The Bread and Butter Letter 2: Dr. Tye Caldwell from ShearShare

Bread and Butter Ventures
Bread and Butter Ventures
3 min readFeb 16, 2021

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A bread and butter letter is a letter of thanks for hospitality…our version is full of gratitude, thank-yous and advice and will feature founders we’ve backed, our team, and friends of B&B.

Dr. Tye Caldwell has been a luminary in the beauty industry for years but only a tech startup founder for a few years. He and his wife Courtney Caldwell co-founded ShearShare, an ML-enabled marketplace that provides access to affordable B2B tools for self-employed stylists, starting with space to work.

ShearShare CEO and Co-Founder Dr. Tye Caldwell

In October, ShearShare announced they had raised $2.3 million from investors including B&B. The funding has made the team even more determined to continue growing. As Dr. Tye, ShearShare’s CEO, shares, “We continue pioneering the future of work for beauty and barbering — the best industry in the world. People can look out for new tools that help industry professionals make a great living working for themselves.”

Dr. Tye spoke with us about some of the people, things, and choices he is most thankful for as an entrepreneur:

Is there a person from growing up who you feel thankful towards?

Yes, two persons who impacted my childhood were my parents, and I feel the most thankful towards them. My mother was always my biggest cheerleader and made me see the best in everything — good, bad, and indifferent. She passed away a couple of months ago, but I know she is proud of the path I’ve chosen.

Who was instrumental at the beginning of your entrepreneurial journey?

I would have to say my wife and cofounder Courtney, and my brother Calvin, who operates our Texas salon. Twenty years ago, I would share with them the vision that is now coming to life. I think having a clear vision and having that support is a major part of staying motivated and positive along the journey. So much is going to happen on your way to success that you’ll need to keep a positive set point.

What books, podcasts, or blogs have really inspired you as a leader?

I am an avid book reader. My favorites are Think and Grow Rich, The 7 Habits Of Highly-Effective People, and Lonely At The Top. I also love to listen to tech and entrepreneur podcasts. As far as blogs, I read blogs that relate to the beauty and barber industry, and tech and business in general.

Who is an unsung person at your company you’d like to highlight?

An unsung person at ShearShare that I’d like to highlight is of course my wife and Co-Founder Courtney. She has been an amazing partner, executioner, and all-around all-star helping to build and grow ShearShare alongside me through my vision.

What do you look back on and thank yourself for doing when you started your company (i.e. what would you recommend to others)?

I thank myself for just jumping, and believing in my vision to start ShearShare when no one else did. I know for sure when you believe in yourself that you should just go for it and not worry about failing, because falling is simply a part of the process. In fact, you can always get back up. As I was . . . and the title of my best-selling book is . . . “Mentored By Failure.”

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