TaxMyVestRSU, ESPP & stock-option tax calculators
Don't Sell Your ESPP Before Watching This
Before you sell your ESPP shares, check this: sell too soon and it's a disqualifying disposition — your discount is taxed as ordinary income at your highest rate. Hold past the qualifying dates and much more of your profit becomes lower-taxed capital gains. The difference can be thousands of dollars.
Watch on YouTube · From the Vest & Nest channel
Transcript
Michael: Before you sell your ESPP shares, check this. ESPP — your employee stock purchase plan — lets you buy company stock at a discount.
Amy: What if I sell too soon?
Michael: Sell too soon, and it's called a disqualifying disposition. You sold too early. Your discount gets taxed as ordinary income, at your highest rate.
Amy: What if I hold?
Michael: Hold past the qualifying dates — two years from the offer, one year from purchase — and much more of your profit becomes capital gains. Capital gains are taxed lower. The difference can be thousands of dollars.
Amy: Where can I see both?
Michael: TaxMyVest.com shows both paths side by side. Free. No signup.
Amy: Thanks for watching!
Michael: Take care, and we'll see you in the next one. Like! Subscribe! and Share!
See both ESPP paths side by side
The ESPP calculator shows the qualifying and disqualifying outcomes for your actual dates and prices — so you can see what waiting is worth before you sell.
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