Podcast Summary: "We Haven't Filed Taxes Since 2020"

Podcast: The Ramsey Show Highlights
Date: March 25, 2026
Host: Ramsey Network (Dave Ramsey, Rachel Cruze, Financial Expert/Coach, Todd)
Duration: Under 10 minutes

Overview

This episode features callers with pressing money and life questions, focusing primarily on a couple’s struggle with unfiled taxes due to years of chaos caused by addiction, and a second caller seeking advice about purchasing a Harley Davidson motorcycle. The hosts—led by Rachel Cruze and Dave Ramsey—deliver practical, urgent financial coaching with a clear, candid tone.

Key Discussion Points & Insights

1. Overcoming Financial Consequences after Addiction

(00:11–05:55)

Background:
The first caller, a stay-at-home mom, shares a candid account of her family's history. Her husband, a small business owner, battled alcoholism for many years, resulting in financial disarray and not filing taxes since 2020. Three years into sobriety, their business is finally thriving, but they face a "looming black cloud" of unfiled tax returns.

Discussion & Advice:

• Urgency of Filing:
  Rachel Cruze immediately stresses the legal severity of not filing taxes:

  "Failure to file income tax returns is a federal criminal offense." – Rachel Cruze [01:08]
  Notably, she distinguishes this from failing to pay taxes, which does not typically result in jail.

• IRS and Filing Strategy:
  Rachel reassures the caller that the IRS is generally lenient when individuals "come out of the cold" willingly:

  "The number of times that the IRS prosecutes someone who comes out of the cold, off the grid, on their own is almost zero." – Rachel Cruze [01:47]

• Action Plan:

  • Immediately contact a reputable tax preparer, preferably a Ramsey Solutions Trusted Pro.
  • Reconstruct the last 3–4 years' tax documentation as accurately as possible, even if records are incomplete.
  • File the overdue returns and address any back taxes with a payment plan if needed.

    "You need to file something because they're probably not going to look at it. They're probably just going to be happy that somebody just showed up and started giving them money." – Rachel Cruze [02:45]

• Employee Classification:
  There’s a red flag regarding tax documentation for 1099 employees in the husband's business. Rachel notes that many entrepreneurs misclassify workers as 1099:

  "I think you're going to find when you delve into this that they're not really 1099." – Rachel Cruze [04:04]
  She suggests the tax advisor address this as well.

• Financial Standing:
  The family is in a relatively strong financial situation post-recovery, with household income back up and their debts mainly in houses, cars, and some credit cards.

  "We're bringing in close to 20 to 30,000 a month... probably making five grand a month [after expenses]." – Rachel Cruze & Caller [05:13–05:28]

• Hopeful Perspective:
  The hosts highlight that in rough years, the family may not owe as much tax as feared. Proactive communication with the IRS is crucial:

  "It may not be as bad as you think when you actually... taxes on it if you didn't make much." – Rachel Cruze [05:34–05:37]
  They encourage, "Come in out of the cold as quick as you can." – Rachel Cruze [05:54]

Memorable Quote:

"People do not go to jail in America for not paying taxes. They do go to jail... for not filing." – Rachel Cruze [01:22]

2. Should I Buy a $50,000 Harley?

(06:07–08:45)

Background:
Todd from Lexington calls in, debating whether or not to buy a new $50,000 Harley motorcycle. He and his wife are nearing retirement. They have no debt, substantial retirement savings, and good cash reserves. Todd's wife is already retired, and he plans to retire in five years.

Discussion & Advice:

• Can You Afford It?
  Rachel responds directly:

  "I would buy the Harley, but I also would tune up my investments and make sure we're putting a good amount because you're making really good money and you could really stack some cash and buy a lot of things later that you want to buy. But right now you can afford the Harley for sure." – Rachel Cruze [07:03–07:13]

• Asset Values and Priorities:
  Rachel brings attention to the disproportionate value of a motorcycle compared to daily vehicles:

  "You understand that your motorcycle is going to be your most expensive vehicle now, right?" – Rachel Cruze [07:54–08:00]
  Todd affirms, and it’s acknowledged that the new Harley will depreciate.

• Retirement Preparedness:
  Rachel advises Todd to consult with a SmartVestor Pro to optimize investments:

  "If you're making 350, you should have more money stacked than what you've got stacked. So I want you to increase your investment goals so that you have got millions later to do stuff with." – Rachel Cruze [08:11–08:45]

Memorable Moment:
Rachel brings some levity to the financial reality:

"Your toy is worth more than your other cars that you drive every day." – Rachel Cruze [08:00–08:05]

Notable Quotes

• "Failure to file income tax returns is a federal criminal offense." – Rachel Cruze [01:08]
• "The number of times that the IRS prosecutes someone who comes out of the cold, off the grid on their own is almost zero." – Rachel Cruze [01:47]
• "I don't care. We have to reconstruct something. The best you can do." – Rachel Cruze [02:37]
• "Come in out of the cold as quick as you can." – Rachel Cruze [05:54]
• "Your toy is worth more than your other cars that you drive every day." – Rachel Cruze [08:00–08:05]
• "If you're making 350, you should have more money stacked than what you've got stacked." – Rachel Cruze [08:11–08:45]

Timestamps for Important Segments

• [00:11] – Caller’s family and addiction backstory
• [01:08] – Legal seriousness of not filing taxes
• [01:47] – IRS approach to voluntary filers
• [02:07] – How to get professional tax help and reconstruct records
• [04:04] – 1099 contractor warning for small business owners
• [05:02] – Family debt and current income assessment
• [05:54] – Urgent advice to contact the IRS proactively
• [06:07] – Caller Todd wants to buy a $50,000 Harley
• [07:03] – Can Todd afford this big purchase?
• [08:00] – The Harley as his most valuable vehicle
• [08:11] – Retirement, investments, and financial priorities

Tone and Takeaways

The hosts remain compassionate, direct, and sometimes humorous, focusing on clarity and actionable advice. Their style combines tough love ("Come in out of the cold as quick as you can") with reassurance and practical solutions, making the episode candid and constructive for anyone overwhelmed by tax or major purchase decisions.