Rufus, Outhouses, and Should we give a $#@%? Or, Do Boomers owe their children a better life?

Send us Fan Mail In this episode, I push back on the idea that Boomers “had it easy” and owe their kids a softer life. Starting with the story of Rufus—a kid who walked into an auto shop two weeks before his 14th birthday to ask for a job—I connect three generations: my dad shoveling outhouses, a young hustler running a repair shop in his teens, and today’s grads struggling with housing and work. We talk college degrees vs trades, starter homes then vs now, participation trophies, Sweden and ...