How to Sell Cash-Secured Puts on AAPL in ThinkorSwim & Track Cost Basis

Introduction: Starting the Wheel Strategy on Apple

The wheel strategy is one of the most reliable income-generating approaches for option sellers. It combines the consistency of cash-secured puts with the premium collection of covered calls, creating a systematic way to generate weekly or monthly income from quality stocks. Apple (AAPL) is a popular choice for this strategy due to its liquidity, weekly options availability, and status as a blue-chip holding.

This article is Part 1 of a four-part series that walks through a complete wheel strategy cycle on Apple. We start at the very beginning: selling a cash-secured put and properly tracking the position. In subsequent parts, we'll cover what happens when you get assigned, how to sell covered calls using your cost basis to pick strikes, and how to track your complete P&L through the full cycle.

The key to successful wheel trading isn't just executing the trades—it's tracking everything accurately so you always know your true cost basis. This knowledge directly informs your strike selection and helps you avoid selling covered calls below your breakeven point. MyATMM provides the tracking infrastructure that makes this systematic approach practical.

Setting Up Your Demo Account in MyATMM

Before executing any trades, you need a properly configured account in MyATMM to track your positions. For this demonstration, we're using a demo account that mirrors the ThinkorSwim On Demand paper trading environment.

Initial Account Setup

Start by navigating to the MyATMM dashboard and selecting or creating your demo account. Since we're simulating a fresh start with ThinkorSwim On Demand (which provides $100,000 in paper trading capital), we need to add a matching deposit.

Go to the Deposits/Withdrawals section and add an initial deposit of $100,000. Make sure to date this deposit appropriately—if you're simulating trades from a specific date, your deposit should be dated before those trades occur. This ensures your performance calculations remain accurate.

Getting the deposit date correct matters more than you might think. If you date your deposit incorrectly, your performance tab will show misleading percentages. For example, a $270 premium on a $100,000 account deposited the same day would show wildly different returns than the same premium on an account that's been active for weeks.

Why Demo Accounts Matter

Paper trading with proper tracking helps you build confidence in the workflow before risking real capital. By logging every simulated trade in MyATMM just as you would with real money, you develop the habits that lead to accurate cost basis tracking when it actually counts.

Selling a Cash-Secured Put in ThinkorSwim

With your MyATMM account configured, it's time to execute the trade. We're using ThinkorSwim's On Demand feature, which lets you simulate trading at any historical date. For this example, we're trading on November 3rd—a Monday—looking to sell a weekly put expiring that Friday.

Finding the Right Strike

Navigate to the Trade tab in ThinkorSwim with AAPL selected. The key decision is strike selection. For at-the-money puts (which typically offer the highest premium relative to risk), look for the strike closest to the current stock price.

With AAPL trading around $270, the $270 strike represents the at-the-money option. For weekly expirations, look at the nearest Friday—in this case, November 7th. The at-the-money weekly put was showing approximately $2.71 in premium, representing about 1% of the strike price for just four days of exposure.

Executing the Trade

To sell a put in ThinkorSwim, left-click on the bid price of the put you want to sell. This opens an order ticket with the position pre-populated as a sell-to-open. Key details to verify:

• Action: Sell to Open (not Buy to Open)
• Quantity: 1 contract (100 shares equivalent)
• Strike: $270
• Expiration: November 7th
• Price: Market or limit at the mid-point

For the best fills, consider using a limit order at the mid-point between the bid and ask. In this case, the order filled at $2.71 per share, generating $271 in premium (before commissions and fees).

Entering the Position in MyATMM

With the trade executed, the next critical step is logging it in MyATMM. This creates your transaction history and enables accurate cost basis tracking throughout the wheel cycle.

Adding the Ticker

Navigate to the Cost Basis page in MyATMM. If this is a new ticker for your account, you'll need to add it first. Click the Add button and enter "AAPL" as the ticker symbol. Once saved, Apple becomes available for position tracking.

Creating the Draft Position

Click "New Position" to create a draft entry for your cash-secured put. The form captures all the essential details:

When you save the draft position, it moves into the Puts section of your cost basis tracking. The system automatically calculates the net credit after applying your default commission and fee settings.

Understanding Commission and Fee Defaults

MyATMM lets you configure default commissions and fees in Preferences. Whether you pay $0.65, $0.50, or $0.30 per contract, the system applies these automatically based on whether you're opening or closing a position. This saves time and ensures consistency across all your trades.

