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Archives

All the articles I've archived.

2026 53
August 25
  • 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.

  • 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.

  • 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.

  • 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.

  • 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.

  • 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.

  • 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.

  • 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.

  • 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.

  • 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.

  • 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.

  • 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.

  • The Layoff Money Playbook

    The first two weeks after a layoff decide the financial outcome. Severance, RSUs, options, COBRA, unemployment, and the 401k moves to make before you sign.

  • The 83(b) Election: Your 30-Day Window

    The 83(b) election has a strict 30-day deadline with no extensions. File it and a future tax bill shrinks to pocket change. Miss it and it can cost six figures.

  • Where to Park Cash

    Cash sitting in a big-bank checking account earning near nothing is the most common, most fixable money leak for high earners. Here's where it should go.

  • Rent vs Buy: The Actual Math

    Renting isn't throwing money away. Most of an early mortgage payment is interest, which is money you never get back either. Here is the real rent-vs-buy math.

  • A Roth IRA for Your Kid

    Your teenager's summer lawn-mowing money can fund a Roth IRA that compounds for 50 years. Here's how custodial Roth IRAs actually work, funding trick included.

  • ISO vs NSO: Options and the AMT Trap

    ISOs and NSOs are taxed completely differently. Get it wrong and you owe a six-figure AMT bill on stock that's now worthless. Here's the full breakdown.

  • The 0% Capital Gains Bracket

    The 0% long-term capital gains bracket lets early retirees harvest gains tax-free. Here's how it works, who qualifies, and the ACA subsidy tension you need to know.

  • Lump Sum vs Dollar-Cost Averaging

    Lump sum beats DCA two-thirds of the time. But DCA beats doing nothing. Here's the math, the Vanguard data, and when each one actually makes sense.

  • Bonds: When to Actually Add Them

    A 28-year-old accumulator probably needs 0% bonds. That changes as you approach your FIRE number. Here's exactly when and how to make the shift.

  • Do You Need International Stocks?

    VXUS vs. VTI-only: the oldest Boglehead argument. Here's what the data says, where Bogle and Vanguard disagreed, and a concrete allocation range to pick from.

  • Health Insurance Before 65

    The biggest unsolved FIRE problem: health insurance before Medicare. Here's how ACA subsidies, MAGI management, and Roth conversions change the math entirely.

  • The Roth Conversion Ladder

    Access your 401k before 59.5 without the 10% penalty. The Roth conversion ladder is how early retirees bridge the gap, here's the full mechanics.

  • Emergency Fund: How Much Is Enough?

    3-6 months is the generic advice. Here's how to calibrate your emergency fund by job stability, income type, and what else you can access in a crisis.

July 17
  • Financial Order of Operations

    Where your next dollar should go, in exact priority order. A deterministic flowchart for engineers who want the math to make the decision, not vibes.

  • Roth vs Traditional: Which One?

    Roth vs Traditional isn't a personality quiz. It's a math problem. Here's the break-even logic, the tax-diversification argument, and when each one wins.

  • Monarch Money: The Best Mint Replacement?

    Mint shut down in 2024. Monarch Money is the best replacement for passive trackers, great net worth dashboard, multi-user support, and solid mobile app.

  • YNAB Review: Is $109/Year Worth It?

    YNAB costs $109/year and has a real 2-3 month learning curve. Here's who it transforms, and who should skip it and use Monarch Money instead.

  • Rolling Over Your Old 401k: A Checklist

    Left a job with an old 401k sitting there? Here's exactly what to do, all four options, the direct vs indirect rollover trap, and a step-by-step checklist.

  • Backdoor Roth IRA: A Step-by-Step Guide

    Earn too much for a Roth IRA? The backdoor conversion still gets you in. Step-by-step 2026 guide with pro-rata rule explained and full Fidelity walkthrough.

  • The Budget That Doesn't Feel Like a Budget

    Stop tracking every coffee. Reverse budgeting automates your savings first, then lets you spend the rest guilt-free, here's exactly how to set it up.

