Alumna Tech Entrepreneur Shares Insights at Women’s Leadership Series Event
“Fail fast,” Courtney Caldwell, MBA’06, told the audience at the most recent Women in Leadership Series event at the Naveen Jindal School of Management. “If you don’t hear anything else from me, then hear ‘fail fast.’ To me, failure is just pivoting. It’s just figuring out another way of doing something you haven’t done before.”
The chief operating officer of McKinney-based ShearShare, Caldwell spoke on “Disruption: How the Startup of the Year Navigates Innovation and Technology in the Digital Age,” at the Feb. 6 series event, which the Jindal School’s Executive MBA program and Office of Development and Alumni Relations hosted.
Caldwell, who did not follow a traditional path to technology, encouraged women to look for inspiration in any field that interests them.
“I never saw myself owning my own company. I never saw myself in technology in this sense. I never saw myself as an entrepreneur,” said Caldwell, whose 20 years in technology marketing included running a consulting firm and serving as director of digital marketing strategy and innovation at Oracle.
Caldwell and her husband, Tye, co-founded ShearShare, an Airbnb-type app that connects salons with licensed cosmetologists and barbers to rent workspace by the day.
“We were the first ones to do this, and it was really by accident,” she said.
Tye, an author with a doctorate of professional barbering from Miracle University in Virginia, has been in the beauty industry for 25 years; Courtney married into it. After they expanded their Plano salon, they had empty chairs to fill. For more than a century, salons have required stylists to sign at least yearlong leases. But when Tye started getting calls from millennials wanting space by the day, the Caldwells decided to give it a try rather than let chairs sit empty.
It was so successful that after three years, Tye asked Courtney to find an app that could book the stylists for them.
“There wasn’t one,” she said. “That was our aha! moment.”
Initially working with a third-party tech firm, they launched the ShearShare app in September 2016 and now have listings in 380 cities and 11 countries, with more than 700 hosts and 1,600-plus users.
The technology news platform Tech.Co named ShearShare its 2016 Startup of the Year. Last year, the company received one of two inaugural $25,000 investments from the UT Dallas Seed Fund. And as one of three 2017 L’Oréal USA NEXT Generation Award finalists, Courtney traveled to New York to pitch the ShearShare vision to a room of 500 marketers from around the world.
“After American Idol style voting, L’Oréal management selected ShearShare to partner for a pilot program,” she said. “Our team is actively working with L’Oréal now to define and execute that program.”
Last month, ShearShare won $100,000 in the Dallas Diversity & Inclusion Investment Challenge hosted by Capital Factory in partnership with DivInc and The Dallas Entrepreneur Center. In addition to the cash investment, ShearShare gets access to top entrepreneurs and mentors, a year of unlimited co-working at Capital Factory’s new Oak Lawn space, and free legal and hosting services.
“We’re hyper-focused on three main areas of our business right now: hiring, growth and product,” Caldwell said. “That’s where the spend will go.”
“We are excited to see Courtney and ShearShare win this great award,” said Bryan Chambers, director of the Blackstone LaunchPad at UT Dallas. “It’s great validation that some of the best and most innovative startups in the region are coming out of UT Dallas, and the UT Dallas Seed Fund is providing financial support to startup ventures that are making a meaningful economic impact.”
Caldwell shared some of ShearShare’s secrets to success with those who attended the Women’s Leadership Series event.
“One of our advisers told us that one of the best things you can do is to hire well,” she said, noting the company now has six employees, having brought tech in-house.
“You have to understand that this thing is going to get bumpy,” Tye added. “When you hire people, you’re hiring for character.”
While everyone knows the golden rule, the Caldwells follow the silver rule at home and work.
“The silver rule in our house is you leave people, places and things better off than you found them,” Courtney said. “This rule was carried over to our startup. That helps us when we are talking to our stylist community — we’re always making sure we leave our community better.”
An audience member asked about being partners in marriage and business.
“What works best for us is we both have our own lane to run in,” Courtney said. “I don’t try to pretend to know more about his area of expertise, and vice versa. And we have to have personal time.”
Downtime, however, does not come easy.
“I’m the kind of person who can work, work, work,” Courtney acknowledged. “One of my mentors gave me a challenge: You’ve got to always make sure you eat well, hydrate well, sleep well, socialize well and move well — even if it’s just walking the dog. Because I do those things consistently, we are really in a good place.”
She said that sometimes, getting started is the biggest hurdle. “When every fiber of your being wants to pursue a certain thing, do as my husband advised me years ago when I was leaving corporate America to start my own consulting firm: Jump and grow your wings on the way down.”
Corinthia Acevedo, a BS’15 alumna of the School of Behavioral and Brain Sciences, appreciated learning from other UT Dallas alumnae’s startup experiences.
“It was very informative, and I enjoyed meeting such a wide variety of talent. The speaker was phenomenal — Courtney’s story was an inspiration,” Acevedo said.
Perhaps most helpful to Acevedo, who recently launched Dallas-based United Security and Defense Solutions with her husband, Christopher, a JSOM marketing student, was hearing about the qualities Courtney and Tye look for in employees: character, motivation, organization and an ability to learn.
“All are things that you cannot find on a résumé,” Acevedo said. “As a woman starting my own company, selecting quality people who share my passion has been my biggest challenge. I plan on learning from their expertise and focusing my search for new talent through their lens.”
Asha Phillips, a BA’08 School of Behavioral and Brain Sciences alumna now a high school counselor in the Garland Independent School District, attended the event with her mom, Kathryn Phillips, MBA’05.
“I would definitely recommend the Women’s Leadership Series to other alumnae,” the younger Phillips said. “The exposure to successful women and hearing their stories is worth attending these events. It’s great inspiration.”
Launched in 2012, the series now includes three events a year. Next up is “Disruption: Creating the Career Change You Want” on May 22 and “Disruption: Thriving in Work, Life and Everything” on Oct. 9.
— Rachel Stowe Master