How to Win a Million Dollars is a madcap, self-deprecating, laugh-out-loud coming-of-age story that reads like David Sedaris meets Heartstopper, told as Ready Player One. It takes listeners on an adventure through the wildly inventive, sometimes-questionable, but always entertaining schemes of a boy who would do anything to make it big.

Growing up as a gay Catholic schoolboy in a tiny Mississippi River town surrounded by cornfields, Luke’s imagination was constantly set on fire by million-dollar daydreams and DIY hustles. Whether it was hunting down the missing Cap’n Crunch or gaming McDonald’s Monopoly, no scheme was too ridiculous, no shortcut too far-fetched. With his trusty Hustler bike and a mountain of determination, Luke didn’t just dream—he plotted.

Set in the 1980s, this is the story of a kid with a knack for scamming, hustling, and occasionally crashing and burning—all in the pursuit of that elusive big win. From navigating a Catholic school playground full of bullies to trying to “make it” out of a blue-collar family, Luke was always on the move, cooking up his next big adventure. Dragging his little sister—turned faithful sidekick—into trouble at every turn, her sweet voice was always in his ear, making us wonder: Is he conning her, or is she saving him from himself?

As Luke grew up, so did the schemes—high school musicals that almost made him a Broadway star, ditching everything for Paris, and even getting cursed by a Hawaiian god. With every plan, the stakes got higher, the twists weirder, and Luke had to ask: Can you beat the system, or does it always beat you?

This whirlwind ride through epic failures and surprising successes proves that sometimes the journey is better than the jackpot. Because maybe, just maybe, there’s still a million-dollar prize out there waiting to be won.