Why I'm Putting Close to a Million Dollars Into The Wheel

Six weeks ago I wired almost a million dollars into a brokerage account and started selling options.

Not because I read a book about it. Not because I watched someone on YouTube do it. Because I spent months back testing a systematic strategy, built the infrastructure to run it automatically, and decided it was time to stop theorizing and start doing it with real money.

This isn't a newsletter about getting rich quick. It's a live document of what actually happens when you deploy serious capital into a disciplined options income strategy — the wins, the losses, the mechanics, and the decisions in real time.

The strategy is called the wheel. You sell cash-secured puts on stocks you'd be happy to own. If they expire worthless, you keep the premium and sell another one. If you get assigned, you own the shares — and then you sell covered calls against them until they get called away. Then you start over.

Simple in theory. Surprisingly nuanced in practice.

The goal is to generate consistent monthly income while staying invested in stocks I'd hold anyway.

Here's where things stand right now:

$128,200 deployed across 4 contracts on 3 symbols (AAPL, SPY, NVDA ×2)

$771,800 sitting in a money market earning ~4.3% while waiting for market conditions to improve

$1,194 realized in the first 6 days

19 open positions across 5 accounts

A fully automated system monitoring every position every 20 minutes

Every Monday I'll publish a portfolio update — what closed, what opened, what the system flagged, and what I decided. No filters. If something goes wrong, you'll read about it here first.

If you're curious how this ends, stick around.

— Keith