Shoulda Bought

Stock Tycoon

1999 Wall Street Time Machine
"Hindsight is 20/20. Mine just became a superpower."
No download, no account. iOS and Android versions coming.
331
months, Jan 1999 โ†’ Jul 2026
485
real tickers, real monthly prices
$0.30
what Apple costs on turn one
1,825
assets, events and characters

You already know what happens.
That is the entire advantage.

A margin call wipes you out in July 2026. You close your eyes, and open them on January 1st, 1999 โ€” thirteen years old, in your parents' kitchen, next to a stack of bottled water someone bought for Y2K.

Real data, not a simulation
Bought Jan 1999ThenJul 2026Return
AAPL$0.3082$308.911,002ร—
NVDA$0.04โ€”huge
ENRN$28.00delistedโˆ’100%
Holo card$120$220,0001,800ร—
Plush bear$75$10โˆ’87%

Every stock, ETF and coin uses its actual split- and dividend-adjusted monthly close. Twenty-eight companies that went to zero are in the list too โ€” trading normally, paying dividends, indistinguishable from the rest. Until they aren't.

THE HINDSIGHT TIMES ยท 2006.08
Subprime Lenders Report Rising Delinquencies
"Contained to a small segment," analysts write.
"Contained. Remember that word. You will hear it for two years."

All 331 months have a real headline and your own instinct about it. The instinct never names a ticker. It just knows something is coming.

Getting rich is the easy part

This is a game about American money, so it is also a game about credit scores, student loans that bankruptcy cannot touch, and a hospital bill that arrives at the worst possible moment.

๐Ÿ“‰

FICO is a main stat

Every loan in the game โ€” card, mortgage, HELOC, margin, and a man named Big Sal who charges 10% a month โ€” is gated by one number you have to protect.

๐Ÿงพ

Tax Day, every April

Short-term gains cost 25%. Hold twelve months and one day, and it is 15%. Selling a winner at eleven months is a real mistake with a real price.

๐ŸŽ“

Debt that never dies

Ivy League costs $200,000. Chapter 7 wipes out everything you owe โ€” except the student loans. That is not a game rule. That is federal law.

๐Ÿฅ

One appendix, $41,749.22

Insurance is a monthly line item you will be tempted to skip. Medical debt is the leading cause of personal bankruptcy in the United States.

๐Ÿญ

The Garage

Found a dot-com in 1999. It is worth 42ร— by February 2000 and nearly nothing by November. You are the only person alive who knows which month.

๐Ÿ’

Who did you marry

Sixty people, four hidden identities. A prenup turns a 50% divorce into 10% โ€” if your Smarts is high enough to get one signed.

Where you start decides what it's worth

Same 331 months for everyone. Not the same game.

ร—3
Trailer Park
Rust Belt. No allowance, no credit file, no safety net. Opening an account at all is an event.
ร—1.5
Suburbs
Ohio, middle class. Five dollars a week and an ordinary credit score.
ร—1
Trust Fund
Manhattan. $250,000 unlocks at eighteen, with the label attached.

Your score on The Rich List is net worth ร— origin multiplier. Starting from nothing counts for more.

What's in it

485 stocks ยท ETFs ยท coins 28 companies that go to zero 331 monthly headlines 117 properties 33 collectibles 60 luxury goods 48 cars 15 bonds & CDs 60 people to meet 34 sporting events to bet 30 boardroom decisions 21 businesses to run 12 side hustles by era 22 achievements