The Canadian Investor - The 7 Biggest Investment Mistakes We’ve Made

Episode Date: October 30, 2025

In this episode, Simon and Dan candidly discuss their worst investing mistakes, emphasizing the importance of acknowledging errors in judgment and the lessons learned from them. They explore themes such as drawdowns, overvaluation, home bias, and the necessity of understanding investments before committing funds. The conversation highlights the significance of position sizing and the emotional aspects of investing, including regret and profit-driven decisions. Ultimately, the hosts stress that while mistakes are inevitable, they can lead to valuable insights that improve future investment strategies. Check out our portfolio by going to Jointci.com Our Website Our New Youtube Channel! Canadian Investor Podcast Network Twitter: @cdn_investing Simon’s twitter: @Fiat_Iceberg Braden’s twitter: @BradoCapital Dan’s Twitter: @stocktrades_ca Want to learn more about Real Estate Investing? Check out the Canadian Real Estate Investor Podcast! Apple Podcast - The Canadian Real Estate Investor  Spotify - The Canadian Real Estate Investor  Web player - The Canadian Real Estate Investor Asset Allocation ETFs | BMO Global Asset Management Sign up for Fiscal.ai for free to get easy access to global stock coverage and powerful AI investing tools. Register for EQ Bank, the seamless digital banking experience with better rates and no nonsense.See omnystudio.com/listener for privacy information.

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Investing is simple, but don't confuse that with thinking it's easy. A stock is not just a ticker. At the end of the day, you have to remember that it's a business. Just my reminder to people who own cyclicals. Don't be surprised. there's a cycle. If there's uncertainty in the markets, there's going to be some great opportunities for investors. This has to be one of the biggest quarters I've seen from this company in quite some time. Welcome back to the Canadian investor podcast. So we have a fun episode here. Everyone, you guys will hear how terrible of investors we are. But no, I kid. You'll hear some of our worst investing mistakes because that is something that we've always done. I've always

been very upfront and I know you, Dan, as well in terms of the mistakes you make. I think it's really important to be transparent and credibility as well because I know as well as you know that there's a lot of people, whether it's on YouTube, other podcasts, TikTok kind of influencers, financial influencers, whatever you want to call them, that seemingly may never, never make any mistakes. And I think that, you know, they're not telling you about the mistakes they're making. They're likely making tons of them like everyone is. Everyone will make mistakes when they're investing. War Buffett makes mistake. I make mistakes. If anything, I might be guilty of talking too much about my mistakes and not enough about my good moves. Yeah. I mean, it's kind of like on my

end, kind of in the spotlight in regards to my portfolio. So a lot of these are, are well known to say like our membership, but on the public side of things, not a lot of people might have known these situations. So it'll definitely be good to talk about because I think it kind of paints things in a more neutral view, especially, you know, how much the markets have ripped over the last few years that, I mean, it is still very possible to make, make mistakes. I'll go over. I mean, there's a few ones from like an actual individual investing perspective and then one I have on kind of a more strategic perspective when I first started. That ended up being a big mistake. But it should be a very interesting episode. And I actually haven't read yours. And I don't think you've

read mine. So they're all going to come pretty fresh here. So yeah, it'll be good. Yeah, there's some that people will recognize that I've already talked about on the podcast. And I guess an honorable mention, probably the biggest financial mistake, none so in an investing mistake. But I wanted to mention it. So I talked about it last year. If people missed that podcast, it was a solo episode that I talked about. And it was something that I was very truthful with and like I'm always as truthful as I can be, obviously, and authentic as I can be. But it was definitely not an easy one to talk about. So if people want to listen to that one, it's called the biggest financial mistake I ever made. So I will link it to the episode in terms of

the link, the internet link for any viewers if you'd like, so you'll be able to listen to it. You can always listen, search it in whatever platform you listen to, whether it's Apple Podcasts or Spotify, but yeah, it's called the biggest financial mistake I ever made. So I won't go over that one, but this one was more about poor financial decisions, buying a house that I probably shouldn't have bought getting over my head with renovation, not having a good plan and so on, so on. So I won't rehash that already did an episode on that. So feel free to go back to that one.

I got some really good positive feedback from it. So it was nice to see when I posted that. The first one here on the list for me is being too heavy in high growth stocks and Bitcoin. So I'm kind of putting these two together. And it's something I've been very upfront about. I probably, like I said, have talked more about my mistakes than my good moves over that time. I've said it quite a few times, but 2022 was a really rough year in terms of my portfolio, so I had 40% drawdown for 2022, way worse than the SMP 500, which was, I think, around 20%.

