“Beauty Deskside” is a new series celebrating Black and Brown founders and their beauty companies or brands.

Courtney Caldwell is the co-founder and COO of ShearShare, a mobile platform that connects salon, barbershop and spa owners with beauty and barbering professionals in need of affordable workspaces. She launched the marketplace in 2017 with her husband and co-founder/CEO Dr. Tye Caldwell. Together they’ve combined their consulting, barbering and cosmetology skills to grow ShearShare’s database of on-demand salon, spa, and barbershop workplace rentals in over 900 cities.

In this exclusive Q&A, Courtney gets candid about tapping into her experience as a successful salon owner in Dallas to support fellow stylists, the early years of bootstrapping before being introduced to the world of investors and venture capitalists who funded dreams and persevering in the face of adversity because “greatness is in my DNA.”

Beauty for Breakfast: What is your first beauty memory?

Courtney Caldwell: My very first memory of beauty is getting ready for church on Sunday mornings as a young girl. After my mom applied her ruby red lipstick from Fashion Fair, she’d sit me down in the middle of the kitchen and press my hair with a hot comb. She’d let me choose my hair accessories for the day but always instructed me to come home from Sunday School with my hair barrettes intact. This special hairstyling time was also where my mother poured everything she had into me, built my confidence, reiterated that I could do and be anything I wanted, espoused what it meant to be a young lady and stated how proud she was of me. For me, beauty is synonymous with community, wellness, love and encouragement.

What was the impetus behind ShearShare? 

Filling empty salon and barbershop space was a problem we were just trying to solve for ourselves. Our salon was well-respected in the Dallas community for nearly 28 years and had an outstanding reputation. In fact, many licensed cosmetologists and barbers would add their name to our wait list for a chance to work out of our shop.

But in 2012, that all changed. When the industry started to shift from employee- and commission-based stylists to more independent contractors, we paid attention to how the market was responding. Around this same time, a stylist called us and wanted to rent one of our empty suites for just a couple of days — no contract, no commission. She had recently moved her salon 45 minutes south, and her clients were already complaining about the long drive. Desperate to not lose her book of business, she found us online and asked if she could use our empty space for the weekend. Since that space was collecting dust and not dollars anyway, we gave it a try. We then found ourselves manually matching stylists to empty salon space for three years before we looked for a solution, couldn’t find one, and decided to build out the technology ourselves.

Fast-forward to 2022, and today ShearShare has listings across more than 900 cities! In each of those communities, we’re helping salon and barbershop owners make money on their excess capacity, and we’re giving licensed pros access to flexible, affordable space to work when and where they need it.

Let’s talk a bit about the early days of your startup. How did you go about pitching ShearShare and building it from an idea?

We actually bootstrapped ShearShare for the first few years because we had no idea there was a world of angel investors and VCs [venture capitalists] who would give you money to go build your dream. So we just did what we knew to do: we emptied out our bank accounts and 401(k) so that we could build a working prototype of our app, a mobile tool that would help salon and shop owners monetize their empty space and keep their small businesses open. An advisor of ours, T.D. Lowe out of Silicon Valley, introduced us to pitch competitions. With every opportunity to explain our vision to a new audience, we learned to refine our messaging in a way that resonated with both users and investors.

Who were the people that most supported you not only financially but with sharing knowledge to maneuver the beauty and salon industry as a Black woman?

There are so many who have supported my journey as a Black woman in beauty, but there are two special individuals who have shaped my navigation of it. The first is my mother, who is my #1 cheerleader. The second is my husband, life partner and co-founder, Dr. Tye. Both have served as models of entrepreneurship for me and set the example for what it means to leave a meaningful legacy. 

What would you say was the most challenging lesson you’ve learned so far?

One of the most challenging lessons I’ve learned so far has been the art of the start. Many of us will have a stroke of genius but ignore it because we immediately count the costs and assume failure. But if you can will yourself to at least take the leap, you’ll grow your wings on the way down.

