◆ Concentrated Stock Retirement Planner

Tax-optimized planning for concentrated stock positions. Monte Carlo analysis with fat tails.

Work-Optional Decision Companion

Can this position make work optional?

Start with the minimum facts needed for a first answer. The planner will tell you whether the plan looks workable now, what could break it, and what to test next before you trust the answer.

Built for people whose life is dominated by one appreciated stock position.
The first answer is fast. The full builder below is where you refine housing, taxes, health costs, and advanced policy rules.
The math stays in the same canonical engine either way, so the quick view and the detailed view do not drift.

Ready for a first answer Fill the fields below, then get the first verdict before opening the full case builder.

First answer

Who You Are

Birth Year

Retirement Age

State

Concentrated Position

Stock Name

Shares Held

Current Price

Average Basis

Other Liquid Assets

401(k)

Roth IRA

Roth Basis

Brokerage

SGOV / Cash

HSA

What You Need

Target Spend

Minimum Spend

The fast answer uses your current builder defaults for growth, inflation, health insurance, Social Security, housing, and advanced tax policy until you refine them.

Full Case Builder

Refine housing, benefits, taxes, Monte Carlo, and advanced withdrawal policy

Use the detailed builder when the first answer is close, fragile, or missing important context.

Not every answer needs this. Open it when you want to audit the assumptions or test more precise scenarios.

Profile

Birth Year Required (1940-2005)

Retirement Target Age Age you plan to retire

Filing Status

Single

Married Filing Jointly Soon

State of Residence

Determines state income tax brackets

Concentrated Stock Position

Stock Name Optional label

Shares Held Must be > 0

Current Price ($/share)

Average Cost Basis ($/share)

Expected Growth Rate

Custom (%/yr)

Stock Type

Volatility (%)

Lock-up Status

Freely Tradeable

Locked Until Year

Other Accounts

401(k) / Traditional IRA

Balance ($)

Growth Rate (%/yr)

Roth IRA

Balance ($)

Basis ($)

First Contribution Year For Roth 5-year earnings clock

Growth Rate (%/yr)

HSA

Balance ($)

Brokerage (Taxable)

Balance ($)

Growth Rate (%/yr)

SGOV / Cash Reserve

Balance ($)

Yield (%/yr)

Income & Spending

Pre-Retirement Income

Annual Earned Income ($) Applies only before retirement age

Retirement Spending

Target Annual Spending ($) After-tax, today's dollars

Minimum Acceptable ($) Spending floor

Social Security

Expected Annual Benefit ($)

Start Age 62 early / 67 FRA / 70 max

Health Insurance

ACA Annual Cost ($) Pre-Medicare, unsubsidized

Inflation Rate (%/yr)

Housing

Home Value

Current Home Value ($)

Appreciation Rate (%/yr)

Mortgage

Remaining Balance ($)

Interest Rate (%)

Monthly Payment ($)

Periods Remaining

Property Tax

Property Tax Rate (%)

Inputs changed since this answer was last run.

Run Monte Carlo to see survival probability

Key Metrics

Decision Memo

Case File Lenses

Confidence & Missing Proof

Modeled Confidently

Key Assumptions

Verify Externally

Tested Improvement Paths

Single-change moves already sampled from this baseline

Strategy Comparison

Comparing SEPP 72(t), Penalty Bridge, and Locked-to-59.5 strategies

Strategy	Survival	Fail Age	Min Spend P25	Lifetime Tax	Flexibility

Spending Sensitivity

Impact of reducing annual spending by $25k

Retire Later Scenarios

Each additional working year adds savings and delays draw-down

Annual Projection

Click any row to inspect that year in detail, including cash sources, taxes, and ending balances.

Year	Age	Real Spend	Tax	Stock Sold	Conversion	SEPP/Trad	Roth Draw	Brok Draw	Unfunded	Stock End	401k	Roth	Brokerage	SGOV	Liquid NW

Advanced Solver Parameters

Monte Carlo Settings

MC Trials

Portfolio Vol (%)

Tail DF (Student-t)

Regime Switching (correlated crashes)

Fat Tails (Student-t distribution)

Stock Sale Strategy

Tax Mode

Custom Gain Budget ($)

Target Allocation (%)

Retain Floor (shares)

Brokerage Target (%)

Early Access Strategy

Early 401k Mode

Draw Start Age

SEPP/Trad Trim Cap ($)

Conversion & Tax Caps

Ordinary Cap (w/ mort) ($)

Ordinary Cap (post-mort) ($)

Roth Conv Cap (w/ mort) ($)

Roth Conv Cap (post-mort) ($)

Phase & SGOV Tuning

Phase 1 Pct

Phase 2 Pct

Phase 1 Cap ($)

Phase 2 Cap ($)

Phase 3 Cap ($)

SGOV Floor (years)

Analysis Running

Elapsed 0s

Running analysis...

Current results stay visible while this runs.

◆ Concentrated Stock Retirement Planner

Can this position make work optional?

Who You Are

Concentrated Position

Other Liquid Assets

What You Need

Filing Status

State of Residence

Expected Growth Rate

Stock Type

Lock-up Status

401(k) / Traditional IRA

Roth IRA

HSA

Brokerage (Taxable)

SGOV / Cash Reserve

Pre-Retirement Income

Retirement Spending

Social Security

Health Insurance

Home Value

Mortgage

Property Tax

Modeled Confidently

Key Assumptions

Verify Externally

Monte Carlo Settings ?

Stock Sale Strategy

Early Access Strategy

Conversion & Tax Caps

Phase & SGOV Tuning

Monte Carlo Settings