The Tim Dillon Show

Snapshot · The Tim Dillon Show

497 - Thomas Massie, Kevin O'Leary, & The American Psyop

Explore episode May 23, 2026

Where this was said

Kevin O'Leary vs. The $28 Lunch — Billionaires Want You to Stop Eating

At 27:10 · chapter starts 24:30

Tim introduces Kevin O'Leary — 'friend of the show, don't sue me' — and plays his clip shaming young workers for their lunch spending habits. O'Leary frames a $28 lunch as financially illiterate: put that money in an index fund at 8–10% annually and in 50 years you'll thank yourself. Tim proceeds to dismantle this argument piece by piece. First, lunch is $28 because the economy is broken, not because workers are reckless. Second, making your own lunch and bringing it isn't dramatically cheaper when groceries are also inflating due to the Iran war. Third, and most importantly, this is part of a broader campaign to strip any remaining pleasure from working-class life — Tim connects it to a previous media story arguing people don't even need a dining room anymore. He mourns the three-martini lunch era at Smith Wollensky's or the 21 Club as a moment when workers had genuine enjoyment built into the workday. Now, they eat a grain-or-green bowl in silence and are told even that is too much. Tim's final image of the O'Leary critique is a worker eating 'organic non-GMO dog food' before returning to an overpriced condo with no dining room to jerk off to violent porn and have a panic attack — and being told not to spend $28 on what barely punctuates this existence.

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