Strategy Before the Trade
Capital gains · Wash sales · Equity compensation · Active trading · Real estate · Liquidity events
Investment tax lensInvestment judgment.
Tax-informed execution.
Tax-informed execution.
- 01Position
- 02Basis
- 03Holding period
- 04Gain or loss
- 05Income impact
- 06State
- 07Timing
- 08Alternatives
- 09Cash flow
- 10Execution
Coordinated outcomeTax-informed investment decision
Choose your starting point
What investment decision are you facing?
The relevant questions depend on what you own, when you acquired it, why you may sell, and how the transaction fits into your broader financial life.
01
I’m selling something with a large gain
Timing, basis, and carryovers usually move the number more than the rate does — and a closing date is easier to move than a bracket.
Model the sale→02I have RSUs vesting
Vest income, withholding that is often too low, basis that brokers report wrong, and a concentration problem arriving at the same time.
Model an RSU vest→03I’m exercising stock options
ISO or NSO changes the character of the income, and an ISO exercise can create AMT on a gain you have not cashed.
Compare an option scenario→04I’m harvesting losses
Replacement purchases, other accounts, and a spouse’s trades can all undo the loss you thought you booked.
Review a harvesting scenario→05I trade frequently
Frequency alone is not enough. Intent, regularity, continuity, and holding periods decide whether this is a business.
Assess trading activity→06I’m selling a property
Gain, exclusion eligibility, and the depreciation that comes back at closing whether or not it was ever claimed.
Model a property sale→07I’m planning a liquidity event
Estimated taxes, charitable timing, diversification, and residency all have to be coordinated before terms are signed.
Plan before the transaction→The core problem
The tax result depends on more than the gain on a brokerage statement.
An investment transaction can be affected by basis, acquisition date, prior losses, income, residency, replacement purchases, compensation arrangements, charitable goals, and the rest of the portfolio.
Tax reporting explains what happened. Investment tax strategy evaluates what should happen, when, and which tradeoffs deserve consideration.
- 01Cost basis and tax lots
- 02Capital-loss carryforwards
- 03Wash-sale rules
- 04Net investment income tax
- 05Concentrated stock positions
- 06Equity compensation and AMT
- 07Trader status and mark-to-market
- 08Depreciation and recapture
Run it now
The rate is rarely what decides a sale. Timing, basis, and carryovers are.
Shifting a closing across a year boundary, or using a carryover you forgot you had, moves the number more than the bracket does. Compare the same sale across two years and see the difference before you sign.
Every financial figure stays in your browser.
Directional scenario differenceCurrent-year tax minus comparison-year tax
Current-year scenario
- 0% band
- 15% band
- 20% band
- Regular federal tax
- Incremental NIIT
- Directional state tax
- Total modeled tax
Comparison-year scenario
- 0% band
- 15% band
- 20% band
- Regular federal tax
- Incremental NIIT
- Directional state tax
- Total modeled tax
Factors affecting the result
Professional-review warnings
Assumptions and methodology
Constants reviewed 2026-07-28. Maintain annually against IRS inflation guidance.
Timing, lot selection, and carryovers move this number more than the rate does. I'll look at yours.
Step 1 · Email me and I'll review the sale before you make it
Use the comparison to ask better questions—not to time an investment by tax alone.
Educational estimate only; not tax, legal, or investment advice. TaxSpectra does not recommend whether or when to buy or sell an investment. Verify basis, holding period, asset classification, losses, income, state treatment, and transaction documents before acting.
Capital gains, RSUs, options, harvesting, wash sales, trader status and property sales each have their own engine.Open the Investor Decision Engines →
Frequently asked questions
Clear answers without portfolio promises.
Should I avoid selling an investment because of capital-gains tax?
Not necessarily. Tax cost is one factor alongside risk, diversification, liquidity, expected return, financial goals, and the reason for selling.
How can I reduce tax when selling appreciated stock?
Considerations may include holding period, tax lots, available losses, timing, charitable giving, income, and state residency. The right approach depends on the full situation.
What creates a wash sale?
A wash sale may occur when a security is sold at a loss and substantially identical property is acquired within the relevant period. Other accounts may also require review.
Are RSUs taxed when they vest or when they are sold?
RSUs generally create compensation income when they vest and may create an additional capital gain or loss when later sold.
Are incentive stock options always taxed at capital-gain rates?
No. Exercise and sale timing, holding periods, disqualifying dispositions, and potential AMT treatment affect the outcome.
Does frequent trading automatically qualify for trader tax status?
No. The determination generally depends on the nature, frequency, regularity, continuity, and intent of the activity.
What is the §475(f) mark-to-market election, and should I make it?
It converts trading gains and losses to ordinary treatment, which exempts you from wash-sale disallowances and lifts the $3,000 capital-loss cap — the reason it saves some traders a great deal. It also gives up capital-gain treatment permanently in practice, and the election has a hard deadline that falls before the year it applies to. It is the rare decision where being a month late costs you the whole year, so it gets decided deliberately and in advance.
Can TaxSpectra tell me which investments to buy or sell?
No. TaxSpectra provides tax analysis and planning, not investment recommendations or portfolio management.
Should I make an estimated tax payment after a large gain?
Possibly. The answer depends on withholding, prior-year tax, current-year income, safe-harbor rules, timing, and expected total liability.
Plan before the transaction
Understand the tax consequences before the transaction becomes final.
Whether you are selling appreciated assets, managing equity compensation, harvesting losses, actively trading, investing in real estate, or preparing for a liquidity event, TaxSpectra can help you evaluate the tax decisions before you act.
Begin with a structured conversation about the investment, proposed transaction, and outcome you are trying to achieve.