Airplane! Jokes, AI Trivia, and the Evolution of Success with Brad Perkins

In this episode, I sit down with my college roommate and longtime friend Brad Perkins, now Managing Partner at Perkins Equity Management, to talk about the twists, turns, and lessons from a life spent leading massive software teams… and why he walked away from corporate life to build something on his own terms.We cover a lot of ground — and yes, plenty of laughs:Why contractors and software developers are way more alike than you thinkThe #1 lesson Brad took from decades in IT leadershipA few classic Airplane! jokes (because we can’t help ourselves)A round of ChatGPT-powered Trivial Pursuit inspired by our college game nightsHow Brad’s definition of success has evolved — and why Mondays feel different nowAnd of course… we wrap it up with a dad jokeIt’s funny. It’s thoughtful. It’s two old friends reconnecting with a lot more wisdom — and still plenty of nonsense.