Today's guest has been a partner and friend to GBH for years. He's a former GM for 16 on Center, a restaurant and venue group in Chicago known for its Michelin Star restaurant, Longman & Eagle, as well as music venues like The Empty Bottle and Thalia Hall.

If Thalia Hall sounds familiar, that's because it's played host to our Uppers & Downers festival basically since its inception. So much of what the festival has become has been substantially shaped by the physical space of Thalia Hall—it's history, and Will Duncan himself.

In this conversation, we're going to talk about some of that, but also how Will has risen through the ranks over the years, from a part-time door guy to GM, to multi-venue manager across the growing empire of bars, restaurants, and venues, and finally launching his own venue as he takes over the historic FitzGerald's venue in Berwyn, Illinois.

He happened to sign the papers for that venue—venturing into his life-long dream of being an entrepreneur in his own right—about a week before COVID-19 turn our world upside down, and places like FitzGerald's shut down.

A dream interrupted. But still kicking.

I've learned a ton from Will over the years. Sometimes explicitly, sometimes just by following his example and experimenting with his kind of team-based leadership. I often describe Will as the most optimistic man in America. But one thing I know is that sometimes optimism comes easy and natural—and sometimes optimism is damn hard work. This conversation is about the work.

This is Will Duncan of FitzGerald's and 16 on Center. Listen in.