Coming at you a day early this week. It's April 15. This can't wait.

(Plus a can't-miss webinar happening tomorrow. More below.)

HAPPY TAX DAY

Every April 15, Donald Rumsfeld mailed a letter to the IRS alongside his tax return.

Same letter. Every year. This is the 2014 version.

"The tax code is so complex and the forms are so complicated, that I know that I cannot have any confidence that I know what is being requested and therefore I cannot and do not know, and I suspect a great many Americans cannot know, whether or not their tax returns are accurate."

This was the Secretary of Defense. Twice. The man who ran the Pentagon.

And he couldn't figure out his own taxes.

He died in 2021. The tax code got worse.

The great @dougboneparth put it best this morning:

Here's what to handle before midnight.

FILE AN EXTENSION IN 5 MINUTES

If your return isn't done, don't panic. File an extension.

Go to directpay.irs.gov. Select "Extension" as the reason for payment. Enter your info. Pay what you estimate you owe.

That's it. The payment IS your extension. No Form 4868 needed.

You now have until October 15 to file.

6 EXTRA MONTHS TO FILE. ZERO EXTRA DAYS TO PAY.

This is where people get burned every year.

The extension gives you more time to file. Not more time to pay.

Interest and penalties start running TODAY on any unpaid balance. The IRS doesn't penalize you for late paperwork. They penalize you for late money.

Not sure what you owe? Estimate high. An overpayment gets refunded. An underpayment gets penalized. Pick the one that doesn't cost you.

CHECK YOUR STATE

Some states piggyback on the federal extension. California, New York, and Illinois accept the federal extension automatically.

Others don't. Virginia and Georgia require a separate state filing.

Don't assume your state follows the feds. Look it up before midnight.

YOUR Q1 ESTIMATE IS ALSO DUE TODAY

Two deadlines. Same day. Different purposes.

If you're self-employed or have pass-through income, your Q1 2026 estimated tax payment is also due April 15.

The extension payment covers 2025 taxes you still owe. The estimated payment covers 2026 taxes you will owe. They are separate obligations.

MY MOVE: THE OVERPAYMENT CUSHION

Here's what I do every year.

I overpay my extension. On purpose.

The IRS applies the overpayment as a credit. I roll that credit forward to cover my Q1 estimate. One payment. Both obligations handled.

I start Q2 with a cushion built in. Costs nothing. Buys margin. I've done it for years.

🎯 TOMORROW AT NOON CT: DEALKILLERS

Last week I introduced Bedrock Quality of Earnings. Tomorrow you get to see the team in action.

Michael Girdley is sitting down with Will McCurdy, CEO of Bedrock, for a live session on how sellers hide problems in the numbers.

Will spent years doing QoE reports at PwC and RSM. He's seen every trick.

What they're covering:

• Where sellers inflate profits before a sale

• The 5 deal-killers in financial due diligence

• How to use findings to renegotiate the price

• Live Q&A

👉 Sign up here

Can't make it live? Register anyway. They'll send you the recording.

Until next time,

P.S. If you haven't filed and haven't extended, directpay.irs.gov before midnight. Five minutes. Do it now.

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