Podcast Summary: Earn Your Leisure

Episode: 9 to 5 Investors: The SIMPLE 5 Year Rule That Builds Real Wealth
Hosts: Rashad Bilal & Troy Millings (iHeartPodcasts)
Date: February 2, 2026

Episode Overview

In this episode, hosts Rashad Bilal and Troy Millings, along with their investment advisor guest, break down the essential "five-year rule" for 9-to-5 investors seeking real, generational wealth. They dismantle the myth of short-term trading leading to lasting riches and emphasize the proven merits of long-term equity holding. The discussion is packed with personal anecdotes, straightforward advice, and sharp critiques of the temptation to flip stocks for fast gains. The tone is direct, honest, and focused on actionable wisdom for working-class investors.

Key Discussion Points & Insights

1. The Five-Year Investment Rule

[01:11]

• The main advice for everyday investors: Pick four quality companies, commit, and hold for five years.

• Long-term holding is the simplest and most reliable path to wealth, no matter your starting point.

• Impatience and the urge to “flip” stocks usually ends in disappointment for the average person.

  "If you're not willing to hold for half a decade, you don't want wealth, you want to flip."
  — Investment Advisor [01:26]

• The real game isn’t in meme stocks or quick wins—it’s in disciplined, patient compounding.

• Institutional investors and regular folks follow the same core principle: hold some positions long term.

  "If you're not holding for five years, you're gambling, truth be told."
  — Investment Advisor [02:15]

2. The Risk of Taking Profits Too Early

[02:40]

• Many investors cut profits short, selling after initial gains instead of letting winners run.

• True outsized returns (think: Bitcoin, Tesla, Nvidia) occur over 5, 10, or even 20 years.

• The advisors urge listeners not to envy tech stock success without reproducing their patience.

  "Would you want to miss out on a 10-year Bitcoin run, a 10-year Tesla run, 10-year Nvidia run and be up several thousand percent? No."
  — Investment Advisor [03:53]

• Trading for short-term gains compared to long-term discipline: the latter, while “boring,” is where wealth accumulates.

  "All the wealth accumulation happens in 5, 10 and 20 year cycles... It's the discipline of holding that gives you the freedom to say what you want and do what you want."
  — Investment Advisor [04:08, 04:28]

3. Investor Discipline and Personal Responsibility

[03:24 & 04:10+]

• The guest openly critiques spending investment gains on luxury or frivolous purchases.

• He emphasizes the importance of not cashing out just for lifestyle: stick to your true long-term goals.

  "To take the money out just to go blow it on bags and go buy Balenciaga... I don't want to hear that."
  — Investment Advisor [05:13]

• Long-term holding brings leverage and negotiating power (i.e., "all the chips in your favor").

  "You can't tell me that you want generational wealth and you won't hold for a generation."
  — Investment Advisor [04:24]

4. Portfolio Construction for 9-to-5 Investors

[05:41+]

• Use shares for long-term asset growth; options can provide income or "cash flow."

• The core rule: if you’re betting on a company's future (options), you should hold the underlying stock, too.

  "If I have an option on, on the company, I must own the company, because I believe in its future growth."
  — Investor/Trader [05:41]

• Cited companies for this approach: Nvidia, TSMC, Meta, Amazon.

• Compare holding equities to keeping valuable intellectual property: sells early, sacrifices long-term value.

  "For the equities, man, hold that. Minimum five years, ideally 10 to 15."
  — Investment Advisor [06:30]

Notable Quotes & Memorable Moments

• On short-term vs. long-term investing:
  "You can't take the shortcut just because you want to f off your money. I'm sorry. I'm sorry. Right?"
  — Investment Advisor [05:38]

• On discipline and freedom:
  "It's the discipline of holding that gives you the freedom to be able to say what you want and do what you want."
  — Investment Advisor [04:28]

• On generational wealth:
  "You can't tell me that you want generational wealth and you won't hold for a generation. Somebody's going to finesse you out of your spot too early."
  — Investment Advisor [04:24]

Timestamps for Important Segments

• 01:11 – The Five-Year Rule Explained
• 02:15 – Short-term vs. Long-term Debate
• 03:24 – Temptations to Take Profits Early
• 04:08, 04:28 – Boring Nature, Power of Holding
• 05:13 – Critique of Lifestyle Spending
• 05:41 – Shares vs. Options, Portfolio Construction
• 06:30 – Final Advice: Hold Equities 5-15 Years

Takeaways for Listeners

• Wealth is built, not flipped.
• Hold top-quality stocks for at least five years—even longer if possible.
• Resist the urge to cash out gains too soon, especially for short-term consumption.
• Use options for cash flow, but retain core shares for long-haul growth.
• Think in decades—if you want generational wealth, you have to stay the course.

This episode delivers no-nonsense, practical advice: the simplest path to true wealth isn’t complex strategy or trendy stocks—it’s timeless discipline and the conviction to let your winners run long enough to change your financial life.