Managing multiple option positions across different brokerages requires systematic tracking to ensure accurate cost basis calculations and premium collection records. In this detailed walkthrough, we'll track option trades executed across four different stocks: Novavax (NVAX), Rumble (RUM), Grab Holdings (GRAB), and Tilray (TLRY), demonstrating how to properly record covered calls and cash-secured puts for weekly income generation.
This session resulted in collecting $205 in option premium for the week, bringing year-to-date premium totals to $784. The process showcases how systematic tracking allows option sellers to maintain accurate records across multiple brokerages while monitoring their weekly average premium collection, which currently stands at approximately $271 per week.
The key to successful option income generation isn't just executing trades—it's maintaining meticulous records that allow you to see your true performance, adjust your strategies, and ensure every dollar of premium is properly accounted for in your cost basis calculations.
Rumble (RUM) presents an interesting case study in this session because positions were opened across two different brokerages—Robinhood and TD Ameritrade—demonstrating the importance of centralized tracking when your option selling activity spans multiple platforms.
The first RUM transaction was a covered call position in Robinhood that required going out significantly further in time than typical weekly options:
This position required a much longer duration because RUM wasn't providing attractive premiums on shorter-dated options at the time. When weekly premiums become too thin to justify the position management overhead, extending duration to monthly options can maintain acceptable premium yields while reducing the frequency of position adjustments.
Key Insight on Premium Erosion: When a stock's premium structure deteriorates significantly—as noted with RUM no longer "putting out premiums like it used to"—option sellers must adapt by either extending duration, adjusting position size, or reallocating capital to more premium-rich opportunities. This flexibility is essential for maintaining consistent income generation.
The second RUM position was a short-term cash-secured put opened through TD Ameritrade with significantly different characteristics:
This weekly put position demonstrates the put side of the wheel strategy, where you're willing to accumulate shares at the strike price while collecting premium. The TD Ameritrade transaction includes the broker's fees already deducted, which eliminates the need for later reconciliation—unlike Robinhood positions that may require adjustment once final settlement occurs.
Having RUM positions in both Robinhood and TD Ameritrade highlights the critical value of centralized cost basis tracking. Without a unified tracking system, it becomes increasingly difficult to:
This is precisely the problem MyATMM was built to solve—providing a single unified view of all your option positions regardless of which brokerage holds them, ensuring accurate cost basis tracking and complete premium accounting.
The Grab Holdings position represents a typical short-duration covered call strategy executed through Robinhood:
| Parameter | Details |
|---|---|
| Transaction Type | Sell to open call |
| Contracts | 2 contracts |
| Expiration Date | December 30, 2022 |
| Strike Price | $3.50 |
| Premium Per Contract | $0.14 |
| Total Premium | $28.00 |
This GRAB position demonstrates the standard process of recording a covered call in your tracking system. The position uses a 10-day duration (expiring December 30) and involves selling calls against existing share holdings to generate income while capping upside at the $3.50 strike price.
The recording workflow shown for both RUM and GRAB positions in Robinhood follows a consistent pattern:
Why Use "Proposed" Status First? The two-step process of first creating a proposed transaction and then moving it to history provides a quality control checkpoint. This allows you to review the details before finalizing, catching any data entry errors before they affect your cost basis calculations. It's particularly valuable when entering multiple transactions in a batch, as shown in this session.
For Robinhood transactions specifically, you may need to return later to reconcile the final premium amount after fees are assessed. Robinhood doesn't always show the exact post-fee premium at order execution, so the initial entry might require adjustment once the trade fully settles.
The Tilray position executed through TD Ameritrade represents another weekly cash-secured put, demonstrating the repetitive nature of systematic option income generation:
This position illustrates selling puts at the $3.00 strike price, indicating a willingness to purchase TLRY shares at that price if assigned while collecting $11 in premium for taking on that obligation. With a three-day duration until expiration, this represents a typical end-of-week option position targeting quick premium collection with minimal time exposure.
