The #1 Investing Mistake Keeping You Broke

13 May 2026 · 7 min · 3 chapters

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In short

The #1 investing mistake: trading long-term “hold” stocks instead of holding them, plus the related error of having no exit strategy.

Guest backgrounds

The episode text mentions SNL’s Mikey Day and head writer Streeter Seidel, but they appear only in unrelated promo segments; the investing discussion is led by Clifford Taylor IV (The Clifford Show).

Key claims

Don’t rotate out of leading companies; fear drives “what’s next” after big gains. Always set an exit plan (e.g., target profit, then take initial capital out and let the rest run). Not having an exit strategy leads to regret and emotional trading.

Notable examples

Nvidia doubling in 2023 while missing later gains; “Sandisk” and “Sandus” discussed; a hypothetical $10,000 invested in 2020; Sanders IPO up ~3400% (Feb 2025 to later price levels).

Written by AI. May contain mistakes. Listen to the episode to check what was said.

Chapters

Tap a time to open that second in VO

The Biggest Investing Mistake

0:45 to 2:04

Discover the common mistake of trading long-term stocks for short-term profits.

“Radio app, Apple Podcasts, or wherever you get your podcasts.”

Importance of an Exit Strategy

2:04 to 6:00

Understand why having a clear exit strategy is crucial for investors.

“I posted it earlier, but I think the biggest investing mistake people are making is trading the stocks you should be holding for long term.”

Balancing Trading and Long-Term Investments

6:00 to 8:10

Learn how to effectively balance between trading and long-term investments.

“I think everyone at EYLU knows my exit strategy.”
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Transcript

Automatic transcript. May contain errors.

0:00This is an iHeart Podcast. Guaranteed Human.

0:31week, my guests, SNL's Mikey Day and head writer Streeter Seidel, help an acapella band with their between songs banter. Where does your group perform? We do some retirement homes. Those people are starving for banter. Listen to Humor Me with Robert Smigel and friends on the iHeart Radio app, Apple Podcasts, or wherever you get your podcasts. Last night, a blown call changed the game. This morning, the internet lost its mind, and nobody's telling you exactly what happened. That's where Sports Slice comes in. I'm Timbo, and every episode, we're cutting through the noise, breaking down the biggest moments in sports, and giving you the real story behind the headlines.

1:07And we're going straight to the source, the athletes themselves, their locker room stories, their reactions in the moment, and the stuff nobody gets to hear. Listen to Sports Slice on the iHeartRadio app, Apple Podcasts, or wherever you get your podcasts. And for more, follow Timbo Slice Life 12 and the TikTok Podcast Network on TikTok. What's up, guys? This is Clifford Taylor the fourth and on my podcast the clifford show i'm bringing you conversations about all kinds of stuff like being an internet famous referee we're in the middle of a game this linebacker you know these kids linebacker walks up to me he goes hey ref my mom wants you to wave at her what quarterback on office blue 42 hey ref mama want you to wave at her what

1:53Where's she at? Hey, Ms. Parker. Listen to The Clifford Show on the iHeartRadio app, Apple Podcasts, or wherever you get your podcasts. Let's go over the biggest investing mistake that people make. I posted it earlier, but I think the biggest investing mistake people are making is trading the stocks you should be holding for long term. 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 leave but the issue is you traded them like 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 of the last few years literally same thing sandus this year um 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 two and three thousand percent on the trade and we're probably going to talk about microndon in a little bit but some of these companies are going to go up four or five thousand percent over a five or six year period and you're going to be stuck on the sidelines with a 200 percent gain win tax and you blew the money on a car or a vacation or somebody who doesn't love your deal.

3:17Something stupid. 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 whole for the long term. And you're blowing the money on liability. It makes no sense to trade an asset to then spend it on a liability. Crazy as hell. 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.

4:04And it sounds like, eh, 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 % 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 we're sitting at what 1289 so Sanders has jumped 3400 % and people have watched week after week like okay there 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? Like 3 ,400%. Was that a better teacher issue or should they have listened the first time?

4:56That's fear. I'm not trying to be mean. To me, that speaks to fear. That speaks to fear. And 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, what should I do? There's no exit strategy. 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, you tell me. Well, did you try to gain 20 %? Because if you did, then you hit that metric.

