Nicolas DiDonato CPA

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Nicolas DiDonato CPA Strategic Wealth Management & Advanced Tax Advisory. Unifying complex accounting with proactive financial planning so you keep more of what you build.

08/19/2026

Stop writing checks to charity if you own appreciated stock! 🛑📉

When you donate stock you’ve held for over a year directly to a charity, you unlock a powerful “double deduction”:
1️⃣ Deduct the full fair market value on your tax return

2️⃣ Completely eliminate capital gains tax on the growth

💡 The Pro Move: Love the stock? Buy it right back immediately with cash! You reset your cost basis to today’s price, keep your portfolio intact, and wipe out previous unrealized gains without running into wash-sale rules (which only apply to losses).

👉 Comment "DOUBLE DEDUCTION" below if you want more tax-smart wealth strategies!

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08/15/2026

If you have Incentive Stock Options (ISOs), exercising and holding your shares can create a tax bill even when you haven’t received any cash.

The biggest issue is AMT.

You could exercise your options, pay Alternative Minimum Tax based on the value of the stock, and then watch the stock price fall. You may receive an AMT credit, but depending on your future tax situation, it can take years to use.

And taxes aren’t the only concern. Holding a huge percentage of your net worth in one company—even the company you work for—creates significant concentration risk.

Before exercising ISOs, we recommend modeling:

• Exercise and sell
• Exercise and hold
• Estimated AMT exposure
• Available cash to pay the tax
• Concentration and diversification risk
• Potential future tax savings

If you have ISOs and want a tax projection before you exercise, we can help.

Click the client intake form in our profile to get started.

08/14/2026

Day traders: Stop letting Wash Sale rules wreck your tax return. 📉🚫

If you qualify for Trader Tax Status (TTS), making a Section 475(f) Mark-to-Market (MTM) election completely changes the game:

🛑 No more $3k capital loss limit — trading losses become fully deductible ordinary business losses against other income.

❌ Eliminates the wash-sale headache entirely on trading positions.

💼 Full business expense deductions for platforms, data feeds, and equipment.

⚠️ Timing is everything—the IRS has strict deadlines and rules to elect MTM. Don’t wait until tax season to figure this out.

💬 Are you trading under investor rules or business rules? Let’s discuss below.

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Concord, MA
01742

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