Riding the Options Roller Coaster

Summary

Earn Your Leisure – "Riding the Options Roller Coaster"

Podcast: Earn Your Leisure — iHeartPodcasts
Date: November 11, 2025
Hosts: Rashad Bilal, Troy Millings, Trader Coach, CJ Toledano, Dave Chance
Featured Guest: Dave Shands

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Episode Overview

In this episode, the Earn Your Leisure crew dives deep into the ups and downs of options trading, using Dave Shands' first-hand experiences as a lens. The show focuses on learning through real-life trading, managing both the emotional and strategic sides of investment, and highlights the value of planning, patience, and research. With a blend of therapy-like honesty and actionable financial wisdom, the group discusses exits, profits, using AI for analysis, and the mindset needed to endure the "roller coaster" of the options market.

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Key Discussion Points & Insights

1. The Emotional Journey of Options Trading

• Dave Shands' Options Experience: Dave shares how he entered his first options play on AMD at the urging and guidance of CJ and the team. The contract saw significant volatility:

  "The AMD call was a roller coaster. It was up, then it was down, then it was down really bad. He stayed with it..." – CJ Toledano (03:42)

• Learning from Losses: Dave reflects on past losses leading into earnings, particularly with Netflix:

  "I have earnings call past trauma, bro. I've experienced trauma... Netflix hooked me." – Dave Shands (05:41)

• Highlighting Real Returns: Despite volatility, Dave ended up with significant gains:

  "I'm up 378%. Up $22,000. Things are happening right now." – Dave Shands (04:35)

2. When Is The Right Time To Sell?

• The panel discusses anxiety around selling before a company's earnings report, a common pain for options traders.
• CJ Toledano stresses the importance of having a plan:

  "Knowing when to sell is something that a lot of people have questions about. Making 300% and not wanting to lose money is a valid concern for sure." (04:47)

• Trader Coach advises long-term thinking and planning your exit before entering:

  "When you got into the option, did you know what percentage gain you wanted to get before you exited it?" (05:56)

• Dave admits:

  "No, I didn't." (06:36)

• Dave Chance emphasizes taking partial profits:

  "If I bought 10 contracts... if I get to 100%, then my initial investment comes out." (09:02)

3. Patience, Planning, and Not Missing Upside

• The danger of selling too soon is discussed; waiting can yield greater returns, but it's emotionally tough.
• CJ's wisdom:

  "You can never lose by taking profit." (10:26)

• Importance of “buying time”—getting contracts that allow you to benefit from multiple earnings cycles and potential tax advantages.

  "If you do something out to June next year, that's at least four to five earnings reports. It gives yourself time." – Dave Chance (19:49, 20:02)

4. Leveraging AI & ChatGPT for Trading Insights

• CJ encourages using AI for daily investing insights:

  "You should be having daily conversations with ChatGPT...it's going to give you a very educated sentiment of everything that's happening." (10:31)

• AI can act as your personal briefings center, similar to how a CEO gets updates:

  "You can structure AI to have briefings on a daily basis on all your investments. So that way you're at very least highly educated..." (16:20)

• Using AI to review sector performance, compare companies, and obtain projections.

5. Evaluating the Bullish Case on AMD

• The group reviews why AMD is currently strong, citing innovations, AI momentum, sector performance, new products, and strategic partnerships.

  "Did they have any Catalyst events inside the quarter? Well, yeah, they announced that they're partnering with this company called OpenAI." – Dave Chance (18:26)

6. Growth Mindset in Trading

• Shift from “What should I do?” to “What does the data say?”

  "I need to ask a really immature question of like, what should I do versus finding out what's happening..." – Dave Shands (20:44)

• The importance of learning so you can educate others; staying disciplined regardless of market news or who’s in political office.

  "Regardless of what's going on in the world, biggest piece of advice, your targets for your exit have to remain the same." – Trader Coach (22:58)

7. Trade Management: Taking Profits, Adding Positions

• Stacking Calls: Using profits to “stack” more positions in the same company if confidence is high.

