Earn Your Leisure Podcast: "Biggest Investing Mistakes of the Year & How to Avoid Them"

Hosts: Rashad Bilal & Troy Millings
Date: December 10, 2025

Overview

In this episode, the hosts break down the most significant investing mistakes of the year 2025 and offer practical advice on how listeners can avoid similar pitfalls. Through candid, real-world examples and listener questions, the conversation centers on missed opportunities, strategies for capitalizing on market downturns, and the importance of identifying the next big sectors. The episode blends actionable financial education with the hosts’ trademark pop-culture references and relatable tone.

Key Discussion Points

1. The Costliest Mistake: Missing Major Market Opportunities

Timestamps: 03:29 – 04:13

• Missed the April Run:
  • Investor 2 identifies the biggest mistake as failing to invest during the significant market dip in April:

    “For me, it was two things. Number one, anyone who missed out on that April run, I don't know if you're ever going to have a better opportunity… For the first time in a long—maybe since COVID—did you have such a chance to almost have a guaranteed win.” (03:32)

  • Both hosts agree that not deploying capital when high-quality stocks were deeply discounted was a huge lost opportunity.

2. Ignoring the Downtrend—Not Sticking to the Plan

Timestamps: 04:13 – 04:57

• Market Doubts Early in the Year:
  • Investor 1 notes that in January, investor sentiment was low, and skepticism toward AI and companies like Nvidia led to missed gains:

    “Nvidia is not real… It's not real. The whole AI thing isn't real. And we saw all of these companies drop.” (04:19)

  • The importance of adhering to a predetermined investment plan during market fear is emphasized:

    “Let’s just stick to the plan… Let’s find some indexes to invest in, let’s find some ETFs… and let’s build from there.” (04:46)

3. The Power of ETFs and Leverage

Timestamps: 08:29 – 09:33

• Biggest Gainers:
  • Investor 1 highlights the remarkable performance of indexes and ETFs, especially those related to semiconductors, referencing their personal move into leveraged ETFs:

    “I actually did a leverage ETF—it was the first time I did that in semiconductors because I believed in space so much. That’s up over 900.” (08:54)

  • Consistent message: Document your strategy and act decisively when opportunities present themselves, even during modest corrections (like November’s 5% pullback).

4. The Need to Hunt for the Next Big Sector

Timestamps: 09:33 – 10:39

• Looking Forward, Not Backward:
  • Investor 2 urges all investors to be proactive in seeking the next breakout sector:

    “If you're not spending all your time figuring out which company is going to boom next in 27, you are going to be sadly mistaken. I don’t know if we’ll ever go back to when value investing is ever needed or popular again.” (09:37)

  • Focus on revolutionary companies and sectors, citing historical examples like Nvidia (chips) and Apple (smartphones):

    “When we think of this chip race, we think Nvidia. When we think of smartphone, we think of Apple.” (10:22)

5. Technical Notes: Stock Splits and Adjustments

Timestamps: 10:39 – 11:28

• ETF Splits and Option Adjustments:
  • Hosts address recent 2-to-1 splits in popular ETFs (XLU, XLK) and remind investors these splits affect both shares and options contracts:

    “So if you had one share, that now turned into two shares… and that goes for options contracts.” (10:41)

  • Temporary confusion in brokerage account balances post-split is normal; hosts also touch on their own losses as a reminder that setbacks are part of investing:

    “Yeah, I’ve had a losing trade… I talked about where my entry was and where I was going to exit if it got to that point and it got to that point and it’s fallen ever since.” (11:14)

Notable Quotes & Memorable Moments

• On Opportunity Cost:

  “Any capital that you did not deploy in April when we were screaming to buy is probably the biggest mistake of the year.”
  —Investor 2 (04:02)

• On Market Volatility and Mindset:

  “It was a 5% pullback. Another opportunity, another opportunity.”
  —Investor 1 (09:08)

• On Staying the Course:

  “You got the script, stick to it.”
  —Investor 1 (09:30)

• On Forward-Thinking Investing:

  “You need to hunt for the next company that will have a meteoric rise, that is sustainable, that would be life-changing to the economy.”
  —Investor 2 (10:10)

Takeaways & Practical Advice

• Act During Fear: Great opportunities often arise when others are fearful—if you have conviction, stick to your plan in downturns.
• Diversification via ETFs: Index and sector ETFs, particularly in high-growth areas, offered some of the largest gains; consider leveraging but recognize the risks.
• Research the Future: Don’t rest on past winners—actively look for the next breakout company or sector.
• Track and Adjust: Understand the mechanics of splits, ETFs, and options; be ready for technical quirks in your portfolio and accept losses as part of the game.

Suggested Listening Segments

• Biggest Mistake Discussion: 03:29–04:13
• Planning and Mindset: 04:13–04:57
• ETFs and Leverage Example: 08:29–09:33
• Searching for Next Sector: 09:33–10:39

The Earn Your Leisure hosts deliver a direct, energetic discussion full of real-life tactics, self-reflection, and actionable wisdom for both new and experienced investors. If you missed 2025’s big run-ups, this episode outlines exactly how not to make that mistake again.