  • Savings Rate: The Only Lever That Matters

    Your savings rate determines your retirement timeline faster than investment returns ever will. Here's the math, the table, and how to calculate yours honestly.

  • Fidelity vs Vanguard vs Schwab: Pick One

    Fidelity, Vanguard, or Schwab? The honest answer for a 3-fund portfolio: pick any of them. Here's what actually differs and what to stop worrying about.

  • Lean FIRE vs Fat FIRE: Pick Your Number

    Lean FIRE, Fat FIRE, Barista FIRE, ChubbyFIRE, the full spectrum mapped with real dollar targets so you can stop theorizing and pick your actual number.

  • Reading Your RSU Grant Without a Lawyer

    RSU grant agreements look like legal gibberish. Most of it doesn't matter. Here's what to actually read, and the questions to ask HR before you sign.

  • Total Market vs S&P 500: Does It Matter?

    VTI vs VOO, FSKAX vs FXAIX, the total market vs S&P 500 debate explained with actual numbers and 30-year projections. Spoiler: you're overthinking this.

  • ESPP: Don't Leave Free Money on the Table

    Your ESPP is a 15-32% guaranteed return hiding in your benefits portal. Here's the math, the tax rules, and why you should nearly always sell immediately.

  • Coast FIRE: The Lazy Path to FI

    Coast FIRE means your investments are already on autopilot to retirement, no more contributions required. Here's the math and why it changes everything.

  • Asset Allocation by Age: A Practical Guide

    The 110-minus-age rule is a solid starting point, most people ignore it. What it means, why young investors should skip bonds, and allocation by decade.

  • Tax-Loss Harvesting: Free Money (Sort Of)

    Tax-loss harvesting offsets capital gains and cuts your tax bill, if you follow the wash-sale rules. Here's the VTI→ITOT swap and the honest math on deferral.

  • 401k Math: What You're Actually Saving

    Maxing your 401k doesn't cost $23,500. At a 35% tax rate it costs $15,275. Here's the math, the 2026 limits, and how to stop leaving money on the table.

June 11
  • The 4% Rule: Does It Still Hold?

    The 4% rule is the foundation of FIRE planning, but it has real caveats most people ignore. Here's what the original research actually says and when to adjust.

  • Side Income Taxes for Software Engineers

    Side income hits harder than W-2: you pay SE tax plus income tax. Here's the Schedule C breakdown, the SE tax math, SEP-IRA limits, and quarterly estimates.

  • Why Index Funds Beat Active Management

    Most active funds underperform their benchmark over 15 years. The math on expense ratio drag alone should end the debate. Here's why index funds win every time.

  • Stock Options vs RSUs: Which Is Better?

    ISOs, NSOs, RSUs, your offer letter has all three and explains none of them. Here's what each type means, how it's taxed, and which you actually want.

  • Your FIRE Number: How to Calculate It

    Your FIRE number is annual expenses × 25. Here's where that formula comes from, what most people undercount, and how to actually make the target work.

  • The Home Office Deduction, Demystified

    W-2 remote workers can't claim the home office deduction post-2017 TCJA. Here's who can, how the simplified vs regular method math works, and when each wins.

  • Mega Backdoor Roth Explained

    The mega backdoor Roth lets you funnel up to $46,500 extra into a Roth account per year. Most plans don't support it. Yours might. Here's the full mechanics.

  • The 3-Fund Portfolio: All You Need

    Three funds. That's all it takes to build a complete, diversified portfolio. Here's the exact tickers at Fidelity, Vanguard, and Schwab, plus how to allocate.

  • Quarterly Taxes: Don't Get Wrecked in April

    Owe $1k+ in taxes after withholding? You're supposed to pay quarterly. Here's the safe harbor rule, 2026 due dates, and the math on $30k freelance income.

  • The HSA Triple Tax Advantage

    Your HSA is the only account with three tax advantages. Here's how to turn it into a stealth IRA, and the math that makes it worth maxing every single year.

  • RSU 101: Sell or Hold? The Math

    RSUs are taxed as income at vest, not when you sell. Here's the math on concentration risk, your tax hit at vest, and why selling immediately usually wins.