OverEngineeredFi
Personal finance for people who over-engineer everything else.
The boring passive portfolio is mostly right. Here's the framework behind that — and an honest account of where I've deliberately broken it, what it cost, and whether it was worth it.
Recent Posts
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NQDC Plans: Worth the Employer Risk?
Non-qualified deferred compensation can cut your tax bill, but the balance is an unsecured IOU from your employer. Here is when an NQDC plan is worth the risk.
13 min read -
State Tax Residency When You Move
Moving from California or New York to Texas? Your old state may still tax you. Domicile, the 184-day test, the convenience rule and audits, with 2025 numbers.
13 min read -
Direct Indexing: Worth the Fee?
Direct indexing costs 3 to 13 times more than an index ETF and only pays off through tax-loss harvesting. Here's the break-even math for tech-worker incomes.
13 min read -
Concentrated Stock: Sell or Exchange Fund?
Exchange funds defer tax on a concentrated stock position for 7 years but cost 1%+ a year and require $500k+ minimums. Here's when they actually beat selling.
11 min read -
Which Account to Drain First
Taxable, then traditional, then Roth is a fine default at 65 and a costly one at 45. The bracket-filling alternative, with the 2026 tax math worked out.
18 min read -
Donate Stock, Not Cash
If you give to charity and hold appreciated stock, writing a check is the worst option. Donating shares skips capital gains tax and still deducts full value.
14 min read -
I Bonds and TIPS
A normal bond fund does nothing when inflation spikes: the coupon is fixed and inflation eats it. I Bonds and TIPS exist to solve exactly that problem.
11 min read -
The IPO Lockup Playbook
The lockup lifts, your double-trigger RSUs vest all at once, and the 22% flat withholding doesn't cover what you'll actually owe. Here's the IPO game plan.
11 min read -
Betterment vs Wealthfront vs DIY
Betterment and Wealthfront charge about 0.25% to automate a portfolio you could build yourself for less. The real dollar cost, and who it is worth paying for.
10 min read -
Term Life and Disability Insurance
Your ability to earn is your biggest asset, and it's probably uninsured. What disability and term life you actually need, and the whole-life pitch to decline.
9 min read -
QSBS: The $10M Tax Break
QSBS lets qualifying startup stock skip federal capital gains tax on millions in profit, but exercise late or structure a buyout wrong and you lose it entirely.
11 min read -
529 Plans and the Roth Rollover
The old objection to 529s, what if my kid skips college, just got a lot weaker. The SECURE 2.0 Roth IRA rollover changes the entire funding calculation.
11 min read