In short, I was too heavy in Bitcoin, Ethereum, and growth stocks. Don't get me wrong. I have still strong conviction in Bitcoin, but the reason why I'm putting this here is that they're kind of so far, and maybe it will change a bit more as we go forward, but these tend to be pretty correlated. So what ended up happening is, you know, the market really tanked in 2022, but especially growth stocks. And some of the names that had in terms of growth stocks were Teledoc Square, PayPal, Lulomen,

Etsy, Tencent, Axon, Axon, Pinterest. And adding all those up, Bitcoin, Ethereum, and all those, I think, I'm just kind of ballparking it here, but it was probably around 80% of my portfolio at the peak. so end of 2021 and had very little cash no gold in my portfolio so really concentrated in assets that will tend to move in a similar fashion whether it goes up or like I learned the hard way down as well so it was great on the way up but the drawdown was definitely rough I mean people need to understand that 40% drawdown means that you need to get 67% returns just to get back to that same level so I was fortunate so anyone following on

on joint TCI will see that I've had really good returns over the last few years. So I made that and then some in 2023, 2024 and 2025. And to be fair, and sometimes I might be, I guess, maybe I was just raised with not being pretty humble and I don't like to talk too much about my successes. But to be fair for me is I did have 64% returns in 2020 and 30% in 2021. So just to put things into context. But in terms of learning, I need to be better diversified in different asset types,

especially assets that don't have a super strong correlation to one another. My portfolio looks much different now than it used to, and it still has a big Bitcoin allocation, but not as large as it used to, definitely not at the peak in terms of percentage of my portfolio. I have a substantial gold allocation now, decent cash position around 50% in treasury bills, so that will cushion the volatility as well. I do have some equities name.

I did have some back then, but it was a smaller portion that are more on the value side, stable businesses, reasonable valuations, and mix with some index funds. So that should help soften the blow in the event of a market correction. And there's no doubt I'll still experience volatility, but it should be more contained than it was because of some of these adjustments that I did. Yeah, I mean, the drawdown aspect is kind of a big element of this. I mean, I remember numerous, even potentially people on YouTube, like 50 plus percent drawdowns during the 2022 market. Obviously, like 2020, 2021, they had huge runups.

But again, once you look at it from a 50 percent perspective, you need 100 percent off those lows just to get back to where you are. And I mean, back in 2022, nobody really could have said that the markets would rebound this fast. So obviously it's been, you know, a bit of a cushion in that regard. But I mean, if you get, say, a drawdown of that level and then the markets go back to 10% annual returns over the next, you know, you're looking at a decade just to get back to where you're at. So I think a lot of people tend to focus on the gains, like achieving the gains when in reality what the mitigation more so needs to be placed on reducing drawdowns because those are really are what is going to hit you hard. in terms of a potential recovery. I mean, I've never really. Or maybe maximizing your risk-adjusted returns.

I think that's probably the best way. There's a reason why there's a term like that. Risk-adjusted returns is, you know, sure, you can be looking at some awesome returns, but when if when there's drawdowns, a drawdowns are super magnified, there's like a really big discrepancy between the two. It may not be the most optimal strategy. Yeah, like if you're drawing down double or triple the index, I mean, your portfolio is, I mean, that's hyper concentrated and probably risk on assets. I mean, I've never really had this issue. I mean, you've seen my portfolio. I do have a lot of probably defensive, you know, lower, lower growth holdings that I know are not going to, you know, have me seeing the 20, 30% returns. A lot of these tech names have earned. But I also know that if the markets do correct, 30, 20, 30,000. 40% they're probably not going to have a lot of that volatility.

I hold those regardless, whereas a lot of people try to kind of time this growth end and then maybe rotate into stocks like that when things get rough. I kind of just choose to hold them all the time, which kind of levels out my portfolio returns. I mean, obviously they're not as big as a lot of people this year, 30, 40% due to the AI names. But I think, I mean, if you've been doing this for a very long time, I think you come to appreciate the lower volatility over the drawdowns, then you do the big gains during the

bull markets as well. Yeah. Yeah, exactly. Having cash on hand is essential for any business. Traditional business accounts hit you with high fees while paying little to no interest on the cash you need for day-to-day operations. That was our experience too, until we switched to the new EQ bank business account. Now, every dollar earns high interest with no monthly fees and no minimum balance. You also get free everyday transactions like EFTs, bill payments, mobile check deposits, and 50 outgoing and 100 incoming free interackey transfers. And to sign up, quick and fully online, no branch visits because, let's be honest, no business owner has time for that. We use it for our own business and it's the first account that actually helps

our money work harder while keeping operations simple. Check it out today at EQBank. to buy a stock but don't want to shell out hundreds or even thousands for a single share. With QuestTrade's new fractional shares, you can invest any dollar amount and build a diversified portfolio instantly. No delays, no trade fees, no excuses. Want to put $10 into a stock trading at $100. No problem. Quest Trade has you covered. They're the first broker in Canada to offer real-time commission free trading for U.S. fractional shares in ETFs. It's simple, powerful, and finally available in Canada. Head to quest trade.com to open and fund an account. Use code TCI and you get $50 to get you started. One of my favorite trips this year was a cottage stay on Airbnb

less than an hour away from Ottawa. Every morning, my daughter would run straight to the lake, sometimes splashing, other times poking at the water with her little pink net, trying to catch frogs. Getting her out for dinner was always a challenge, but after days like that she went down so easily at bedtime. That gave my wife and I the chance to finally unwind in the hot tub and watch a sunset together. Having a cozy place to come back to made the whole trip feel effortless and special. It also got us thinking about our own place. If someone else's home could be such a a perfect fit for us, maybe ours could be for another family too. Hosting our home on Airbnb would let them make their own memories in our beautiful neighborhood while giving us a little

