All Seasons

Season 2018

• S2018E01 Groupon's Andrew Mason: Pt. 1, The Rise

  • October 1, 2018

• S2018E02 Groupon's Andrew Mason: Pt. 2, The Fall

  • October 8, 2018

• S2018E03 Sophia Amoruso: From Nasty Gal to Girlboss

  • October 15, 2018

• S2018E04 Nina Jacobson: How to Make a Hit in Hollywood

  • October 22, 2018

• S2018E05 Golden State Warrior Andre Iguodala

  • October 29, 2018

• S2018E06 Relentless: How One Guy Brought the Internet to America's Schools

  • November 5, 2018

• S2018E07 Smart Out Loud: How Janice Bryant Howroyd Learned to Own Her...

  • November 12, 2018

• S2018E08 The Man Behind the Iconic Apple Stores: Ron Johnson

  • November 19, 2018

• S2018E09 The Accidental Technologist: Caterina Fake

  • November 26, 2018

• S2018E10 How One Mom Tried to Reunite Migrant Families

  • December 3, 2018

• S2018E11 Ira Glass: The Man Who Launched a Thousand Podcasts

  • December 10, 2018

Season 2019

• S2019E01 The Secret Early Lives of Sam Esmail

  • February 11, 2019

• S2019E02 How a Revolution Turned into America’s Number One Radio Station

  • February 18, 2019

• S2019E03 Bringing Brands Back to Life

  • February 25, 2019

• S2019E04 Black Sheep of Wall Street: Henry Blodget

  • March 11, 2019

• S2019E05 How to Fire People

  • March 18, 2019

• S2019E06 The Decades-Long Hunt for the Golden State Killer

  • March 25, 2019

• S2019E07 The Tragedy Expert

  • April 8, 2019

• S2019E08 How Anna Chlumsky Got a Second Act

  • April 15, 2019

• S2019E09 An Early Facebook Insider Reckons with What He Built

  • April 22, 2019

• S2019E10 Showing Up at Your Dream Job Uninvited

  • May 6, 2019

• S2019E11 Exiled from the Industry He Helped Create

  • May 13, 2019

• S2019E12 How a Hollywood Newcomer Shook Up Prime Time

  • June 3, 2019

• S2019E13 Don’t Underestimate Gretchen Carlson

  • June 10, 2019

• S2019E14 A 90s Sitcom Star's Fight for the Future of Black TV

  • June 17, 2019

• S2019E15 The Scared Child Inside Every Leader

  • July 8, 2019

• S2019E16 The Woman Who Brought Politics to Teen Vogue

  • July 15, 2019

• S2019E17 The Cost of Having a Conscience in the Senate

  • July 22, 2019

• S2019E18 How a Stay-At-Home Mom Started an Empire

  • August 19, 2019

• S2019E19 From Hustling Dice to the Heights of Global Fashion: The Dapper Dan Story

  • September 9, 2019

• S2019E20 Being an A$$hole: The Final Frontier for Women on the Screen

  • September 16, 2019

• S2019E21 How Coming Out Made Shane McAnally a Nashville Star

  • September 23, 2019

• S2019E22 The Cyclist Who Blew the Whistle on Doping

  • October 7, 2019

• S2019E23 Nick Kroll Gets Out of Character

  • October 14, 2019

• S2019E24 Ira Glass: The Man Who Launched a Thousand Podcasts (Rebroadcast)

  • October 21, 2019

• S2019E25 The Man Who Changed the Future of Florida Elections

  • November 4, 2019

• S2019E26 The 32 Seconds that Changed This Mayor’s Life

  • November 18, 2019

• S2019E27 How Earlonne Woods Podcasted His Way to Freedom

  • December 2, 2019

• S2019E28 Michelle Phan: The Original Internet Influencer

  • December 9, 2019

• S2019E29 The Woman Who Took On Larry Nassar and USA Gymnastics

  • December 16, 2019

Season 2020

• S2020E01 The Secret Early Lives of Sam Esmail (Rebroadcast)

  • January 20, 2020

• S2020E02 The Church of John Green

  • February 17, 2020

• S2020E03 The Secret to Writing a Children’s Book

  • March 16, 2020

• S2020E04 What's Happening Around Gimlet: Science Vs - Will Chloroquine Save Us?

  • March 30, 2020

• S2020E05 What’s Happening Around Gimlet: Reply All - The Attic and Closet Show 2

  • April 6, 2020

• S2020E06 What's Happening Around Gimlet: Every Little Thing - Essential Workers Call In

  • April 13, 2020

• S2020E07 How Megan Phelps-Roper Left the Westboro Baptist Church

  • April 20, 2020