JD, GSM & Going All In

Simon sits down with his pal Fisch to enjoy a nice glass of rosé and discuss some of his favorite things about Chicago.Also, the dogs make their long-anticipated pod debut.

The one where the ghost of Steve Jobs ruins a great conversation about Spanish reds and the fundamentals of shaping the youth athlete.

In a wide-ranging conversation, Simon yaps with his brother Stuart about doing something you love, and wanting to be better at drinking wine.

Simon talks with his three daughters about sparkling reds, where they find hope, and the future of our great nation.

Simon chats with Kelly, a career educator, who's seen the school system from every angle. They share a bottle of a Chardonnay Sauvignon Blanc blend that really shouldn't exist, which Simon proves by recommending its ultimate food pairing...hot dogs.

After enlightening me for 53 odd years, you'd think Dad would take his foot off the gas, but no. Just another in a lifelong series of exceptional conversations with one of my heroes. The wine was pretty swell too.Cartograph 2021 Transverse Pinot Noir.

The long-awaited 3rd installment, where Simon continues to butcher French words, and learns about committing.

Simon enjoys a delightful bottle of Ridge Zinfandel with his friend Surrey, as they discuss how to make the most out of your time on this earth.

Simon and his first guest break down the importance, value, and work of meaningful adult friendships, while enjoying a lovely Sancerre from La Garrenne.

Simon clumsily shares his reason for creating Podcast, and even more clumsily breaks down a zinfandel from Seghesio Vineyards.