  "I've stacked Nvidia calls from $20...to $45, to $80, to 100...As I see that price and the announcements and catalyst events, I keep stacking." – Dave Chance (24:13)

8. Building a Portfolio

• Dave currently holds options in AMD, Netflix, Micron (MU), Meta, and ASML.

  "So you got MU, you got Netflix, I got Meta...I got ASML." – Dave Shands (25:41)

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Notable Quotes & Memorable Moments

• "I'm up 378%. Up $22,000. Things are happening right now."
  – Dave Shands (04:35)

• "Earnings can definitely hurt, especially if it's options, because whatever you feel in the stock, you're gonna feel three times more in options."
  – CJ Toledano (06:48)

• "You can never lose by taking profit."
  – CJ Toledano (10:26)

• "I always say, like, I like to get 100% return if I'm investing...my initial investment comes out."
  – Dave Chance (09:02)

• "You should be having daily conversations with ChatGPT because it's not going to tell you exactly what's going to happen, but it's going to give you a very, a very educated sentiment of everything that's happening in the world."
  – CJ Toledano (10:31)

• "Your targets for your exit have to remain the same...It takes a lot of the frustration. If you take profit, you don't lose that way."
  – Trader Coach (22:58)

• "If I believe in the company and the fundamentals are there and the technicals are showing me that this is something that's going to continue, I do it...I keep stacking."
  – Dave Chance (24:13)

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Important Timestamps

• 03:42 – Introduction of Dave Shands' journey with options
• 04:35 – Dave reveals his 378% return ($22,000 gain)
• 05:41 – Emotional discussion on loss aversion and earnings trauma
• 06:36 – Admission of not having an exit plan
• 09:02 – Discussion on profit targets and scaling out positions
• 10:26 – Value of taking profits and leveraging ChatGPT
• 16:20 – Using AI for personalized investment briefings
• 18:26 – Deep dive into AMD’s bullish case and sector analysis
• 22:58 – Critical advice on maintaining exit targets
• 24:13 – The “stacking calls” approach to growing positions
• 25:41 – Dave lists his current options holdings

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Tone, Flow, and Style Highlights

• Friendly, humorous, and supportive atmosphere; plenty of jokes about trading “therapy” and “testimonials.”
• Transparent, educational, and approachable; the show brings listeners into genuine, sometimes vulnerable discussions about winning and losing money.
• Actionable advice mixed with stories; the team stresses planning and discipline with relatable, real-life examples.

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Summary for New Listeners

"Riding the Options Roller Coaster" is a must-listen for anyone learning about options trading, blending firsthand testimony, expert coaching, and the realities of emotional investing. The panel, especially through Dave Shands’ candid journey, reveals how strategy, patience, and a commitment to learning—plus leveraging new AI tools—are key to surviving and thriving in volatile markets. If you want to learn how real investors make (and sometimes lose) real money, and how to translate lessons into practical next steps, this episode is an entertaining and insightful ride.

Transcript

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[Dave Chance]

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[Trader Coach]

Novel.

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[CJ Toledano]

To continue this con. What's up my brother?

[Dave Shands]

Ah, everybody's good, man.

[Trader Coach]

I got Some advice for you to.

[Dave Chance]

The show at this point.

[Dave Shands]

No, yeah, absolutely, man. Listen, I am. Listen, Y' all ever need to add a testimonial or something, bro?

[Trader Coach]

I do right now.

[Dave Shands]

I'm up on call. First off.

[CJ Toledano]

Dave shut my brother. So Dave. So we had a conversation offline, but, you know, I think that the. What you said is vitally important because I'm pretty sure it's a lot of people that kind of feel the same way. So I'll give. I'll give the audience the background. They're not familiar. Dave shands. This was six months ago, maybe January 11th. January, yeah. And Dave shares. I walked Dave Shands to his first option play. He never made an option play before, right?

[Dave Shands]

Absolutely.

[CJ Toledano]

I was like, yo, like, you didn't like. But long story short, he got into an AMD call, and the AMD call was a roller coaster. It was up, then it was down, then it was down more, then it was down really bad. He stayed with it, called me a few times. Accent, should he sell? He's like, yo, if you sell, let me know because I'm in the call with him.

