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

Updated: May 23



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.

4. How does one know when it’s time to quit their 9-5 and go all-in with their business?

C: You’ll never really know the exact time, but you will know when it's the right time.

It’s like becoming a parent or getting married. You can read a hundred books on the topic but you’ll never find answers on when it’s the perfect time for you. However, when you feel it in your gut, you have to do it. People can talk you out of that feeling of confidence very easily. So, when you get that gumption to do it, go with it.

5. What is your biggest piece of advice to that young entrepreneur who is still working their 9-5 but building their business from 5-12? 

C: Be sure to create a healthy routine and build relationships now.

Try to find a routine because it will help give you clarity when prioritizing all of the tasks you need to accomplish. Every day my husband and I wake up, drink some hot ginger, and then meditate. This helps us clear our minds before we open our laptops. We can then narrow down our focus every day to those things that truly matter. 

Also, take advantage of the relationships you’re building in your 9-5. Those relationships are going to help drive your 5-12. You won’t have an answer to every question, but you’ll be able to find your way to the person who does have the right answer.

6. There’s no specific guidebook for entrepreneurship, how did you figure it all out?

C: By being resourceful and figuring things out as we went. No book will lay out what your entrepreneurial journey is going to be. You won’t know a lot of things, but you'll always know what feels right. When my husband came to me with the idea of building an app, there wasn’t a question...the answer was, “let’s do it.” We just had to jump and grow our wings on the way down. We failed a lot but always ended up figuring it out. 

If you think about it, we are always figuring things out as we go. Your everyday experiences as a parent, a spouse, or significant other is teaching you how to be resourceful. Don’t discount your own day-to-day experiences because living, working, and sharing your life with someone are valuable teaching moments. We’re all just figuring it out as we go. 


7. What has been the most successful marketing strategy for ShearShare?

C: A combination of face-to-face interaction and word of mouth. 

Once salon owners started signing up for ShearShare, even if it was just two or three in one city, we would fly to them. We’d meet them face to face to get them excited about ShearShare. In those meetings, we would build genuine relationships with our fellow salon and barbershop owners. They saw that we were real people willing to get our hands dirty and meet them where they are. 

Those face to face meetings would be like a little fire that started in that city. The few people we met with would become like a ShearShare army for us and would tell their salon friends about ShearShare. Then those friends would spread the word.  Word of mouth was huge and still makes up about 40% of how people still find us today.


8. What are your thoughts on the “No sleep, grind all day and night” entrepreneur mentality?

C: I can answer this because I’ve been the “I’ll sleep when I’m dead” person. It’s a big lie. People have to realize your company/your marriage/your children are only as healthy as you are. Not just physically but mentally, emotionally, and spiritually. If you’re not feeding yourself good things, only bad will ensue. If you’re not taking care of yourself, it will be visible and can be seen in so many different aspects of your life

So you have to be pushing yourself to invest in you so you can invest in other people. That means getting sufficient sleep, exercising even if that’s just a walk around the block, socializing well, and hydrating. You have to do the work to figure out what works for you and then stick to it.

9. How does a young entrepreneur stay encouraged after facing a significant amount of rejection?

C: Out of the 250 investors we met with, ShearShare has fewer than 10. So we’ve had our fair share of no’s. You have to have a positive disposition to want to try your hat at entrepreneurship.

The founders who succeed are the ones who have the “I'm going to figure this thing out” mindset. When they hear “no” they hear “not right now.” We heard no’s from investors who have now invested in ShearShare. That’s why it’s important to stay positive, establish those relationships, and come back when the time is right. 

Staying grounded and having that support system is important as well. My husband, my son, and I leaned on each other a lot; we had to keep each other going.

10. What part of entrepreneurship made you the most uncomfortable?

C: The risk! I am a calculated person and being a military brat, everything in my life has always been very regimented. I have to plan, I have to schedule, I even highlight calendars with certain color markers.

Once I got into this thing called ShearShare, I threw all of that out of the window. I had to learn to be okay with waking up every day and saying, “Okay God, whatever you throw at me today, just give me the resources and energy to get it done.” As an entrepreneur, your life will never be regimented. But it’ll be exciting.

More About Courtney:

Courtney founded ShearShare with her husband Dr. Tye Caldwell in 2017. Before ShearShare, Courtney worked in corporate America building winning teams in the technology and marketing space. After recognizing she was ready for change, Courtney launched her boutique consulting firm where she dominated in international sales and marketing. Courtney was named a 2019 Outstanding Young Alumna by Southern Methodist University’s Cox School of Business, a 2018 Dallas Business Journal Women in Tech, the 2017 L’Oréal Women in Digital Award Winner, and received an Honorary Doctorate Degree from Miracle University. Courtney resides in McKinney, Texas with her husband and son. You can keep up with Courtney and the ShearShare gang on Twitter @ShearShareCOO and Instagram @ShearShare.

More About ShearShare:

Also known as Hairbnb, ShearShare is the largest provider of on-demand salon and barbershop space rentals. The ShearShare app gives licensed beauty and barbering professionals the freedom and flexibility to rent workspace by the day in cities all over the world, while salon and barbershop owners make money on unused space. 

ShearShare started somewhat by accident. A stylist called Dr. Tye and asked if they could rent out a chair in his Plano, Texas, salon. From there, Courtney and Tye started manually connecting stylists to salons across the country. When they looked for an app that could make these connections for them, there wasn’t one. Thus, the birth of ShearShare. 

ShearShare is operating in 600 cities and 11 countries, is the first Texas startup to win Google Demo Day, won L’Oreal’s Women in Digital NEXT Generation award, and won the 2019 Diversity & Inclusion Challenge presented by Capital Factory. They have been mentioned in Forbes, Black Enterprise, Inc Magazine, and in Google’s Annual Economic Impact Report.



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