The Business Lessons My Dad Never Meant to Teach Me: What Grief Taught Me About Success, Wealth, and Entrepreneurship

Every car ride sounded the same.

My dad and I would sing If I Had $1,000,000 by the Barenaked Ladies.

Sometimes we were driving to one of my sporting practices.

Sometimes we were just sitting outside in the backyard.

Every single time we got to the chorus, I’d laugh and tell him,

“One day I’m going to have a million dollars.”

He’d smile.

“I hope you’re right.”

Looking back now, I realize we weren’t singing about money.

We were singing about possibility.

At the time, I thought success meant becoming wealthy enough to retire my dad.

My dad and I spent our lives chasing two very different definitions of wealth.

He owned five pairs of Levi’s jeans and wore them until they literally didn’t fit anymore. If someone suggested buying another pair, he’d shrug and say, “Why would I buy something I don’t need? I’d rather save it for a new golf club”

Meanwhile, I dreamed big.

I dreamed about building businesses. I dreamed about financial freedom. I dreamed about a beautiful home where family would always feel welcome, a backyard with a pool full of kids and friends, and one day, the ability to give my own children opportunities I had never imagined for myself.

Most of all, I dreamed about retiring my dad.

I wanted to be the one to tell him that after decades of working as a mechanic for Frito-Lay, he never had to worry about another paycheck again.

I thought that would be the greatest gift I could ever give him.

I never got the chance.

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