A senior engineer at Amazon walks into year 3 of her 5/15/40/40 grant with $540k of RSU income landing in one calendar year. Here is how the numbers shook out.

An Apple senior IC maxing ESPP at $23,750 per year ran the math on holding for qualifying disposition versus selling at purchase. The answer was not obvious.

A retiring Apple engineer with $1.8M of AAPL inside his 401(k) evaluates Net Unrealized Appreciation treatment versus standard rollover. The math was close.

A Google PM moves from San Francisco to Austin in the middle of a vest cycle. California still wants its share of the RSU income. Here is how the workday allocation worked.

A French-American engineer at Stripe works through US-France tax treaty rules on RSU vests while living in San Francisco. Treaty tie-breakers, foreign tax credits, form filings.

A Databricks director with $4M of pre-IPO equity plans a 10b5-1 structure that can trigger at IPO. The design decisions around cooling off and lot selection.

Two senior ICs, one at Amazon and one at Google, with combined $600k of annual RSU income face 37% bracket pressure. Here is how they coordinated withholding.

A bootstrapped C-corp founder hits year 4 of a 5-year QSBS hold and gets an acquisition offer. Here is how he modeled waiting versus taking the deal.

An early engineer at an AI startup modeled exercising $200k of ISOs against AMT. Here are the four options we ran and the AMT-neutral threshold we found.

A senior engineer laid off from a pre-IPO company has 90 days to exercise her ISOs. The AMT math said $140k. She decided in 6 weeks.

A VP Engineering at a late-stage pre-IPO company sits on 4 years of double-trigger RSUs as the S-1 filing approaches. Here is the tax waterfall we built.

A Meta engineer gets a competing offer while sitting on $900k of unvested RSUs. Here is how we modeled the counter-offer and the buyout negotiation.

A staff engineer at Meta pulls $800k of annual RSU income and discovers the 22% supplemental withholding leaves a six-figure shortfall. Here is how he covered it.

A Microsoft senior engineer with $450k of RSU income tries to qualify for a $1.2M jumbo mortgage. Lenders treat RSU income inconsistently. Here is how we made the package.

An Nvidia senior engineer with $3.2M of employer stock, up 5x from grant, ran the math on diversifying versus holding. Here is the decision framework.

An OpenAI engineer holds Profit Participation Units with no clear precedent for tax treatment. Here is the framework we used to plan around the ambiguity.

An early employee at a newly-public SaaS company faces lockup expiry with $1.8M of previously-triggered RSUs. Here is how we built the first year of liquidity.

A Meta staff engineer takes a 12-month sabbatical and uses the income dip to convert $180k of traditional IRA to Roth at the 22% bracket.

A founder sold QSBS six months before the 5-year mark and used IRC §1045 to roll gain into replacement QSBS. Here is how the 60-day window played out.

A senior AE at Snowflake blew through quota and hit accelerators that pushed total comp above $1M. The 37% supplemental threshold matters differently in sales.

A Stripe engineer holds $2M of double-trigger RSUs as IPO rumors heat up. Planning for the cliff means modeling withholding, AMT, and sale-to-cover mechanics before S-1.

A Tesla senior engineer holds 12,000 options at a near-zero effective strike after a prior 3-for-1 split. Here is how we timed the exercise around AMT.

A Meta engineer transferred London to Menlo Park mid-vest. HMRC claimed trailing UK tax on equity earned during UK service. Here is how the treaty worked out.

A Seattle-based senior IC works remotely for a California-headquartered employer. California asserts he is a resident. Here is how we documented otherwise.

A YC founder with $13.9M of QSBS gifts shares into a Spousal Lifetime Access Trust before a Series C secondary. Here is how the gift-tax and QSBS stacking math worked.