One significant operational advantage mentioned during the recording process is that TD Ameritrade transactions show the exact net premium after fees upfront. This eliminates the reconciliation step required for Robinhood transactions:
This transparency in fee structure makes TD Ameritrade transactions slightly easier to track and record, though the difference is minor when using proper tracking software that accommodates both approaches.
The NVAX position represents a more complex scenario that many option sellers eventually face: managing a position that has moved significantly against you while continuing to generate premium income.
As noted during the recording: "We're in this a little deep. The prices continue to fall and we're dollar cost averaging down. We're still selling calls and I have gone through here and entered some of the calls but we're not getting much premium so I didn't record it. But we're still playing the put side and the put side we're still getting full premiums down there."
This candid assessment reveals several important aspects of real-world option selling:
Despite the challenging situation, the session's NVAX transaction demonstrates continued premium collection:
| Parameter | Details |
|---|---|
| Transaction Type | Sell to open put |
| Contracts | 1 contract |
| Expiration Date | December 23, 2022 (this Friday) |
| Strike Price | $11.00 |
| Premium Collected (Gross) | $90.00 |
| Premium After Fees | $89.34 |
At $89.34 in premium for a single weekly contract, this NVAX put represents by far the largest premium collected in this session. The substantial premium reflects both the volatility in NVAX and the risk premium associated with potentially acquiring more shares of a stock that has already declined significantly.
Key Lesson on Position Management: When a position moves against you, the wheel strategy can still function to reduce your cost basis through continued premium collection. While not ideal, this approach allows you to methodically work down your average cost while maintaining exposure for potential recovery. However, this strategy requires strong conviction in the underlying company and careful position sizing to avoid overconcentration.
The NVAX example highlights several considerations when managing positions that have moved significantly against you:
After recording all the week's transactions, the session concludes with a performance review using the dashboard's premium tracking and projection features. This review process is essential for understanding whether your option selling activity is meeting your income goals.
The week's activities resulted in the following premium collection:
The platform's projections tab reveals important trend information: "Right now we're weekly averaging about $271 dollars a week based off everything we've collected and everything we've done so far."
This $271 weekly average provides crucial context:
Understanding Premium Variability: Weekly premium collection will naturally fluctuate based on market volatility, the number of positions expiring and being rolled, and strategic decisions about which opportunities to pursue. The $200-per-week range mentioned appears to be a consistent baseline, with the overall average around $271 suggesting periodic larger premium collection weeks that pull the average higher.
With December 20th positioning in the final weeks of the year, the year-to-date total of $4,486 in premium collection demonstrates sustained option income generation throughout the year. The month-by-month breakdown visible on the dashboard allows for analysis of seasonal patterns and identification of particularly strong or weak periods.
This type of historical tracking becomes invaluable for:
This session's demonstration of tracking five option positions across two brokerages and four different tickers highlights exactly why purpose-built option tracking software is essential for serious option sellers.
Without a unified tracking system, managing the type of activity shown in this session becomes increasingly complex:
MyATMM addresses these challenges with features specifically designed for option sellers:
The platform was built by an option seller who faced these exact tracking challenges, which is why it focuses exclusively on the features that matter for covered call and cash-secured put strategies rather than trying to be a general-purpose portfolio tracker with hundreds of features you'll never use.
Options trading involves significant risk and is not suitable for all investors. Selling covered calls and cash-secured puts can result in substantial losses, including the potential loss of your entire investment. The positions described in this article, particularly the NVAX example of averaging down into a declining position, represent strategies that carry substantial risk and may not be appropriate for all traders.
Past performance does not guarantee future results. The premium collection amounts and percentages discussed are historical examples and should not be interpreted as indicative of future returns. Market conditions, volatility levels, and individual stock performance vary significantly over time.
This content is provided for educational purposes only and should not be considered financial advice or a recommendation to engage in any particular trading strategy. Always consult with a qualified financial advisor before making investment decisions, and never risk capital you cannot afford to lose.
Stop juggling spreadsheets and multiple brokerage platforms. MyATMM provides the centralized tracking, automatic cost basis calculations, and performance analytics you need to manage your option selling business professionally.
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