a napkin, managing their award-winning salon, and leading global marketing teams.

Who Is ShearShare? Partners Turned Business Partners

The founding duo are more than business partners: They’ve also made the ultimate partnership in marriage. Courtney and Tye Caldwell founded ShearShare in an effort to solve a problem they were having at Tye’s salon in Texas, the retention and signing of long-term beauty professionals in an industry that’s drastically changing.

In the past, back in the days when Tye was just starting out, industry professionals would often stick with a location for years, anywhere from a decade or more; however, now professionals find it difficult to make commitments for more than six months at a time. Having just expanded Salon74 by Tye, Tye had more space to fill, but the industry was shifting. Regardless of their reputation and awards, licensed beauticians were on the move.

“Being in the industry for almost a quarter of a century, you learn to recognize trends and change with the times,” said Tye.

Amidst trying to solve the problem, Tye began receiving calls from stylists in North Dallas and even other states who wanted to borrow a seat in his salon for a day or two. The stylists had clients relocate to that part of Texas and wanted to continue to support them in some capacity. The issue? Borrowing or renting space for such a short period of time isn’t, or wasn’t, something being done in the industry.

“We were still trying to fill our empty salon suites the old way– by having stylists sign long-term contracts,” said Tye. “But we soon realized that we could make some money on our space rather than none. We said ‘let’s try it out, it can’t hurt.’ Then it kept happening over and over again. We were manually matching stylists to salons at first, but at state number 5, we thought there had to be something out there to scale this. There has to be an app for that.”

At the time there was not only no app to solve the problem, there were no existing platforms that could really do what the industry needed. The Caldwells discovered both a problem and a challenge, and considered what it would be like if they created it.

“What would we even call it? I remember we were on a plane to California for vacation, reading magazines…and started thinking of possible names for the app. Tye said that we have to have Shears in it to represent the beauty industry, so Shears made the list. I added that owners are essentially sharing their space, so Share made the cut. That’s how we landed on ShearShare! . But we closed the book on the app idea for two years,” said Courtney.

Flash Forward to 2015, when the team revisited the idea. They sat down, started drawing on a napkin, and even sketched out what the app would look like screen-by-screen. The Caldwells then began researching how to find someone to build the app. Through the advice of a friend, the duo was referred to a development team in Silicon Valley that built out their concept, mirroring what they doodled on the napkin. Flash forward to today, they have revenue coming in, and people are ecstatic. They have disrupted the beauty space.

“People will always see your glory but will never know your story,” said Tye.

The story for the Caldwells is one of hard work, planning, and sacrifice. Although they have found both growth and success, it was not without its challenges.

“We spent so much time, energy, and effort on building ShearShare from the ground up… I can’t tell you how many nights we ate rice and beans, saving wherever possible. People never see that, though. They only see the highlight reel,” said Courtney.

Challenges of Bootstrapping and Growth

For all entrepreneurs, there is a point of no return when they must decide to fully pursue their ideas and dreams or continue on their path.

“Why not us? Why not take this and make it a staple in this particular space in the industry? We’re solving a real problem that has not been solved–helping cosmetologists and barbers find space to work,” said Tye. “We knew it would take a lot of sacrifice and financial responsibility. So, we put our heads together and took it to the next level.”

The team already had a successful salon, which means this would not be their first rodeo. As seasoned business owners, they knew there would be bumps and bruises along the way, and would have to work through them as they arrived.

“Bumps and bruises will come, but as soon as you have a bad day, expect the next to be better,” said Courtney. “It makes it easier to get through the not-so-good days if you are prepared financially. Even before drawing on the napkins, we made some tough decisions. We paid off all of our debt. We paid off our house. We removed as many financial obstacles as we could because we didn’t want to have an excuse to stop. We wanted to be different.”

And different they are. Although they are bootstrapped, the team is also now positioned in such a way that would allow them to seek outside investments purely to focus on growth and scaling.

“Having a path to success is huge. Taking on investors is a nice-to-have now, and it would literally be pouring gas on a fire that we already started. We talk to our users everyday, so we know that the right investment would only help ShearShare take off like a rocketship,” said Courtney. Beyond saving and scaling, there is also a need to educate the industry.

Converging Paths

As kids growing up we often hear stories of wanting to go to the moon, maybe even being a fireman, but for Tye Caldwell, he always wanted to make his own way. Courtney jokingly referred to Tye as unemployable, but only in the sense that he doesn’t allow barriers to come between him and success.

“I’m the 7th of 8 kids. I learned how to share at an early age and always wanted to do my own thing,” said Tye. “As a young man, I did a variety of odd-jobs around town, always doing something to make money. And then I picked up a pair of scissors when I was 11 and gave someone a  haircut. When my friend introduced me to a full clipper set, that’s when I fell in love with the art. Beauty is a must. Growing up, my mom would tell us to always look your best because you never know who’s watching. That’s always stuck with me.”

Prior to fully pursuing what he loved, Tye went to school for sports medicine, and then worked in a hospital for a short stint. From there Tye decided to go to school for what he was truly passionate about, something that he would do for free, but wouldn’t mind getting paid for, either. In barber and beauty school, he rose to the ranks of  student-teacher, learned to run the floor, and taught others how to cut and do hair, along with other beauty services. Post-school, he worked in a salon, and on his first day, working 9am – 9pm, only made $10.

“Most people would have quit. But I pivoted, I knew I had to , keep coming back. Somehow I just felt that success would come one client at a time,” said Tye. He never really wanted to own a salon, but also knew that he wanted to be an agent of change, offering customers the best service experience possible. That led him to open Salon74 by Tye almost twenty years ago.

For Courtney, she belongs to beauty by marriage. Although the salon is a family business, her area of expertise is technology marketing.. “Marketing is something I wanted to pursue as soon as I got to college, even going back to school to earn my MBA. I had a knack for making things appeal to a certain audience, so marketing was where I invested my time. And because digital marketing moves so fast, I fell in love with being able to drive results quickly,” Courtney said.

Courtney went on to work for Oracle’s Digital Strategy & Innovations team and then decided to consult, working for global software brands and even a private equity firm. Two years after the napkin doodle and countless manual matches of beauty professionals to salons, the partners knew it was time to do something together.

“When we were matching stylists to empty salon chairs manually, we knew there had to be a way to pull in tech and systematize what we were doing. That’s where we overlapped and haven’t looked back since. We both get to do something we love every single day,” said Courtney.

“That’s the beauty of working together,” said Tye. “We have an awesome team. We work so well together because Courtney knows what needs to be done from an operations and marketing standpoint, and I take care of the industry knowledge. That makes for a really good company and a really good culture.”

Creating a Legacy

For startups, not all of them are transparent about their end goal. For Courtney and Tye, they want ShearShare to be their legacy.

“We truly feel that this is the legacy we are supposed to leave. It’s not something we ever thought about [selling], not even now,” said Courtney. “ Tye and I never considered those avenues because beauty and tech are what we know. ShearShare is something we feel in we want to leave for the generations coming behind us.

“We are doing our part to help the industry become greater and keep businesses open,” said Tye. “Our goal is to help [licensed cosmetologists and barbers] extend their ability to make a living long-term.  Instead of limiting themselves, we want industry professionals to gain success one empty chair at a time.”

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Written by:
Elliot is an award winning journalist deeply ingrained in the startup world and is often digging into emerging technology and data. When not writing, he's likely either running or training for a triathlon. You can contact him by email at elliot(@) or follow him on Twitter @thejournalizer.
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