Don't F---- with the tax man. I know of a peer that was playing a dangerous game with their books and taxes. I asked my accounting professor what might happen, and I used AI to reframe his response in the second person:
Let me be absolutely clear: if you think you can just “opt out” of paying taxes or doing bookkeeping because you don’t feel like it, you are playing a reckless and incredibly dangerous game. The IRS does not tolerate willful neglect. Failing to file or pay taxes isn’t just irresponsible—it’s illegal. You are exposing yourself to civil penalties that can rack up fast—5% per month for failing to file, and 0.5% per month for failing to pay, both capping at 25%, plus interest on top. That’s the light end of the consequences. Once you are flagged, audits can go back years, and if the IRS suspects willful evasion, they can escalate things to criminal charges. That means fines, prosecution, and yes—prison time. People have gone to jail for much less than simply deciding they don’t “feel like” filing.
And it doesn’t stop there. If you ignore the IRS long enough, the agency can start levying your bank accounts, garnishing your income, and seizing your assets—business and personal—without ever stepping into a courtroom. Unlike most creditors, the IRS doesn’t need a judgment to take your money; they just do it. And here’s the part that should really keep you up at night: tax debt is one of the few types of debt that cannot be discharged in bankruptcy. There is no reset button. That tax liability will follow you for years—possibly decades—with interest compounding the entire time. Even if your business fails and you try to wipe the slate clean, the IRS will still be there, waiting to collect, with the full force of the federal government behind them.
If you are serious about being an entrepreneur, you need to act like it. If not, be prepared for the reality check that’s coming—one that starts with a letter and ends with a lien. I strongly encourage you to fix this before it becomes a catastrophe. But if you stay on this path, the fear of God may come too late.
Let me be absolutely clear: if you think you can just “opt out” of paying taxes or doing bookkeeping because you don’t feel like it, you are playing a reckless and incredibly dangerous game. The IRS does not tolerate willful neglect. Failing to file or pay taxes isn’t just irresponsible—it’s illegal. You are exposing yourself to civil penalties that can rack up fast—5% per month for failing to file, and 0.5% per month for failing to pay, both capping at 25%, plus interest on top. That’s the light end of the consequences. Once you are flagged, audits can go back years, and if the IRS suspects willful evasion, they can escalate things to criminal charges. That means fines, prosecution, and yes—prison time. People have gone to jail for much less than simply deciding they don’t “feel like” filing.
And it doesn’t stop there. If you ignore the IRS long enough, the agency can start levying your bank accounts, garnishing your income, and seizing your assets—business and personal—without ever stepping into a courtroom. Unlike most creditors, the IRS doesn’t need a judgment to take your money; they just do it. And here’s the part that should really keep you up at night: tax debt is one of the few types of debt that cannot be discharged in bankruptcy. There is no reset button. That tax liability will follow you for years—possibly decades—with interest compounding the entire time. Even if your business fails and you try to wipe the slate clean, the IRS will still be there, waiting to collect, with the full force of the federal government behind them.
If you are serious about being an entrepreneur, you need to act like it. If not, be prepared for the reality check that’s coming—one that starts with a letter and ends with a lien. I strongly encourage you to fix this before it becomes a catastrophe. But if you stay on this path, the fear of God may come too late.
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