A big, fat loophole

Anthony's bags, with everything he took to Cambodia.

What if we told you there was a way to walk away from your debts with no financial consequences? There’s just one big catch.

Capitalism is a complex system, and by 23, Anthony was totally bought-in.

“I was the No. 1 advocate, evangelist, gung-ho, fist-pumping capitalist,” he said. “I remember a friend of mine … called me Johnny Corporate.”

Anthony, whose real name we’re withholding for privacy reasons, had a meteoric rise. He skipped college for a promotion at the wireless company he’d worked for in high school; by 21 he was earning six figures, and by 23, he was managing employees all around the Midwest.

Then the Great Recession hit, and Anthony had a long way to fall. He hadn’t saved anything. He couldn’t get a job that paid anything close to his old one. He maxed out credit cards and took out loans, joining the wave of older Americans who enrolled at for-profit online colleges. He accumulated a lot of debt.

Like, a lot of debt. Enough that Anthony started looking for loopholes. Defer student loans forever? Bankruptcy? Anthony used to be the No. 1 capitalist, but now he was starting to feel scammed by the system, and he kept looking for a way to claw his way back to his old life.

“We live in an ecosystem of complex systems,” he said. “And eventually, if looked at long enough, all systems can be gamed.”

On today’s show we’ll follow Anthony’s path deep into debt and look at how he eventually gamed the system. He walked away from his debts, never looked back, and so far has avoided any financial consequences. It’s the story of the ultimate loophole, one that might leave you wondering if Anthony is the scammer or the one being scammed.

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