Model your tech money like you model systems
RSUs, liquidity events, and retirement trade-offs explained with assumptions engineers can stress-test, and the math shown.
Recent articles
Practical articles you can apply to your own equity and tax situation.
- RSU Vesting and the Tax-Withholding Shortfall Nobody Warns You About
Your company withholds shares at a flat supplemental rate on every RSU vest. For most engineers in mid-to-high tax brackets, that rate is not enough — and the gap shows up as a surprise bill.
- ISO vs. NSO: Stock Option Basics Every Engineer Should Model
Two option types, two different tax triggers, two different risk profiles at exercise. The type printed on your grant agreement changes the entire decision tree.
- AMT Planning for Startup Equity: A Systems View
The alternative minimum tax behaves like a second tax system running in parallel to your normal return. For engineers exercising ISOs at a startup, understanding both systems is not optional.
- Mega Backdoor Roth 401(k) Mechanics, Step by Step
The standard 401(k) limit and the total plan limit are two different numbers. The gap between them, if your plan allows after-tax contributions and in-plan conversions, is the mega backdoor Roth.
- Comparing FAANG-Style Benefits Packages Beyond the Headline Number
Two offers with identical base salary and similar equity grants can differ by tens of thousands of dollars a year once 401(k) match structure, HSA contributions, and vesting cliffs are modeled properly.
- Negotiating Equity Refreshers: What Actually Moves the Number
Refresher grants are not automatic, and the process that determines their size is more mechanical — and more influenceable — than most engineers assume.
- 83(b) Elections for Early-Stage Equity: The Window You Can't Reopen
You have 30 days from grant to file an 83(b) election. Miss it, and a decision that could have been nearly costless becomes permanently more expensive.
- Engineer-to-Manager Compensation Transition Planning
Moving from IC to manager changes your equity refresh cadence, your bonus structure, and sometimes your leveling entirely — often before your paycheck reflects any of it.
- Geographic Arbitrage and Remote-Work Tax Residency Basics
Moving to a lower-cost-of-living or no-income-tax state as a remote engineer sounds simple. The tax-residency mechanics of actually making the move stick are not.
- Target-Date Funds vs. Self-Directed 401(k) Allocation for Tech-Industry Risk Profiles
A target-date fund assumes your only risk exposure is the stock market. An engineer with a large RSU position at the same employer as their paycheck has a second, correlated risk that default glide paths ignore.
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