
My name is Courtney Caldwell, and the Cofounder & COO of beauty-tech startup, ShearShare,’s app works like an Airbnb for barbers and cosmetologists—instead of renting houses, they’re renting salon and barbershop stations. Now, the company is going one step further by not only helping their clients with rentals, but also with finances. In short, ShearShare connects “SOLOPRENEUR” barbers and cosmetologists with studios renting salon and barbershop space. Prior to cofounding ShearShare, Inc., Google Demo Day winner 2018, Tech. Co’s Startup of the Year, and a YC Fellowship and 500 Startups alum, I managed an award-winning salon with my husband and cofounder, which was the genesis behind ShearShare. Before that, I ran a boutique consulting firm where I fast-tracked international sales and marketing success for brands such as Zendesk, Zenefits, and Qualtrics.
Courtney: I spent nearly two decades building winning teams in tech marketing and has held leadership positions in both early-stage and late-stage technology organizations: vice president of marketing for Marketing Advocate, global director of Oracle’s worldwide digital marketing strategy and innovations group, head of digital demand generation and JAPAC field marketing at RightNow Technologies. My leadership in demand and revenue generation at RightNow Technologies was instrumental in the $1.45B acquisition of the company.
I recently received an honorary doctorate degree from Miracle University and is the 33rd African-American female to raise $1 million in venture funding. I was named to the Inc. magazine 2019 Female Founders 100 list, is the first African-American female to be named the SMU Cox School of Business Outstanding Young Alumna, the 2019 Ada Lovelace Female Tech Founder of the Year, is a 2018 Dallas Business Journal Women in Technology, and the 2017 L’Oreal Women in Digital NEXT Generation Award winner. I volunteer with various children’s, education, and civic organizations, and serves on the Advisory Board for Ogle Cosmetology School, the Alumni Board for Southern Methodist University, the President’s Council at SMU, the Board of Trustees for Texas Military Institute, and the Board of Directors for the UT-Dallas Entrepreneurship Council. I live in McKinney, Texas, with my cofounder husband, Dr. Tye Caldwell, and I am to mom to our 19-year-old son, Trey.
What were the biggest initial hurdles to building your business and how did you overcome them?
Having to believe in our idea more than the hundreds of "no's" we heard from investors.
What books are you currently reading? And your recommendation for entrepreneurs to read?
Do pause: you are not a to-do list: Author: Robert Poynton
Think and grow rich: Author: Napoleon Hill
Did you ever deal with contention from your family and friends concerning your entrepreneurial pursuits?
YES
How did you handle it?
Although they don't understand what we do every day, we keep going because we know that Shearshare is our legacy to leave.
What would you do differently in hindsight?
Nothing.
What would you say was the single most influential factor in your business success?
Our support and faith in each other as cofounders
What advice would you give to an upcoming entrepreneur locally and internationally?
4 tips below:
- Believe in yourself and prove it.
- Uncover alternative methods to funding your business.
- Your company is only as healthy as you are.
- Find supporters who believe in your vision and share your values.