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

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.

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.

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)

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.

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.

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.