A Twenty-Something's Guide to Entrepreneurship with Courtney Caldwell

Updated: Jan 22

Courtney Caldwell will be the first to tell you that you don’t have to know everything about business to become a successful entrepreneur. You just need to have the confidence to jump and grow your wings on the way down. 

Courtney is the Co-Founder and COO of ShearShare. ShearShare is the first on-demand salon and barbershop space rental app. Since Courtney and Dr. Tye Caldwell launched ShearShare in 2017, it has disrupted the beauty industry. Not only is the app operating in 600 cities and 11 countries, but it has also won a strategic partnership with L’Oréal and is the first Texas start-up to win Google Demo Day.

Successful businesses aren’t built in one day; it's a humble journey of trial and error. Courtney didn’t come from an entrepreneurial or tech background, but she believed in her ability to figure it out. A fun example: Courtney didn’t know much about venture funding when she started ShearShare, yet she is now the 33rd black woman to raise over $1 Million in venture funds. 

If you are a young entrepreneur just trying to figure it out, you’re not alone. Here are 10 questions with Courtney Caldwell that will give you guidance on pitching investors, knowing when to leave your 9-5, and ditching the toxic, “sleep when you’re dead” entrepreneur mentality.

1. How does a startup that “started by accident” gain attention from top brands like Google and thrive in Silicon Valley?

C: The idea behind ShearShare naturally thrived in Silicon Valley because west coast investors are used to seeing big audacious ideas. The expectations of venture capitalists and angel investors vary by region. In California, they want to know how you can take over the world and own the market—think Uber and Airbnb.

It’s almost like the crazier the idea the better. They recognized that my husband and I were the team to make it happen because we had such a unique pedigree that no one else had.

2. Why is it so important to just “jump” rather than try to perfect your product?

C: If we had waited to build an elaborate app before launching to the public, ShearShare would still not exist. If you think you need to make something perfect before you launch, it's never going to happen.

We didn’t know anything about building an app when we first started. In fact, we drew the ShearShare app design on Chipotle napkins. We never thought that we needed to be an expert in artificial intelligence or machine learning before we jumped. We just knew that there was a problem and we wanted to build the solution.

Do not spend your time trying to make something perfect. No matter how perfect you think you’re making it, you’ll always be one step behind your customer. Something will always need to be updated and changed. The faster you can get something out in the market, the better, because you can give customers something to respond to and improve upon it from there. 

3. Top 3 tips for pitching to investors?

C: We’ve had over 250 meetings with investors. Here’s what I’ve learned: 

1. Have confidence in yourself and your product. Your energy is going to enter the room before you do. So if you walk into a room unsure of your idea, investors will eat you alive. Make sure you love what you do and believe that nobody else can do it as well as you can.

2. Be prepared for the basic questions. Be ready to talk about the problem you’re trying to solve and the solution you’re building for it. Be prepared to talk about your team (if you have one) and why you guys are uniquely qualified to build this product. Finally, be prepared to show some traction. That doesn’t have to be revenue, maybe you gathered over a thousand sign-ups within the first 24 hours of launch. Show how you’ve generated some type of engagement.

3. Know your total addressable market. Investors want to know how big your idea can get. It’s not because they’re hungry for the money, but because they have to look at their overall portfolio and see where you fit in. When talking about the total addressable market, it can’t be people who own purple cats because that’s not big enough for investors. It has to be big and repeatable.