extra money to put towards our next trip. And the nice thing is the flexibility hosting provides so we can decide when it makes sense to host our home. Your home might be worth more than you think. Find out how much at Airbnb.ca. slash host. So for you, what's, was that the first mistake or we just comment? No, no, yours. Okay. I'll go into the first mistake. Dan doesn't make mistakes. Yeah. No, I don't have any. My notes are blank. No, yeah, I've, uh, so the first one I'll go into is probably, it's from a financial perspective is probably not trusting my first instinct, especially when it comes to something like valuation. So I kind of go by the rule that, and I mean, I can't remember what investor said this. I might have been munger Buffett, but you don't want to

trim your flowers and water your weeds. So effectively what this means is you don't want to sell your winners and buy more of your losers, which I mean, if valuations are in any sort of reasonable range, I tend to agree with, like, let's just say for a quick example, if a company is typically traded at 25x earnings and it goes up to 30 or 35x, I'm probably not going to sell. I'm probably not going to trim unless maybe it's grown a bit too big allocation wise, but there's been quite a few times in my investing career where I've probably oversimplified this and it's ended up costing me a lot of money. And I'll go over one quick example. There's been numerous ones, but one quick example is I ended up buying a nano cap stock back in 2020 called Good Nature products. And I mean,

what the company effectively did, they produced like environmentally friendly consumer packaging. So you can think of the main business model being kind of revolved around groceries or restaurants. So like the to-go containers that were typically styrofoam, these would have like biodegradable elements to them or like compostable grocery bags, compostable packaging for like the vegetables you buy at the grocery store. So I did invest in this company pretty much on a speculative basis, but it did have some sort of fundamental backing to it. I kind of thought this trend would continue, I guess, so to speak. I mean, globally there's a lot of incentive to get rid of plastics. So I ended up buying around $10,000 into this company. My average cost basis was, I think it was around 30 cents.

It might have even been lower. The bulk of my purchases were actually made around 15 cents. I wanted what ended up happening was this company absolutely rocketed in terms of price. I mean, they're kind of broke now. So I couldn't easily access a stock chart, but it went from, I think it went from 15, 20 cents to like $1.80. in the, like, three, four months. So I was, I was sitting. A dream.

Yeah. That's a dream right there, yeah. And like, this is kind of what I mean by that main mistake where, yeah, you don't want to trim your flowers and water your weeds. But this was a situation where I should have known better. I mean, it was, it, the valuations of the business got to the point where it just, it was never going to be sustainable. I mean, the company was growing revenue.

They were, they were taking on debt. I mean, debt was cheap back then. they were making acquisitions, but I didn't sell. I held my entire position and eventually rates escalated. A lot of restaurants and consumer companies kind of faced a lot of pressure. Good nature sales pretty much bombed. Their items were not cheap. And if it, and if, you know, if it isn't enforced by, you know, regulatory bodies to kind of have these biodegradable or more environmentally friendly products, it's pretty much the easiest expense for a business to cut out. I even remember going to some restaurants in 2021, that 2020, 2021, that ended up actually

charging you for these to go boxes if you use them because they were so expensive. But they still, they eventually got bought out by a private equity company and shareholders pretty much got nothing. They still operate, but privately, I think the company effectively just kind of took on all their debt and kind of said shareholders are going to get nothing. But I mean, from a financial perspective, I would imagine this is probably one of the biggest mistakes I've ever made. I mean, when you're thinking about potential gains, like, I had this in my TFSA. So you can imagine a $10,000 investment sitting on a 10 plus bagger in your TFSA. If I would have

actually booked the profits there and invested that money, I mean, you're talking, like, you're probably talking. You're probably talking about, yeah, like, if I would have taken that money and probably, you know, let's say I sold it and just bought an index fund for the next 20, 30 years. you're probably talking about like $300,000, $400,000 extra that I would have had in my TFSA. But, I mean, I got a little bit too caught up in it. It probably, I mean, it's probably prone to happen to me again. But this is probably a hard set example of why I try not to do this anymore. If things get too stretched, I just sell other situations, I guess I can say, would be Canada Goose.

I did end up taking profits in that one when it ran up a whole bunch. I believe it was in like 2017 or 2018. light speed as well. Same example, I kind of took some profits off, but I left a lot of the positions kind of open and ended up, you know, even though I fundamentally knew that this could not continue, I just kind of held on to the positions thinking it could and it ended up costing me. Yeah, I think, I mean, you probably got caught up in the narrative a bit, right? And I mean, that's fine. Like my second point is, is that as well. So I guess for you, the learning is just maybe when Val valuations get too stretched, at least take a good chunk of profit, at the very least trim or potentially sell the whole position if it just doesn't make sense anymore, right? In terms of valuation. And I think like a lot of people will probably take this a bit too literal. Like I said, if a company typically trades at 25x and it's trading at like 35, I really, I would not trim in that situation, but in the case of you see these massive runups, at some point like the story just doesn't make sense. But it's also very hard from a mental perspective to see a company go up this fast and it kind of begin, you start to think, like, if I sell now, is it going up another 10x? It's a mental battle at that point. But if you just stick to, you know, the fundamental understanding of a business in general, I mean, it, it's much easier for me now to cut this. Like, if this happened today, I would have cut this. Like, no question. It wouldn't have even been a thought. But back then, it ended up costing me because I mean even now like yeah I'll go with my second one which which aligns with that yeah so yeah so my second one definitely is very similar to that so my second mistake not that I wanted to cut you off or having a little bit of technical issue with a connection here but

