All Episodes

August 27, 2025 117 mins

In this follow-up episode of If By Whiskey, Jason and Mark keep the conversation on A.I. rolling—minus William this time, but with even more whiskey-fueled skepticism. We dive deeper into what artificial intelligence really means for freedom, work, and wealth in a world where politicians think slapping a regulation on silicon chips is the same thing as “protecting” humanity. From cubicle-crushing automation to the possibility of robo-bureaucrats who never sleep, we wrestle with whether A.I. is the greatest tool of liberation since the printing press… or just the newest excuse for central planners to tighten the leash. Pour yourself a glass and settle in—this round is all about decoding tech hype, deflating utopians, and asking the question that really matters: will A.I. make us freer, or just make the taxman faster?

🎙️ New to streaming or looking to level up? Check out StreamYard and get $10 discount! 😍 https://streamyard.com/pal/d/5888413371072512

Mark as Played

Advertise With Us

Popular Podcasts

Stuff You Should Know
Dateline NBC

Dateline NBC

Current and classic episodes, featuring compelling true-crime mysteries, powerful documentaries and in-depth investigations. Follow now to get the latest episodes of Dateline NBC completely free, or subscribe to Dateline Premium for ad-free listening and exclusive bonus content: DatelinePremium.com

The Breakfast Club

The Breakfast Club

The World's Most Dangerous Morning Show, The Breakfast Club, With DJ Envy, Jess Hilarious, And Charlamagne Tha God!

Music, radio and podcasts, all free. Listen online or download the iHeart App.

Connect

© 2025 iHeartMedia, Inc.