Pessimistic at Best

Welcome to Pessimistic at Best, a podcast for those with a penchant for frequent frustrations, personal gripes, unpopular opinions, honest observations, and the like. Hosted by Sam, your resident Pessimistic Patty, this weekly show operates on the belief that no complaint is too small.

Each week, Sam sits down with a guest to explore the good, the bad, and the ugly. A surprisingly good country album by your favorite pop artist, a bad bang trim you gave yourself during a manic episode, a military homecoming video on the internet that made you ugly cry. The list is endless, and therein lies the beauty. Come on in, we saved you a seat!

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Pessimistic at Best

We've Been to the Year 3000

April 28, 2026 • Sam Georgson

0:00 | 56:35

POV: It's 2006, the Jonas Brothers have just released their debut album, It's About Time, and you briefly leave your body. Caroline and I get into her music origin story, her earliest fandoms, and how that eventually led to building the Chicago Show Calendar.

Then we get into the Good, the Bad, and the Ugly: Ditching Spotify and starting fresh on Qobuz, the way people undervalue small businesses, and music industry PR literacy ft. the Geese psyop discourse.

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