STARTUP INTERVIEW SERIES: Meet Courtney at ShearShare
Coming in strong with the second episode of the WIN Startup Interview Series: meet Courtney at ShearShare! An award winning marketer and first time tech co-founder of ShearShare – a mobile platform that matches stylists to empty salon spaces.
We sat down with Courtney to chat about her story and experience converting the bootstrapped written-down operation into a widespread mobile platform servicing 71,000 stylists across 1,017 cities. Sharing a positivity that is hard to tear away from, Courtney expresses that her biggest take away from 9 years piloting her first venture is to do it scared. And we couldn’t agree more.
Where did the idea for ShearShare come from?
The idea behind ShearShare is two-fold: monetizing the 40% of empty salon and barbershop space that goes unused every day, and giving stylists the opportunity to rent flexible, affordable space to work by the day. As award-winning salon owners, it was really our own problem to solve. My husband is a 30-year industry veteran and celebrity barber-stylist who earned his Doctorate degree in Professional Barbering & Cosmetology. He's also the first African-American male member-elect to sit on the PBA (Professional Beauty Association) Advisory Board.
In 2012, we added individual suites to our open concept salon. All of a sudden we weren't getting people to sign long-term contracts to lease the spaces, which is typical in our industry. We thought, “well, this is really odd, we've never had an issue filling our workspace with talent before.”
Around this same time, a stylist gave us a call and said, “Hey, I have clients up your way who are complaining about the longer drive to get to me at my new location. Can I just rent out one of your empty suites on a Friday or Saturday?” I honestly laughed at the idea. In what world would a salon owner rent to a stylist for a day! But my husband said, “Well, hold on. That space is just sitting there lying dormant. I'd rather it make some money than collect dust. Let's give it a try.”
Thank God we did, because that stylist started asking us to do the same thing for her in other cities. We would go on Google and start cold calling fellow salon owners. And for three years, we found ourselves manually matching stylists to empty salon spaces! One day my husband said eight words that changed our life: “I think this needs to be an app.” When we sold ShearShare, we were helping more than 71,000 small businesses stay open in more than 1,017 cities across the country. I can proudly say that we did the work to support the backbone of the American economy.
How has being a part of the WIN ecosystem helped or impacted you? Curious how you've leveraged the WIN ecosystem?
We came into the WIN ecosystem right around the time we were exiting ShearShare. You first go from doing this singular task for a minimum of 120 hours a week for nearly a decade to waking up one day and not having a team, a product, a Board meeting, or a fire to put out. It is a very surreal accomplishment. I'm humbled by the love I've received from the WIN network and have been able to leverage WIN by talking to other accomplished women who have really leaned into their new chapters. Being able to chat with them about their own processes, I found myself back in school, now working towards earning my doctorate degree in business administration. I was put in touch with several women, including a professor at Columbia University. I'm happy to say that the WIN community has its own page in this new life chapter I'm writing for myself.
And then angel investing. I feel like I have a strong sense of what investors look for because I've sat on the founder side of the table, but being able to spend time with other investors and understand their diligence process has helped to refine the way that we look at our personal investment thesis.
What were some of the biggest challenges you faced in getting the startup off the ground? And how did you overcome some of those?
I think a lot of people have a brilliant idea but don't take that first step to actually launch it. I'm glad that we did it scared, grabbed each other's hands, jumped off the mountain and decided to grow our wings on the way down! That's really the first challenge: getting over the what-if-this-fails question? I always told myself that if the worst thing that could happen is that I go back to Corporate America, I owed it to myself to bet on our abilities. Our second challenge was figuring out how two, non-technical cofounders were going to build an award-winning tech company. There was no book for that back then.
One night we were sitting at Chipotle, sharing a veggie bowl. My husband said, “look, if we're going to be serious about this app thing, what would it even look like?” He pulls out a Chipotle napkin, and we start drawing the different screens the app. We kept that napkin after all these years. It's sitting in the same frame with our US patent. It's pretty cool to say that you're a patented founder, especially because 1.3% of patent holders in the United States are African-American.
Soon after Chipotle, I had a conversation with a lady that I met randomly on LinkedIn. Her name is T.D. Lowe, a very well-respected venture capitalist. It was she who introduced us to a third-party engineering team out in Silicon Valley and encouraged us throughout our startup journey. I remember unfolding our little Chipotle napkin in the meeting and sliding it across the table, telling the engineers, “we need you to build that.” And that is how ShearShare became real on the App Store. I fondly remember those conversations, and I think, what happens if we hadn't gone to Chipotle? What happens if we hadn't drawn on the napkin to make it real? What happens if I hadn't answered that random LinkedIn request from T.D.? All those things became a part of a very important story.
How were you leaning on the startup community and where were you finding them?
