How the GOP Operatives Behind ‘Ruthless’ Turned a Niche Podcast Into a Right-Wing Media Sensation

Isaac Schorr Aug 22nd, 2025, 10:03 am

They would have you believe it was destiny.

About five years ago, Shashank Tripathi , better known by his social media moniker, Comfortably Smug , instantly hit it off with GOP operatives Josh Holmes , John Ashbrook , and Michael Duncan at an off-the-record happy hour he hosted in Washington, D.C. — “The guest list remains confidential,” he told Mediaite — and in short order approached them with an idea.

“I’ve got a deck about an idea of a podcast that uses satire to skewer the left. And a media company that really focuses on that idea. Because debating the left is absurd when they have absurd ideas, they should be mocked. And I put it d

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