The Deductibles // June 2026

📅 The Deadlines Worth Getting Ahead Of

A few dates are coming. The difference between a proactive firm and a reactive one shows up in what happens before them, not after.

• September 15, Q3 estimated payment. Wait until you're scrambling and you risk underpayment penalties on income you could have planned around months earlier. A mid-year projection tells you the number now, while there's still time to adjust.

• September 15, extended partnership and S-corp returns. If you extended, the months between filing and this date are prime planning time. The real question is whether anyone is using them.

• October 15, extended individual and C-corp returns. Same test. A good extension buys time for strategy. A reactive one just postpones the data entry.

Not sure if your current setup is adjusting estimates based on real data? That's exactly what a Gelt tax strategist can help you figure out. Schedule a call →

🎯 The Summer Planning Window Most Firms Skip

Here's the mechanic that makes timing everything. When a business restructures (an S-election, a new entity, a smarter income setup), the savings only apply to income earned after the change is in place. You can't reach back and reallocate income you've already earned. A structure set up in summer works for most of the year. The same move in December captures a few weeks of benefit while still costing a full year's corporate return.

That's why the calendar matters as much as the strategy. The moves below take time to do right, and the runway to do them is now, not in Q4:

• Withholding and estimated payment true-up. Six months of real income is enough to see where you'll land and close the gap before it becomes a penalty.

• Retirement contribution pacing. A solo 401(k), SEP, or defined benefit plan can shelter real money, but only if it's funded on a schedule that starts now, not in a December rush.

• S-corp reasonable compensation. The right salary-to-distribution split can save thousands in payroll tax. Set it wrong and you either overpay or put the election at risk.

• Entity structure and cost segregation. An entity change or a cost segregation study can move six figures for the right owner, and both need lead time to execute before year-end.

• Charitable planning. Planned early, giving opens up smarter, better-timed options. Left to December, it's whatever's left.

None of this happens on its own. It happens when someone is actually looking at your situation in the middle of the year.

🤖 From Our CEO: What AI Can't Replace in Your CPA

Tal Binder, Gelt's CEO, takes on a question a lot of business owners are quietly asking: if AI is this good, do I still need a human tax expert?

His answer: AI is excellent at the high-volume, rules-based work, categorizing, reconciling, filing accurately. But a clean return is the floor, not the ceiling. Accuracy doesn't lower your bill. The strategy, judgment, and trust that change your outcome are still human, and that's exactly where a firm should be spending its time.

It's a useful lens for whoever does your taxes now: are they handing you a correct return, or actually changing the number?

📖 Read Tal's full take: AI won't replace your CPA

🎙️ New Podcast: Why Proactive Planning Beats the March Scramble

On the latest Tax Talk Unfiltered, Gelt's Spencer Carroll, CPA sits down with senior tax managers Julie Susskind and Adam Bolitho to break down why the moves that lower your bill happen months before anything gets filed.

They get into the strategies most people miss by waiting, pacing retirement contributions instead of cramming them in December, timing charitable giving, and the S-corp and PTE chain reaction, plus a real example: an owner who came in mid-year with short-term rentals and recovered more than $50,000, because the timing left room to do it right.

It's a window into how a proactive team actually thinks.

🎧 Watch the episode: Tax Talk Unfiltered

📖 Or read the companion article: Proactive tax planning and why timing matters

📰 Gelt in the News

The case for proactive, year-round planning is getting picked up:

• Kiplinger: Rachel Richards, CPA on why Q2 is the start of next tax season, not the calm after the last one.

• Entrepreneur: CEO Tal Binder on why a surprise tax bill is rarely a tax problem, and the four breakdowns behind it.

• Medical Economics: Spencer Carroll, CPA on how to actually use a tax extension. More time to file, not more time to pay.

📻 On the airwaves: Spencer Carroll, CPA also joined the Financial Freedom for Physicians and BootstrapMD podcasts on physician tax strategy.

The Bottom Line

If your tax advisor's last contact was a deadline reminder and not an idea, you're getting compliance, not strategy. There's still half a year left to change what you'll owe, and this is the window to do it.

Talk to our expert tax team now. Schedule a call →

🔗 Let's Connect

📧 Send us a message — share your ideas, questions, or topics you'd like to see in future editions with us at [email protected]

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