Podcast Summary: Earn Your Leisure

Episode: The Psychology Behind Winning Trades & Stop Loss Secrets

Release Date: November 4, 2025
Hosts: Rashad Bilal, Troy Millings (with frequent contributor Ian)
Podcast Network: iHeartPodcasts

Overview

In this episode, Rashad Bilal and Ian (with Troy Millings referenced in show notes but not the aired conversation) dissect the psychological factors behind successful trading, the nuances of effective stop loss strategies, and the dangers of comparison and fear in trading. The discussion leans into actionable advice for traders—especially in futures and options markets—while emphasizing the importance of mindset and pre-defined trading plans.

Key Discussion Points & Insights

1. The Danger of Too-Tight Stop Losses

(02:47 - 04:13)

• Rashad warns futures traders of the pitfalls of placing stop losses too tightly. He recounts a story of someone who "missed out on like 60 grand having a stop loss at 1200 bucks," illustrating how over-protectiveness can hinder trades.

  "Having too tight of a stop loss damn near is worse than having no stop loss at all."
  — Rashad (03:39)

• When traders set stops too close, they can get "liquidity swept," exiting positions just before the trade goes in their favor.

• Key point: Determine your maximum loss and profit target before entering a trade.

2. Emotional Cycle: Regret and Planning

(04:13 - 04:45)

• Ian reflects on the "terrible feeling" of being stopped out, only to see the trade play out as he originally anticipated.

• Rashad highlights the frustration: "It [the price] goes down and then goes where you knew it was going to go. Oh my God." (04:17)

• The segment underscores the need for having a plan and sticking to it, especially considering the volatility of futures and options.

3. Setting the Right Thresholds: Context Matters

(04:45 - 05:41)

• Ian explains how stop losses vary by asset:
  - With equities, a 20% stop often signals a correction,
  - In options/futures, dramatic moves can happen in minutes or seconds.

• He gives examples:

  • He's been more flexible (removed stops) for companies he deeply understands, like Nvidia, because "I understand the company, I understand how the market moves, I understand the long term vision for it, which is why we always buy time." (05:08)

• Typical stop loss thresholds for options: "when I'm doing an option call, 30 to 40% I feel like is a safe space."
  — Ian (05:21)

4. Importance of Planning Exits

(08:43 - 09:13)

• Ian emphasizes, "Once it hits a threshold. I gotta go. Yeah, I gotta go. I don't love [the trade]." (08:43)
• Rashad follows: "You have to know the exit because you can't figure out how to assemble a plane on the way down. ...It doesn't work that way in real life. You crash out every time." (09:12)
• Critical point: Have an entry and exit plan before executing any trade.

5. The Psychology of Trade Management

(09:13 - 10:34)

• Rashad ties tight stops and poor planning to fear and lack of market understanding:

  • "It's fear. A lot of it is not knowing your entry, not knowing your exit when you're going to profit." (09:45)

• He encourages trading "one way in, one way out" for data and consistency.

• Ian expands on the psychological element:

  • "The fear comes because of the lack of education and experience, which is understandable." (09:59)

• Social media can amplify comparison and FOMO (Fear of Missing Out).

6. How Social Comparison Affects Traders

(10:31 - 11:34)

• Ian wonders if seeing others’ profits online hurts or helps traders psychologically.

• Rashad responds: "No one wants to lose money and then no one wants to have somebody make more money than them." (10:35)

• The risk of overtrading and overleveraging increases when comparing yourself to others.

• "Just focus on your race... Keep your eyes on your own paper." (10:55)

  "That's a bar right there. The risk of making money."
  — Ian (11:02)

• Rashad cautions that constant comparison leads to unhealthy habits: "When you start to have too much comparison, that's when the FOMO and the over trading and the over leveraging really kicks in." (11:15)

Notable Quotes & Memorable Moments

• On Stop Losses:
  "Having too tight of a stop loss damn near is worse than having no stop loss at all."
  — Rashad (03:39)

• Emotional Cycle of Getting Stopped Out:
  "It to go down and then go where you knew it was going to go. Oh my God."
  — Rashad (04:17)

• The Need for a Plan:
  "You have to know the exit... because you can't figure out how to assemble a plane on the way down. ...It doesn't work that way in real life."
  — Rashad (09:12)

• On Social Comparison in Trading:
  "No one wants to lose money and then no one wants to have somebody make more money than them."
  — Rashad (10:35)

• Self-Focus:
  "Just focus on your race... Keep your eyes on your own paper."
  — Rashad (10:55)

• On the True Risk:
  "The risk of making money. Like you already said, the risk of making money, which is like, damn, that just sounded crazy just now. But like, that's what we're at."
  — Ian (11:02)

Timestamps of Important Segments

• 02:47 – Rashad opens with the dangers of tight stop losses
• 03:39 – Notable: "Having too tight of a stop loss..."
• 04:13 – Ian and Rashad discuss the emotional impact of stops
• 04:45 – Ian elaborates on thresholds and asset differences
• 05:21 – Typical options stop loss tolerances
• 08:43 – Ian and Rashad on the necessity of exit planning
• 09:45 – Rashad outlines the role of fear and planning
• 10:31 – Social comparison and FOMO effects
• 10:55 – The importance of staying in your lane

Takeaways

• Stop loss placement should consider volatility and asset context, not just arbitrary amounts.
• Trade with a plan: define your maximum loss, profit targets, and do not "assemble the plane on the way down."
• Social comparison fuels bad trading habits; ignore the noise and focus on your own process.
• Fear and lack of education lead to mistakes—improve your knowledge and experience to manage both.

Earn Your Leisure delivers a fusion of practical, psychological, and strategic trading wisdom in this episode, offering both education and encouragement for traders determined to master their mindset and execution.