Episode Overview

We all have a ‘worst trade ever’ moment. In this episode I detail what was my worst trade ever, and it isn’t the traditional kind of worst trade where you blow up the account – instead it was completely different and just a horrible case of bad timing, to say the least.

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Available on: Apple Podcasts | Spotify | Amazon | YouTube


Episode Highlights & Timestamps

  • [0:00] Owning Your Trading Mistakes
    Ryan introduces a new series where he opens up about his own bad trades, explaining why sharing these moments can teach valuable lessons about emotions and decision-making in trading.
  • [1:12] Emotions in Trading Are Inevitable
    He discusses the myth that traders must be emotionless, sharing his Myers-Briggs personality type and explaining how emotions, when understood and managed, can actually help identify market sentiment.
  • [3:06] When Emotion Meets Market Euphoria
    Ryan connects emotional awareness to recognizing greed and fear in the markets, emphasizing that traders who harness emotion can better understand how others react during euphoric rallies.
  • [4:11] The LinkedIn Trade That Still Hurts
    He recounts his worst trade ever, being stopped out of LinkedIn minutes before it was acquired by Microsoft, illustrating how timing, emotion, and discipline collide in trading.
  • [10:43] Accepting the Emotional Side of Trading
    Ryan reflects on the lessons learned from that loss, acknowledging the frustration but reinforcing that emotion is part of the process and that discipline and perspective ultimately lead to growth.

Key Takeaways from This Episode:

  • Everyone Has Bad Trades: Even seasoned traders make mistakes; what matters is learning from them rather than hiding them.
  • Emotions Are Normal: Every trader experiences fear, greed, and frustration at times; acknowledging those feelings instead of denying them helps you make clearer, more rational decisions in the market.
  • Harness Emotion as a Tool: Understanding your own emotional reactions can help you anticipate how others behave in the market.
  • Stay Disciplined with Stops: Following stop-loss rules consistently protects your account, even when it stings.
  • Perspective Brings Growth: Every painful trade can strengthen your mindset if you analyze it honestly and apply its lessons going forward.

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Full Episode Transcript

Click here to read the full transcript

0:00
Hey, everybody, this is Ryan Mallory with Swing Trading the Stock Market. Now, guess what? I’ve been pondering this new series that I want to do, and I’m not saying I’m gonna do it every week, but, you know, it might be once a month or a couple of times a month, or you might not hear me continue this series for maybe a couple of months depending on what we’re dealing with with the stock market and the other subjects that I’m addressing.

0:21
However, I want to start talking about my bad traits, and I have them, and some of them have some fascinating stories that really show you how raw and emotional trading can be, because I know what what it’s, what people say out there. People are like, oh, you gotta be an emotionalist, is that emotionalist?

0:39
It’s not emotionalist, it’s a emotionless, an emotionless person when it comes to the stock market. You can’t feel nothing, you can’t feel fearful, you can’t feel greedy, you can’t feel nervous or anxious. That’s a bunch of crap.

0:55
It really is. You’re going to feel nervous, you’re gonna feel greedy. There’s gonna be times where you feel fearful, you’re gonna get shaken out of trades. You’re a human being. And anybody that says, oh, I trade without emotion, that’s bull crap. Absolute bull crap. Now some people control their emotions better.

1:12
I’m actually an emotional person. I feel emotions a lot more than people would normally feel, right? I’m pretty good at disguising them, but if you did like a Myers-Briggs test, right? And I think it’s a really cool test. If you haven’t done it, I highly recommend the Myers-Briggs test. So I I do the Myers-Briggs test and it comes back as an INFP.

1:30
It means I’m introvert, but some of you may be surprised by that because I mean, I do a lot of, uh, talking on the interwebs, right? Or the, uh, I have a YouTube channel and this podcast, obviously, and, and I put myself out there, but I am, I’m very introverted and it’s easy for me to like talk on this podcast because I’m not standing in front of an audience, but even in front of an audience, I feel fine, but In social settings, I can feel a little bit anxious at times, right?

1:56
And what’s funny about that is when I go out with some friends or if I, you know, go grab a drink with a few buddies of mine, you can actually see some of my anxiety come through by the way I hold myself. It’s like, uh, if you see me with a beer in my hand or a drink in my hand, you’ll see me, I’ll start spinning the cup around.

2:12
I just keep spinning it the whole time while I’m talking to somebody. I can’t like stop doing that. It’s just kind of like a nervous twitch, right? So people People act like you’re not supposed to have emotions or that if you’re an emotional person, you can’t trade. That’s not true because I’ve been trading since, gosh, like 11 years old, and, uh, I’ve been doing SharePlanner for now like 13 years.

2:29
This month, it was 13 years because I started in May of 2007. I don’t even remember the exact date. I guess some people keeping records of that. I don’t know what the exact date was. I’m sure I got it laying around somewhere. I just know it was May 2007, right? SharePlanner has been around for a long time.

