How to Enter Employer Stock and Equity Compensation in Boldin

Equity compensation can be a big part of your retirement picture, but it rarely fits neatly into a single income box. Each type has its own taxable event, and some aren't subject to payroll taxes at all. This article shows you how to enter each type accurately. You can enter it yourself, or let Boldin AI make the entries for you.

Quick reference

Type	When it's taxed	FICA?	How it enters your plan
RSU / PSU	Vest date (ordinary income)	Yes	Job income + contribution to a Capital Gains account
NQSO	Exercise date (ordinary income on the spread)	Yes	Job income + contribution to a Capital Gains account
ESPP	Sale date	No	Job contribution to a Capital Gains account
ISO (held)	Sale date (long-term capital gains)	No	Lump sum pension (non-taxable) to a Capital Gains account
ISO (sold same year)	Exercise year (ordinary income on the spread)	No	Lump sum pension (taxable)
ESOP	Distribution (ordinary income)	No	Tax-deferred account

GOOD TO KNOW

Using Boldin AI: Copy the prompt for your equity type, replace everything in [brackets], and paste it into Boldin AI. Each prompt asks Boldin AI to show you the entries before saving, so you can check them first.

Cost basis: Contributions, windfalls, and lump sum pensions directed to an account all add to its cost basis automatically.

RSUs and PSUs

How they work: On each vest date, the value of your vested shares counts as ordinary income. Federal tax, state tax, and FICA all apply. Your employer usually withholds shares to cover taxes and deposits the rest in your brokerage account. PSUs work the same way, except the number of shares depends on performance targets.

Enter it with Boldin AI

COPY THIS PROMPT INTO BOLDIN AI

Please add my RSUs to my plan using these steps:

1. In Assets and Debts, create an Investment account called "[Company] RSU" with the Capital Gains tax treatment. Set the current balance to $[current value, or 0] and the cost basis to $[cost basis, or 0]. Set the rate of return to [X%].

2. In Income, add a job called "[Company] RSU." Add an income stream of $[gross vest value] with the start and stop date both set to [vest date].

3. Calculate the after-tax value of the vest by subtracting FICA plus federal and state income tax at my plan's rates. [Optional: My statement shows $[net amount] was deposited after withholding. Use that instead.]

4. Add a contribution from this job of the after-tax amount to the "[Company] RSU" account.

Repeat steps 2–4 for each of these vests: [date – $amount, date – $amount, …]

Before saving, show me each entry and your after-tax calculation.

For PSUs: Use the same prompt with your expected payout amount and date. If the payout is uncertain, use a conservative estimate.

Enter it yourself

Go to My Plan > Assets and Debts. Add an Investment account with the Capital Gains tax treatment, and label it clearly, for example "ACE RSU."
Go to My Plan > Income and add a job for your RSUs.
Add an income stream for the gross vest value, with the same start and stop date.
Add a contribution of the after-tax value to your RSU account.

Non-Qualified Stock Options (NQSOs)

How they work: Your employer grants you the right to buy shares at a fixed strike price once they vest. When you exercise, the spread counts as ordinary income, subject to FICA. The spread is the market price minus the strike price, times the number of shares.

If you'll exercise and hold the shares

COPY THIS PROMPT INTO BOLDIN AI

Please add my NQSO exercise to my plan using these steps:

1. In Assets and Debts, create an Investment account called "[Company] NQSO" with the Capital Gains tax treatment. Set the rate of return to [X%].

2. Calculate the spread: ([market price] − [strike price]) × [number of shares].

3. In Income, add a job called "[Company] NQSO." Add an income stream for the spread, with the start and stop date both set to [exercise date].

4. Calculate the after-tax value by subtracting FICA plus federal and state income tax at my plan's rates.

5. Add a contribution from this job of the after-tax amount to the "[Company] NQSO" account.

Before saving, show me each entry and your calculations.

If you'll exercise and sell right away: Ask Boldin AI to complete steps 2 and 3 only. The proceeds flow into your plan as income.

Enter it yourself: Follow the RSU steps above, using the spread as the gross income amount.

Employee Stock Purchase Plans (ESPPs)

How they work: You buy company stock through after-tax payroll deductions, usually at a 10–15% discount. Nothing is taxed at purchase. At sale, part of your gain counts as ordinary income (with no FICA), and the rest is a capital gain.

Qualifying sale (held 2+ years from the offering date and 1+ year from purchase): the ordinary income portion is limited to the discount, and the rest is a long-term capital gain.
Disqualifying sale (sold sooner): the discount at purchase is ordinary income. Any gain or loss after purchase is a capital gain.

Enter it with Boldin AI

COPY THIS PROMPT INTO BOLDIN AI

Please add my ESPP to my plan using these steps:

1. In Assets and Debts, create an Investment account called "[Company] ESPP" with the Capital Gains tax treatment. Set the current balance to $[current value] and the cost basis to $[total amount I've paid for my shares]. Set the rate of return to [X%].

2. Under my job "[job name]," add a contribution of $[amount] per [month/year] to the "[Company] ESPP" account, starting [date] and ending [date].

