Meet Cassidy Maestas

We were lucky to catch up with Cassidy Maestas recently and have shared our conversation below.

Cassidy, thank you so much for making time for us. We’ve always admired your ability to take risks and so maybe we can kick things off with a discussion around how you developed your ability to take and bear risk?

The ability to take risks is not merely about doing something just to say you’ve done it. It’s about understanding the meaning of the risk.

When I was younger, I would take risks simply for the sake of the accomplishment. I enjoyed the feeling of being admired for doing what others wouldn’t, were scared of, or knew wasn’t a risk worth taking. As I matured, I started taking a more “adult” approach to risk-taking.

This approach is rooted in knowing and trusting in something beyond what you can touch or see. For me, it’s the belief that if God put a path in my mind, I am capable of whatever that risk entails.

I watched my father take calculated risks. I may not have known it then, but I see now that every risk he took was prayed on, carefully thought out, and backed by the discipline he practiced daily.

Before moving forward with any risk, I always ask myself, “why?” I don’t allow others’ actions to determine my stance on the subject, and I keep an open mind. I pray about it, always.

Let’s take a small detour – maybe you can share a bit about yourself before we dive back into some of the other questions we had for you?

I have been a barber for ten years, and over the last few, I’ve dedicated myself to mentoring and helping elevate my mind and the minds around me.

I initially started doing hair simply to pay the mortgage and cover our bills. I had no idea that years into my career, this industry would fundamentally change my life. The shift happened as soon as I made a promise to myself: that this risk—the risk of enrolling in cosmetology/barber school—would be well worth it!

I am so grateful to be able to tell you today that the risk was absolutely worth it. I have hit all my goals thus far. I never would have believed you if you had told me I would be booking out 90 days in advance, that I’d soon be sponsoring school sports, or that I would have clients on recurring appointments. I probably would have laughed and said, “God, I certainly hope so!”

Where I stand today is a place of “Thank you, God,” every single day. My dreams have become reality, and my craft has allowed me to help so many people. Being trusted at the level I am with other human beings is a feeling I truly cannot put into words.

I focused my brand on being rooted in enlightenment and comfort. I wanted the brand to feel like a space—a sanctuary—and not something that could simply be “bought.”

P.S. Keep an eye out so you don’t miss what’s next with Grateful Heads Barber!

Looking back, what do you think were the three qualities, skills, or areas of knowledge that were most impactful in your journey? What advice do you have for folks who are early in their journey in terms of how they can best develop or improve on these?

Three Pillars of My Barbering Journey

Looking back over my ten years in the industry, the most impactful growth wasn’t just in mastering the shears; it was in developing three core qualities that turned a job into a vocation: Intentionality, Discipline, and Empathy.

1. Intentionality (The “Why”)

When I started, the goal was survival (paying the bills). As I matured, my approach evolved into one of Intentionality—the practice of deeply understanding the “why” behind every major decision, or risk. This is the difference between blindly taking a risk and taking a calculated risk. I learned this from watching my father: every big move was first prayed upon and thought out.
Impact: This quality allowed me to define my brand, my goals (like booking out 90 days), and the desired experience for every client, ensuring my effort was always moving me toward a defined future, rather than just reacting to the present.

2. Discipline (The Practice)

Discipline is the engine that converts intention into reality. For me, this wasn’t about being strict; it was about consistency in the small things. It was showing up, practicing when I was tired, and treating the one client I had on slow days with the same care and focus as a full book. It also meant sticking to the hard work of building recurring appointments and perfecting my craft.
Impact: Discipline built the deep confidence necessary to mentor others. It created the reliable quality that resulted in client trust, pre-booked appointments, and the financial stability I initially sought.

3. Empathy (The Space)

In barbering, you are trusted with more than just a person’s appearance; you are trusted with their time, their headspace, and their stories. Empathy is the foundational quality for building a brand rooted in “enlightenment and comfort.” It means actively listening, being present, and making the chair a sanctuary—a space, not a transaction.
Impact: This focus on being present and empathetic is why clients become loyal and why I feel “blessed to be surrounded by” the art and the humanity of my studio. It moves the relationship beyond commerce and into community.

For those just starting their journey, focus on cultivating these three areas immediately. They are skills, not just inherent traits, and they can be practiced every single day.

To Develop Intentionality:
Define Your Non-Negotiables: Decide what success looks like outside of money. Do you want to be a mentor? Do you want to be booked six weeks out? Write it down, and ask yourself “why” that goal matters before taking the next step toward it.
Study the Calculated Risk: Learn to weigh potential loss against potential gain. If a risk aligns with your core “why,” it’s worth the commitment.

To Improve Discipline:
Master the Fundamentals: Practice your basics until they are second nature. Find one area you struggle with and commit to 15 minutes of dedicated practice on it every day for a month. Consistency is the key to mastery.
Respect Your Schedule: Treat your open days, slow times, and prep time with the same respect as your booked appointments. This practice builds professional resilience.

To Cultivate Empathy:
Focus on Presence: be fully present. Put your phone away. Ask meaningful questions and, more importantly, listen to others.
Create the Space: Look around your space. Does it feel like a transaction hub or a refuge? Adjust your environment, lighting, and routine to cultivate the comfort and safety that makes individuals feel enlightened and at ease.

What was the most impactful thing your parents did for you?

This question holds significant weight for me. I am blessed with a single parent: my dad.

When I say my DAD is the GOAT, I promise you, he truly is that guy. My father has literally given me everything I have ever dreamed of; I have never had to go without. Even during the hardest times, my dad was doubling down to ensure we were taken care of.

He is my light, my guide, and the person I trust wholeheartedly. His word is better than any contract. He has always been the highest example of “you are not where you came from.” He built a life for himself, and with that foundation, he built a life for me.

But the most impactful thing he has ever done for me is that he gave me space. Space to grow. Space to learn. Space to run. And space to return. The freedom he gave me allows me to flourish and bloom into the woman God has designed me to be.

Contact Info:

• Instagram: @gratefulheadsbarber

Image Credits

Tayla, Kelsey, Denea, myself