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Should I buy employee stock options?

Employee stock options can be a valuable benefit when you join an early-stage company, especially if youre among the first employees. While the potential payoff is huge, theres also a risk that you could lose everything if the company fails.

What percentage should I contribute to employee stock purchase plan?

The max contribution is $25k, but sometimes employers will put a cap on salary that can go toward your ESPP. If you havent ever contributed to your companys ESPP before, select a percentage of your pay that feels comfortable (maybe 1-5% of your salary).

Should you max out your employee stock purchase plan?

If you have no debt and youre contributing up to the company match in your 401(k) PLUS saving money, you should definitely max out the amount you can contribute to your ESPP. This will result in you substantially growing your net worth.

Do I need to report ESPP on my tax return?

Your ESPP is taxed when you sell shares. You have taxable ordinary income to report as well as any capital gain/loss from the sale. As you file your taxes, youll want to consider if you made a qualifying or disqualifying disposition.

Should I cash out my ESPP?

If you are risk-averse, you might consider selling your ESPP shares right away so you dont have overexposure in one stock, particularly that of your own employer. ESPP shares can put you in an overexposed position. If the stock value goes down, you may suffer losses and in extreme cases, even lose your job.

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