[Dave Chance]

Can we add a piece of this story?

[Trader Coach]

Yeah.

[Dave Chance]

I'm getting the call. Like, yo, bro, you sure about this?

[Dave Shands]

Rashad didn't pick up, bro. Like, yo, what are we doing, bro?

[Dave Chance]

Just trust me on this one. Just trust me on this.

[CJ Toledano]

So fast forward to now. He's up 300. How much you up? 300 and what?

[Dave Shands]

Well, today I'm down 15 percentage wise.

[Trader Coach]

How much you up? Since you've been in there? I want to hear this, y'.

[Ryan Reynolds]

All.

[Trader Coach]

Since you got two plaques on the wall talking about, I'm down 15.

[Dave Shands]

But I'm up 378. Up $22,000. Things are happening right now.

[Dave Chance]

He's giving out dollar amounts.

[Dave Shands]

Okay, say hello. Thank you.

[CJ Toledano]

So she has a 338 in less than one year. Okay. But you, you had a vital. You text me today, and you was concerned about AMD going into earnings. So you said, should you sell? So this is something that, like I said, a lot of people knowing when to sell is something that a lot of people have questions about. Making 300 and not wanting to lose money is a valid concern for sure. So these are all things that I'm sure a lot of people have the same questions about. Right. And you. I just think it's dope because you're a content creator and you're in the space and you're learning in real time. So we're going to talk about our Advice to you, but what's your emotions right now as far as this option trade? So far?

[Dave Shands]

I have earnings called past trauma, bro. I've experienced trauma.

[Trader Coach]

In which company?

[Dave Shands]

Netflix, bruh. Netflix hooked me. You hear me?

[Trader Coach]

But let's help with your trauma. Let's fix your life.

[Dave Shands]

Yeah.

[Trader Coach]

Nvidia earnings and Netflix earnings are different from amd, so I know that pain is still there. But first and foremost, when you got into the option, did you know what percentage gain you wanted to get before you exited it?

[Dave Shands]

You asked me this in front of people. These are like behind the scenes conversations, bro.

[Trader Coach]

We're coaching. Welcome to Traders Therapy.

[Dave Chance]

New segment.

[Trader Coach]

Traders Therapy.

[Dave Shands]

No, I.

[Dave Chance]

This is the trading hot seat.

[Dave Shands]

That might be a show.

[Trader Coach]

Hey. Yeah, yeah.

[Dave Shands]

No, I didn't. No, I didn't.

[Trader Coach]

Okay.

[CJ Toledano]

You know, well, you know, the earnings cooked a lot of people meta. Notoriously, I mean, they just, they just dropped 80 last week, which was unbelievable.

[Trader Coach]

Yeah.

[CJ Toledano]

Before that meta, they had the worst drop in history a few years ago. A few years ago. So that, that earnings can definitely hurt, especially if it's options, because whatever you feel in the stock, you're gonna feel three times more in options. Call. So. Okay, so that's, that's a valid concern that you have.

[Dave Chance]

Quick question, Dave, around the Netflix, because did you buy the call leading into earnings or you've been in the call already?

[Dave Shands]

No, I've been in it. I've been in it. And then it was like a. Okay, yeah, it was a fly. But then I, I was buying down though, like when it dropped. Okay. It won't come up. Yeah, I'm still getting cooked right now, but it's part of.

[Dave Chance]

You believe in the company.

[Dave Shands]

Yeah, absolutely.

[CJ Toledano]

Okay. All right, so. So Dave Shands wants to know, should he sell AMD before earnings? What's the unanimous decision?

[Dave Shands]

Let me tell you what happened. So I said it before the call, and then one of y' all on speaker was like, yo, the call. It's the next year. So he didn't give me financial advice, but the way he said it was, it's secure. I said, okay, I' ma chill.

[Trader Coach]

You have another year to work through whatever precipitous decline or upside that they have. And a thing that we're trying to stress to you because you're starting off well, you're like, oh, Tani, you starting off with a home run. Stay in for the long term because not only will your confidence get built off of this win, look how many people in your family lives you'll be able to guide and help through the same kind of situation. So don't get out early. And I think it's a mistake for any trader or any investor to only look at the short side, because what if you miss out on another 120% to the upside?

