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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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 -
Should Your Side Gig Be an S-Corp?
Below about $50,000 in net profit, an S-corp election costs more than it saves. Here's the salary-split math, the real costs, and the breakeven number.
10 min read -
RSU Taxes When You Move States
Move from California to Texas, vest RSUs a year later, and you can still owe California tax on part of that vest. How state sourcing for equity works.
9 min read -
Rebalancing: When and How
Rebalancing is risk control, not a return booster. How drift actually happens, the calendar-plus-band approach, and how to do it without a big tax bill.
11 min read -
Mortgage Payoff vs Investing
Extra principal or invest the difference? Compare your mortgage rate to your after-tax return first, then let liquidity, taxes, and psychology break the tie.
9 min read -
HDHP vs PPO: Open Enrollment Math
Open enrollment math most people skip: comparing HDHP and PPO by worst-case totals, not premiums. The four numbers that decide it, and the HSA swing factor.
10 min read -
Solo 401k vs SEP IRA
For most tech workers with 1099 side income, the solo 401k beats a SEP IRA. The math, the shared deferral limit, and the backdoor Roth trap that decides it.
11 min read