so we don't run too late because I feel like that could easily be an hour and a half episode in terms of our mistakes but for me it would be not selling or trimming enough when the valuations were clearly way too stretched so kind of the same thing you're talking about here the best example for me was teledoc i don't know what my exact returns were on paper but the peak it must have been like four or five x the money i had made a big chunk of it was in my tfsa all the signs were there trading a crazy multiple tons of hype around it was during the pandemic so all these work from home or log down stocks whatever you were calling them there was a whole lot of hype behind them On top of that, Teledoc was making ridiculous acquisition, paying insane valuations.

The one that comes to mind is Livongo, you know, years after they ended up riding off most of it. And of course, it's easy in hindsight to say now, but looking back, I think it would have been pretty prudent for me to at least trim a larger part of that position. In my defense, I did trim a bit. And I think overall I made a smell profit for Teladog, but not very big considering the run-up that it had. And really, similar to you, right? The company sees its valuation go to like really stupid levels, is what I wrote here. It's probably best to take some profits or some chips off the table. It's even more true if the company's not very profitable, barely profitable.

I mean, I'm definitely more now. My criteria is much more strict when it's come to investing in not profitable companies. I will rarely, rarely do it now. And if I do, it's going to be a very small allocation to my port. portfolio. But yeah, very similar for my second one to you probably of less magnitude, I would probably say. But it was still, I think, 10, 15% of my portfolio at that point. So pretty, pretty big for a company and could have made a lot more money if I had been more disciplined. But it is what it is. You learn from it. That's that's what you can hope, right? If you make a mistake, you learn from

them. But what's your next one here? So I think the next one would have been kind of boiling down to when I first started investing, and that probably would have been being too Canadian focused. So when I first started investing, it was pretty much like the golden age of Canadian financial bloggers, personal finance bloggers, things like that. And on the Canadian side of things, like the vast majority of these bloggers were not only Canadian heavy on the equity front, but also dividend heavy. So I mean, a lot of these bloggers' main focus was to grow their income stream. I mean, we've seen a lot of that in relation to, like, fire, like financial independence, retirely, like, you know, grow your income stream. Now it's morphed into those covered calls.

Yeah. Yeah. Yeah. And I do kind of, I'll mention that a bit later on because I think that's kind of the new side of this. And like, as someone who is fresh into the space, I mean, it's safe to, you're probably going to adapt the strategy you see most. I mean, if everybody's doing it, it's probably going to be the best way. I mean, that would be the assumption of somebody just starting out. And I kind of did this for the better part of like six, seven years.

I had pretty much a portfolio of 100% Canadian equity and the bulk of it was centered around income. I mean, back then, I would have been firmly in the kind of basket of people who actually did believe that dividends create additional value. And it's kind of funny because, you know, I get into a lot of debates with dividend enthusiasts now. And like a decade ago, well, maybe a little bit long. than a decade ago, I would have been in the exact same situation they were arguing the points they were. But I had a bit of a wake up call in 2016. I was kind of getting why I've been not kind of getting. I was getting crushed by the S&P like overall, just index wise, too much Canadian exposure. And if you were investing back then, like from 2009 to 2016, I mean, the TSX got

absolutely killed by the S&P 500. I think the S&B posted like triple the returns. So I mean, at that point, I kind of, I kind of thought, like, what, what the heck am I doing here? It was, it was a fairly quick transition for me. I felt at that point, I was pretty good at analyzing Canadian equity. So I kept a lot of that, but I ended up buying, like, I turned a massive amount of my portfolio into XAW, which is effectively, it's a global ETF with large exposure to the U.S. That doesn't include Canada. But, I mean, I guess a real lesson here would be that, like, home bias for, you know, the first six, seven years of my career. investing career probably cost me a lot of money. And again, as you had mentioned, I'm kind of

seeing the same mentality today spread across a lot of the high income ETFs. I mean, investors with 20, 30, 40 year time horizons, like trying to build up their passive income stream, which is exactly the strategy I utilized back then. That's kind of what I was aspiring to do. I didn't have a lot of money back then, but I did, I did have a five-figure portfolio. So I mean, investing it. Maybe not a lot of money, but a lot of charisma. Yeah. I always said that. Yeah. Yeah. Yeah. Yeah. I mean, like, if you think about it, even on a five-figure portfolio, if I would have just bought the S&P, like how much more money that would be, like today. Yeah. So yeah, that was a big mistake that I, happy I moved on from. Yeah. And I think good thing to mention here before I move on to my third one is you have to get comfortable. And we talk maybe once or twice about that, but you have to get comfortable with regret when you invest, whether it's regretting, selling too early, whether it's. It's regretting, not investing in a company that you have on your watch list. Like you have to get comfortable with that.

