Gambling for Shoes

Jack picks his favorite NFL teams to gamble on and favorite stand-up comics to watch in this circular reasoning extraordinaire!

After a week in gambling jail, Jack returns to prove he's a changed man and ready to make smart picks.

Jack licks his wounds after a brutal week 2, compares Chicago to Venezuela, and attempts to get vulnerable about comedy. Plus fooh-ball!

Jack toasts himself over a Week 1 victory, denounces sneakerhead culture, and tells his first Chicago train story. Plus shoes!

The podcast returns! Jack talks strategy against street criminals, tells his first Chicago comedy story, and predicts the future for Week 1 of NFL fooh-ball.

Back from Denver, Jack brushes off his airport funk, shares another weird moment in stand-up comedy, then details his tumultuous relationship with Twitter. Plus shoes!

Jack defends ties in soccer, weed, and getting mad at someone during a comedy show. Plus shoes!

Back from Chicago, Jack details picking a fight with college kids on St. Patrick's Day, says a prayer for Kanye, then makes a bet to win more shoes.

Jack mixes comedy and baseball for the first time in a rant about high school sports, then makes the case for being selfish. Plus shoes!

Jack talks about why he started comedy, what it feels like to bomb in your 30s, and tries his hand at motivational speaking. Plus shoes!