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Life, Values & Legacy: Our Chat with Brittany Cobb of Dallas

Brittany Cobb shared their story and experiences with us recently and you can find our conversation below.

Hi Brittany, thank you so much for taking time out of your busy day to share your story, experiences and insights with our readers. Let’s jump right in with an interesting one: What makes you lose track of time—and find yourself again?
Pinterest! I love this platform to get inspired, dream and see all the pretty things out there!

Can you briefly introduce yourself and share what makes you or your brand unique?
My name is Brittany Cobb and I grew up in Southern California. I moved to Texas to attend college at SMU, and after a decade of writing about fashion, decor, and more, I founded what would become Flea Style in 2009. There are now Flea Style locations spanning three states and counting, each one home to The Original Hat Bar.

Flea Style provides immersive experiences blending shopping, dining, and creativity. We’re most known for our hat bars that welcome customers to create the hat of their dreams with our exclusive, custom designs and one-of-a-kind accessories (many of which I curate and find at flea markets).

Whether it’s through custom hat making, curated vintage finds, or supporting local makers, we foster a community of stylish, independent-minded shoppers. Flea Style is headquartered in Dallas, where I live with my children, Landry and Barrett.

Appreciate your sharing that. Let’s talk about your life, growing up and some of topics and learnings around that. Who taught you the most about work?
I learned so much watching my dad build his business when I was an impressionable teen. Around middle school, he left his longtime career in construction and started his own financial planning business. He risked so much for his future, and worked 24/7 to make it happen. I saw him build his clients, brand and business from the ground up (way before helpful tools like social media, blogs and AI). He was always vocal about life lessons and I now realize how much I sponged from our talks. I also learned so much from the unspoken — time away from his family, Saturday meetings — and how you have to pour every ounce into your business in the early days to hopefully build it for success and self-sustaining status in the later days. Although he worked all the time, he still made my brothers and me feel seen and special. His priorities were always straight and that is one of the best work lessons you can learn.

Is there something you miss that no one else knows about?
Prior to starting Flea Style, I was a freelance journalist and interior decorator. Both careers — although totally different — required no employees and gave me total freedom of my schedule. Sometimes, if I’m being totally honest, I miss the days I wasn’t responsible for so much and could do as I wish when I wish.

For example, I love to travel and visit my family in California. I have really had to put that on the back burner building my business the past six years. I never imagined I’d have over 75 employees and be managing so many balls in the air when I started this company. There are definitely times I miss the simpler days.

With that said, I wouldn’t trade my position today for the world. Nobody can prepare you for the pressure and expectations on a business owner building a brand. I’m up for the challenge each and every day, but sometimes long for those moments I had more independence and freedom for work/life balance.

Sure, so let’s go deeper into your values and how you think. Where are smart people getting it totally wrong today?
I think a lot of people overthink things or strive for perfection versus just starting with the tools they have. Oftentimes, this causes a delay or failure to launch.

I believe that speed is the answer to business. The quicker you can start something, you often beat your competitors. It might not be perfect, but usually those problems that still need ironed out are the exact failures or lessons that teach so much and lead to future success.

This belief is the foundation of Flea Style (and my past businesses). My degree is in journalism and I was held to a tight deadline most of my career working for a daily newspaper and e-newsletter. The speed needed to hit my deadlines 100% is the same pace I use for my business and personal life.

With that said, this doesn’t mean you should be sloppy or careless. It’s more about cutting out the overthinking and non-priorities. I get so much done with this mentality!

Before we go, we’d love to hear your thoughts on some longer-run, legacy type questions. What do you understand deeply that most people don’t?
I believe at my core that change is a good thing. When you believe that, everything is easier and less heart-breaking.

I have had to face, pivot and accept so many changes for my business and personal life over the years. If I resisted change, I wouldn’t be where I am. Because I embrace it and get motivated by it, I’ve moved forward with a positive attitude and excitement.

I believe accepting change is the true key to a happy life and successful business. It doesn’t mean there aren’t hard times when facing or dealing with change, it just means that you have perspective that it will work out and it’s supposed to be part of your story.

I have a plaque in my kitchen that says, “I trust the next chapter because I know the author.” We’re all the author of our life. When you believe change is a good thing so is each chapter, even when there are dark times.

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Image Credits
All photos from our in-house photographer Nichole Stephens

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