[Dave Shands]

Yeah, that's my question too. Yeah, but so how do you know? So the last time I was on market Mondays, like, we had the testimonial joint shot up and I only have two contracts. And one of the advice was like, yo, you could just sell one and then keep the other. But if I'd have done that, I'd have missed out on a whole bunch of money. So how do I know, like, what's the top? Or do I just ride it out, period? Or am I looking for something?

[Dave Chance]

I think that's what the, the intern. Knowing where you're going to exit the position before you enter it plays in. Right. So I always say, like, I like to get 100 return if I'm investing. And so if I bought 10 contracts, or like you did, you bought two contracts. If I get to 100, then my initial investment comes out. So one gives me. It gives me the capital to say, all right, if the one that I still have remaining continues to grow now I can re enter perhaps a later position because I believe in the company so much and maybe get three contracts. Right? Because it's going to be a little bit cheaper. So you always got to have the position mapped out, which is why I would say buy time. Right. So when you bought that, and I think it's important, your story is important, your testimony is important, because this wasn't a home run at first.

[CJ Toledano]

Right.

[Dave Chance]

Like, I think people need to realize that, like when it, when you bought the call, it actually pulled back because D.C. happened at the end of January.

[CJ Toledano]

Right.

[Dave Chance]

And then April 7th happened and we saw a pullback. But you didn't sell.

[Trader Coach]

Right.

[Dave Chance]

You kept it. So it actually was a negative contract that actually turned out to be a 300. Which is why when we started the show was like, well, what's your stop loss? Well, if they put a stop loss, he would have sold all that and missed out on all the upside.

[Dave Shands]

Right. But also if I, if, like, let's say, for instance, my target was to be up 200, if I'd have hit the 200 and I'd have sold, I.

[CJ Toledano]

Would.

[Dave Shands]

Be upset, you know, like right now.

[CJ Toledano]

Yeah, for sure. So the thing about is this. You can never lose by taking profit.

[Trader Coach]

That thing.

[CJ Toledano]

Also Chat, GBT is your mentor, so you should be having daily conversations with Chat GPT because it's not going to tell you exactly what's going to happen, but it's going to give you a very, a very educated sentiment of everything that's happening in the world. And the good thing with Chat GBT is that after, at the end of it, because how I use Chat gbt, I, I asked it a question and it types it out. But I'll hit the record because nine times out of ten I'm too busy to read a bunch of different stuff. So voices it, it's like a voice, it'll say okay. And then they say okay. Now is this, is this sufficient or do you want more? So it'll tell you the, the traps, the, the highlights, what to look forward to, you know, are they still bullish on the situation as far as the market sentiment? What are all of the analysts saying in aggregate? What is, what's fueling it is the AI. It's the AI crave. Right? What's what could be potentially harmful to it? What's the so do you have a better instead of guessing right, instead of guessing to say is it gonna go up? It's not gonna go up. Who knows? You can have daily conversations so it's almost like you're getting so like a CEO gets daily reports from his company because they don't, they don't know exactly everything that's going on in the company.

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[CJ Toledano]

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[Trader Coach]

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[Trader Coach]

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[CJ Toledano]

If a company's so big you can't know everything that's going on so the leadership has to report. It's like government leadership has to report to the person to give them a briefing. Got it. So you can structure AI to have briefings on a daily basis on all your investments. So that way you at very least highly educated, you watch Market Mondays and now you can say okay, I made 300, I'm gonna take some off the table, I'm gonna let some ride. 4. I got another 18 months. I'm pretty confident that it's still going to go up. It might pull back in the short term, but I have a high level of confidence that over the eight next 18 months the stock is going to be higher than it is right now today.

[Trader Coach]

And in the spirit of Invest Fest, even though you didn't ask Dave a good prompt act as a world class investor. Based on our last five years data, what's the average that AMD goes up over a three month or one year period in this option and it will start to break down the options and how much they will go up to know if you are have some meat left on the bone pause or if there you should start to take profit. You don't have to guess because it'll tell you the exact calculation of how much each option future asset classes went up and went down. So you can know if you're up 300. If the average is hypothetically 315, you know how much more room you have to go if you want to maximize or if you want to take the money off the table.

