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- The Deductibles // August 2025
The Deductibles // August 2025
Labor Day reminder: don’t let taxes take more than their share ⚖️

Hi there deadline dorks!
Labor Day may mark the unofficial end of summer, but when it comes to taxes, the work is just getting good. This month is all about honoring your hard work by putting deadlines to work for you—keeping cash moving, sharpening your strategy, and making sure you head into fall in control, not catching up.
The Highlights -
📅 September’s stacked deadlines
💸 Estimated taxes done right
📢 in partnership with All The Hacks - Live Q&A on running a business
🔥 Fresh strategies to level up your tax game
💬 What we’re hearing from our Gelt community
⚠️ Upcoming Deadlines
📆 September 8:
Last day to send your individual tax information and guarantee filing by October 15.
📆 September 15:
Q3 Estimates for individuals
Extended deadline for S Corporations
Extended deadline for Partnerships
📆 September 30:
Extended deadline for trusts
If we were you, we’d check in with our CPA, if they haven’t done so yet.
💸 Estimated Taxes Done Right
The IRS expects tax to be paid as you earn income. If you’re earning income from businesses or investments that don’t have taxes taken out automatically, that’s where quarterly estimates come in.
The IRS lets you stay penalty-proof by paying a safe harbor amount of:
90% of this year’s expected tax, OR
110% of last year’s tax (100% if your household income was under $150K).
As long as you pay the safe harbor amount, you’re protected from penalties even if your final tax bill is higher.
Here’s the opportunity: penalties aren’t really “penalties,” they’re about 8% annualized interest. That means you can weigh whether it’s smarter to send cash to the IRS now, or keep it working harder in your portfolio or business.
Just FYI - Gelt clients get full support in estimating the cost of not making a payment automatically, so they can make an informed decision.
👉 Bottom line: estimates aren’t just compliance, they’re a cash flow strategy.
📢 Hosted by Chris Hutchins: 5 Tax Moves for Business Owners
Tax rules are shifting, and 2025 is the year to act. From deductions and credits to business structures and retirement accounts, the right strategies today can shape your financial future tomorrow.
Join us for a free live event with ATH on Thursday, September 18, from 12:00–1:00 PM PT.
We’ll break down the five moves every business owner should know to reduce taxes and build long-term wealth
Strategies Worth Knowing
📈 Qualified Small Business Stock (QSBS – Section 1202)
QSBS is one of the most powerful tax breaks in the code, and most people don’t even know it exists. If you hold qualifying startup stock long enough, you can exclude millions in gains when you sell.
Recent updates made it even better:
Partial exclusions start earlier (50% after 3 years, 75% after 4 years).
Full 100% exclusion at 5 years.
The per-issuer limit is now $15M, and larger companies (up to $75M in assets) can qualify.
👉 Founders, early employees, and investors: if you’re involved with a startup that might qualify, confirm their QSBS eligibility now and track acquisition dates carefully. This can be the difference between a life-changing exit and a life-changing tax bill..
🏠️ Home Office Deductions Done Right
If you run a business from home, part of your housing costs - utilities, insurance, even cleaning - can often be deducted. Too many people skip this because they assume it’s complicated or risky. It’s not.
There are two legitimate ways to calculate your deduction:
By square footage → If your office takes up, say, 8% of your home’s space, you can deduct 8% of eligible expenses.
By number of living areas → If you’ve got 5 living areas and use one exclusively as an office, that’s 20% - which can sometimes be more favorable.
👉️ Bottom line: don’t overthink it. Document your setup, sign up for Gelt and we can run both methods to make sure you don’t leave money on the table.
💝 Charitable Remainder Trusts: A Triple Win
If you’re sitting on a concentrated stock position, a real estate asset, or even a business interest, a CRT can be transformational.
Here’s the play:
You contribute the appreciated asset.
You avoid immediate capital gains when it’s sold.
You get an upfront charitable deduction.
You (or your family) receive income from the trust for years.
The remainder goes to charity at the end.
👉 CRTs turn a tax headache into a triple win: current tax savings, a long-term income stream, and a lasting legacy. Pair with a donor-advised fund if you want flexibility in how the charitable dollars are deployed.
💬 What’s Happening in Our Gelt Community
🏡 The Augusta Rule
Under the Augusta Rule, you can rent your personal residence to your business for up to 14 days per year. That rent is tax-free to you and deductible to the business.
🌟 Many of our clients are taking advantage of this for board meetings, client dinners, or offsites. Way to go!
💝 Charitable Giving, Done Smarter
Another theme: should I gift cash or stock? The smart answer is often stock. By donating appreciated assets, you avoid capital gains and still deduct the full fair market value.
🌟 For larger moves, donor-advised funds let you bunch multiple years of giving into 2025, securing a bigger deduction now while spreading out grants over time.
👨👩👧 Hiring Family Members
One of the simplest plays we’ve been helping clients with: putting family on payroll. It shifts income into your kids’ lower tax brackets, creates deductible wages, and even allows Roth IRA contributions for them.
🌟 One founder client recently shaved five-figures off their bill while setting their teen up with tax-free growth for decades.
🗞️ Gelt in the News
Explore where we’ve been featured this month:
Observer – Spencer discusses Why “Permanent” Tax Cuts Are a Temporary Advantage for High-Net-Worth Investors
HIT Consultant – Tal shares The Top 3 Tax Mistakes High-Earning Physicians Make
Go Banking Rates – Rachel reveals 5 Ways To Lock in Benefits From Trump’s New Tax Bill
Want to Reconnect?
🧪 Good news: all it takes is picking up our last email thread. I’ll take it from there. 🧠✨ Or email me at - [email protected]