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Real Estate Investor With 27 Properties Hasn't Filed Taxes in a Decade: "Most of That Income Is in Cash"

MarketDash Editorial Team
23 hours ago
A Minnesota landlord pulling in up to $15,000 monthly from 27 rental properties hasn't filed federal taxes since 2016. Now he needs a mortgage and discovers lenders have questions about that.

Here's a situation that starts bad and gets progressively worse: A Minnesota real estate investor named Claude called into The Ramsey Show on Wednesday with what you might call a self-inflicted financial crisis. He owns 27 rental properties, most of them paid off. He's collecting $10,000 to $15,000 per month in rental income. And he hasn't filed federal taxes since 2016.

The Cash Income Problem

Claude recently bought a home through private financing and now wants to convert it to permanent financing. There's just one small issue: mortgage lenders tend to ask for tax returns. It's kind of their thing.

When pressed by co-host George Kamel about his income, Claude offered this memorable explanation: "I haven't, I don't really, on paper, I guess, show making a bunch. Most of that income is in cash and you've spent it."

That's not exactly the answer that makes tax professionals sleep easy at night.

The IRS Doesn't Forget

Kamel didn't mince words about the severity of Claude's situation. "The last people you want on your back is the IRS. They can destroy your life. I know that's right. And so I would not ignore this any longer," he warned.

His advice was straightforward: hire a CPA or enrolled agent immediately to calculate the tax liability and explore payment plan options. Co-host Jade Warshaw added simply, "You got to do this with integrity, my guy."

A Pattern of Tax Troubles

Claude wasn't the only caller facing tax compliance issues that day. Tyler, who owns a Florida moving company, reported $1.9 million in revenue with rising profits. Dave Ramsey counseled him against chasing write-offs through unnecessary purchases, suggesting he focus on paying down personal debt and work with an accountant on legitimate depreciation strategies.

Another caller, a single father earning $80,000, confessed to three years of unfiled returns. Ramsey estimated he could owe around $60,000 plus penalties and stressed a critical distinction: it's the failure to file, not the failure to pay, that can lead to criminal charges. The legal risk isn't theoretical.

The common thread across these calls? Taxes don't disappear just because you ignore them. Whether you're running a moving company, collecting rent checks, or working a regular job, the IRS eventually comes calling. And when they do, having professional help and a plan beats hoping the problem solves itself.

Back to News

Real Estate Investor With 27 Properties Hasn't Filed Taxes in a Decade: "Most of That Income Is in Cash"

MarketDash Editorial Team
23 hours ago
A Minnesota landlord pulling in up to $15,000 monthly from 27 rental properties hasn't filed federal taxes since 2016. Now he needs a mortgage and discovers lenders have questions about that.

Here's a situation that starts bad and gets progressively worse: A Minnesota real estate investor named Claude called into The Ramsey Show on Wednesday with what you might call a self-inflicted financial crisis. He owns 27 rental properties, most of them paid off. He's collecting $10,000 to $15,000 per month in rental income. And he hasn't filed federal taxes since 2016.

The Cash Income Problem

Claude recently bought a home through private financing and now wants to convert it to permanent financing. There's just one small issue: mortgage lenders tend to ask for tax returns. It's kind of their thing.

When pressed by co-host George Kamel about his income, Claude offered this memorable explanation: "I haven't, I don't really, on paper, I guess, show making a bunch. Most of that income is in cash and you've spent it."

That's not exactly the answer that makes tax professionals sleep easy at night.

The IRS Doesn't Forget

Kamel didn't mince words about the severity of Claude's situation. "The last people you want on your back is the IRS. They can destroy your life. I know that's right. And so I would not ignore this any longer," he warned.

His advice was straightforward: hire a CPA or enrolled agent immediately to calculate the tax liability and explore payment plan options. Co-host Jade Warshaw added simply, "You got to do this with integrity, my guy."

A Pattern of Tax Troubles

Claude wasn't the only caller facing tax compliance issues that day. Tyler, who owns a Florida moving company, reported $1.9 million in revenue with rising profits. Dave Ramsey counseled him against chasing write-offs through unnecessary purchases, suggesting he focus on paying down personal debt and work with an accountant on legitimate depreciation strategies.

Another caller, a single father earning $80,000, confessed to three years of unfiled returns. Ramsey estimated he could owe around $60,000 plus penalties and stressed a critical distinction: it's the failure to file, not the failure to pay, that can lead to criminal charges. The legal risk isn't theoretical.

The common thread across these calls? Taxes don't disappear just because you ignore them. Whether you're running a moving company, collecting rent checks, or working a regular job, the IRS eventually comes calling. And when they do, having professional help and a plan beats hoping the problem solves itself.