[CJ Toledano]

That's it.

[Dave Chance]

So the, the you got a port. So tomorrow is earnings. So you're talking about earnings formula fear. But you got to look at how the market has performed and how that sector has performed. So we can look at Broadcom and we can look at Micron, we can look at all these semis and see how they performed and then we can ask ourselves what's the sentiment for the sector, right? And then what still is the bullish sentiment around AI have data center expansions increased? Well, we just heard Amazon saying they're about to go over 120 billion.

[Dave Shands]

Right.

[Dave Chance]

We just heard Meta, which pulled back because they said our capex is going to increase in spending. And so that AI story is still there, the data center story is still there. And then you look at what's happened in the quarter for amd. Yeah, they've been on a nice run. Did they have any Catalyst events inside the quarter? Well, yeah, they announced that they're partnering with this company called Open AI who actually owns Chat GBT. Right. And so now they have a 10 stake. So it's more advantageous for Open AI to perform. And we're seeing it. They're right about to hit a billion monthly. Monthly users having a 10 state. Well, where are they going to get that compute from? Yes, it's going to be from Nvidia, but it makes even more sense to have something that's going to cost less, which they can have in house. Right, which is amd. And in addition they have new products. Right. So we've been talking about this on market Mondays for a while, but the M1 350 is about to start getting into that cycle of revenue. Right. So that's that GPU that is the next tier. Right. So when we talk about Nvidia and we're talking about obviously Hopper, but now Blackwell and Barwell Ultra in a few few months, AMD is now putting that, that second tier GPU in market and the people who can't afford at this level will be able to get at this level. So you take all that into account, you see that the moves that they're making, you see that Lisa sue is becoming more visible. You see the partnership she's, she's having, it feels like there's a bullish case. So we'll see. I like it. But the reason why I like to say buy time is because you buy in those Catalyst events. So when you did it in January, I'm already calculating out, if I do something out to June next year, that's at least four to five earnings reports.

[Trader Coach]

It gives yourself time.

[Dave Shands]

Right?

[Dave Chance]

That's at least four to five of them that we're going to calculate inside there. They're going to be innovation inside there. There's going to be partnerships announced inside there, there's going to be volatility that's going to be priced inside there. And so we're using all that to our advantage when we make that call when it goes out over a year, plus the tax incentives Right. If you would have bought a January contract, there's going to be some short term capital gains. Whereas now when you're in June is long term capital gains. Because the great thing is like, yeah, you've made this money, right, that 300 or 400 potentially by tomorrow. But if you got to pay capital gains tax on that, then you got to make sure that when you get those gains that are realized, that you have the money to pay those taxes as well, which is a lot of people have to remember inside.

[Dave Shands]

Inside of investing, I realized that I need to ask a really immature question of like, what should I do versus finding out what's happening and even ask you all the questions. I know people come up to you, yo, should I buy this?

[CJ Toledano]

Or.

[Dave Shands]

I think the next conversation that I have with you all will be backed by some reasoning of what I'm doing saying, okay, I see this, I see this, I see this. What do you make of that in terms of my question asking? Because then I'll get a better answer versus yo, what do you think I should do? So.

[Trader Coach]

But it's still a great question you have.

[CJ Toledano]

You have to be educated to ask the question. Yeah, yeah. I like this segment with you, Dave. Yeah, we should have you back as a regular at least once a month because now you people can actually see your trading journey in real time and go through all of the aspects as far as the emotional and ups and downs. But before you leave, my last thing is the bitcoin situation. Remember we was on stage and you asked Ian about bitcoin. I think it was like, I don't know where it was at. 80, 70, around that range. And he was like, nah, it's a good time to buy. And then you was like, well, how do you know? Like, how are you sure? So bitcoin, now it's been, like I said, it's been hovering around $110,000. So from that, from that standpoint, in less than a year, bitcoin was. Is up $40,000. So did you buy.

