September Stock Market Moves: Buy the Dip, Hold Reserves & Key Strategies for the Fall

Summary

Earn Your Leisure Podcast

Episode Title: September Stock Market Moves: Buy the Dip, Hold Reserves & Key Strategies for the Fall
Date: September 2, 2025
Hosts: Rashad Bilal and Troy Millings

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Episode Overview

In this episode, Rashad Bilal and Troy Millings break down essential strategies for the stock market as September rolls in—a month historically known for volatility. Drawing from both personal experience and market data, they cover why consistency, preparation, and simplicity—rather than timing or over-analyzing—lead to generational wealth. The conversation delivers actionable advice for navigating September’s pullbacks, the importance of buying regularly, the role of holding cash reserves, and key calendar dates like quadruple witching.

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Key Discussion Points & Insights

1. The Power of Consistent Buying

(01:51 – 03:40)

• Main Point: Buy shares every month—regardless of market movements.
• Host B:
  • "We are going to buy every single month. Now, if we have a dip, which we had a little bit of pullback...the biggest lesson is to be able to buy a certain amount of shares every month regardless of what the market is doing. That includes crypto."
  • Emphasized that the execution of buying is more important than gathering all possible information.
  • Notable Quote:
    "The ratio of execution of buying is more important than the ratio of information that you take in." (02:41)
  • Stock Picks: Named Microsoft, Nvidia, Netflix, and Google as core media/tech investments, dismissing others like Paramount or Disney for simplicity’s sake.
  • Approach: Keep stock picking simple, focus on “the big four,” and use pullbacks as opportunities.

2. Importance of Holding Reserves

(03:40 – 04:40)

• Host C:
  • Advocated for the importance of having liquid funds ready: "Make sure you have money to invest. Having reserves is important."
  • Explained that this lets you take advantage of pullbacks and great prices, especially around periods of volatility.

3. Upcoming Market Volatility: Quadruple Witching

(03:56 – 05:14)

• Key Date: September 19th – triple/quadruple witching, when options, futures, index options, and single stock futures all expire.
• Host C:
  • "September 19, circle that on your calendar. That is an expiration date where all simultaneously will expire."
  • Warns that this week typically brings volatility due to profit-taking and corrections.
  • This coincides with possible interest rate decisions, amplifying the importance.
• Advice:
  • Stay out of trades a few days before expiration; don’t hold into that actual date.
  • Use this volatility as an entry point if you have cash reserves.

4. Specific Price Levels and Market Timing

(05:14 – 05:56)

• Host B:
  • Target level for SPY: "Spy gets back to 6.38.45. That's the area I would like to potentially enter."
  • Advocated not worrying about short-term drawdowns: "If you're looking to hold for a long term, five years, like you won't even remember any drawdowns or pullbacks that you have."
  • Long-Term Perspective: September and August are historically good months to buy if you plan to hold for years—especially ahead of the anticipated Christmas rally and into January.

5. Options Trading and Live Education

(05:56 – 06:23)

• Host C:
  • ("Yeah. So anybody that's been with us and watching some of these contracts...") Discussed exercising options contracts and reinvesting capital, noting that practical education will be shown live for VIP classes.
  • Reinforces the community aspect and hands-on education strategy of Earn Your Leisure.

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Notable Quotes and Memorable Moments

• On Strategy Simplicity:
  "Buy every month and if we have a great pullback in September, it's your time to execute." – Host B (03:26)

• On Information vs. Action:
  "The ratio of execution of buying is more important than the ratio of information that you take in." – Host B (02:41)

• On Reserves and Opportunity:
  "Have reserves. That would be my two words." – Host C (04:38)

• On Volatility Dates:
  "…quadruple witching, which is going to happen this month. It happens in the third month of each quarter, the third week. So September 19, circle that on your calendar." – Host C (03:57)

• On Long-Term Outlook:
  "When everyone says I want to buy the dip—from a mathematical standpoint, September and August will give you those entries …if you're looking to hold for a long term, five years, like you won't even remember any drawdowns or pullbacks that you have." – Host B (05:46)

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Key Timestamps

• 01:51 – Buy the Dip vs. Buy Every Month: Why buying consistently trumps market timing; naming core stocks.
• 03:40 – Importance of Reserves: Why cash on the side matters and practical strategies for September.
• 03:57 – Quadruple Witching Alert: Markets to watch; advice on trades around high-volatility dates.
• 05:14 – Entry Points and Long-Term Thinking: SPY target, why September is prime for long-term buyers.
• 05:56 – Options Contracts and Live Teaching: VIP community benefits and upcoming live education demonstrations.