It's going to happen. And you just have to be comfortable that it's going to happen. You're not going to make all the right moves. No one will. And that's okay. It's just, you just have to be comfortable with that. I know sometimes it takes a little bit of time, but I think it's important to reinforce here. Because clearly, obviously there is some regret in our, like, mistakes.

like you we talked about like imagine the money if I sold Tel Doc invested that in something else you know you think about that by the end of the day look I think we're both pretty pretty happy with our overall returns sure it could have been better but yeah it could have been a lot worse so you have to also focus on on your right moves but the next one here is investing in something that I don't understand so I've been guilty of doing that not very frequently but a few times So this is the first time I talked about this specific investment on the podcast. Most people will know when it comes to crypto that I basically stood to Bitcoin. I have a little bit of Ethereum and that's it.

But to give some context, I did invest ones in shitcoins. And I'm using shit coins because it's very appropriate here. And apologies if I'm offending anyone with that term. So I have a friend who has been in crypto since 2011, 2012. He's the guy, so good props to him because he's the one that got me first interest in Bitcoin back in 2013. I bought my first, I think it was half a Bitcoin or close to a full one back in 2013. It was this, it changed called Cripsy, ended up going under, so I lost it. Obviously, it would be worth a whole lot today, but whatever.

That it is what it is. That's not the mistake itself. So back in 2018, he kept talking. talking to me, wouldn't shut up about it, about Bitcoin and Ethereum. At that point, Ethereum was a thing. And he had gotten early, had gotten some pretty good returns for those familiar with the crypto space. You'll know that in 2017, it was a big bull market. Bitcoin ran up to like, I think, close to $20,000, U.S. and Ethereum, I think, was close to a grand, maybe more. I think it may have been 17, but I'm just going on memory here. And then after the Big Bowl

market it really crashed and then I had the little bit spare money so I decided to a dollar cost average and obviously without that buddy that is actually one of my better investment and we will be doing a second part or where we talk about our better investments and that will be part of it there but the context is that the market peak in 2021 when crypto all coins defy decentralized finance for those not familiar with that name was going through the roof. fee wouldn't shut up about this project called the Radix and finally I'm like okay

I'm going to put one Ethereum in it I had like a decent amount at that point so I'll put one Ethereum in it didn't really understand it it was a token on the Ethereum blockchain so put one Ethereum in it well that investment

is not worth roughly $50 and if I had just kept that Ethereum it would be worth $4,300 right now So clearly it was not a good investment. I still have this thing, but I don't know. I feel like the transaction costs are not even worth selling it. So we'll see.

Maybe I get lucky at some point and just takes off. But obviously not the end of the world. But, you know, it definitely thought me a good lesson that especially, you know, it's easy sometimes to get hyped up by friends, family, things like that, taxi driver or Uber driver. But make sure you do your due diligence, understand what you own. It's not a mistake I've made very. often. I usually have a pretty good understanding of the investments I do. But this one, I guess the FOMO got the better of me and it cost me a few thousand dollars. Yeah, I mean, I guess in

the one case, this kind of would have worked out for me a bit in regards to Bitcoin because I eventually just, I just bought it. I had no idea how it worked. Like, I had a lot of people previously that were kind of pushing it on me in like 2017, 2018, and I finally bought it. I think it was in 2020 but I think this kind of boils down to a lot of equities as well because like if you don't know what you own ultimately if something happens you're not you're not going to know how to kind of judge that situation so it's not even only in the crypto space yeah exactly if you don't know what you own and there's a big pullback like how do you know if you should be selling or it's a good buying opportunity right like you don't really know so no definitely a good good lesson

for me a mistake but at the end of the day I think mistakes are fine as long as you learn from them. Having cash on hand is essential for any business. Traditional business accounts hit you with high fees while paying little to no interest on the cash you need for day-to-day operations. That was our experience too, until we switch to the new EQBank business account. Now, every dollar earns high interest with no monthly fees and no minimum balance. You also get free everyday transactions like EFTs, bill payments, mobile check. deposit and 50 outgoing and 100 incoming free interackey transfers. And to sign up, quick and fully online, no branch visits because, let's be honest,

no business owner has time for that. We use it for our own business and it's the first account that actually helps our money work harder while keeping operations simple. Check it out today at eQbank.ca slash business. Want to buy a stock but don't want to shell out hundreds of even thousands for a single share? With QuestTrade's new fractional shares, you can invest any dollar amount

and build a diversified portfolio instantly. No delays, no trade fees, no excuses. Want to put $10 into a stock trading at $100. No problem. Quest Trade has you covered. They're the first broker in Canada to offer real-time commission-free trading for U.S. fractional shares in ETFs.

It's simple, powerful, And finally available in Canada, head to quest trade.com to open and fund an account. Use code TCI and you get $50 to get you started. One of my favorite trips this year was a cottage stay on Airbnb less than an hour away from Ottawa. Every morning, my daughter would run straight to the lake, sometimes splashing, other times poking at the water with her little pink net, trying to catch frogs. Getting her out for dinner was always a challenge, but after days like that she went down so easily at bedtime.

