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The $40 trillion national debt is growing while Social Security goes broke—because wealthy Boomers are collecting over $100k in benefits per year

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Despite having a net worth of $400 million, Kevin O’Leary still shops at Walmart for $29 jeans: ‘I’m always looking for a great deal’

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Welcome to the 'upper-middle-class trap': why $300,000 a year doesn't feel like winning anymore

1

The $40 trillion national debt is growing while Social Security goes broke—because wealthy Boomers are collecting over $100k in benefits per year

2

Despite having a net worth of $400 million, Kevin O’Leary still shops at Walmart for $29 jeans: ‘I’m always looking for a great deal’

3

Welcome to the 'upper-middle-class trap': why $300,000 a year doesn't feel like winning anymore
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Personal Finance
The $40 trillion national debt is growing while Social Security goes broke—because wealthy Boomers are collecting over $100k in benefits per yearplaceholder alt text
By Joshua HongAugust 27, 2026
Success
Despite having a net worth of $400 million, Kevin O’Leary still shops at Walmart for $29 jeans: ‘I’m always looking for a great deal’placeholder alt text
By Preston ForeAugust 27, 2026
Success
Welcome to the 'upper-middle-class trap': why $300,000 a year doesn't feel like winning anymoreplaceholder alt text
By Nick LichtenbergAugust 27, 2026
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