Earn Your Leisure Podcast: "YOU CAN’T TRADE STOCKS IF YOU’RE SCARED — GROW SOME BALLS!"

Release Date: December 5, 2025
Hosts: Rashad Bilal, Troy Millings
Podcast: Earn Your Leisure
Theme: Behind-the-scenes financial insight into entertainment, sports, entrepreneurship, and personal finance; with an emphasis this episode on the psychology and conviction needed for successful trading and investing.

Episode Overview

This episode centers around overcoming fear in stock and futures trading, developing emotional intelligence, and understanding when and how to size up positions for meaningful returns. The hosts challenge listeners to move beyond hesitant, small-scale trading and embrace bold, decisive strategies supported by research and discipline. The conversation also emphasizes the crucial balance between risk management, conviction, and emotional stability required to thrive in volatile markets.

Key Discussion Points and Insights

1. Trading Tip of the Week: “You Can’t Trade Stocks If You’re Scared”

(03:44)

• The Futures Trader emphatically encourages traders—especially in futures—to drop the fear and start taking bigger, well-calculated risks.

• Many new options traders are taking bigger swings than seasoned futures traders, which the hosts see as a missed opportunity for those with more expertise.

  "For my futures traders? I want to be very honest and say I want you guys to have less fear and more kahunas..." — Futures Trader (03:44)

2. Position Sizing and Targets in Futures Trading

(03:44)

• Key Strategy: Targeting 33 contracts on S&P 500 futures for 42 ticks (~10 points) can earn over $17,000 per trade.

• Rationale: Doing this even a few times a month can be life-changing. Sticking with just 1-4 contracts prevents substantial growth.

• The importance of learning when to increase size is highlighted.

  "You can't play the one to four contract game forever because you're going to miss your window of actually making real money that can change your life..." — Futures Trader (04:23)

3. Courage vs. Risk Management in Trading

(04:48)

• The Investment Advisor agrees with upping trade size, but underscores the need for “mitigated risk”—increasing size only when capital and conviction are aligned.

• Having small size in big moves feels disappointing in hindsight.

  "Having two contracts go to a thousand percent sucks when you could have had like five, right? ...you gotta have the capital." — Investment Advisor (04:51)

4. Emotional Intelligence: The True Key to Trading and Investing

(04:51)

• Emotional intelligence is described as the overarching theme for successful investment—not just numbers or strategies.

• Navigating volatility, losses, and gains all require a steady mindset.

  "That's overwhelming. The theme that has just been coming back into my conversations is the emotional intelligence. And in life, that's necessary, right?" — Investment Advisor (04:51)

5. Responding to Volatility and Drawdowns

(10:05)

• Navigating sharp market volatility is a psychological test. Some panic sell, some hold, and others look for new opportunities.

• The hosts advise: trust your research, believe in the company, and stay committed to your plan during downturns.

  "Have emotional discipline. But when you do your research, have conviction in it. Trust what you did." — Investment Advisor (10:58)

• Long-term perspective is emphasized—market turbulence is temporary, time in the market is key.

  "The day that you run up 60%, you should feel the same exact way [as when you drawdown]." — Investment Advisor (11:21)

6. Strategic Use of Leverage and Position Sizing

(11:37)

• Advanced traders with long-term portfolios can start strategically increasing risk for higher returns once their base is secured.

• Shorting is discussed: only short when the market’s actually falling. Otherwise, follow the dominant trend.

  "Know when to put on risk. You have to have your long term portfolio set up first." — Futures Trader (11:37)

7. Tactical Trading: Obeying Market Direction

(12:22)

• Trade with the trend: only short in clear downtrends, and otherwise go long.

• Examine market direction across month, week, and day timescales for confirmation.

• The hosts note the market falls faster than it rises—presenting unique shorting opportunities during downturns.

  "Only short when the market is falling and go long when it's going up. That's why I say you have to obey direction." — Futures Trader (12:22)

8. Options vs. Futures: Suit Your Personality and Strategy

(13:12)

• Options and futures offer different risks and advantages.

• Investment Advisor shares a personal preference for calls over puts and for not being aggressively bearish on assets that generally trend upward.

  "There's no reason to go short an asset that normally goes long... There's no reason to continually short an asset that goes up in perpetuity." — Futures Trader (13:22)

Notable Quotes & Memorable Moments

• “Have some balls to trade.” — Futures Trader (04:42)
• “Emotional intelligence... that's necessary, right? To navigate through the world, to navigate through relationships, to navigate through business.” — Investment Advisor (04:51)
• “Have emotional discipline. But when you do your research, have conviction in it.” — Investment Advisor (10:58)
• “Only short when the market is falling and go long when it's going up. That's why I say you have to obey direction.” — Futures Trader (12:22)
• “There's no reason to go short an asset that normally goes long.” — Futures Trader (13:22)

Timestamps for Important Segments

• 03:44: Futures trading tip, sizing up, and having courage in the market
• 04:51: Importance of emotional intelligence and risk management
• 10:05 – 11:37: Navigating volatility, drawdowns, and long-term conviction
• 12:22: Trend-following and the logic behind trading only in line with market direction
• 13:22: Options vs. futures, and the fallacy of perma-shorting bull markets

Conclusion

This episode delivers a tough-love message to aspiring and active traders: true growth and opportunity lie on the other side of fear. By developing emotional intelligence, scaling positions with conviction, and respecting market direction, traders and investors can set themselves apart in volatile—and lucrative—markets. The dialogue captures the blend of practical, strategic, and psychological advice that defines Earn Your Leisure's unique approach to financial literacy.

For anyone building wealth through trading and investing, this episode provides straight talk about courage, research, and controlling your emotions—essentials for surviving and thriving in today's dynamic markets.