The Psychology Behind Winning Trades & Stop Loss Secrets

4 Nov 2025 · 8 min

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Podcast Summary: Earn Your Leisure - The Psychology Behind Winning Trades & Stop Loss Secrets

Episode Overview In this episode of "Earn Your Leisure," hosts Rashad Bilal, Ian Dunlap, and Troy Millings explore the intricacies of trading across futures, options, and equities, emphasizing the psychological aspects of trading and the strategic use of stop losses.

Key Themes

  1. Stop Loss Strategies
  2. Importance of Stop Losses: Setting a stop loss that is too tight can lead to missed opportunities for gains.
  3. Real-Life Examples: The hosts discuss cases where traders lost potential profits due to overly cautious stop losses, stressing the need for a balanced approach.
  4. Threshold Awareness: Understanding the volatility of the asset is crucial; different assets may require varying stop loss strategies.
  1. Developing a Trading Plan
  2. Pre-Trade Planning: Importance of knowing your entry point, exit strategy, maximum loss, and profit target before entering a trade.
  3. Trading Mindset: Emphasizes that trading is not solely about numbers but also involves a psychological battle against fear and comparison.
  1. Psychological Factors in Trading
  2. Fear of Missing Out (FOMO): The impact of social media on traders can create pressure that leads to poor decisions and overtrading.
  3. Running Your Own Race: Rashad highlights the necessity of focusing on personal goals and strategies rather than comparing oneself to others.
  1. Practical Insights from the Hosts
  2. Troy's Trading Experience: Shares insights from his options trading, emphasizing how different stocks should have tailored stop loss strategies.
  3. Ian's Perspective: Points out that sometimes it's advantageous to remove stop losses altogether for certain trades, especially when confident about long-term growth.

Key Takeaways

  • Avoiding Tight Stop Losses: Traders should refrain from setting stop losses too tight, as this can hinder profit potential and lead to regret.
  • Plan Before Entering Trades: A well-defined trading plan can significantly improve trading outcomes.
  • Mindset Matters: The psychological components of trading, including FOMO and fear, can lead to detrimental trading behaviors.
  • Focus on Education: Continuous learning and understanding market dynamics are crucial for successful trading.
  • Community Support: Engaging with trading communities can provide insights, but it's essential to filter information and focus on individual goals.

Conclusion The episode combines financial education with relatable anecdotes, encouraging listeners to prioritize personal trading strategies and cultivate the right mindset for successful trading. The hosts advocate for a balanced approach to trading that considers both technical strategies and psychological resilience.

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Transcript

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0:00This is an iHeart Podcast. Guaranteed Human Run a business and not thinking about podcasting? Think again. More Americans listen to podcasts then add supported streaming music from Spotify and Pandora and as the number one podcaster iHeart's twice as large as the next two combined. Learn how podcasting can help your business. Call 844-844-IHEART This episode is brought to you by PNC Bank. A lot of people think podcasts about work are boring and sure, they definitely can be but understanding a professional's routine shows us how they achieve their success little by little, day after day. It's like banking with PNC Bank.

0:37It might seem boring to save, plan, and make calculated decisions with your bank, but keeping your money boring is what helps you live a more happily fulfilled life. PNC Bank, brilliantly boring since 1865. Brilliantly boring since 1865 is a service mark of the PNC Financial Service Group, Inc. PNC Bank, National Association member, FDIC. So starting off with trading, what's futures trading tip of the week? I don't know if I went over this in full detail before, but to my futures traders, having too tight of a stop loss is almost worse than having no stop loss at all. a lot of times um when we're looking to get into a move we're looking to protect our account um and both of you can speak at this from the options perspective but sometimes you can have a stop loss that is so tight that you don't even give yourself room to be able to let the move fully mature um so i know somebody last friday who probably missed out on like 60 grand having a stop loss at 1200 bucks like i get it if you're trading a bunch of contracts you want to have protection but you need to put your stop loss in places where the brokerages and competition won't hit your liquidity sweep zones and stop loss zones and hunt there and also too like we were talking to one of our good friends before this you have to know the exit before you get in so if you're going to lose six thousand bucks but the upside is 60 grand why cut it off at 1250.

2:15You go into it knowing, put this in chat, go into it knowing what your maximum loss will be and what your maximum profit target will be, but having too tight of a stop loss, damn near it is worse than having no stop loss at all. It's a terrible feeling. It's a terrible feeling. For it to go down and then go where you knew it was going to go? Oh my God. Yeah, it's tough. I think that's why a part of that plan, we always talk about having a plan is figure out what that threshold is. I know some people don't have a strong threshold, so it might be a 20 % pullback. But especially when you're talking about equities, that's a, I mean, that's a correction, right?

