Over the years, I’ve shared many of the most valuable lessons I learned—lessons that shaped my thinking, my decisions, and my approach to life and business. Many came from my dad, whose nickname was Chubby. In honor of Chubby being the first to teach me the difference between being educated and being smart, I call them “Chubby Rules.”
Chubby believed that while education was important, knowing how to apply knowledge intelligently was essential. He would often tell me, “Greg, it’s important to be educated, but it’s essential to be smart.” That stuck with me.
Over the years, I’ve picked up additional wisdom from other smart people—entrepreneurs, leaders, mentors—who reinforced and added to what my dad taught me. Together, those insights formed a set of thinking guides—rules for applying knowledge in ways that helped me make better decisions, fewer mistakes, and know what to do when others didn’t have a clue.
I decided to take a few of the lessons I learned over the years and enter them into ChatGPT to see how artificial intelligence, a technology of today and the future, would present them. The lessons may have come from my past, but they are being presented to you by AI, a modern technology. Think of it as timeless human wisdom presented by a new technology.
With that, here are 12 of my favorite “Chubby Rules” presented to you by AI—distilled into brief, easy to remember phrases with a thumbnail description below. I gave AI those Chubby Rules in my words. You are reading them in AI’s words.
1. Say It Before You Forget It
When you think something nice about someone, let them know before you forget.
A compliment unspoken is a missed opportunity to make someone’s day and strengthen a connection.
2. Don’t Trade Time for Money to Be Wealthy
Wealth comes from ownership, not hourly wages. Invest in assets, create systems, and build businesses that make money while you sleep.
3. People Criticize What They Aren’t Part Of
It’s human nature—those on the outside tend to judge. Don’t let criticism from non-players affect your game.
4. Because You Can Doesn’t Mean You Should
Just because an opportunity is available doesn’t mean it’s the right one. Discernment is the key to avoiding unnecessary distractions.
5. Take a Chance on Being Better Than You
Your biggest competition isn’t other people—it’s the version of yourself that’s content with staying the same.
6. Care More About Others Than Yourself
Ironically, the more you focus on adding value to others, the more success, fulfillment, and loyalty come your way.
7. Do What’s Right, Not What’s Popular
Leaders don’t follow trends—they create them. Politicians take polls, but true leaders make them.
8. It’s Really Dumb to Think You’re Smart
The moment you believe you have nothing left to learn is the moment you stop growing. Stay humble. Stay curious.
9. Make Money So You Can Make a Difference
Money isn’t the ultimate goal—impact is. The more resources you have, the more you can contribute to causes that matter.
10. Free Isn’t Better If Better Isn’t Better
A deal is only “a deal” if it is a good value. Sometimes, paying more upfront will be a better value in the long run.
11. Brief and Brilliant Beats Big and Bloated
Clarity wins. Whether in business, writing, or life—simplicity and impact always outshine complexity and fluff.
12. Learn Something About Everything and Everything About Something
Chubby emphasized to me that I should strive to be the best in the world at one thing, while also enhancing my ability to converse and relate to other people by having some knowledge of many things.
My Offer To You: Make my 12 Chubby Rules your own. The technology of the future may be AI, but without wisdom from the past AI would only be “A” because it would have no intelligence.
