Off the Beaten Jack

This week I'm in Portland, staying with Darryl Purpose - one of the world’s best blackjack players, now a folk singer-songwriter. We talk about card-counting, earning a living as a gambler, his music, creating art when you don’t understand the rules and how his mum supported him on these very different paths.

A trip to the pub leads me to an embalmer and funeral director named Kelly, who invites me to stay with him and his wife Cleo. We discuss the unique circumstances of how they met, growing cannabis, the emotional impact of killing someone (in self defence), and becoming desensitised to death by working with dead bodies. Oh, and guns...

Elkhart, Indiana is a town living in the shadow of its 1970s heyday. My host Evan and I discuss how these changes have played out in the community, as well as guns, Midwestern stereotypes, the Amish and how we can better love our fellow man.

In episode one, I reflect on how the pandemic forced me to dwell on where I am in my life - feeling I’ve left things too late - and how I’d like to change that in the coming year. I speak to my mum about Couchsurfing, and her experiences as a host when it first started, as well as her tips as I prepare to cross America in the dead of winter to pursue a long-held dream.

In part two of my Portland adventure, I go through intensive training with Darryl Purpose - learning to count cards and play blackjack basic strategy. Then we make our way to the casino, where I stake my last few hundred dollars and try to turn it into thousands. Will I lose everything or take the house for all it’s worth?