Earn Your Leisure – "Riding the Options Roller Coaster"

Podcast: Earn Your Leisure — iHeartPodcasts
Date: November 11, 2025
Hosts: Rashad Bilal, Troy Millings, Trader Coach, CJ Toledano, Dave Chance
Featured Guest: Dave Shands

Episode Overview

In this episode, the Earn Your Leisure crew dives deep into the ups and downs of options trading, using Dave Shands' first-hand experiences as a lens. The show focuses on learning through real-life trading, managing both the emotional and strategic sides of investment, and highlights the value of planning, patience, and research. With a blend of therapy-like honesty and actionable financial wisdom, the group discusses exits, profits, using AI for analysis, and the mindset needed to endure the "roller coaster" of the options market.

Key Discussion Points & Insights

1. The Emotional Journey of Options Trading

• Dave Shands' Options Experience: Dave shares how he entered his first options play on AMD at the urging and guidance of CJ and the team. The contract saw significant volatility:

  "The AMD call was a roller coaster. It was up, then it was down, then it was down really bad. He stayed with it..." – CJ Toledano (03:42)

• Learning from Losses: Dave reflects on past losses leading into earnings, particularly with Netflix:

  "I have earnings call past trauma, bro. I've experienced trauma... Netflix hooked me." – Dave Shands (05:41)

• Highlighting Real Returns: Despite volatility, Dave ended up with significant gains:

  "I'm up 378%. Up $22,000. Things are happening right now." – Dave Shands (04:35)

2. When Is The Right Time To Sell?

• The panel discusses anxiety around selling before a company's earnings report, a common pain for options traders.
• CJ Toledano stresses the importance of having a plan:

  "Knowing when to sell is something that a lot of people have questions about. Making 300% and not wanting to lose money is a valid concern for sure." (04:47)

• Trader Coach advises long-term thinking and planning your exit before entering:

  "When you got into the option, did you know what percentage gain you wanted to get before you exited it?" (05:56)

• Dave admits:

  "No, I didn't." (06:36)

• Dave Chance emphasizes taking partial profits:

  "If I bought 10 contracts... if I get to 100%, then my initial investment comes out." (09:02)

3. Patience, Planning, and Not Missing Upside

• The danger of selling too soon is discussed; waiting can yield greater returns, but it's emotionally tough.
• CJ's wisdom:

  "You can never lose by taking profit." (10:26)

• Importance of “buying time”—getting contracts that allow you to benefit from multiple earnings cycles and potential tax advantages.

  "If you do something out to June next year, that's at least four to five earnings reports. It gives yourself time." – Dave Chance (19:49, 20:02)

4. Leveraging AI & ChatGPT for Trading Insights

• CJ encourages using AI for daily investing insights:

  "You should be having daily conversations with ChatGPT...it's going to give you a very educated sentiment of everything that's happening." (10:31)

• AI can act as your personal briefings center, similar to how a CEO gets updates:

  "You can structure AI to have briefings on a daily basis on all your investments. So that way you're at very least highly educated..." (16:20)

• Using AI to review sector performance, compare companies, and obtain projections.

5. Evaluating the Bullish Case on AMD

• The group reviews why AMD is currently strong, citing innovations, AI momentum, sector performance, new products, and strategic partnerships.

  "Did they have any Catalyst events inside the quarter? Well, yeah, they announced that they're partnering with this company called OpenAI." – Dave Chance (18:26)

6. Growth Mindset in Trading

• Shift from “What should I do?” to “What does the data say?”

  "I need to ask a really immature question of like, what should I do versus finding out what's happening..." – Dave Shands (20:44)

• The importance of learning so you can educate others; staying disciplined regardless of market news or who’s in political office.

  "Regardless of what's going on in the world, biggest piece of advice, your targets for your exit have to remain the same." – Trader Coach (22:58)

7. Trade Management: Taking Profits, Adding Positions

• Stacking Calls: Using profits to “stack” more positions in the same company if confidence is high.

  "I've stacked Nvidia calls from $20...to $45, to $80, to 100...As I see that price and the announcements and catalyst events, I keep stacking." – Dave Chance (24:13)

8. Building a Portfolio

• Dave currently holds options in AMD, Netflix, Micron (MU), Meta, and ASML.

  "So you got MU, you got Netflix, I got Meta...I got ASML." – Dave Shands (25:41)

Notable Quotes & Memorable Moments

• "I'm up 378%. Up $22,000. Things are happening right now."
  – Dave Shands (04:35)

• "Earnings can definitely hurt, especially if it's options, because whatever you feel in the stock, you're gonna feel three times more in options."
  – CJ Toledano (06:48)

• "You can never lose by taking profit."
  – CJ Toledano (10:26)

• "I always say, like, I like to get 100% return if I'm investing...my initial investment comes out."
  – Dave Chance (09:02)

• "You should be having daily conversations with ChatGPT because it's not going to tell you exactly what's going to happen, but it's going to give you a very, a very educated sentiment of everything that's happening in the world."
  – CJ Toledano (10:31)

• "Your targets for your exit have to remain the same...It takes a lot of the frustration. If you take profit, you don't lose that way."
  – Trader Coach (22:58)

• "If I believe in the company and the fundamentals are there and the technicals are showing me that this is something that's going to continue, I do it...I keep stacking."
  – Dave Chance (24:13)

Important Timestamps

• 03:42 – Introduction of Dave Shands' journey with options
• 04:35 – Dave reveals his 378% return ($22,000 gain)
• 05:41 – Emotional discussion on loss aversion and earnings trauma
• 06:36 – Admission of not having an exit plan
• 09:02 – Discussion on profit targets and scaling out positions
• 10:26 – Value of taking profits and leveraging ChatGPT
• 16:20 – Using AI for personalized investment briefings
• 18:26 – Deep dive into AMD’s bullish case and sector analysis
• 22:58 – Critical advice on maintaining exit targets
• 24:13 – The “stacking calls” approach to growing positions
• 25:41 – Dave lists his current options holdings

Tone, Flow, and Style Highlights

• Friendly, humorous, and supportive atmosphere; plenty of jokes about trading “therapy” and “testimonials.”
• Transparent, educational, and approachable; the show brings listeners into genuine, sometimes vulnerable discussions about winning and losing money.
• Actionable advice mixed with stories; the team stresses planning and discipline with relatable, real-life examples.

Summary for New Listeners

"Riding the Options Roller Coaster" is a must-listen for anyone learning about options trading, blending firsthand testimony, expert coaching, and the realities of emotional investing. The panel, especially through Dave Shands’ candid journey, reveals how strategy, patience, and a commitment to learning—plus leveraging new AI tools—are key to surviving and thriving in volatile markets. If you want to learn how real investors make (and sometimes lose) real money, and how to translate lessons into practical next steps, this episode is an entertaining and insightful ride.