For this example, with a $0.50 commission and $0.01 in fees, the net credit from the $271 gross premium becomes $270.49.

Moving to Permanent Transaction History

The draft position serves as a staging area. Once you've verified all details are correct, click the button to move it to your permanent transaction history. This action:

• Calculates the final net credit including all fees
• Generates the transaction description automatically
• Sets the transaction date based on your entry
• Updates all summary metrics

After clicking "Add Transaction," the entry becomes part of your permanent record, and you'll see all the summary figures update immediately.

Understanding the Summary Metrics

With the position logged, MyATMM displays several important metrics that inform your trading decisions going forward.

Shares from Puts

This metric shows how many shares you're obligated to purchase if all your cash-secured puts are assigned. With one contract at the $270 strike, you're committed to buying 100 shares if AAPL closes below $270 at expiration.

Collateral

Selling a cash-secured put requires setting aside capital equal to the strike price times 100. For the $270 put, that's $27,000 in collateral. This money remains in your account but is reserved to cover the potential share purchase.

Cost Basis with Puts

This is where tracking becomes powerful. Even though you don't own any shares yet, MyATMM calculates what your cost basis would be if you get assigned. The $270 strike minus the $2.70 net premium gives you a projected cost basis of approximately $267.30 per share.

With just one position, this calculation is straightforward. But as you continue selling puts, rolling positions, and potentially getting assigned multiple times, this metric keeps track of your true breakeven point—something that becomes invaluable for strike selection on future trades.

Dashboard Reconciliation with Your Brokerage

One of the most valuable features in MyATMM is the ability to reconcile your tracked positions against your actual brokerage account. This verification ensures you haven't missed any transactions and that your cost basis calculations are accurate.

The Total Brokerage Figure

On the MyATMM dashboard, the Total Brokerage field shows your calculated account balance based on all tracked deposits, withdrawals, and transactions. After adding the $100,000 deposit and receiving $270.49 in premium, this should show $100,270.49.

Matching Your Broker

In ThinkorSwim, the Cash and Sweep Vehicle shows your available cash. After selling the put and receiving premium, this should match the MyATMM Total Brokerage figure. In a live account with real commissions, these numbers should match exactly.

In On Demand mode, ThinkorSwim doesn't track commissions, so the broker shows $100,271 while MyATMM shows $100,270.49 (accounting for the $0.51 in commissions and fees). This small discrepancy is expected in simulation mode.

Capital Left Metric

The Capital Left figure shows how much buying power remains after accounting for collateral requirements. Starting with $100,270 and reserving $27,000 for the put collateral leaves approximately $73,270 available for other trades.

This metric serves as an important safety check. As long as Capital Left stays above zero, you're not using margin. When it goes negative, you know you've exceeded your cash and are borrowing from your broker—something many wheel traders prefer to avoid.

Performance Tracking Across Time

The Performance tab in MyATMM organizes your results by year, making it easy to track your progress and calculate returns accurately.

Year-by-Year Tracking

Since our simulated trade occurred in November 2025, clicking on the 2025 tab shows that year's activity. The Performance tab displays:

• Total Deposits: $100,000
• Total Premium Collected: $270.49
• Net Working Capital: $100,270.49
• Performance: 0.27% (premium / deposits)

Accurate Performance Calculations

Getting your deposit dates right ensures meaningful performance metrics. With a $100,000 deposit dated November 1st and $270 in premium collected shortly after, the 0.27% return reflects the actual capital deployed during that period.

If you had dated the deposit on the same day as the current date, the calculation would be skewed because the system would think you just deposited money today but had collected premium in the past—leading to inflated or nonsensical percentages.

What's Next: Part 2 - Handling Assignment

This article covered the first step in the wheel strategy: selling a cash-secured put and tracking it properly. But the real complexity—and where accurate tracking becomes essential—starts when that put gets assigned.

In Part 2 of this series, we'll walk through what happens when AAPL drops below the $270 strike and you're assigned 100 shares. You'll learn how to:

• Process the assignment in MyATMM
• Understand how premium received affects your true cost basis
• Track shares acquired through assignment separately from direct purchases
• Prepare for the next phase: selling covered calls

Assignment is where tracking really starts to matter. Without accurate records, you won't know your true breakeven point, making it impossible to select safe covered call strikes. MyATMM handles these calculations automatically, but understanding how they work helps you make better trading decisions.