5:35If it was 40%, 100%, when you got there, what did you do? because some people say, well, oh, man, if I sell it at 50 and I watch it go to 70, I'm going to be upset. I'm like, well, what was the goal when you entered the position? Then you can't be upset. You set the metric for yourself. Nobody made it for you. And so the mistake I'm seeing a lot, especially this year, especially over the past four weeks, is having no exit strategy. It's so important. Like, you got to know what it is. I think everyone at 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?

6:10a little bit, but once I get it, what do I do? All right, I'm taking my initial investment out, and let's the rest run. Let's do it. Every time. There's no question about it. Have your extra energy. I'm going to be real. Some of you are going to trade your way into poverty. You're rotating out of the best companies on earth, and the crazy part is you're seeing best of both worlds. You're seeing people get 1 ,000 % return long-term, and you're 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 what is anthropic coming at what does open ai come in what is spacex come in at as a result and how far will they fly and i think you can um do both and it i think that's something that people should consider as well as Like if you believe in a company.

7:08Got to do both. Trading, to me, how I look at it, trading, it gives you leverage. So small amounts can turn into large amounts. Yes. 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 your total framework that you think you're comfortable having more risk. And now you can trade Google as well. 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 going to invest it. I mean, you can't just invest, that's fine too. But if you are a trader, then it's like, okay, I'm going to have the positions that I hold long-term and then I'm going to have a position that I'm going to feel comfortable trading.

8:00And then a certain amount of money as well. A money allocation that you feel comfortable losing because trading is volatile or you feel comfortable having it go up and then go down. Like you got to, 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 emotionally attached to it. So 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 it's going to go up 500%. And usually what happens when you do that is that you lose everything.

8:47Departation, yeah. 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 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 some money and trade the company. If you really have done the research, you feel good about it, and you feel like this is something that you want to just kind of have, you know, that leverage to have outstretched the gains than you would get in a traditional just buy a whole situation.

9:29All facts. Another podcast from some SNL late night comedy guy, not quite. Unhumor me with Robert Smigel and friends, me and hilarious guests from Bob Odenkirk to David Letterman help make you funnier. This week, my guests, SNL's Mikey Day and head writer Streeter Seidel help an acapella band with their between songs banter. Where does your group perform. We do some retirement homes. Those people are starving for banter. Listen to Humor Me with Robert Smigel and friends on the iHeartRadio app, Apple Podcasts, or wherever you get your podcasts. Last night, a blown call changed a game. This morning, the internet lost its mind, and nobody's telling you exactly what happened.

10:08That's where Sports Slice comes in. I'm Timbo, and every episode we're cutting through the noise, breaking down the biggest moments in sports, and giving you the real story behind the headlines. and we're going straight to the source, the athletes themselves, their locker room stories, their reactions in the moment, and the stuff nobody gets to hear. Listen to Sports Slice on the iHeartRadio app, Apple Podcasts, or wherever you get your podcasts. And for more, follow TimboSliceLife12 and the TikTok Podcast Network on TikTok. What's up, guys? This is Clifford Taylor IV. And on my podcast, The Clifford Show, I'm bringing you conversations about all kinds of stuff, like being an internet famous referee.

10:44We're in the middle of a game. This linebacker. This linebacker walks up to me. He goes, hey, ref, my mom wants you to wave at her. What? Quarterback on office blue, 42. Hey, ref, my mama wants you to wave at her. What?

11:03Where's she at? Hey, Ms. Parker. Listen to The Clifford Show on the iHeartRadio app, Apple Podcasts, or wherever you get your podcasts. What's up, fam? It's Isaiah Thomas. And I'm CJ Toledano. It's our favorite time of the year on our podcast Point Game, the playoffs. We're digging into the biggest surprises of the season. And I'm looking back on some of my greatest playoff moments. If we didn't talk ever again, I was fine. You just understood. That's how personal it got. Wow. Then after that game seven, Marquis coming to you, he's like, you know, I love you, dog. You know, it's all love. This was just playoffs.

11:37This was just basketball. So listen to Point Game on the iHeartRadio app, Apple Podcasts, or wherever you get your podcasts. This is an iHeart Podcast. Guaranteed Human.

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