That gave my wife and I the chance to finally unwind in the hot tub and watch a sunset together. Having a cozy place to come back to made the whole trip feel effortless and special. It also got us thinking about our own place. If someone else's home could be such a perfect fit for us, maybe ours could be for another family too. Hosting our home on Airbnb would let them make their own memories in our beautiful neighborhood while giving us a little extra money to put towards our next trip. And the nice thing is the flexibility hosting provides so we can decide when it makes sense to host our home. Your home might be worth more than you think. Find out how much at Airbnb.c.ca. slash host.

What's the next one on your list here? So I kind of had like making decisions just kind of based on profit numbers, like kind of round, like kind of arbitrary profit numbers. And I don't know why I used to do this. Who doesn't like round numbers, right? I don't know why I used to do this, but I, I did this like up until very recently, probably like 20, 21. And I like, I used to love booking profits on nothing more than just kind of total return amounts. Like, you know, you'd buy a stock. If it hits 100% return, you'd sell it for nothing more than just, you know, you're up. You've doubled your money. And one of the, this, I kind of thought of this point because Shopify would have been one of the very prominent examples of this. Like, I started buying Shopify

pretty early. I think it was 2017 or, or 2018. It's pretty hard to figure out my actual cost and dollar I sold that just because of the split. I know I sold at around $600 pre split, but I just can't remember what I had bought it at. But I do remember being up, it was pretty close to 400% and I mean like I sold the company just based off nothing more than this round number that I was up 400% like I was happy with a 400% gain so I ended up selling it and moving on and obviously Shopify did end up running up quite a bit I ended up leaving a ton of money on the table that like I still really liked as a company but for some reason like that profit number kind of got in my head like obviously it feels good to book profits it would probably be

due to a combination of things too, like loss aversion would be one of them. Nobody wants to be that person that had 300, but now they have nothing. I mean, obviously I did that with- For context, it's probably been a three to four baggers since you sold, just so people kind of, yeah, understand. Yeah, and the thing is, is like there was absolutely nothing company-wise that told me to sell. I just sold because I was up that amount. I just wanted to book that profit. And I can't remember what I bought with it, but I would almost guarantee it hasn't

produced as good of returns as Shopify. And I mean, I think there's like a situation where kind of the saying like nobody ever went broke taking profits, which is 100% true. I still made, you know, I still made that amount on Shopify, but there's also an element of opportunity cost. And I kind of, I don't know, I look back at this right now on how I mean, stupid it was because I just kind of associated price with the value of the stock. I mean, a stock you buy today that runs up 300% but earnings are up 300% you're effectively you're sitting on the same price as you were when you bought it previously but I have eliminated it from my like my thought process now it's crazy I did this for for so long but I solely fundamental standpoint now I

I really don't care if I'm up 100% 500% thousand percent if I look at a stock and I can confidently say I'd buy the stock today I just I don't book profits unless I it's somehow of a allocation issue. Like, it's too much in my portfolio. But I think there's a bit of a difference between trimming a position as a form of risk control and just trimming a position just to feel good. And, yeah, Shopify reminds me of that a lot because I got in early, made a bit of money. But now if you think about like why I sold and how much money I left on the table with

that one, it just seems silly to even think that I had that thought process. Yeah, I mean, I think it is interesting, though, how. a lot of people I think you know we were talking about dividend investors too I think sometimes there is these mental blocks or mental hurdles or just these mental concepts that people will have investors will have that kind of prevents them from making optimal or more optimal decisions so I think it's just a it's a good reminder where even though sometimes the math will be clear that it shows that it's not a good decision to make, for whatever reason mentally, it feels good to do that. And it's good to identify those.

It's not always easy to change that behavior, but I think the first step is at least identifying those. And we talked about covered calls, ETFs, but a lot of, and we'll have a guess, maybe you'll hear this after the guess I'm not quite sure, but we'll have a guess come on to talk about, though, and provide some more data, very analytic kind of. guess about covered calls but at the end of the day people just focus so much on the income they're getting but they don't realize that there's a lot of capital destruction involved too and they just focus on the one part when mathematically everything shows that if you used a strategy and you had maybe some cash aside to be able to do some withdrawals and actually pay yourself that income

that mathematically it would be a much better outcome but the mental aspect behind it of getting that income is I guess reassuring and look I'm not blaming people that are using this strategy for that reason because our brains will play tricks on us and I think it's important for me it's very important to try and follow the math behind it and use that as a guiding line but it's not always easy and I think that was just a good example of that. Yeah, I think it's the element of, like they say, a bird in hand is worth two in the bush. Like you have, you know, a realized return and, you know, the future is unrealized, like, unrealized, unknown. So a lot of people take the realized returns.

And obviously, yeah, again, I was happy with that amount of money I made. But ultimately, if I had just kind of, you know, thought about the future instead of just having that money in my hand today, it probably would end it up better. And I mean, for a while, I was actually correct. because, you know, it took a few years, but Shopify eventually bombed, and I don't know why. I never bought it back. But, I mean, even if we look to today's prices, it's, yeah, left a lot on the table. And yeah, it's something that's made all the time because realized returns are realized. And you don't know what the stock market's going to do in the next year, two years.

