The Deductibles // May 2026

⚠️ Deadlines That Matter This Quarter

📅 June 15 – California PTET prepayment If your business is electing PTET in California for 2026, the prepayment is due June 15. Greater of $1,000 or 50% of your 2025 PTET liability. Under the new rules (SB 132), missing it costs you 12.5% of the credit, not the whole election, but a real number on a real deduction.

📅 June 15 – New York PTET Q2 estimate For entities that elected NY PTET by March 15, the Q2 estimated payment is due June 15 through NYS Online Services. Missed the March 15 election? NY PTET is off the table for 2026 entirely, your next window is 2027.

📅 June 16 – Q2 federal estimated tax payments 2026 Q2 estimates are due. The number you owe depends on your year-to-date income picture, not last year's. A surprising number of underpayment penalties trace back to owners paying off stale safe-harbor numbers when their business has grown.

📅 June 16 – U.S. citizens abroad Automatic two-month extension to file 2025 returns.

📅 September 15 – Q3 estimated payments On the radar but not urgent yet.

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 Books Problem Most Owners Don't Know They Have

Read the summary below and check out our latest video about what good bookkeeping looks like in practice. 👉 Watch it here

Here's the pattern we kept hitting across the 2025 filing season, at every revenue level from $250K solo operators to multi-million dollar operations. The owners who paid the most in tax weren't the ones with the worst businesses. They were the ones whose financial picture was too messy to support real strategy.

It looks like this:

• Revenue and expenses tracked in a spreadsheet, sent over at year-end

• Personal and business expenses commingled on the same credit card

• A QuickBooks file no one has touched in months

• Payroll booked as guaranteed payments, or vice versa

• Receipts living in an email inbox waiting to be sorted

Why this drains money

A tax strategist is only as good as the data they're working with. When books are clean, we can identify deductions, model entity decisions, optimize timing, and run real planning. When they're not, the engagement gets eaten by reconstruction. The deductions still on the table when April 15 hits are the ones easy enough to find in chaos. Everything else gets left behind.

We watched this play out in real dollars this season. Same business size, same industry, same income, the client with clean monthly books paid materially less in tax than the client whose books got pulled together at the eleventh hour. Not because their CPA was smarter, but because their CPA had something to work with.

What good looks like

• A separate business bank account

• A separate business credit card

• A bookkeeper closing your books monthly (not a CPA, not you)

• Clean separation of personal and business expenses from day one

🎯 Four Mid-Year Moves with Real Dollar Impact

These aren't tips. They're the moves we're actually running with clients right now.

1. Cost segregation on real estate. If you own qualifying property (short-term rentals, real estate professional status, business-owned real estate) a cost segregation study can accelerate years of depreciation into the current year. On a $1M property, that's typically $150K to $300K in first-year deductions. The catch: it has to be done before you file your 2025 return to apply to that year. Mid-year is when to scope it.

2. Form the LLC now if S-corp is on the horizon for 2026. S-elections only backdate to the entity's formation date. We see this every fall: an owner crosses $100K in net income, comes to us as a great S-corp candidate, but doesn't have an LLC. We can elect, but only back to when the LLC was formed, which often means losing six to ten months of self-employment tax savings. Get the LLC in place now, even as a dormant placeholder. That preserves the option.

3. Clean books, or no real strategy. The single biggest reason owners miss deductions isn't ignorance. It's that their books are too messy for their CPA to find anything in the first place. A separate business account, a separate business credit card, and a bookkeeper closing your books monthly. Without that foundation, any tax strategy is theoretical.

4. Bonus depreciation is back to 100%. Fully restored, no current phase-out on the horizon. For owners considering a significant equipment purchase, heavy vehicle, or business asset in a strong-income year, accelerating the purchase into 2026 can shift the timing of a large deduction into a year that needs it. The math gets meaningful quickly on six-figure purchases.

If these strategies are relevant to you: Schedule a call with Gelt today →

🤝 The Gelt Partner Ecosystem - New Additions

Most tax firms stop at the return. Gelt goes further with a vetted partner network that connects bookkeeping, wealth management, banking, spend management, and investment strategy back to our clients tax plan — so the strategy actually gets executed.

Recent additions include:

• Prometryx — Tech-enabled bookkeeping with dedicated support for reporting, AP/AR, and year-round tax-ready books. Learn more or contact [email protected]

• Peterson Rogers Private Wealth — Personalized wealth management and financial planning for high-net-worth individuals, families, and business owners. Learn more or contact [email protected]

• Brex — Financial operations platform for banking, cards, and spend management. Gelt clients receive 50,000 bonus Brex points upon activation. Learn more

• Mercury — Modern banking and financial software platform offering Gelt clients up to $1,000 in rewards plus expedited onboarding and support.

• Eckard Enterprises — Direct-access oil and gas investment opportunities backed by 40 years of industry expertise. Learn more or contact [email protected]

Check out all of our partners on our partner page! Linked here

📰 In the News

📰 Entrepreneur Media 
Gelt CEO Tal Binder was featured in Entrepreneur with a piece on the timing question most business owners get wrong: when to actually evaluate your CPA. The short version: tax season has no room to think, year-end has no time to act, and Q2 is the only window where you have both a full year of evidence and enough runway to influence what happens next. If you've ever wondered whether your current tax preparer is the right fit, the timing of that question matters more than the answer.
👉 Read the piece

📰 MoneyLion 
Rachel Richards, CPA was featured in MoneyLion on the investing mistake even high-net-worth investors make: ignoring the tax side. Wealth doesn't fix the problem, it usually makes it bigger. Rachel walks through the patterns she sees across high earners, from year-end loss harvesting done as panic instead of strategy to charitable giving used as a feeling instead of a tool.
👉 Read the piece

🔗 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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💼 Explore our Partner Ecosystem to see how we extend beyond the return