This video is a slightly edited recording from Theta LIVE on December 17, where host John Einar Sandvand was joined by Paul Gundersen, Lee Lowell, and Brian Terry for a live panel discussion. Together, they explored how they actually trade the Wheel, Covered Calls, and Cash-Secured Puts – and which mistakes they see most often among retail options traders.

Watch the panel discussion

The panel

This Theta LIVE panel brings together Paul Gundersen, Lee Lowell, and Brian Terry — three experienced options traders who all use the Wheel, Covered Calls, and Cash-Secured Puts as core income strategies, but in different ways.

Paul Gundersen is known for his systematic, data-driven approach to the Wheel. Lee Lowell has decades of market experience and focuses on conservative, high-probability put selling. Brian Terry actively trades income strategies, emphasizing practicality, discipline, and repeatability.

• The Wheel: Theta Profits interview with Paul Gundersen
• Selling Puts: Theta Profits interview with Lee Lowell
• In the Money Covered Call: Theta Profits interview with Brian Terry

Why this topic matters

The Wheel, Covered Calls, and Cash-Secured Puts are often described as “simple” options strategies. And mechanically, they are.

However, as this discussion makes clear, most long-term underperformance stems from how these strategies are executed, rather than from the strategies themselves.

In this Theta LIVE session, the panel shares how they each trade these strategies, including how to avoid mistakes that quietly can erode returns over time.

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Here are some of the typical trading mistakes that the panel touches upon in their presentations and discussions:

Mistake #1: Chasing premium instead of managing risk

One of the strongest themes throughout the discussion is the danger of selling options too aggressively.

Lee Lowell emphasizes the importance of staying within a clearly defined risk zone, selling far enough out-of-the-money to allow for directional error. The panel agrees that many traders get into trouble by chasing a higher premium without adjusting for risk.

The takeaway is simple: high win rates and steady income come from conservative positioning, not from pushing strikes too close to the current price.

Mistake #2: Selling options on stocks you don’t want to own

Both Paul Gundersen and Brian Terry stress that stock selection is foundational to income strategies.

Selling a cash-secured put should never be about premium alone. The panel repeatedly highlights the importance of understanding the underlying business and being comfortable owning the shares if an assignment occurs.

When traders skip this step, assignment becomes emotional and reactive, which often leads to poor decisions.

Mistake #3: Treating an assignment as a failure

Assignment is one of the most misunderstood parts of the Wheel strategy.

With his In The Money Covered Call strategy, Brian Terry reframes the assignment as a planned transition, not a mistake. The goal, he explains, is not necessarily to keep the stock forever, but to continue generating income through the next phase of the strategy.

Paul adds that viewing assignment as part of the process, rather than something to avoid at all costs, makes it much easier to stay disciplined and consistent.

Mistake #4: Staying too long in the wrong phase of the Wheel

Paul Gundersen makes an important distinction between different phases of the Wheel. He explains that his most profitable trades tend to occur when he remains near the “top” of the Wheel, selling puts and generating premium without tying up capital in long stock positions for too long.

Letting covered calls drag on indefinitely can reduce capital efficiency and slow down income generation.

Mistake #5: Rolling without a clear plan

Rolling positions is another area where many traders struggle.

The panel emphasizes that rolling should be mechanical and rule-based, not emotional. Paul discusses accepting small debits to improve positioning, while Lee highlights the importance of avoiding unnecessary risks, especially around earnings.

Rolling works best when it is part of a predefined process, not a last-minute reaction to price movement.

Mistake #6: Accidentally taking earnings risk

Lee Lowell is particularly clear on this point: earnings introduce a type of risk that income strategies are not designed for.

The panel agrees that many traders unintentionally hold positions through earnings announcements, exposing themselves to outsized moves that have little to do with probability or edge.

Avoiding earnings — or having a clear plan around them — is a key part of keeping income strategies consistent.

Mistake #7: Strategy hopping and unrealistic expectations

Brian Terry cautions against jumping from strategy to strategy or comparing results to exaggerated claims seen online.

Mastery, he argues, comes from doing a few things well and repeating them consistently, not from constantly chasing the next idea.

The panel reinforces that realistic expectations and discipline are what allow these strategies to work over time.

This is only an excerpt of the long discussion. Watch the full video for much more depth.

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Where to connect to the speakers

Lee Lowell

Lee was interviewed on Theta Profits in October 2025 about his conservative way of selling puts.

You find his website Smart Option Seller here.

Paul Gundersen

Paul has done thousands of Wheel trades over the last years. He was interviewed in-depth about his strategy in October 2025.

You can reach out to Paul on his website

Brian Terry

Brian trades several income strategies. Our interview with him about In The Money Covered Calls was the first video published on Theta Profits.

You can reach Brian through the Facebook group Conservative Covered Calls