You don't even three months, things like that. Yeah, there's an argument to be made to take some profits, take some chips off the table. So the next one for me, position sizing too small because it's a starter position or I'll add later. Well, what I notice is that oftentimes I never do. And I've had some really great returns, like one that comes to mind is Axon, which was I think a 10x for me. But the reason that's a mistake here is because I think if I remember correctly, when I started that position was like 0.5% of my portfolio. So yes, I ended up getting really good returns, but even at 10x there is not that much of a needle mover for your portfolio. Yes, it will definitely, you know, it doesn't hurt, but it's also not great. Another example is ASML I bought in late 2020, around $400 per share, ended up selling it at around $1,000 per share as things were getting really frothy. Booked a nice 2.5x profit. I bought it back, not too long ago because I thought the valuation had calmed down quite a bit, but again, it was less

than 1%, so yes, a nice profit, but doesn't really move the needle because the position is too small. And of course, you don't want to go too big for risk your investment. Axon was trading a high valuation, ASML, not cheap either, but you also want to make it so, you know, if you do get a multi-bagger, it does move the needle for your portfolio. And I've made that mistake, like, a lot of times, unfortunately, kind of ashamed to admit it, but I have that mistake, multiple times. So now what I've been doing over the last year, year and a half or so is I have to make the position at least 1%. I'm not saying like making a riskier bet on a company that's trading at higher multiple or maybe on the verge of profitability, whatever it is. I'm not saying making it

5 or 10%, but at least 1% has been a good guiding and kind of forcing me to be comfortable with making that investment. So so far I've been sticking to that. I think a few times I was probably at 0.9, but never as low as a 0.5%. So I've been pretty good at sticking to that and realizing that yeah, some of these multi-baggers could have been really, really been a big tail win for my portfolio. Unfortunately, because of the sizing was too small. But again, that is for me you also don't take it as me saying like oh it should be 10% right like I'm just saying it was so small that it didn't move the needle all that much I used to do that all the time I think a lot of people do that like they like they look at a company they want and they say oh

I're going to get a starter position then kind of add to it as I go and then the stock price increases and then that plan just falls to pieces because they don't want to buy at a higher price so they never buy again I would say if you're going to absolutely stick to that strategy where you're going to start a position and say, you know, accumulate it to what you want it to be over the course of whatever timeline it may be. That's all, it's, I mean, it's not a bad strategy, but very few people fall through with it, myself included, because you buy it and then you're like, okay, I'll add to it in a couple months. And then it's up 40%. You're like, I'll add to it when it comes down a bit. And then it never does. And yeah, it's, yeah, like now I used to do this

a lot too, but now if I just want to buy a company, I just buy it. I just find the money for it. and I buy whatever position sizing I want. Yeah, yeah. And I think for you, you only had those three big mistakes, right? Yeah, that's all I got, yeah. Yeah. So, well, I have some honorable mentions here and just some final thoughts and feel free to chime in.

So the honorable mention number five, not buying because valuation and being too high. So this is one that I've done quite a few times, but I don't. The regret part, you know, it sucks. but I don't have too much regret. Costco is one that comes to mind that we recently talked about in earnings because it's a company that I have always liked, but I always thought it was a bit overvalued for more of a retail play, trading in the 30 to 40s in terms of P.U. or price of free cash flow, well, it turns out that it probably requires a premium, and if

I had bought it at that time, I'd be sitting on quite the winner. But my biggest learning here is that I think it's okay to invest in a company, in a high quality company that's slightly overvalued. And I think the keyword is slightly because if it's really overvalued, then you can get into some pretty poor investments, even though the company is really solid. But for me, I think is sometimes, you know what, slight overvaluation for a high quality company, probably something that I should consider. consider a bit more but again I think it's it's always a fine line so that's why I don't have too much regret because that instinct of not overpaying for companies has definitely saved me a lot of money on other types of companies so it's a bit of a mixed feeling here but Costco is the one that I am always reminded like oh I should have should have bought it when uh you know in 2020 or

2019 when it was still maybe a bit overvalued but not really that bad yeah I think like the thought, like the thought process there is correct. So like obviously you're not always going to be happy with the result. But I mean, you definitely don't want to be overpaying for companies. I mean, in terms of me and in terms of value, like I used to do this a lot, like just kind of take value at the valuation of a stock kind of at face value. But now I just look at what the market has historically paid for a company. And I kind of judge the valuation based off that. I mean, we had a point where, you know, the market had been paying 30x for. Costco's earnings for 10 years. So it's the market is probably much better at pricing these

stocks than a lot of retail investors are. So I mean, I think if you judge it based off that aspect, you can kind of get a better idea. I don't really try to put much emphasis on me doing it on my own. I'll just look at what the market has typically paid for a company like this. And I mean, again, we have a situation with Costco post-pandemic where it probably deserved an even higher valuation over what it had historically traded at just because of the pickup in popularity. So from that perspective, you kind of need to judge that yourself too. But the market is pretty efficient at valuing companies. So I kind of base it off that. Yeah. No, that's a good approach. And I think I'm doing that more to is just looking at historical

valuations and then kind of having a sense on what the range is. That's kind of normal. buying it if it's within that range or not and I like the company so my final thoughts here those are just kind of five kind of I use more overarching mistakes obviously I had a quite a for some of these I had a few examples but there's other that come to mind for no specific reason I for most of these I lost money so PayPal allied property reed two names I've talked about before Terhira Diamonds is the company I've talked to about a couple of times on the podcast where I was 18 and invested in this junior minor, $2,000 at the time, and it was a whole lot of money for me back then, especially when you factor in inflation

on top of that. But as a young person, you don't have as much money typically lost all my money. But the reason I didn't add that one is that I think it was a good thing in hindsight just because it really made me realize, you know what, I think it would have hurt me to have like a multi-bagger in that first investment because I think it would have hurt my process for future investments and made me think that I was a genius. Unfortunately, like a lot of people I think think they are right now. Yeah.

