Nick Kroll
Jake
A bankrupt businessman tries to restore good relations with his sister and her family.
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Nick Kroll
Jake
Rose Byrne
Justine
Bobby Cannavale
Danny
Matthew Paddock
Teddy
Caleb Paddock
Teddy
Paula Garcés
Blanca
Joel McHale
Hudson
Caitlin FitzGerald
Kat
Jane Krakowski
Miss Jenn
Mike Birbiglia
Braden
Greg Johnson
Business Dude
Bobby Moynihan
Paul
Seth Barrish
Doctor
Jason Mantzoukas
Herman
Cara Cooper
Real Estate Agent
Paul Urcioli
Georgia's Dad
Sarah Steele
Sarah
Josh Charles
Phil
