60s | Still Cracking Jokes, Still Breaking Systems
At this point, I use humor the way other people use meditation—except instead of deep breathing, I’m making AI question its life choices. Because let’s be real, AI is powerful, but it’s also clueless. (Ever seen an AI-generated hand? Nightmare fuel.) The world is in a constant state of freakout mode over technology, but here’s the real punchline: humor is the only thing that makes any of it make sense.
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50s | The “Wait, Am I the Old Guy Now?” Era
One day, you’re ahead of the curve, and the next, some 25-year-old with an NFT collection is calling you a “legacy thinker.” The joke? Everyone thinks they’re the disruptor—until they get disrupted. Instead of fighting it, I leaned in. Because humor isn’t about knowing everything, it’s about calling out the nonsense and keeping a straight face while everyone else panics. And wow, was there a lot of nonsense to call out.
40s | The “Rewriting the Playbook” Phase
This was the decade where I realized most businesses treat marketing like a hostage situation: Confuse them until they comply. Jargon, overcomplicated strategies, meaningless buzzwords—every pitch was just a fancier way to say absolutely nothing. So I did the only logical thing: I started treating business strategy like a comedy set. Cut the fluff, get to the point, and if people laugh in recognition, you’re onto something.
30s | The “Why So Serious?” Years
Tech was booming, and every company was convinced their software was the next revolution—meanwhile, no one could figure out how to reset a router. The problem? Businesses were so obsessed with what they were building, they forgot why people should care. I spent this decade showing people that the same principles that make a joke land—timing, clarity, and not wasting people’s time—are the same ones that make a message stick.
20s | When Comedy Met Technology
Some people graduate college and get a real job. I started writing jokes for radio stations using email in the 80s—when email was still some sketchy nerd experiment. And guess what? It worked. Why? Because humor has always been the fastest way to get people’s attention, and technology has always been a tool for getting there first. Everything since then has been a remix of that same play: use the latest tools, but don’t take them too seriously.
The Bottom Line
After four decades of watching people panic over the next big thing, I can tell you this: the tech changes, but people stay predictably weird. They get overwhelmed, they overcomplicate things, and they take themselves way too seriously. But humor? Humor slices through the nonsense, keeps people engaged, and makes things actually work. And that’s why it’s always been my secret weapon.
How Dare I
Give me a challenge to make you laugh about your business.