What if the Iran War Never Ends?
What if the Iran war never really ends—but instead settles into a dangerous, permanent limbo? In this episode, Ravi Gupta sits down with former Deputy National Security Advisor Jon Finer to unpack the...
6 Maj 42min
Grading Mamdani
Ravi Gupta sits down with Bradley Tusk to break down New York City’s mounting budget crisis, a $6B deficit, and the tough choices facing Mayor Mamdani. They dig into the city’s $40B education system—w...
4 Maj 54min
Can You Predict a Recession?
What if everything you’ve been told about recessions is wrong? On this episode, Ravi Gupta sits down with economist Tyler Goodspeed to challenge the classic “boom and bust” narrative—arguing that down...
1 Maj 46min
Nobody Lasts That Long
Ravi sits down with legendary music biographer Bob Spitz, who pulls back the curtain on rock’s biggest icons and the forces that made them endure. From secret blues records on military bases to the ca...
23 Apr 1h 2min
Cuba Libre?
When Ravi Gupta was a struggling high school student, he pulled Jon Lee Anderson’s biography of Che Guevara off his mom’s bookshelf—and it became the first book that truly grabbed him, shaping how he ...
16 Apr 51min
Iran Ceasefire, Hasan Piker
Ravi Gupta breaks down what he sees as a major U.S. loss in Iran, arguing that Trump’s threats and ceasefire ultimately left Iran with more power and America with less. He also shares clips of Hasan P...
8 Apr 46min
How to Make and Lose a Million Dollars
Ravi Gupta sits down with Alexander Hurst, author of Generation Desperation, to unpack his journey from $300 to over $1 million—and the identity he built around the life that money seemed to promise. ...
1 Apr 1h 6min
Iran Quagmire + AI Politics
What happens when Americans fear AI more than Trump, ICE, or either political party? In this provocative conversation, Catherine Bracy joins Ravi to unpack why voters are deeply skeptical of artificia...
18 Mars 50min