2:44
Uh, the podcast has not. Uh, the podcast is about 2017, I think, so going on what you’re number 3. But the, the cool thing is, if you are emotional, you can be a successful trader. You just gotta know how to harness it and sometimes they can actually help you because when you see the fear and you see the see the greed in the market, you actually know what that’s like, what kind of thinking that some of these people are doing.

3:06
And like right now we have this S&P 500, that’s 40% off of the March lows, and there’s a lot of greed out there right now. And if you’re an emotional person, but can harness those emotions, you can also know what it’s like for some of these retail traders that are in the market right now that you know what they’re feeling and you know how stupid that they’re probably being right now by not locking in some profits, by not raising their stock losses, and the likelihood of there being a bloodbath for Because let’s, let’s face it, these retail traders, they are not going to come away with all their money.

3:35
They’re, they’re all gonna lose their money. I mean, not, not every single person. Some of them will get lucky and be able to cash out, but it’s kind of like Bitcoin mania. You don’t even really hear people talking about Bitcoin right now because all the rage is the stock market. Everybody’s wanting to get into stocks, trade those. It’s almost like the people who were in Bitcoin back when Bitcoin was trading at like $19,000 a coin.

3:55
They’re now all trading stocks, and they’re all hyped up about it. They know what they’re doing. Stocks goes in infinity, money printer goes burr, whatever. But you can’t be emotional. And so the reason why I talk about all this is because I want to talk about one of my worst trades ever. I think it’s actually my worst trade ever.

4:11
And It’s not because it from a percentage standpoint, I lost a lot on the trade. I think you can go back on my website’s past performance, and I didn’t do this before I recorded it, but I think I lost like 3% on the trade or something like that. So it wasn’t like a big trade, it was like an average loss. But the story behind it is what’s so amazing.

4:28
So, I’ll take you back to June 10th, 2016. It was a Friday afternoon. And so, for some of you who have been trading me with in the, in the trading block or back then it was called the Splashone. You’ll know this story well because you were there when it happened. I think I was pretty quiet.

4:45
When it happened, because I, I was mad, very mad. And I’ll get to that as to why, but it was June 10th. I wouldn’t say I was on top of my game with trading at this particular time. I was doing OK, but I wasn’t like, you know, the market was choppy, stuff like that. We were heading into an election year.

5:01
There was a lot of volatility, uncertainty and everything else at that point in time. A lot of people thought at that time that Donald Trump got elected, the stock market would completely crash. In fact, if you go back to election night, it did. They had it limited down when he started winning like Florida and Ohio and everything else, they shut it down for the whole night.

5:17
And then it rallied back the next morning and recovered all its losses for the most part. But I was long on LinkedIn, OK, this was when it was publicly traded. The symbol at that time was LNKD. Stock trade wasn’t really doing much for me. It had been kind of like sideways for a while. I’ve been in it a few days.

5:33
And then it just like started like going south towards the close. And of course, you know me, I’m, I’m a zealot when it comes to using my stop losses. I’m gonna follow them. And I did it with LinkedIn. So it was like, I don’t know, like 5, 10 minutes before the, before the bell was about to ring.

5:49
And all of a sudden you get that little think or swim sound that, OK, you’ve been stopped out of a trade. I’m like, oh, man, I wish I could have seen what would at least have happened, you know, holding over the weekend that I wouldn’t have gotten stopped out on it. And how prophetic that was, right? Because I get stopped out, kind of bummed about it.

6:08
The month of that, that particular month wasn’t unprofitable, but it wasn’t really that profitable per se. I woke up, kid you not. On Monday morning And this is when I was like working out of my house.

6:26
I turn on CNBC, have that going, and there was this headline that said breaking, and I swear I looked at this headline for at least a solid 5 minutes, and it wasn’t registering to me what I was reading. And so I kept on reading it and reading it.

6:41
I’m like, what am I seeing here? Is this a dream? Like, am I in a dream state? And what the headline said is, Microsoft acquires LinkedIn. Let me tell you, I was so pissed, so pissed. I was fuming mad, and it’s still, it, I don’t even know if it really had sunk in yet.

7:01
I just thought to myself, how can that be possible? I was literally 5 minutes away from holding this over the weekend and having L and KD getting bought out in the pre-market by Microsoft. So I’m just, I’m just looking at the screen.

7:18
I’ve got my Mountain Dew, I was drinking Mountain Dew in the mornings at the time. Now I’m on the ice coffee. I’ve given up the Mountain Dews, right? But I’ve got this Mountain Dew in my hand. I’m just really not even sure what to do. I know. How, how do I even trade?

7:34
Even if I’m, I finish up on the day 2, 3%, how can I even be happy? Because when I looked at the, the price on LinkedIn, the stock price, it was up 60%. Yes, that’s 60% from where it closed on Friday.

7:53
It was just, I know it was one of those like surreal moments. It’s like that did not just happen. I was literally in it 5 minutes earlier. I almost had this moment of desperation where I wanted to call my broker and say, look, look, I was just in there 5 minutes before the, the bell closed.

