amazing dad stories

52 Amazing Dad Stories

I’ve written a lot about my amazing dad, Chubby. Like me, Chubby was plump as a kid. He eventually lost the weight, but his nickname stuck.

Chubby grew up with no money, no father, no education, and no connections. Yet through hard work, extraordinary values, and uncanny street savvy, he built one of the most successful real estate firms in Cincinnati.

Why stories about amazing dads?

Like many fathers, Chubby sacrificed so I could have a head-start in life, advantages he didn’t have. As a tribute to him, I wrote a book about 52 remarkable dads (including Chubby) and the lessons they taught their kids.

The book is 5-star rated and available on Kindle and Amazon. But you don’t have to buy it because I set up a free download for my readers at

One of my favorite stories from the book is titled, “Two Hatted Dad.” It’s about a father and son in business together, and how Dad dealt with an irresponsible son.

This story resonates with me because I worked with my dad and my three sons each worked with me. I hope you enjoy.

Two Hatted Dad

My dad wears two hats. It started like this.

“Tom, join me in the hot tub. Let’s talk,” said my dad. Pretty cool, I thought. Hot tubbin’ with dad. A father-son chat. Why not?

I had worked at Dad’s store for months. He took me on when I bailed out of college.

Dad wasn’t pleased when I quit school, but he swallowed hard and gave me a job. Because of his success, I figured I had it made.

My name is Tom Leonard. My dad is Stewart Leonard. He’s quite a guy.

My father started his business in 1969. Back then it was a small dairy store with seven employees. It’s now the “World’s Largest Dairy Store” with 2,000 employees.

I’d been working for months in the store. “Start at the bottom,” Dad said. So I did. Stocking the shelves. Sweeping up. That was my gig.

One day the phone rang. Great news. My buddies were headed to Ft. Lauderdale for Easter break. Heck, I thought, I’d been working hard and needed a vacation.

I asked Mr. Barry, our store manager, if I could take a few days off.

I could hardly believe what he said!

Mr. Barry was nice, but firm. The answer was no. Something about the busy Easter weekend. He needed my help.

No? I was the boss’s son. My dad owned the place. I didn’t have to listen to that. So I took off anyway.

Man, what a blast. My friends and I showed that Florida town what fun is all about.

Wearing two hats is not easy.

So now back to that hot tub with Dad. I arrived with a smile (and a tan from my trip). I shucked off my jeans and pulled on my shorts.

My father was waiting, submerged to his shoulders. I plopped into the tub. Pretty cool! “So what’s up, Dad?” I asked.

Here’s what happened.

Dad said, “You know Tom, being both a father and a boss in a family business is a tough job. I have to wear two hats.”

Then Dad reached behind him, picked up a red baseball cap and placed it on his head. He continued, “Tom, on the one hand, I’m your dad.”

Then Dad turned, removed the red hat, grabbed a white hat from the ledge, and put it squarely on his head. He went on:

“On the other hand, I’m also the boss. As the boss, I have to treat all of my employees fairly.

Your manager told me you asked for vacation. He told you no. You didn’t listen. You went anyway. So I hope you understand that I have to treat you the same as our other employees. Tom, you’re fired.”

My mind went blank. Fired by Dad? How would I live? Where would I work? I’d quit school and had no real skills.

But Dad wasn’t through. What did he do?

Wearing two hats takes guts.

My father proceeded to take off the white “boss hat” and put on the red “dad hat.” Then he said, “Son, I hear you just lost your job. What can I do to help?”

With Dad’s help and encouragement, I went back to college, earned my degree, and now operate my own business. Come by and say hi. It’s Tom Leonard’s Farmer’s Market in Richmond, Virginia. It’s all thanks to my dad.

About the Contributor

Tom Leonard is the founder of Tom Leonard’s Farmer’s Market. His store has been recognized by Richmond Guide as #1 in the “Top 15 Things to Do with Kids” in Richmond. Richmond Magazine named it #1 in the “50 Best Food Finds” in Richmond and the #1 place to purchase produce. If you see Tom, be sure to say I said hello. He is a fantastic guy who contributed a wonderful story to my book.