Their Son Wants A Bailout After Racking Up $200,000 In Taxes, Interest, And Penalties. Dave Ramsey Says, 'I Probably Wouldn't' Step In Today

Thu, Sep 11, 2025, 1:01 PM 3 min read

Jeff and his wife are in their early 70s, comfortably retired in Indiana with a net worth of about $2.3 million. But now they're facing a painful decision: Should they sell off property or mutual funds to bail out their son, who owes more than $200,000 to the IRS?

Their 40-something-year-old son returned to Indiana from Los Angeles 11 years ago to take over Jeff’s insurance agency. Back in California, he’d gotten into tax trouble while working in the music industry as an independent contractor. Jeff helped him set up a repayment plan and assumed the lesson was learned.

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It wasn't.

“Many times I’d ask him if he was on this, and he’d just blow up and wouldn’t talk to me about it,” Jeff told Dave Ramsey and Jade Warshaw on a recent episode of “The Ramsey Show.”

Three months ago, his son called again with bad news: He hadn’t filed any state or federal taxes for the past four years and hadn't paid any estimated taxes for 2023. He also failed to pay 941 withholding or unemployment taxes.

Jeff estimated that half of the $200,000 his son now owes is from penalties and interest. His son recently resigned from the insurance job and is now in a new sales role earning about $75,000 a year plus bonuses.

“He has no business being self-employed, obviously,” Jeff said.

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This isn’t the first time Jeff and his wife have stepped in. Years ago, they had to pull their son out of high school and send him to a survival camp. They co-signed a car loan he couldn't keep up with. They paid for a private school in California.

“It’s just been one thing after another,” Jeff said. “I’m okay with no being the answer,” Ramsey interjected.

“Jade and I are both saying sadly, I probably wouldn’t,” he said. “Warshaw added that he was an adult earning a decent living, not living in poverty, and needed to take responsibility for himself.

Jeff had considered covering the tax bill using part of his son's future inheritance. But the numbers didn't add up, and he grew concerned about the IRS putting a lien on the family home.

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Ramsey pointed out that this and the bailout question are two separate issues. “Do I change the will in a few years? I might. You can change it now, you can change it later.”