Tools & blog
Free calculators, and plain-language posts on the tax questions tech professionals and business owners ask us every week.
Calculators
Tech professionals
- RSU taxes, explained: why 22% withholding leaves you owingHow RSUs are taxed at vest and at sale, why the flat 22% withholding usually falls short, and how to avoid a big bill and penalties in April.
- ISOs and AMT: how to exercise stock options without a surpriseHow incentive stock options are taxed, why exercising can trigger the Alternative Minimum Tax, and how to plan exercises, holding periods and the AMT credit.
- RSU cost basis wrong on your 1099-B? How to avoid paying tax twiceWhy brokers often report a $0 or missing cost basis for RSU and ESPP shares on Form 1099-B, how it makes you pay tax twice, and how to correct it on Form 8949.
- ESPP taxes: qualifying vs disqualifying dispositionsHow employee stock purchase plan shares are taxed, the difference between a qualifying and a disqualifying sale, with worked examples, and how to report it correctly.
- NSO taxes: how non-qualified stock options are taxedHow non-qualified stock options (NSOs) are taxed at exercise and at sale, why withholding often falls short, and how to time exercises to manage the tax.
- Estimated taxes for tech employees: safe harbor, deadlines and penaltiesWhen tech employees with RSUs or option income need to pay estimated taxes, how the safe harbor rules avoid penalties, and the federal and California deadlines.
- Year-end tax checklist for tech professionalsThe tax moves tech employees should review before December 31: ISO exercises and AMT, tax-loss harvesting, charitable gifts of stock, retirement accounts and estimates.
Tax + financial planning
- Should you sell RSUs when they vest?Selling RSUs at vest usually adds little or no tax. Here is how the tax works, why holding is like buying your employer’s stock, and a simple way to decide.
- How tax planning and financial planning work together for stock compensationWhy decisions about RSUs, ISOs and ESPP shares need both a tax plan and a financial plan, with five examples where coordinating the two changes the answer.
- Diversifying a concentrated stock position without a big tax billPractical, tax-aware ways for tech employees to reduce a concentrated position in their employer’s stock: lot selection, spreading sales, losses, gifts and more.
Business owners
- S corp vs LLC: taxes, salary and when to electWhat changes when an LLC elects S corp status: self-employment tax, reasonable salary, QBI, retirement plans, costs and the Form 2553 deadline.
- How an S corp election works: Form 2553 step by stepWho can elect S corp status, how and when to file Form 2553, what happens if you miss the deadline, and what changes in your business after the election.
- S corp reasonable compensation: how to set your salaryWhat reasonable compensation means for S corp owners, the factors the IRS looks at, common myths like the 60/40 rule, and how salary affects QBI and retirement.
- The Augusta rule: renting your home to your businessHow the Augusta rule (Section 280A(g)) lets business owners rent their home to their business for up to 14 days a year tax-free, and how to document it properly.
- PTE tax elections: the SALT cap workaround for business ownersHow state pass-through entity (PTE) taxes let S corp and partnership owners deduct state income tax despite the SALT cap, who benefits most, and what to watch for.
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