She Shed or Man Cave? (with Kathryn Hahn)

Actor Kathryn Hahn joins Sam from her “she shed” to talk about how important it is to try a decision on for size before you make it and how she’s very good at getting rid of stuff (except for her kids’ art projects). They talk about taking jobs to pay off student loans, the distinct wetness of pre-…

Red States or Red Carpets? (with Heather McMahan)

Comedian Heather McMahan joins Sam to talk about how she’s what you would get if Joan Rivers and Conan O’Brien had a baby, why she chose to self-produce her comedy special Breadwinner and the importance of being your own yes-man. They also talk about the joys of the human body, like ovarian cysts b…

Gourmet or Go Home? (with Ruth Reichl)

Renowned restaurant critic, food writer, and magazine editor Ruth Reichl joins Sam to talk about why taking a job as the editor-in-chief of Gourmet Magazine was such a hard decision, and how it ended up changing her life. They talk about getting paid to do a job you would do for free, her new docum…

Red, White, and Blue or Green…Card? (with Lauren Ash)

Fellow Canadian and actor Lauren Ash joins Sam to talk about why she continues to live on a Green Card rather than apply for US citizenship, and why on her 40th birthday she decided to try a career in music. She talks about why she’s not as easily swayed as when she was younger but how small decisi…

Shy Voter or Vocal Voter? (with Errin Haines)

With less than two weeks until Election Day, editor-at-large of The 19th* Errin Haines joins Sam to talk about news coverage leading up to the most significant election in recent memory and whether or not shy voters will make a surprising difference. They talk about the importance of being open to …

Dishwasher or Daredevil? (with Jenny Slate)

Jenny Slate sits down with Sam to talk about the difference between FOMO and regret and how sometimes you need to bust through a wall to take a big swing. Jenny talks about how she is naturally risk averse and giving birth was the most dangerous (and best) situation she ever put herself in. They ta…

Monthly Magazines or Nonstop News? (with Joanna Coles)

Joanna Coles, the Chief Content Officer of The Daily Beast sits down with Sam to talk about deciding to leave the never-ending cycle of daily news for a slightly more dependable pace of monthly magazines…and then returning to news after two decades away. They talk about seeing George Clooney in the…

Basketball Star or Bipartisan Leader? (with Governor Maura Healey)

Massachusetts Governor Maura Healey joins Sam to talk about trading her career as a (yes) professional basketball player in Austria for law school and later to serve as Attorney General and Governor of Massachusetts. They talk about how Governor Healey happily works across the aisle with non-crazy …

Seat-Filler or Superdelegate? (with Jon Cryer)

Jon Cryer joins Sam to talk about how he chooses his acting roles when he knows saying yes to one job means having to turn down another, and tells Sam about a huge role he passed up. They also get into it about a raccoon that steals his delivery food, why he gets recognized at the Frankfurt airport…

List Maker or List Keeper? (with Mackenzie Davis)

Actor Mackenzie Davis joins Sam to talk about how she took a semester off from college to model–hated it–and ultimately decided to go back to school and fast track her degree so that she could start acting. They bond over seeing baking directions as meditational, learning lines while cooking, and h…