"YOU CAN’T TRADE STOCKS IF YOU’RE SCARED — GROW SOME BALLS!"

Summary

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.

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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.

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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)

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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)

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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

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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.

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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.

Transcript

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What.

[Jacob Goldstein]

About the trading tip of the week?

[PNC Bank Narrator]

What's the trading tip of the week.

[Futures Trader]

For my futures traders? I want to be very honest and say I want you guys to have less fear and more kahunas. The thing I do love about the options market is that people who just started options trading, they're like eight contracts and they're going to hold. Meanwhile, futures traders play it too small. So a target that I love is 33 contracts. Go for 42 ticks on the S P 500. That's a little bit over 10 points. That should put you like over 17 grand per trade. And if you get two or three of those in a month, you'll be a okay. But the lesson for this week, you have to learn when to put on size. 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 that you can then put into the market or buy an amazing property like Rashad did on a discount. You have to have enough cash flow to be able to do so. So 33 contracts is the target I love. Go for 42 ticks, you'll be at 17 and some change per trade. Do that three times a month and you'll be okay. But have some balls to trade.

[Investment Advisor]

Have some coons. I'm with you.

[Futures Trader]

You do?

[Investment Advisor]

I'm all about the mitigated risk. But yeah, having two contracts go to a thousand percent sucks when you could have had like five, right? It just. Yeah, you gotta have the capital. I just want to add to this because I've been. I've been having conversations with people, especially since the last options class, about emotional intelligence. I feel like that 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? To navigate through the world, to navigate through relationships, to navigate through business, you need to.

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Ugh. Stressing me out. Why are all the people I love so hard to shop for?

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Actually surprise you with categories like best gifts for the mom whose idea of a sensible walking shoe is a stiletto.

[Futures Trader]

Psst.

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[Investment Advisor]

Have it. Investing it.

[Futures Trader]

It.

[Investment Advisor]

It's also needed, right? So, like, when we see. When we have volatility like we did two weeks ago, like, how are you reacting to that? Like what, How. How do you feel when you see your account go down, right, it draws down because the entire stock market went down. Are you moving, right? Are you budging? Are you selling? Like a lot of people that. Some people. I shouldn't say a lot. Some people will sell. Some people will say, oh, we've been here before. Some people, this is their first time, and they're like, hey, there's no way to start my investing journey right? But this is why we always talk about long term. This is always why we talk about buy time. Because when you buy time, you're buying into it. The volatility of the market, you can't control that. We had this conversation the other day. I'm like, yo, we made an investment. I'm like, look, we got time. We got. We got some time on our hands. This is a strong company. We gotta really believe in the company, believe in the research. It's like, have emotional discipline. But when you do your research, have conviction in it. Trust what you.

[PNC Bank Narrator]

What you did.

[Investment Advisor]

Trust what you did.

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And even if, right.

There'S a drawdown.

[Investment Advisor]

Or it hits that threshold, remember, you had your plan, right? If it was 20, 30, 40. I know some people, 50. All right, well, get back in, get back, and there'll be another opportunity. If you believe in that country, if you trust the research that you've done, have conviction, but have the emotional talents to say, you know what? I understand what this feels like. Because the day that you run up 60%, you should feel the same exact way.

[Futures Trader]

Yep.

[Investment Advisor]

Right? It should be even killed. Have your seat belt on. Trust the research, trust what you're doing, and just be patient.

[Futures Trader]

And on the feature side, like, 33 contracts for NASDAQ is 33,000es the 16,500. I'm not saying it's a small chunk of change, but I know some people who are doing a hundred thousand dollars elsewhere and get 9%. And it's like, if you're able to get 2 to 400% inside of a trade or two at some point, know when to put on risk. If you have your. You have to have Your long term portfolio set up first.

[Investment Advisor]

Yeah.

[Futures Trader]

And even with this drop this happened if you've bought in March, in April and last, you should still be up a tremendous amount. Now you can put on some risk. And if the market's falling to the downside and you're shorting, you should be up even more.

Stick to your game plan.

[Investment Advisor]

Do you like to show the market.

[Futures Trader]

Hell yeah. When it's falling. And it's a great lesson. 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.

[Investment Advisor]

Yeah.

[Futures Trader]

Look at that. Month, a week, then day. Obey it always. But when the market is falling, the market is going to fall faster than it can rise.

[PNC Bank Narrator]

Right.

[Futures Trader]

You got to take advantage of it.

[Investment Advisor]

I'm just not only in, in futures is for sure. I've just never, I've never been a, a big put guy.

[Futures Trader]

It's probably not worth the risk. But the futures market is evenly weighted, right?

[Liberty Mutual Narrator]

Right.

[Futures Trader]

Because they only care about the transaction and liquidity inside of it. So you're getting in and out inside of a day anyway.

[PNC Bank Narrator]

Yeah.

[Futures Trader]

So you're just playing the true direction.

[Investment Advisor]

That's why I say in the futures market makes a lot of sense.

[Futures Trader]

Yeah.

[Investment Advisor]

I just don't have the move around so much and like I said, volatility happens puts. And if people do that, great. You can make money both ways.

[PNC Bank Narrator]

Right.

[Investment Advisor]

When the, the market goes up, you can make it on calls, you can make it on puts.

[PNC Bank Narrator]

On the way down.

[Liberty Mutual Narrator]

Yeah, great.

[Investment Advisor]

If you're skilled at that, great. If that's your strategy, great. I just never have been big on it.

[Futures Trader]

There's no reason to go short an asset that normally goes long. Michael Burry I love you dealer. There's no reason to continually short an asset that goes up in perpetuity.

[Investment Advisor]

Yeah, yeah.

[Futures Trader]

Speaking of that. Yeah, speaking of the asset that goes up.

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[Bowen Yang]

This is Bowen Yang from Las Culturistas with Matt Rogers and Bowen Yang.

[Matt Rogers]

Hey, Bowen, it's gift season.

[Bowen Yang]

Ugh, stressing me out. Why are the people I love so hard to shop for?

[Matt Rogers]

Probably because they only make boring gifts guides that are totally uninspired. Except for the guide we made in.

[Bowen Yang]

Partnership with Marshall's, where Premium gifts Meet Incredible Value.

[Matt Rogers]

It's giving gifts with categories like Best Gifts for the Mom Whose idea of a Sensible Walking Shoe is a Stiletto.

[Bowen Yang]

Or Best Gifts for Me that were so Thoughtful I really shouldn't have.

[Matt Rogers]

Check out the guide on marshalls.com and.

[Bowen Yang]

Gift the good stuff.

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