The #1 Investing Mistake Keeping You Broke

Summary

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Earn Your Leisure Podcast: "The #1 Investing Mistake Keeping You Broke"

Date: May 13, 2026
Hosts: Rashad Bilal & Troy Millings
Key Theme: Why trading long-term winners too soon—and not having a clear exit strategy—keeps investors from building real wealth.

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Episode Overview

In this episode, the Earn Your Leisure team digs into the most common investing pitfall keeping people from wealth: selling great companies too early and not having a clear exit plan. The discussion covers the psychology behind these mistakes, missed opportunities in recent years, the emotional traps of trading, and practical steps toward a healthier investment strategy—including the possibility of balancing both trading and long-term holds.

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Key Discussion Points & Insights

1. The #1 Investing Mistake: Trading Long-Term Winners

• Key Point: Many investors sell stocks in high-potential companies for quick wins, missing out on far greater long-term returns.
• Memorable Example: “Someone told me, hey, I had a hundred thousand dollar trade in Nvidia in ’23, I doubled my money. But look how much money you miss on the back end.” (Financial Analyst, 02:48)
• Perspective: The biggest market leaders typically continue leading; people lose out by trading them for a short-term gain instead of holding.

2. The Power of Compounding & Missed Opportunities

• Case Study: Referenced companies like Sandisk and Nvidia have gone up as much as 3,000–4,000% over 5-6 years, but most investors only realize modest short-term profits.
• Quote: “We just watched a company IPO in February of 2025. It is now up 3400%.” (Investment Enthusiast, 04:01)
• Lesson: Long-term perspective drastically shifts potential wealth outcomes.

3. Lack of Exit Strategies Hurts Investors

• Issue: Many investors don’t set clear sell targets; as a result, they either miss further gains or sell in a panic.
• Anecdote: Many reach out after making money, asking, "What should I do now?"—exposing the lack of planning.
• Advice: “If you set your metric at 20%, at 40%, at 100%—when you get there, what did you do?” (Investment Enthusiast, 05:45)
• Personal Strategy: Investment Enthusiast aims for 100% gain, pulls out initial investment, lets the rest run.

4. Trading vs. Investing: The Balance

• Financial Analyst’s View: Trading has its place (leverage, learning), but not at the cost of missing long-term wealth: “Some of you are going to trade your way into poverty.” (Financial Analyst, 06:31)

• Risks Highlighted: Chasing quick trades with all your capital is emotionally taxing and prone to disaster.

• Investor Framework: Foundational long-term positions in solid companies should come first; speculative trading should only be with disposable money.

  Quote:
  “It’s not gambling. That’s when you go into the realm of gambling—when you have $10,000 to your name and you put $10,000 on a one-day trade hoping it goes up 500%. Usually what happens in those cases is you lose everything.”
  — Investment Advisor (08:45)

5. Building a Healthy Investment Plan

• Portfolio Structure:
  • Core: Solid, long-term holds in reliable companies (e.g., Google).
  • Risk/Flex: A designated portion for trading, only what you can afford to lose.
• Emotional Management: Avoid becoming emotionally attached to risky short-term trades.
• Research is Key: If you truly believe in a company and have done due diligence, it’s possible to both invest for the long term and tactically trade.

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Notable Quotes & Memorable Moments

• On long-term vs. trading:
  “It makes no sense to trade an asset to then spend it on a liability.”
  — Financial Analyst (03:37)

• On regret and goals:
  “If I sell it at 50 and watch it go to 70, I’m gonna be upset. I’m like, well, what was the goal when you entered the position? Then you can’t be upset.”
  — Investment Enthusiast (05:36)

• On investor psychology:
  “That speaks to fear. And it’s, that’s something that’s very common in our community.”
  — Investment Enthusiast (05:09)

• Practical allocation advice:
  “Allocate how much money you feel comfortable out of your investment portfolio to trade… If you do want to trade, make sure you have solid foundational companies for your long-term hold.”
  — Investment Advisor (08:25)

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Timestamped Highlights

• [02:20]–[03:51]: Why trading long-term winners is the biggest mistake; cautionary examples from Nvidia, Sandisk.
• [04:01]–[05:03]: Missing out on generational returns; the psychological barrier of long-term thinking.
• [05:36]–[06:30]: The crucial importance of having clear exit strategies.
• [06:31]–[07:28]: The risk of “trading your way into poverty”; market cycles and future opportunities.
• [07:29]–[09:39]: How to balance trading and investing; portfolio structure and emotional discipline.

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Summary Takeaways

• Hold, don’t fold: The greatest wealth in investing is built by holding strong companies for years, not chasing quick trades.
• Plan your exits as much as your entry: Define your exit/goal before investing to avoid emotional mistakes.
• Balance is key: Combine a strong long-term portfolio with a small, well-defined trading allocation—never gamble all your capital.
• Do your research and stay patient: True conviction comes from research, not guessing the “next big thing.”

This episode provides both a reality check and a roadmap for those looking to build sustainable wealth through smart, patient investing.

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Transcript

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[Investment Advisor]

let's go over the biggest investing mistake that people make.

