Prepare to be disappointed!
In this episode of The Education Road, we chat with Ian Kalman, founder and creative director of Bald Guy Greetings, the irreverent, hilarious, and wildly relatable greeting card company found in hundreds of stores across North America.
Ian kicks things off with what he calls “a road full of questionable choices that somehow worked out,” and that phrase couldn’t sum up his story better. From dreaming of writing witty ad copy in college to running a nationally recognized greeting card business, Ian’s journey proves that the best careers often start as happy accidents.
He takes us back to his time at San Jose State University, where he majored in advertising and minored in psychology, a combination that would later help him connect with audiences on a deeply human level. After graduating, Ian landed his dream job in advertising, working on iconic campaigns for Budweiser, E*TRADE, and the Oakland A’s.
But everything changed with a birthday cake.
What started as a joke written in frosting sparked an idea: What if greeting cards were actually funny? On a plane ride shortly after, Ian began jotting down card ideas — 60 in total. Twelve of them became the first Bald Guy Greetings collection, and the rest is history.
Mike and Ian talk about the early struggles of starting a business without a roadmap. No entrepreneurship courses, no investors, just a writer who wanted to make people laugh. Ian admits that his college education didn’t prepare him for payroll, taxes, or packaging orders, but it did teach him creativity, persistence, and empathy.
Ian also opens up about his creative process, describing it as spontaneous and joy-driven. He keeps hundreds of ideas in his phone notes, drawing inspiration from overheard conversations, awkward social moments, and life’s little absurdities. With over 350 cards in circulation today, his brand has become a cult favorite for people who prefer laughter over sentimentality.
“If it makes me laugh, I’ll make it. I’d rather fail on my own terms than succeed at something that doesn’t feel like me.”
It’s that authenticity that’s made Bald Guy Greetings such a success and why so many customers, like Mike’s own family, refuse to buy any other cards.
By the end of the episode, you’ll see why Ian’s self-proclaimed “questionable choices” were anything but. His story is a reminder that passion, persistence, and a sense of humor can take you further than any perfect plan ever could.