Early May in Chicago, I had the delightfully daunting task of bringing a little comic relief to the main stage at CFA Institute LIVE 2025. Sharing the same stage with Nobel Laureates and star economists felt daunting, but I quickly realized my job wasn’t to outdo the experts—it was to offer something different.
My topic? Not the usual parade of AI breakthroughs and buzzwords, but the hilarious, head-scratching, and sometimes hair-raising ways artificial intelligence can go spectacularly wrong—especially when it comes to your money.
Why “Artificial Stupelligence”?
Let’s face it: the world is awash with serious books about AI. But for every algorithm that promises to revolutionize finance, there’s a story (or three) of a machine that misses the mark in ways that are equal parts absurd and alarming. That’s where “Artificial Stupelligence” comes in—a humorous guide to AI’s not-so-genius moments, and a reminder that our digital helpers are only as clever as their creators.
The Greatest Hits (and Misses) from the Presentation
I kicked things off with a story many in the audience could relate to: my visit to an Amazon Go store, where the promise was pure AI magic—no checkout, no humans, just seamless automation. The reality, however, led to an “AI aha moment” that fundamentally changed the way I view these technological marvels.
When Chatbots Go Off-Script
We then explored the world of customer service chatbots, like the one in the UK that, when asked to write a poem about itself, turned into both a poet and a whistleblower. It’s a reminder that when AI goes off-script, the results can be both hilarious and a little unsettling—especially when you consider that similar technology is entrusted with managing your investments.
When Algorithms Run Amok
But the consequences aren’t always so innocent. I shared how, in finance, a single fake tweet once triggered trading algorithms to wipe billions off the market in seconds—no human double-checking, just machines in overdrive. And let’s not forget the AI-powered loan officers making questionable decisions based on outdated stereotypes or odd patterns, sometimes penalizing you for meal prepping or rewarding you for just being male.
The Real Lesson: AI Needs Us
So what’s the lesson? AI is not magic. It’s a tool—one that needs supervision, diverse data, and a healthy dose of skepticism. We need to build responsible systems, always verify before we trust, and remember that the best results come when human wisdom and technology work together.
The Human Factor
As I wrapped up, I reminded everyone that while AI can crunch numbers at lightning speed, it can’t replace critical thinking, empathy, or leadership. That’s where we come in.
If you left my session with a smile and a bit more skepticism about the next AI headline, then mission accomplished. And if the term “Stupelligence” sticks with you, my work here is done.
Thank you, CFA Institute, for the stage—and may your tweets never crash the market.
“Artificial Stupelligence: The Hilarious Truth About AI” is available on Amazon as an eBook, paperback or hardcover version.