[Financial Analyst]

I posted it earlier, but I think the biggest investment mistake people are making is trading the stocks you should be holding for long term. Like I've had people reach out to me and say same thing. What's the next SanDisk Nvidia AMD one we'll talk about later. The ones that are leading now will lead. But the issue is you traded them. Like someone told me, hey, I had a hundred thousand dollar trade in Nvidia and 23 I doubled my money. But look how much Money you miss on the back end of the last few years. Lily, Same thing. Sandisk this year. And I know I may be a little bit biased towards futures, but if you look at the history of the biggest companies we're now looking at, some companies go up 2 and 3,000% on the trade and we're going to talk about Micron in a little bit. But some of these companies are going to go up 4 or 5,000% over a five or six year period and you're going to be stuck on the sidelines with a 200% gain win tax and you blew the money on a car or a vacation or somebody who doesn't love you deal something stupid. Yeah, stop trading the stocks that you should be holding for a long period of time and once again, the ones that are going to do incredibly well in the future are doing incredibly well now. Hold for the long term and you're blowing the money online. It makes no sense to trade an asset to then spend it on a liability. Crazy as hell.

[Investment Enthusiast]

Yeah, you hear those stories, right? And we've posted it a few times. If you would have had $10,000 in 2020 and invested in such and such company, it would be this amount today. And you're like, oh, well, I wasn't doing it in 2020. And then if they scale out to a longer term vision, they say, well, if I invested in 2010, I'd have 1.4 million. And it sounds like that is so out of reach. But we're living in a time where we just watched a company IPO in February of 2025. It is now up 3400%.

[Financial Analyst]

Yep.

[Investment Enthusiast]

Like, and it wasn't like, where did this thing come from? Never heard of it before. Literally we said it here and that was at 195 today was sitting at what, 1289. So Sanders has jumped 3, 400. And people have watched week after week, like, okay, here it's going up, it's going again. I wonder if it'll pull back and watched it and missed. Right? And to me I'm like, okay, well the next question I'm going to get is, well, what's the next one? I'm like 3,400%.

[Financial Analyst]

Was that a better teacher issue or should they have listened the first time?

[Investment Enthusiast]

That's fair. That's more.

[Financial Analyst]

I'm not trying to be mean.

[Investment Enthusiast]

No, no, I'm just saying that's fair to me that that speaks to fear. That speaks to fear. And it's, it, that's something that's very common in our community. To answer the question, I'll come back to it. But to answer the question of the biggest mistake that I'm seeing and I get this call probably three to four times a day is easily what should I do? There's no exit strategy within some people. If they end the calls, they've made money. The next question is, what should I do? Well, what's your exit strategy? I don't know, what should I what? You tell me. Well, did you try to gain 20? Because if you did, then you hit that, that metric. If it was 40, 100% when you got there, what did you do? Because some people will say, well, oh man, if I sell it at 50 and I watch it go to 70, I'm gonna be upset. I'm like, well what, what was the goal when you entered the position? Then you can't be upset. You set the metric for yourself, nobody

[Investment Advisor]

made it for you.

[Investment Enthusiast]

And so the mistake I'm seeing a lot, especially this year, especially over the past four weeks, is having no exit strategy. That's so important. Like you gotta know what it is. I think everyone in Eylu knows my exit strategy. Everyone here should know it. Like I'm looking for 100%. If I don't get it, am I disappointed? A little bit. But once I get, what do I do? All right, I'm taking my initial investment out and lets the rest run. Let's do it every time. There's no question about it. Have your.

[Financial Analyst]

I'm going to be real. Some of you are going to trade your way into poverty. They're rotate like you're rotating out of the best companies on earth. And the crazy part is like you're seeing best of both worlds. You're seeing people get a thousand percent return long term and you seeing it being done in trading in four or five years, especially post economic crash. Some of these companies are going to be too expensive too. Because if SK Hynix and Sandisk is priced where it is now, where does Anthropic come in at? What does open AI come in? What is SpaceX come in at as a result? And how far will they fly?

[Investment Advisor]

And I think you can do both. And I think that that's something that people should consider as well. It's like if you believe in a company, gotta do both trading. To me, how I look at it, trading, it gives you leverage. So small amounts can turn into large amounts.

[Investment Enthusiast]

Yes.

[Investment Advisor]

So but you need a foundational base. So if you have Google, right, like you can have a long term portfolio in Google and then you have a portion of, of your total framework that you think you're comfortable being, having, having more, more risk. And now you can trade Google as well. I don't, I don't think you should look at it as like one or the other of like I'm either going to trade it or I'm gonna invest it. I mean you can't just invest, that's fine too. But if you are, you know, a trader, then it's like okay, I'm gonna have the positions that I hold long term and then I'm gonna have a position that I'm going to feel comfortable trading and then a certain amount of money as well. A money, money allocation that you feel comfortable losing because trading is volatile or you feel comfortable, you know, having it go up and then go down. Like you gotta, you can't not advisable to put every single dollar that you have into trading because from an emotional standpoint you're going to be too, too emotionally attached to it. So it's not, it's not gambling. I think that's when you kind of go into the realm of gambling. When you have $10,000 to your name and you put $10,000 on a one day trade with the hopes that is going to go up 500%. And usually what happens when you do that is that you lose everything. You know, you're not thinking from a rational standpoint. So allocate how much money you feel comfortable out of your investment portfolio to trade. If you do want to trade, make sure you have solid found solid foundational companies that you have in your long term hold. And if you feel really great about a company, then yeah, do both. Buy the company long term hold and then take, take some money and trade the company. If you really have done the research, you feel, you feel good about it and you feel like this is something that you want to just kind of have, you know that lever to have outstretched gains than you would get in a traditional just buy a whole situation.

[Investment Enthusiast]

All facts.

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