Reading about the wheel strategy and actually placing your first trade are very different things. The first trade is where theory meets the reality of picking a stock, reading an options chain, choosing a strike, and hitting the button. This guide walks through every step so there are no surprises when you get there.
Step 1: Open Your Brokerage Account and Get Options Approval
If you don't have a brokerage account yet, see our broker comparison guide and choose based on your situation. Apply for options Level 2 approval (or the equivalent at your broker), which allows selling cash-secured puts. Fund your account with at least the minimum capital for your target stock — see the capital requirements calculator for exact figures by ticker.
Step 2: Choose Your First Stock
Use the criteria from our best stocks guide: moderate IV Rank (25-50%), liquid options chain, price your account can support, and a company you'd be genuinely comfortable holding for several months. Before finalizing your choice, check the latest earnings report and 10-Q analysis on MoneySense.ai to confirm there are no material red flags hiding in recent filings.
Step 3: Read the Options Chain
Open the options chain for your chosen stock. Go to puts expiring approximately 30-45 days out — this is the expiration window where theta decay is most efficient for CSP sellers. Find the strike price with a delta of approximately 0.25-0.30. This gives you roughly a 70-75% probability of the put expiring worthless while still offering meaningful premium income.
Step 4: Place Your First Cash-Secured Put Order
Select "Sell to Open" on your chosen put contract. Use a limit order at the midpoint between the bid and ask price — don't market-order options. The mid-price is almost always achievable with a little patience. Confirm that your broker is holding the full strike × 100 in collateral. Once the order fills, you're officially running the wheel.
Step 5: Log the Trade in OptionWheelTracker Immediately
Create a free OptionWheelTracker account and start a new campaign for your ticker the moment your trade fills. Log the CSP with the net premium, strike price, expiration date, and contract count. Your ACB tracking begins immediately — and from this point forward, every premium you collect, every roll, and every assignment updates your campaign automatically. Starting your tracking log from trade one is significantly easier than trying to reconstruct history months later.
Step 6: Manage the Position
Check in every few days. If your CSP reaches 50% of its original premium, consider taking profit or rolling forward. If it approaches expiration worthless, let it expire and sell a new one. If you get assigned, move to selling covered calls above your ACB. Every trade gets logged, your campaign grows, and your ACB tracks automatically.