Doing What You Love and Loving What You Do: Dale Basista, Founder Dale's Leatherworks

I’ve recently fallen into one of my weirdest passions, and that’s saying a lot—just ask my wife. One day, I’ll be watching video after video about intermittent fasting; the next, I’m watching videos on boots. That’s right—boots. It drives her nuts.

She’ll come in, and I’ll be watching some video on the latest waxy flesh boot from Truman Boot Company or the limited run of Cordovan Shell boots Grant Stone has just announced. She doesn’t get it. Actually, I can’t say I do either. The only thing I know is I’m into boots. I love ’em. Little did I know, there’s an entire content creator niche dedicated to handcrafted boots.

During my scratching of this itch, I landed on the YouTube channel of a mild-mannered guy out in Baltimore named Dale Basista. Dale is the Founder of Dale’s Leatherworks. He’s also creating a space on his YouTube channel for other purveyors and lovers of heritage-style boots.

I’m a proud subscriber of Dale’s channel, and I guess you could say I’m a fan. Having just met him on my podcast and had a great conversation, I can now add “friend” to my description of Dale.

There’s an old saying: “Do what you love, and you will never work a day in your life.” Well, Dale Basista loves boots. Specifically, Dale likes handcrafted heritage-style boots. Don’t believe me? Check out his YouTube channel, and you will see a portion of his collection displayed on a wall behind him. It’s a collection any boot lover would be envious of—yours truly included.

I’ve recently started paying attention to heritage-style boots. It came as a personal preference I’ve developed for buying high-quality goods. I prefer to buy fewer things that will last longer. I also love buying from brands that have a story behind them.

This is what made me a fan of the brand Rag & Bone. Yes, their jeans are ridiculously expensive, though certainly not the most expensive on the market. But there’s more to it than just jumping on a trend train. Marcus Wainwright started Rag & Bone as a response to his inability to find a pair of jeans he really liked.

What was his answer to this dilemma? Simple—make his own. Not long after moving to New York from the U.K., Wainwright set out to make himself a pair of jeans. He spent time sourcing denim from the garment district of NYC, and after much trial and error, the story of Rag & Bone began.

There’s a similarity in this story with that of Dale Basista. As someone who himself appreciates small-batch handmade goods, he decided he wanted to make his own leather courier bag. So that’s exactly what he did. I have great admiration for this.

I find it courageous for someone to take their hobby and passion to a higher level. Dale has done that. In this conversation, we discuss brands we like, how Dale got started, and what’s next. I’m so glad I reached out, and Dale accepted. This is, I hope, the first of many more conversations to come with my friend Dale Basista.