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Episode Tone

Energetic, straightforward, and educational with a pragmatic focus. The hosts blend technical knowledge with accessible, real-world advice, making complex market moves digestible for both novice investors and seasoned listeners.

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Summary for Listeners

This episode arms you with actionable strategies for the notoriously choppy month of September. The message: keep it simple, stay consistent, maintain reserves, and don’t get spooked by volatility—especially with key events like quadruple witching and potential rate moves on the horizon. If you’re building generational wealth, the time-tested play is to buy monthly, focus on a shortlist of high-quality stocks, and think years—not days—ahead.

Transcript

[A]

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[B]

What is the market advice for September? Based off of historical data, by September we're gonna make everything real simple. We'll need all the complicated answers when the market moves 3 1/2 standard deviations. No, if the market drops in August and September, we're going to buy in August and September. Rashad, guess what? On the months when it's up in April and January, what are we going to do? Going to buy in April and January. We're going put in chat. We're going to buy every month. We are going to buy every single month. Now if we have a dip, which we had a little bit of pullback, some people were worried about bitcoin. You shouldn't be. But the biggest lesson is to be able to buy a certain amount of shares every month regardless of what the market is doing. That includes crypto. We're hovering at like 109 and some change, we should hit 107 or 106 on Bitcoin. But the key is to buy every month. And also the ratio of execution of buying is more important than the ratio of information that you take in. It's great to know all the information in the world, but some of the people I've seen have the biggest returns and the most amount of shares. They just buy and don't look at all the information and say, okay, I know these are the four I'm going to invest in. Like I was talking earlier, if you're media, Microsoft, Nvidia, Netflix, Google are the only four you need in media. Well, what about Paramount? Extra Plus? Not an equation. Disney, Love Disney, the corporation, shout out to everybody on the executive board, yada yada. But those are the big four. Make it simple. Buy every month and if we have a great pullback in September, it's your time to execute.

[C]

Yeah, I, I figured you was going to go that route. I had buy but I switched mines up. I put have reserves, right? So like make sure. I know people invest in every month, but make sure you have money to invest. And so having reserves is important. We talked about the interest rates and we'll know about that in the next couple weeks.

[B]

Yeah, this month.

[C]

But I think something that gets looked over, especially in the futures market, definitely in the options market is quadruple witching, which is going to happen this month. So it happens in the third month of each quarter, the third week. So September 19, circle that on your calendar. That is an expiration date where all simultaneously will expire. So the options markets will have expiration dates on that date. Futures markets, ETF indexes, they all have it around that time. And what you'll see is people will sell to take profits. All right, so you're going to see sometimes a downtrend or a nice correction or a pullback around that time. But that's all part of the game, right in this to make money. And so when people make money and they take profits, this is what happens. And so circle that day, September 19th, around that week you might see some volatility and that will happen at the same time, presumably when we'll know about the interest rate hike or, you know, maybe not a hike. So it should be an interesting time. There will be some volatility here, but have some reserves in the event either way, because like you said, this is, you want to make sure that you're getting at the right price, which is why you're inside A stock club. But you want to make sure that you're getting it for the long term so you can get some really generational prices and keep them for the long term. So have reserves. That would be my two words.

[B]

Yeah. Spy gets back to 6.38.45. That's the area I would like to potentially enter. And then also with Quiet Witch and coming up, you want to be out three or four days before the expiration. You don't want to hold them into that actual date. And I know sometimes it can be fearful to hold for a long period of time, but when everyone says I want to buy the dip. From a mathematical standpoint, September and August will give you those entries. If you're looking to hold for a long term, five years, like you won't even remember any drawdowns or pullbacks that you have. But September is a definitely a great time. Especially going into the fourth quarter and into the Christmas rally.

[C]

Yeah.

[B]

And into January. You're going to be okay. Hope for the long term.

[C]

Yeah. So anybody that's been with us and watching some of these contracts tomorrow, I would have did it today if the market was open. But tomorrow I'm gonna have to, you know, exercise some of these contracts. I'm probably not going to exercise them to add more shares. We'll probably take capital and reinvest. So either we're going to do that. I know we're doing something special for our VIPs. I'm actually going to probably show that during the class so people can see what it looks like to sell an options contract.

[A]

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[C]

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[D]

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[A]

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[D]

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[E]

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[A]

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[D]

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[E]

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[D]

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[E]

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[D]

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[E]

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[B]

Yes.

[E]

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