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Will Cain Country

Kevin O’Leary Says THIS Is Why People Stay Broke - Is He Right? (ft. Jack Mac & Rep. Andy Ogles)

Will Cain Country

FOX News Podcasts

News, Society & Culture, Sports News, News Commentary

4.72.1K Ratings

🗓️ 21 May 2026

⏱️ 71 minutes

🧾️ Download transcript

Summary

Kevin O’Leary struck a nerve with younger internet users when he called out indulgent lunch expenditures, but does he have a point, or is it just more “boomer slop” (as Tinfoil Pat puts it)? Will and The Crew are joined by Barstool’s Jack Mac, Host of 'Unpack With Jack Mac,' to break down the internet’s outrage over Mr. Wonderful’s concerns surrounding Gen Z’s financial habits, before taking a look at yet another heater to come out of Maine's Democratic Senate candidate Graham Platner’s Reddit account. Plus, Congressman Andy Ogles (R-TN) breaks down the ASSIMILATION ACT; a bill he says will help crack down on H-1B fraud and fix America’s broken immigration system. Subscribe to ‘Will Cain Country’ on YouTube here: ⁠⁠⁠⁠⁠Watch Will Cain Country!⁠⁠⁠ Follow ‘Will Cain Country’ on X (⁠⁠⁠@willcainshow⁠⁠⁠), Instagram (⁠⁠⁠@willcainshow⁠⁠⁠), TikTok (⁠⁠⁠@willcainshow⁠⁠⁠), and Facebook (⁠⁠⁠@WillCainNews) Follow Will on X: ⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠@WillCain⁠ Learn more about your ad choices. Visit podcastchoices.com/adchoices

Transcript

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0:00.0

Attention all passengers.

0:04.0

The Uber ride for Jeff's rugby team will depart in five minutes from Platform 15.

0:10.0

Your ride comes with six toilets and a refreshments carriage that you'll empty within five minutes.

0:16.0

Thank you for booking your tickets on Uber.

0:20.0

Trains on Uber. Trains on Uber.

0:22.6

Some follow the noise.

0:25.0

Bloomberg follows the money,

0:26.8

whether it's the funds fueling AI

0:28.4

or crypto's trillion dollar swings.

0:30.9

There's a money side to every story.

0:33.5

Get the money side of the story.

0:35.6

Subscribe now at Bloomberg.com.

0:53.7

Senate candidate for Maine.

0:57.0

Graham Platner keeps churning out the hits.

1:00.0

This time, mocking an American soldier wounded in Afghanistan.

1:08.0

Democrats, you got some gems running to represent you in Washington, D.C.

1:16.6

Kevin O'Leary says don't spend $28 on a lunch when you're making $70K.

1:22.5

And for that, the internet is mad with Barstools, Jack Matt.

1:39.1

It is Wilcane Country.

1:41.1

Streaming live at the Wilcane Country YouTube channel, the Willcane Facebook page.

1:45.8

But here, it's your leisure on demand.

1:48.1

Simply hit Follow.

...

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