From Sree Tripuramallu · 2026—
Letters
Essays on wealth, tax code, equity, and the parts of money that never make sense. Written for readers who want to understand the math, not just be told what to do.
- 23
Take the Thousand, Skip the Rest
Should I open a Trump account for my child?
Trump accounts hand your child $1,000 for free. Adding your own money is where the deal falls apart.
- 22
One Good Year
Why wasn't enough tax withheld on my RSUs?
A stock vest is withheld at a flat 22%, whatever bracket you're in. Last year's small tax bill hides the shortfall for exactly one year.
- 21
Payable on Arrival
Do I need to make estimated tax payments?
Income tax is due four times a year, not once in April. A salary satisfies all four automatically; everything else is yours to send.
- 20
The tax break you can photocopy
How do I avoid capital gains tax when I sell my startup stock?
Qualified small business stock erases federal tax on the first $15 million of startup gains. Each trust you gift shares to gets its own $15 million.
- 19
The Second Set of Books
How do I avoid AMT on my stock options?
The IRS calculates your taxes twice and keeps whichever answer is bigger. Exercise stock options and the second calculation is the one that gets you.
- 18
The Thirty-Day Window
Do I need to file an 83(b) election?
On stock you buy before it vests, one form is the difference between owing nothing and owing millions.
- 17
The Half-Million-Dollar Decision
Should I take Social Security at 62 or wait?
Wait from 62 to 70 and the Social Security check grows 77%. Most people grab the small one anyway — betting against their own longevity.
- 16
One Dollar Over the Line
Will a Roth conversion raise my Medicare premiums?
A Roth conversion is ordinary income, and Medicare reads your income from two years ago to set its premium surcharges. The thresholds are cliffs, not ramps: one dollar over costs about $2,300 a year.
- 15
Your 401(k) Isn't All Yours
Will my 401(k) make my Social Security taxable?
Every dollar in a traditional 401(k) is taxed on the way out, and at 73 the IRS forces it out — pushing up to 85% of your Social Security into the tax base. Roth conversions before 73 defuse it.
- 14
The Tax Bomb You're Inheriting
What happens when I inherit my parents' 401(k)?
A quiet 2020 law turned inherited retirement accounts into a 10-year tax bill, landing in your highest-earning decade.
- 13
Don't Roll Over
Should I roll over my old 401(k)?
The hidden tax advantage sitting inside your 401(k).
- 12
The Loss Bank
Is tax-loss harvesting actually worth it?
Harvesting losses to pay $0 in capital gains on a tender offer.
- 11
You Shouldn't be Investing in the S&P 500
Isn't buying the S&P 500 diversified enough?
A third of an S&P 500 fund is just seven tech companies. If one of them signs your paycheck, the 'diversified' fund quietly doubles your employer bet — concentration you never chose.
- 10
Squeezing more juice from your 401(k)
Should I max out my 401(k) early in the year?
The 401(k) setting most people never consider
- 09
The Sticker Price Is a Lie
What will a house actually cost me per month?
A framework for buying your first home
- 08
Using Donations to Offset Capital Gains
Can I donate stock to avoid capital gains tax?
How donations reduce income to owe less capital gains
- 07
The Health Savings Account Paradox
Should I use my HSA to pay medical bills or invest it?
Why you should never use your HSA to cover medical expenses
- 06
The tax code secretly loves your second child
Can I open a 529 before my child is born?
A 529 quirk lets parents stack six figures for a child before they're born.
- 05
The Fallacy of Savings Accounts
Is a high-yield savings account worth it?
The true cost of having a high yield savings account
- 04
The Invisible $500K tax in your 401(k)
Are target-date funds worth it?
The default-setting trap that quietly eats retirement nest eggs.
- 03
How Anthropic engineers will lose 56% of their equity
How much of my stock options do I actually keep after taxes?
Paper wealth and actual cash are two very different things.
- 02
The Phantom Tax
Why do I owe taxes on sports betting if I broke even?
Making $0 in profit still generates a tax bill.
- 01
Tax laws are penalizing couples for tying the knot
Will getting married raise my taxes?
The SALT cap doubled to $40,000 — but not if you're married.
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