2:56Yeah. When you talk about futures and options, that could be five minutes. That's a blip on radar. Yeah. Right? Like that could be in five minutes. And so you got to take that into account how volatile that these assets move or these derivatives move. And so 20%, it feels like, all right. Run a business and not thinking about podcasting? Think again. More Americans listen to podcasts than ad-supported streaming music from Spotify and Pandora. And as the number one podcaster, iHeart's twice as large as the next two combined. So whatever your customers listen to, they'll hear your message. Plus, only iHeart can extend your message to audiences across broadcast radio.

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5:15Now, like I said, depending on the company, that'll change. My company, I've changed that for. Microsoft, I've changed that for. But like Super Micro, right? Once it hits a threshold, I gotta go. I gotta go. I don't love, I'm not in love with the option trade. It makes sense and I feel like can make money but if it's not making money then there's like there's another opportunity where we can put that capital so have a plan before you enter any position we can say it but most people still don't do it right like we talked about our close friend made money and now it's trying to figure out what should i do you have to know the exit you gotta have a planter yep because you can't figure out how to assemble a plane on the way down i know they love to say that in silicon valley like figure out how to build a plane on the way down it doesn't work that way in real life you don't crash out every time and also too even with the the asset they were trading the es mini the s p 500 i'm like if you knew the market was falling why have such a tight stop and we've been falling but it's fear it's fear a lot of it is not knowing your entry not knowing your exit when you're going to profit and then the other part that isn't talked about enough is you're doing so many different things and when you're trading you end up getting confused on how this is going to pan out.

6:34That's why I say trade one way in, one way out all the time. So you can have a huge data set to know what the outcome is going to be. There's that psychology. We were talking about it before, but it's that psychology. The fear comes because of the lack of education and experience in it, which is understandable. What is the other side of that when you see people win? If you're watching people, especially when you watch people on social media, it's like, man, they've had percentage gains, they've had percentage gains. Psychologically, do you think that works as a detriment or is it more advantageous to say oh i should be involved i often like wonder like how people do that maybe both rashad what you think yeah for sure i think it psychologically definitely plays a part as far as investing is concerned because no one wants to lose money and then no one wants to have somebody make more money than them.

7:28So it's a catch-22 because you don't want to lose money, but then the risk of making money so you constantly kind of, you know, run your own race. Yep. Keep your eyes on your own paper. I think that that's a bar right there. The risk of making money. You remember what he said? The risk of making money, which is like, damn, that just sounded crazy just now. But that's where we're at. because you're seeing other people post their games but not always their losses and on top of that when you start to have too much comparison that's when the fomo and the over trading and the over leveraging really kicks in it really kicks in just focus on your race earners what's up you ever walk into a small business and everything just works like the checkout is fast the receipts are digital tipping is a breeze and you're out the door before the line even builds Odds are they're using Square.

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From the publisher

In this Market Mondays clip, Rashad Bilal, Ian Dunlap, and Troy Millings dive into the nuanced world of trading futures, options, and equities, sharing hard-earned wisdom about stop losses and trading psychology. Ian explains why setting a stop loss that's too tight can sometimes hurt you more than having none at all—citing real examples where traders missed big gains due to overly cautious exits. Troy shares practical insights from his own options trades, discussing thresholds, volatility, and adjusting your strategy based on the company you’re dealing with, whether it’s Nvidia or Microsoft. Together, the hosts talk about the importance of having a clear plan before entering any trade—knowing your entry point, exit, maximum loss, and profit target. They emphasize that trading isn’t just about numbers, but also about mindset: comparison, fear of missing out (FOMO), and the psychological impact of watching others post their wins on social media. Rashad weighs in on running your own race and reminds us not to let other people’s gains dictate our strategy. Tune in for relatable stories, actionable tips, and that signature Market Mondays mentality: focus on your goals, your education, and your own long-term vision in the market. Don’t let fear or comparison ruin your trades—trade smarter, not harder. 👇 Drop your thoughts and trading strategies in the comments! Have you ever experienced a stop loss regret or let FOMO influence your decisions? Let’s discuss! **Hashtags**: #MarketMondays #FuturesTrading #StopLoss #OptionsTrading #TradingPsychology #InvestingTips #RiskManagement #IanDunlap #RashadBilal #TroyMillings #FinanceEducation #RunYourOwnRace #TradingPlan #StockMarket #OvercomingFOMO

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