Editor’s Note
Welcome to the first issue of this newsletter. I have been wanting to do this for a while. One email a month that makes the tax and money side of your life feel a little less overwhelming and a lot more manageable.
I am sending this to current clients and a few people I have had the pleasure of connecting with recently. If we have not worked together yet, consider this a small taste of how I think about this stuff. And if it is not for you, there is an unsubscribe link at the bottom, no hard feelings at all.
My practice specializes in equity compensation and tax complexity, but that complexity shows up in a lot of different places. For some of you it is RSUs, stock options, or a pending liquidity event. For others it is running a business, navigating complex deductions, or trying to make smarter decisions about what you keep at the end of the year. Each month this newsletter speaks directly to both. You will always find something relevant to your situation.
No jargon. No noise. Just what you actually need to know.
Matt Curtin, CPA
ON THE CALENDAR
June and Upcoming Dates to Know
June 15: Q2 Estimated Tax Payment Due
If you are self-employed, own a business, or have significant investment or equity income, your second quarter estimated payment is due. Before you send that payment, make sure the number actually reflects where your year is headed, not just what you paid last year. If you are unsure, reply to this email.
Ongoing Through June: Mid-Year S-Corp Salary Review Window
June is the sweet spot for reviewing reasonable compensation for S-corp owners. Adjustments made now can still be implemented before year-end. Waiting until December leaves very little room to maneuver.
September 15: Business Return Extended Deadline
If your partnership or S-Corp filed an extension back in March, September 15 is your deadline. That is closer than it sounds. If we have not started gathering your business documents, now is the time to get moving.
MARKET MINUTE
What’s Happening and What It Means for You
After a strong 2025, markets have been choppier this year. The conflict in the Middle East has been the dominant story, with the situation involving Iran disrupting global oil supply and pushing Brent crude prices as high as $140 per barrel at points this spring. Prices have since pulled back to around $92 on ceasefire optimism, but headline-driven volatility remains elevated. Tariffs and policy uncertainty have added to the turbulence throughout.
The good news is that corporate earnings have held up better than expected, with S&P 500 earnings growth tracking nearly 28% year over year through Q1. The honest take: short-term market noise rarely changes what you should be doing with your financial plan. What it can do is create planning opportunities worth paying attention to, and that is what the next section covers.
THE PLANNING ANGLE
What This Market Means for Your Situation
Your situation is specific. Here is what is most relevant depending on where you are coming from.
FOR EQUITY COMP PROFESSIONALS
The Tax Trap Hiding in Your Vesting Schedule
This is one of the most common and costly mistakes I see, and market volatility makes it more urgent right now.
The withholding problem: When RSUs vest, most companies automatically withhold 22% for federal taxes. For professionals in higher tax brackets, that is often not enough. The gap between what was withheld and what you actually owe tends to show up as a surprise bill every April. If that happened this year, now is the time to fix it before the next vesting event.
Why market swings matter here: Volatility directly affects the value of your shares at the moment they vest, which changes your tax bill in ways that are hard to predict without a plan. A vesting event during a market dip means less income recognized. A vesting event during a rally can push you into a higher bracket than expected. Neither outcome should catch you off guard.
On concentrated positions: If a significant portion of your net worth sits in a single company's stock, the tax planning around any future sale becomes complex fast. Understanding the tax implications of that position now, before you are forced to act, is something worth putting on the agenda. That is a conversation I can help frame even if the investment decision itself belongs with a financial advisor.
Worth knowing: The IPO market is active this summer. If you hold pre-IPO equity or options at a company approaching a public offering, the 90 days surrounding a lockup expiration are some of the most consequential from a tax standpoint. The decisions around timing and sequencing that sale against your other income can make a significant difference in what you actually keep. If that situation applies to you, this is worth a dedicated conversation before the window opens.
FOR ENTREPRENEURS
Your Q2 Payment Deserves a Real Look This Year
Most business owners and self-employed professionals set their estimated tax payments once and leave them on autopilot. That works in stable years. This is not a stable year.
If your revenue is up, your deductions have changed, or you have made any structural moves in 2026, the number you paid in April may be meaningfully off in either direction. Underpaying creates a penalty situation next April. Overpaying means you gave the IRS an interest-free loan for months.
The bigger opportunity right now: The One Big Beautiful Bill Act (OBBBA) restored 100% bonus depreciation for equipment placed in service after January 2025. If you have been considering a major purchase for your business, the tax case for doing it before year-end is strong. That changes the math on your full-year projections and your estimated payments at the same time.
June is also the right time for S-Corp owners to review reasonable compensation. The window to make changes that matter for 2026 is open now. It closes faster than most people expect.
QUICK HITS
A Few Other Things Worth Knowing
The QBI deduction is now permanent. The OBBBA made the 20% qualified business income deduction permanent for pass-through owners. If you have a pass-through business of any kind, this is one of the most valuable deductions in the tax code and it is not going away. Make sure your planning is built around it.
529 plans got more flexible. The OBBBA broadened qualified expenses for 529 accounts, giving families more ways to use the funds without penalty. If you have a 529 and have been unsure whether your planned expenses qualify, the answer may have changed in your favor.
Withholding mismatches are more common than you think. Several OBBBA changes that began in 2025 carry into 2026, and many people have a gap between what their paycheck withheld and what the law now allows. If your tax situation changed this year, a quick review now prevents a larger surprise later.
FROM MY DESK
Let's Keep the Conversation Going
If anything in here is relevant to your situation and you want to dig deeper, just reply to this email. That is exactly what this is here for.
Looking forward to being in your corner every month.
Matt Curtin, CPA
P.S. If you know someone dealing with equity compensation or tax complexity who could use a clearer picture, feel free to forward this along. They can reply to this email to get on the list.
Visit us at kindledplanning.com