Finding Your Why

An entrepreneur’s take on staying strong

Finding Your Why

The key to success might just be finding your why. For Dan Caldwell (founder and president of MMA gear giant, TapouT), success is all about supporting his family.

The ’80s were an awesome time to be alive. Disco was turning to heavy metal, roller skating became skateboarding and the official presidential limousine went from a Ford to a Cadillac Fleetwood. I was only 10 years old, but I remember that my grandma Margie loved her Cadillac.

My grandma was a hardworking single Hispanic mom who grew up in San Antonio, Texas. She was shrewd, outspoken and business minded. For as long as I can remember, my grandmother always owned a Cadillac. Her car was never new—but for her generation, the Cadillac represented success.

One day, I was playing with one of my grandma’s car windows when it stopped working. She told me that the car was just getting old. So with all the confidence I could muster, I told her that I was going to buy her a brand-new Cadillac when I grew up—and the windows were all going to work!

Everyone has a why. When we set goals for ourselves, we tend to focus on having a big business, cars, houses, fame, et cetera. But these things, like money, aren’t our true why. It’s what we want to do with that money that is our why. “I want to provide for my family,” for example. Finding your why is essential for success.

In 2006, TapouT (a sports clothing brand that began as a modest distributor of MMA clothing) was growing fast but also experiencing extreme growing pains. For the past 10 years, we hadn’t had enough money to pay salaries. I’d been supporting my son and daughter while living in a two-bedroom condo, barely able to pay the bills. But all that changed in September 2006, when a private equity group infused $10 million into the company. I remember feeling like all the struggle and pain had been worth it.

It was a Wednesday morning in San Antonio when a well-dressed car dealer knocked on my grandmother’s door. Still in her nightgown, she was embarrassed to come outside. The car dealer was holding two dozen roses and the keys to the brand-new white Cadillac parked in her driveway. I don’t think she quite knew what was going on at first. She kept trying to fix her hair and asking, “What’s happening?” And then she saw the Cadillac and broke down crying.

When you chase a dream, first make sure you know your why. And then use it to carry you through hard times, when thoughts of quitting creep into your head. Give your why a face. Make it personal! Once you get there, you’ll be able to move mountains.

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