[Dave Shands]

I didn't buy it, bro. Like, leave me alone. No, I'm sorry. Would you listen to your boy? I know, man, I know. I didn't have faith.

[Trader Coach]

You don't have faith in me.

[Dave Shands]

It will never happen again, bro. It'll never happen again.

[Trader Coach]

Thank you. At that time, that was a hell of a time. That was a layup time. But it's okay.

[Dave Chance]

I just. I just showed Shoddy a text I got from a dude in my neighborhood, and it says, today I'm the Dave Chance. Am I lying? It says, oh, whatever the dude's name is. I said laugh out loud. Dave Shanty's like, yo, yeah, I'm gonna be him. So people are hearing your story on market Mondays every week and they're like, that's gonna be me.

[Trader Coach]

I like this, bro.

[Dave Shands]

Yeah, this is yo, that, that chat, man. I hope they was listening to that chat. GPT like just finding out what's going. The wealth of the world is on it.

[Trader Coach]

Also, to get a. Regardless of what's going on in the world, biggest piece of advice, your targets for your exit have to remain the same.

[Dave Shands]

Yeah.

[Trader Coach]

So regardless what happens with Trump or whoever wins next, that Peter Teal picks my targets and futures remain the same year round. It takes a lot of the frustration. That's why Rashad kept saying, listen, if you take profit, you don't lose that way. So if your first target is 100% and your second is 400, it doesn't matter who's in office. Those should always be your targets.

[Dave Shands]

Let me ask this, though. Let's say, for instance, you hit your target, but you see something that gives you confidence to stay in. Are you in a disciplined space where he's like, yo, I'm just going to take it and then maybe go back in. Or based on what's happening, do you let it ride?

[Trader Coach]

You should always follow your plan and then start to size up.

[Dave Chance]

Yeah. If, if I. And this is great because we talked about this last week as well. If I've hit my target and I've taken out my initial investment and it's a strong company. Like, I literally have done this probably 5 or 6 times. I like to call it. I start stacking my calls, right. So, like, I've done it with Nvidia and I shout out to everybody that. That gave me the congratulations. I've stacked Nvidia calls from $20, which are obviously stock split, take into account.

[Trader Coach]

Yep.

[Dave Chance]

To $45 to $80, to 100 to. I have probably eight calls on Nvidia. And as I see that price and the announcements and the Catalyst events and the innovation that they announced, I keep stacking. I've done it with Micron, I've done it with Broadcom.

[CJ Toledano]

Right.

[Dave Chance]

I've done it with Celestica. If I believe in the company and the fundamentals are there and the technicals are showing me that this is something that's going to continue, I do it right. So, like, I always invest the money. Like, I don't treat it like a checking account where it's like yeah, we made 20,000. We made 30,000. No, I'm looking at like, okay, where do I deploy more content? Right? Can I go back into this position and grab some more contract track so we can let this run? Can we do 100 again?

[Trader Coach]

Then you can talk real crazy on them hot seats. What made you pick this dumbass business? You can't even break it your beard off. How you a barber.

[Dave Chance]

How many companies are in the portfolio in terms of your. Your options? Like portfolio. How many companies are in there?

[Dave Shands]

Option? I have one. I got. I'll just tell you. I got amd. Yeah, I have Netflix.

[Trader Coach]

So it's nasty.

[Dave Chance]

Don't be mad at that.

[Dave Shands]

Mu is going crazy.

[Dave Chance]

So you don't even know. I said Micron five times. That's. That's Micron.

[Dave Shands]

Mu's.

[CJ Toledano]

Yeah.

[Dave Shands]

Ridiculous.

[CJ Toledano]

I don't think so. Who.

[Dave Shands]

Can you get that one, huh?

[CJ Toledano]

So you got Mu, you got. You got Netflix. I got Metal Meta. That was recent.

[Dave Shands]

Yeah, I got asml. I just got asml.

[Dave Chance]

Today, today, today, today.

[Trader Coach]

So you got four.

[Dave Shands]

Yeah, five.

[Trader Coach]

Stay right there. Just four is a sweet spot.

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[CJ Toledano]

Shins my brother, man. Thank you for joining us.

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[Trader Coach]

Lenovo.

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