3. My plan buys shares at a [X%] discount. Calculate the annual value of that discount and add it each year as a windfall directed to the "[Company] ESPP" account.

4. I plan to sell my shares on [sale date]. Add up the total discount from step 3, then add a one-time expense on that date called "[Company] ESPP – tax on discount." Set it equal to the total discount times my federal and state ordinary income tax rates for that year.

5. On [sale date], transfer $[amount, or the full balance] from the "[Company] ESPP" account to my [savings account name].

Before saving, show me each entry and your calculations.

WHY STEP 4?

Boldin counts the discount as part of your cost basis, so it won't tax the discount when you sell. The expense in step 4 covers that tax. If you don't have a sale date in mind yet, skip steps 4 and 5 and add them later.

Enter it yourself

Go to My Plan > Assets and Debts. Add an Investment account with the Capital Gains tax treatment, and enter your balance and cost basis.
Go to My Plan > Income and add a contribution from your job to the ESPP account.
Go to My Plan > Income > Windfalls and add the discount value, directed to the ESPP account.
Go to My Plan > Expenses and add a one-time expense in your sale year for the tax on the discount.
Go to My Plan > Money Flows and add a transfer on your sale date.

Incentive Stock Options (ISOs)

How they work: ISOs have no regular income tax and no FICA at exercise. If you hold the shares 2+ years from the grant date and 1+ year from exercise, your entire gain is taxed at long-term capital gains rates when you sell. That gain is the sale price minus the strike price.

AMT ALERT

The spread at exercise can trigger Alternative Minimum Tax (AMT). Boldin doesn't model AMT. If you're planning a large exercise, talk with a CPA or tax advisor before you exercise.

If you've already exercised and hold the shares

COPY THIS PROMPT INTO BOLDIN AI

In Assets and Debts, create an Investment account called "[Company] ISO" with the Capital Gains tax treatment. Set the balance to $[current value] and the cost basis to $[strike price × number of shares]. Set the rate of return to [X%]. Show me the entry before saving.

If you'll exercise in the future and hold the shares

COPY THIS PROMPT INTO BOLDIN AI

Please add my future ISO exercise to my plan using these steps:

1. In Assets and Debts, create an Investment account called "[Company] ISO" with the Capital Gains tax treatment. Set the rate of return to [X%].

2. In Income > Pensions, add a Lump Sum pension called "[Company] ISO exercise" for $[market price at exercise × number of shares], dated [exercise date], directed to the "[Company] ISO" account. Set the tax treatment to No.

3. I'm paying the strike price in cash, so add a one-time expense of $[strike price × number of shares] on [exercise date].

4. Calculate the spread: ([market price at exercise] − [strike price]) × [number of shares]. I plan to sell on [sale date]. Add a one-time expense on that date called "[Company] ISO – tax on exercise spread." Set it equal to the spread times my federal long-term capital gains rate, plus my state income tax rate and the 3.8% Net Investment Income Tax if they apply to my income that year.

5. On [sale date], transfer $[amount, or the full balance] from the "[Company] ISO" account to my [savings account name].

Before saving, show me each entry and your calculations.

WHY STEP 4?

Boldin counts the full value at exercise as your cost basis, so it won't tax the gain between your strike price and the exercise value. The expense in step 4 covers that tax. Boldin taxes any growth after exercise automatically when you sell.

If you'll exercise and sell in the same year

COPY THIS PROMPT INTO BOLDIN AI

In Income > Pensions, add a Lump Sum pension called "[Company] ISO sale" for $[(market price − strike price) × number of shares], dated [sale date]. Set the tax treatment to Yes. Show me the entry before saving.

This taxes the spread as ordinary income with no FICA, which matches how the IRS treats a disqualifying ISO sale.

Employee Stock Ownership Plans (ESOPs)

How they work: An ESOP is a retirement plan, similar to a 401(k), that invests mainly in company stock. Your employer funds it, not you. Distributions are taxed as ordinary income and are subject to RMDs.

Enter it with Boldin AI

COPY THIS PROMPT INTO BOLDIN AI

Please add my ESOP to my plan using these steps:

1. In Assets and Debts, create a tax-deferred 401(k) account called "[Company] ESOP" with a balance of $[vested balance]. Set the rate of return to [X%].

2. My company contributes about $[amount] per year until [date]. Add these as annual windfalls directed to the "[Company] ESOP" account.

Before saving, show me each entry.

TIP

Plan around your vested balance only. If you don't know your company's contribution, skip step 2 and update your balance each year.

Planning a future sale (all account types)

To model selling shares on a specific date, for example to diversify, use a transfer. Selling from a Capital Gains account triggers capital gains tax on the gain.

COPY THIS PROMPT INTO BOLDIN AI

On [date], transfer $[amount, or the full balance] from my "[Company] ___" account to my [savings account name]. Show me the entry before saving.

Still have questions?

Equity compensation decisions, especially exercise timing, AMT, and holding periods, can have real tax consequences. For more help:

Ask Boldin AI.
Use Support Chat by clicking your initials in the upper right corner of your plan.
Consider a coaching session or a Boldin Advisors engagement.