Going back to the third-party engineering team that built our MVP . . . that CEO told us about a pitch competition that was happening for Startup Grind. We had two days to decide if we would buy a last-minute flight to Silicon Valley. We ended up doing it. We had no pitch, no presentation. My husband, son, and I stood in front of a room of about 100 people and had never pitched before. But we had a story and shared that: this is our problem, this is the solution we created, and this is how we think we'll make money. It was a world we knew nothing about, so it was a bit terrifying. But that's another good thing about us, is that we do it scared.
Someone in the crowd found us later and told us about a new pitch competition. The prize was $100,000 plus some ancillary items. Long story short, we ended up winning that pitch competition and getting tons of free press. One of the winnings was being fast tracked into the 500 Startups application process. We were accepted into Batch 19 and learned all about the startup world through that accelerator program. We had no idea what the heck a term sheet was, how to speak investor-ease, or how to set up your legal paperwork. We ended up graduating from 500 Startups and getting our very first investment. That is how ShearShare started, and we've been leaning into that amazing network ever since.
There's something to be said about bootstrapping your business before you start getting investments. Because we didn't know anything about the startup world, we didn't know the “typical” founder process. But I'm glad that we had three years of doing ShearShare manually before we had our first investor meeting. That investor said, “I believe in you guys, and I believe in this idea, here's the money to go build it.“ We knew the questions that the salon owners and stylists were asking because it was all listed on our 8.5x11 yellow notepad that we had been writing on for years. I'm grateful for that hard time, because it kept us really close to the market that we have the honor of serving.
If you could go back and change something, would you and what would that be?
I wish fundraising was a meritocracy. I don't know why they call it FUN-draising. There's no fun in it. Tye and I had 143 meetings before we got our first, “Yes.”
That's 143 times walking into a room full of zeal and excitement, ready to pitch and thinking, “oh! this one's going to be it,” and then hearing, “no.” But after that first yes, it was like we were off to the races! I'm part of a special elite group, as they would say. This group is the best list to be on, but also the saddest: it's the number of African-American women who have raised more than a million dollars in venture capital funding. I'm number 33. And I shouldn’t know my number, right? Ask Mark Zuckerberg; I bet he has no idea what number he is. But I know exactly how many women before me and after me raised that amount of VC funding. The great thing is that there are many more.
And that's kind of strange to me. Women can take $1 and stretch it. When you parlay that skill set into startups, the world gets more fiscally-sound businesses that are managed superbly well. Women have demonstrated throughout history that we can do a lot with a little. I can't say that I miss the sleepless nights or the 120-hour workweeks for nine years straight, but I wouldn't dare change my experience for anything. I think that you have to be a little obsessed with solving your particular problem in order to truly impact an entire industry, and that's what we did.
What is one thing that you wish you knew when you started building the app and turning it into the business that it is today?
I wish I would have thought more about the end game in the early days of ShearShare. You hear from multi-time founders who have the exit in mind before they even register their business. They know which milestones to reach and when as they position for an exit, what strategic brands to reach out in a quarter, in a year. They know which partnerships to confirm within the next six months so they can attract certain M+A targets. When you're a first time tech founder, everything is so new. You're just trying to help as many people as possible, keep costs low, mitigate risks, and grow revenue. You don't really think seriously about the end game until somebody brings it to you.
What would be your first piece of advice for first-time founders?
I say, do it scared.
Then you need to surround yourself with people who believe in you and will speak life into you. There are so many things that are going to hit you across the head that’ll look like a sign to stop. And it's not. It just means that you're finding your way through. Find the right tribe, the right community that is just as crazy as you are, and who's doing hard stuff every day. You have to be around other people with huge, crazy, massive ideas, because being in that community is going to make you believe that you can build yours, too.
Then it's a lot of self talk. Our brains don't know the difference between a truth and a lie, and so whatever we tell ourselves, we will believe and we will make it happen. If I get up in the morning and think “I'm the best startup founder, I'm going to exit this company, I'm going to sell to XYZ,” every cell in my body will move to make that happen. On the flip side, if I wake up in the morning and say, “I'm so tired, sales dropped, we're tanking,” you're going to make that happen. No matter what, you have to feed what you want to live and starve what you want to die. Simple as that.
How would you describe any changes that you've seen in the kind of innovation landscape over the last couple of years, specifically for women.
I'm always a glass-half-full kind of personality, and I truly believe that optimism is a competitive advantage. I choose to see only the good when there's a lot of not so good out there. But what I see in my fellow female founder groups, is that more women are betting on themselves a lot more these days. From that perspective, the landscape is definitely changing. We're betting on ourselves a lot earlier and are confident when we jump. One of my Board members, Arian Simone of Fearless Fund, talks about African-American women being “the most founded, but the least funded.” As women, we represent some of the most brilliant minds and ideas, and I love that for innovation! Reach out to me any time at www.bookthecaldwells.com.