They think they are geniuses because they started investing in the last five, six years and they're day trading and the only thing they've seen is day trading in a bull market, never experiencing really a deep bear market. I think that's really dangerous. I think, you know, if you're in that situation, make sure you're on. with yourself because this kind of, this is not really the norm what we've seen over the last four or five years and even more so since 23, 24, 25. So I'm kind of happy that happened because it really made me more aware of having a better process. Some of the other names, I lost money,

Pinterest, Tencent, K-Web, the crane shares ETF, the Chinese tech ETF. More recently, buying Nvidia in April during the Liberation Day aftermath and then selling it pretty quickly as a trade. Quick 15% profit, but probably would have doubled my money by now. So probably should have just bought it and held and written that AI play a little more, not a huge position, but still. So these are just other examples of situation where I lost some money. So definitely mistakes are are plentiful in terms of my investing career or an investing journey, whatever you want to call him. But overall, I mean, we'll talk about some of our good moves and, you know, I'm happy to say that my good moves far outweigh the bad ones. Yeah, I mean, you don't need to be right

every time. I mean, you actually, you can get away with being right only 60% of the time and actually get pretty good returns as long as you kind of mitigate the downside there. I mean, the same situation with nvita i can't remember when i bought it but i bought it it reported like a quarter and it fell five or ten percent on the quarter and i bought it and then i booked it at like a 20 percent gain and that was that was probably over a year ago now and it was just i mean bad decision but i had another one it was a hydrogen play i can't zebeck i think it was called and this was actually oh yeah this actually you told me about that one yeah i wouldn't necessarily say this was a mistake. It was mostly just fraud because the company ended up,

I mean, it was, they were fraudulently reporting revenue on their financial statements. So it was, it was really hard to actually detect this one until it kind of came out. And they were booking revenue for projects that they hadn't even started working on. It was, it was a pretty shady situation, but it's also like, it kind of highlights the fact that there's risk in equity. I mean, even that is not seen on the surface. You could not have known that this was coming. And then, of course, they come out with a whole bunch of revised financial statements. And I mean, eventually the company went bankrupt because the revenue wasn't there.

But yeah, you're going to lose money in the market. Obviously, you have to be right more often than you're wrong. But, I mean, you don't need to be batting 90% plus to actually make any money. It's not you're going to lose money. It's inevitable. Yeah. I mean, even when you think about venture capitalists, right, like for the most part, I mean, I'm probably butchering a little bit the percentage there. But let's say they make 10 investments. There's probably like, I don't know, five, six, seven that'll go to zero. Yeah, five, six, seven that'll go zero. One maybe or two that they'll kind of break even, make a little bit of money. And then they'll have one that'll just crush it and make up for everything else in that. that portfolio. So obviously that's a higher risk approach and they're usually very experienced. The good ones are very experienced and they know what they're doing. But it just goes to show that

you don't need to be batting 100. You just need to hit Grand Slam once in a while, even if you strike out the rest of the time and you will make a good return with that. But yeah, don't take this as I'm saying you should just invest in super risky stuff. But it's an extreme example that, you know, As long as your winners far outweigh your losers, whatever the percentage is, you'll do, you'll do good. Yeah. Yeah, I think the more, like, I think it's over the long term, it's probably better to try and hit singles and doubles rather than grand slams. You'll probably end up better off. But yeah, it's, you don't need, not every stock you buy will be a winner.

Not every ETF you buy will be a winner. I mean, it's just the inevitability of, you know, some companies don't do well. some funds don't do well. Yeah, no, exactly. So I hope you enjoyed this episode. I mean, it was a fun one for us to do, I think, speaking for you a little bit, but it was still kind of fun looking back at some of stupid moves we made.

So it's always interesting. And for me, I've said it before. I've been comfortable living with regret in terms of investing. It's just part of the game. And as long as you learn from your mistakes and don't repeat them over and over, although sometimes, you know, it's harder, are there said than done. But for the most part, the big ones, that's what I take from them is just I learned some valuable lessons. And you know what? I wouldn't go back and change it because

I learned some valuable things. So hopefully you can do the same with your portfolio. And I think it's always important to be honest with yourself too when you look back as a sudden investments and the ones that didn't go well. Just make sure you get value out of it. It's a different kind of value, but it's still value. Yeah, I would definitely go back and change a few of these if I could. Definitely. Yeah, I mean. But yeah, I mean, I hadn't thought about these in quite some time until we dug them back up.

So they're buried deep in my mind. And ultimately, it just kind of made me better. So, yeah. Well, now they will live forever on the internet. So there you go. That's a good way to close it. So I hope you enjoyed this episode. As always, if you're interested in listening to the.

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