Can you expand on how your platform not only helps to minimize the stress of finding affordable chairs to rent in salons and barbershops, but create opportunities to make revenue and ultimately, build wealth and independence?

Whether you’re the salon and barbershop owner or the licensed pro, we’re here to give you one thing: economic mobility. For the owner, ShearShare helps you unlock brand-new revenue by renting out your chair at a price and time that’s convenient for you; for the hairstylist, barber, esthetician, nail tech, makeup artist, braider, microblading artist, and massage therapist, ShearShare helps you save more money by renting affordable, flexible space to work when and where you need it — but without having to sign a long-term booth rental contract or work by commission.

No longer do you have to search the world wide web or hope to hear from a peer that a chair has become available. With the ShearShare app, you can view the available inventory in your city, filter by your licensed specialty, desired amenities, day of week, price point, location, workspace type and more. You type in your credit card information and literally book salon space to work like you book a hotel room!

In addition, we’ve recently partnered with Lloyd’s of London — the largest insurance company in the world — to provide another industry-first: professional liability insurance by the day. For just $5 a day, pros get up to $1 million in coverage and only pay for the days they actually work! By providing access to two of the costliest business tools required to be successful, but on a pay-as-you-go basis, we enable our fellow industry professionals to maximize their earnings potential and build independence.

How do you hope ShearShare makes an impact on the lives of salon owners?

Look, I’ve been there. Even as an award-winning salon and shop owner, I still live the day-to-day challenges and understand all too well the ups and downs of salon ownership. The impact I hope ShearShare makes on the lives of our fellow salon owners is to give them the ability to adapt to new industry work demands while meeting the autonomy requirements of today’s modern stylist. By making their empty chairs and suites available to local pros on demand (and likewise, staffing up to full occupancy at a time and price that’s convenient for them), owners use ShearShare to unlock brand-new revenue. Before ShearShare, there was no app that helped you turn your empty space into extra dollars or manage your most profitable business asset right from the palm of your hand. But now you can lease your empty stations and suites efficiently and safely, get access to tens of thousands of ShearShare-certified professionals, and create more brand exposure to a highly-targeted audience. It’s the new definition of hybrid–designed by YOU, powered by ShearShare.

Congrats on securing new funding! How has that backing helped you to continue to set ShearShare up for success?

Thank you! We’re thrilled at the support we’ve received. Fearless Fund out of Atlanta, Georgia, was the lead investor, and Dave Parker was the senior partner on the deal. We’re using this most recent fundraise to invest in the product, hire talent and expand our market reach so that we keep more of our small businesses open.

What have your ancestors taught you most about perseverance?

To just keep going. When I think about one of my most notable ancestors, Garrett A. Morgan, who invented the automatic traffic light and eventually sold the rights to General Electric for $40,000, I think about the inspiration he had to conjure up in order to create something that didn’t before exist. But he didn’t stop there. Garrett also invented a smoke hood, which became the basis for today’s gas mask, patented an improved sewing machine, started an African-American newspaper in Cleveland, Ohio, opened an all-Black country club and established the G.A. Morgan Hair Refining Company that sold haircare products to Black men and women. I like to think that I’m continuing what he started by giving back to an industry that has fed our family for generations. One of Garrett’s quotes encourages me to keep going and to give it my all on those days where I’m feeling less inspired as an entrepreneur: “If you can be the best, then why not try to be the best?”

You come from a line of influential entrepreneurs. Did you ever feel pressured to accomplish something “major”?

That’s right, and I’m very proud of that fact. I actually don’t feel pressure to accomplish anything major; it’s more like an unspoken expectation. Because I know greatness is in my DNA, I live each day trying to leave people, places and things better off than when I found them.

What is your biggest word of advice for fellow Black women entrepreneurs in the salon/beauty industry?

In all things in life: feed what you want to live, and starve what you want to die.