My Barber's A Badass

It’s been a while, and I apologize for that! But the good news is that I’ve been working on a new design to make this newsletter look more professional and easier to read. In the meantime, I figured I owed you all something special, so here’s a personal story about my badass barber.

For context, I’ve been getting my hair cut by the same barber for the past 16 years (I’m 25 now), so we’ve naturally developed a great relationship. Over hundreds of haircuts, I’ve learned more about his story and journey. If you believe in the American dream, this one’s going to fire you up!

Like many Cubans in the past 60 years, my barber had to leave everything behind and head to America—the land of opportunity. He found a safe haven in Miami, FL, where he’s now been living for 31 years. From the very first day, he’s been cutting hair.

When he started cutting my hair around age 10, I noticed he always had 5x the customers of all the other barbers in the shop. He was hardworking, respectful, and always gave top-notch haircuts, even though he barely knew English. But you could see how hard he was trying to learn, and it was impossible not to respect that drive.

Between the ages of 10 and 17, he was just my barber—a cool guy who cut my hair and kept me entertained with stories. But as I got older and started flipping sneakers and launching businesses, our conversations got deeper. He began picking my brain about real estate, business, investing—anything he could learn to keep the American dream alive for him and his family. And I respected that more than ever.

My family, like many of my friends’ families, has Cuban roots. My grandparents landed in Chicago with nothing, and somehow, through pure grit, they gave their kids (my parents) a shot at success. That determination created a foundation for me and my brother to have an amazing life. So this story hits home for me in a big way.

Yesterday, during my haircut, I had a deep conversation with my barber about his journey. After 31 years in the U.S., he’s created a life that perfectly embodies the American dream.

Since landing in Miami with little money, family, or resources, here’s what he’s been able to accomplish:

• start a family here in the States

• own a fully paid-off home valued at over half a million dollars

• create a book of business with over 400 active clients that will follow him anywhere (seriously his customers are like a cult and I am on of them)

• Send his daughters to a quality education

• Send his oldest daughter to the #2 public college in the US

• Give his daughter the opportunity to study abroad in France for the summer (this one hits the hardest for me what an upgrade from one generation to another by just working hard)

Even with all of his accomplishments, my barber is still constantly learning how to create wealth, and I respect the hell out of that. Right now, he’s taking weekend trips to small beach towns in Florida with his wife, looking to purchase a second home for both retirement and investment purposes. Not only that, but he recently dove into the stock market. Despite starting later in life, he’s working to build an investment portfolio that he can pass down to his daughters, determined to set them up for success.

As I sat there getting my haircut, listening to him break all this down, I couldn’t help but think—wow, this guy is a true badass. He’s faced adversity at almost every turn in life and come out on top, time after time. He’s in his late 50s or early 60s, but every single day—from Monday to Sunday—he’s at the barbershop by 7 a.m., long before anyone else. He cuts hair back-to-back until 6 p.m., always fully booked.

If you love America, business, or just appreciate an underdog success story, this one’s for you.

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