8:09
You’re not gonna hold that against me, are you? It was so, I mean, I, I, I, I know that there’s just no do-overs in the stock market, right? But you have that desperation. The emotions were strong. I remember I went around and walked around the block. I just really didn’t know what to do.

8:25
Well, I knew there wasn’t anything I could do, but here I am in the trading block too. I didn’t, that that was the last place I wanted to go into. Go in there and like, yeah, I was, I was long on it, got stopped out. Sorry, really sucks and it does. It sucked so bad at that time.

8:40
And since then I get a good laugh about it, OK? I mean, I’m always anytime I have a bad trade. Right? If I get stopped out of a trade, I’ll always say, huh, that trade sucked, but you wanna know it was a lot worse? LinkedIn. And I always, I always use the hashtag like never forget June June 13, 2016.

8:59
Uh, yeah, that, that was, that was awful. That was one of the worst moments of my trading. I think it really was. It probably was the worst moment of my trading career and it wasn’t the biggest loss. It was just missing out on such a substantial profit that would have made such a huge impact on that year. Fortunately, there was actually a couple of people who, who did not get stomped out.

9:17
They were using mental stops and because they weren’t watching the price action at the end of the day, they actually held over the weekend. So I guess if there’s like a silver lining or a consolation. it’s knowing that some people held over the weekend, but oh my gosh, me personally, I want that. I want that. I, I mean, it’s hard to get into a stock that ultimately gets bought out, OK, because it just doesn’t happen that much.

9:37
And to be in the stock, only 5 minutes prior to a market close and on Monday they’re bought out. Merger Monday. Remember those? I used to always have a list of mergers on Monday. Man, I’m telling you, I’m, I still get really ticked off about that, that day. And I tell you, my keyboard did not survive that morning.

9:53
It didn’t even survive until the opening bell. It was gone, and it was a wireless keyboard, right? So it was an easy target. I don’t think my mouse survived either. I took that keyboard. I banged it sideways this Sunday on my desk. Oh look, I’m not proud of it, OK? But as traders, like I was saying earlier, you’re still gonna be emotional at times, OK?

10:10
I don’t care how good of a trader you are, you’re gonna feel emotion if you were in LinkedIn 5 minutes before the market close on a Friday afternoon, only to see them get bought out Monday morning in the pre-market. You’re going to get emotional. Yes, I know it looks bad when I say I broke a keyboard over it, but I broke a keyboard over it.

10:26
What are you gonna do? It was upsetting. I put a lot of blood, sweat, and tears into my training, a lot of time. Even do this podcast right now, Thursday night. It’s 9:20. I still got to edit this podcast so that I don’t sound like a bumbling fool. Even that line there, I had to edit a little bit, so I didn’t even sound like I was bumbling on the word bumbling fool.

10:43
The market doesn’t care how much hard work, it’s just gonna penalize you whatever way it wants to, OK? So the market doesn’t owe you anything. You’re gonna be have moments of emotions in the stock market where you get upset about things. It happened to me pretty, pretty hard that Monday morning. That was, that was really upsetting.

10:59
I, I don’t think the mouse survived either. I think In both cases, I was using my warranty on my keyboard and my mouse at Best Buy. Got a new keyboard, got a new mouse. Yeah, they, they actually have warranties there for your, your keyboard and that basically under some, some keyboards, it doesn’t matter how it breaks.

11:19
I mean, you could take a sledgehammer to it and they’ll still replace it. So it was a good warranty, thankfully. Man, I, I just really. Even looking back to this day, that was, that was a really dark, dark, that was a dark day. And you could say, well, Ryan, you didn’t, you didn’t lose any money technically from that trade. I mean, I lost the 3%, but I’m saying like after I got knocked out, it wasn’t like I was holding a stock that was falling 60%, and that’s true.

11:38
It could be far worse things that happens, but to be so close and yet to come up empty-handed. It’s like being in the Olympics, right? And you’re like a downhill skier or whatever, a bobsledder and you, you missed the podium by like 1000 of a second. You come away with nothing. And the only difference was 1000 of a second. You don’t go on the podium, you don’t get remembered. And that’s kind of how it was with the LinkedIn thing.

12:16
But I tell you what, it would have felt good. It would have felt good. It would have been a fun thing to celebrate with traders in the splash zone. That was what it was called back then. It would have been it would have been great to celebrate, but I couldn’t, you know, because I wasn’t in it anymore. But in any case, that was, that was my worst trade. That was my one of my darkest moments in trading ever.

12:33
So I’m gonna try to continue to do this series going forward and we’ll, we’ll try to highlight some other trades. I got plenty of bad trades. There’s bad trades every year, guys. It’s just part of trading, manage the risk though and you’ll be fine. If you have any questions, just feel free to email me, ryan@shareplanner.com.

12:50
Thank you. God bless.


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