Tax Day Countdown: What Business Owners Can Still Do Before March 15 Or April 15

Tax season does not usually fall apart because someone is careless.

It falls apart because someone waited.

In Season 2, Episode 3 of Tax Talk Unfiltered, Spencer is joined by Julie Susskind, Head of Tax at Gelt, and Adam Bolitho, Tax Manager, to break down what procrastination really costs business owners and what you can still do before the tax deadline.

The goal was simple. Help founders and high income professionals avoid last minute mistakes, make smart decisions before filing, and set up a cleaner and more optimized year ahead.

As Spencer put it:

“Garbage in, garbage out. We can’t care about your taxes more than you do.”

Watch The Full Episode

Why Procrastination Costs Business Owners Real Money

Procrastination in tax planning rarely shows up as one dramatic error. It shows up quietly:

• Financial statements that are mostly done but not clean
• Payroll that was not structured properly
• Deductions that were not tracked in real time
• Strategy conversations happening after the year is already closed

Julie explained it clearly:

“Our strategies are only as good as the information you give us.”

When books are half ready, the process slows down. Returns get delayed. Planning gets compressed. Instead of optimizing, your CPA is cleaning up.

For business owners, clean financials are not just about compliance. They are the foundation for strategic decisions. Without them, you lose options.

Tax Filing Versus Tax Optimization

Adam drew an important distinction:

“Filing is simply reporting what’s already been done. Optimization is identifying opportunities during the course of the year and executing them.”

Most people treat taxes as a once a year event. They gather receipts, send documents to their CPA, sign a return, and move on.

That is filing.

Optimization looks different. It includes:

• Quarterly projections
• Retirement contribution planning
• Payroll structuring
• Entity strategy
• Investment decisions aligned with tax impact
• Long term deferral strategy

Adam added:

“The real opportunity in retirement planning isn’t just the current year deduction. It’s the tax deferral over 20, 30, even 40 years.”

If you start thinking about taxes in January, many of your best moves required action by December 31.

At that point, you are documenting history. You are not shaping outcomes.

What You Can’t Do Anymore If You Waited

By February, several strategies are generally locked in because they required year end execution.

These often include:

• Capital loss harvesting
• Charitable contributions for the prior year
• Roth conversions
• Certain S corp payroll corrections
• Deduction timing decisions for cash basis businesses

As Adam said:

“If you don’t start thinking about your taxes until the new year, you’re pretty much just a record keeper.”

Record keeping is necessary. It is not strategic.

What You Can Still Do Before The Tax Deadline

The good news is that not everything is closed.

Depending on your structure, you may still be able to:

Make Retirement Contributions

• IRA contributions before the filing deadline
• HSA contributions if eligible
• Certain employer retirement contributions, particularly for S corps if the plan was established properly

Capture Overlooked Deductions

• Home office deductions
• Vehicle mileage or actual expense tracking
• Health insurance premiums run through the business
• Business expenses that were categorized incorrectly or missed

Use Extensions Strategically

Extensions are often misunderstood.

Julie addressed this directly:

“An extension is a tool the IRS gives you. There’s nothing wrong with it.”

An extension gives you additional time to file. It does not give you additional time to pay. You still need to estimate and pay your tax liability as accurately as possible to avoid penalties and interest.

Extensions can reduce rushed errors and prevent costly amendments.

Julie made this point clearly:

“If we’re comparing risk, I would put an amendment much higher up there than an extension.”

Extensions are normal. Amendments reopen closed years and can invite unnecessary scrutiny.

Avoiding A Cash Flow Crunch On March 15 Or April 15

Surprise tax bills rarely come from nowhere. They usually come from a lack of forecasting.

Adam’s advice was direct:

“Treat taxes like a recurring operating obligation.”

That means:

• Running quarterly projections
• Setting aside funds intentionally
• Using conservative estimates
• Aligning liquidity with expected liabilities

Adam also described working with a client who used portfolio rebalancing to generate cash for a tax payment while improving diversification. That is holistic planning. Tax, investments, and cash flow should not be separate conversations.

Penalties and interest are preventable. Adam described the alternative as:

“Almost like credit card debt to the U.S. government.”

The Reset: How To Make Next Year Easier And More Optimized

If this tax season feels rushed, treat that as feedback.

Julie’s advice focused on systems:

“It’s so imperative that you have the right foundation.”

That foundation includes:

• A real bookkeeping platform
• Clean and updated financial statements
• Proper payroll setup
• Organized documentation
• Regular check ins with your tax advisor

Without clean data, strategy becomes guesswork.

With clean data, tax planning becomes proactive.

That is the shift Gelt pushes every client to make.

The Bottom Line

Between now and the tax deadline, you still have opportunities. More importantly, you have a chance to reset how you approach taxes.

Do not treat tax as a filing activity.

Treat it as strategy.

File accurately.
Pay intentionally.
Plan earlier.

Most firms meet at tax time.

We turn tax strategy into a year round growth lever.

If you are a founder, investor, or business owner who wants cleaner books, proactive projections, and real optimization, Gelt can help you move from compliance to strategy.