Transcript
Podcast Announcer (0:00)
You're listening to tip this past year.
Kyle Grieve (0:03)
Has been a predictably unusual one for me in the markets. Between the tariff tantrum and the AI scare, many of the companies that I own have really been put through the wringer. But after spending hours each day researching investing, I've learned a lot and taken the time to reflect on which of those lessons have really helped me evolve the most in 2025. This episode, like all my previous episodes, won't bother at all guessing with what will happen in 2026. It's about what I've learned that has directly impacted how I think and how I strategize. Now, when reflecting on some of the biggest mistakes I've ever made in my investing career, I realized that two of them didn't really stem from poor analysis. They came from fairly simple psychological errors. It's easy to learn about investing and assume that we'll all act rationally, but the reality is far from it. This episode was an excellent exercise for forcing me to confront where my thinking was too rigid, too emotional, or even too optimistic. One of my biggest thinking shifts was realizing that being confident and being flexible can actually coexist. A more uncomfortable realization was the biggest threat to my portfolio isn't interest rates, geopolitical unrest, or AI, but me and my imperfect thinking. I also share my thoughts on fragility of compounding and the steps that I've taken to protect myself so the compounding engine can just continue working. This episode is packed with how I've turned this thinking into usable tools to help me improve as an investor. And the reason I think these tools work is that nearly all of them have been cloned from the legendary investors I get the privilege of studying daily. I'll walk you through updates of my strategy around things like position sizing, how I wait for investments to play out, and how I say no. So if you've ever felt the urge to act when nothing needed to be done, or felt extreme confidence right before proven wrong, this episode is just for you. Because I feel your pain. This episode will help you learn from my mistakes and give you a few ways to think differently about your own investing. Let's jump right in to what I learned in 2025.
Podcast Announcer (2:00)
Since 2014 and through more than 180 million downloads, we've studied the financial markets and read the books that influence self made billionaires the most. We keep you informed and prepared for the unexpected. Now for Your host, Kyle G.R.
Kyle Grieve (2:17)
Foreign. Welcome to the Investors Podcast. I'm your host Kyle Grieve, and today I'm happy to discuss my nine biggest learnings from my last year, specifically from this podcast. So the podcast game is just super interesting for me because, you know, it's a job where I get to share these incredible lessons with you every episode. But then I can also, you know, pick and choose which of these strategies and mental models that I personally learn from that, you know, the world's greatest investors or minds are using on a regular basis. So today I'm going to go over some of the strategic shifts that I've learned from spending thousands of hours researching the world's greatest investors, companies and fascinating books that I've shared with you in 2025. So let's jump right in and discuss the concept of Flexible conviction. So on the face of it, flexible and conviction are two words that seem very, very strange to put next to each other, don't you think? Flexible means being able to bend, adapt, or change easily without breaking. And conviction refers to a firmly held belief or strong confidence in an idea, principle or decision. But here's the thing. Conviction works very well under specific circumstances, such as things like position sizing. But it can also lead to many errors in my thinking. If I have too much conviction in an idea, it makes me do things such as size, positions too large. Maintain conviction in an idea where maybe the thesis is deteriorating or exposing myself to increased risk. And these three things add up to me losing money or having reduced returns, which is an area of investing that I'd obviously love to protect myself as much as possible. But don't get me wrong, conviction 100% matters and it matters a lot. But what I really learned this year, especially from someone like Anthony Bolton, was that conviction must be re earned at very regular intervals. So what I used to focus on was strong convictions strongly held. When I looked at a business that I owned, such as Alibaba, I think I followed this framework. I'd get an idea in my head, I'd gain conviction. And then I didn't think that I allowed myself to be very flexible until, unfortunately, it was just too late. While I thought that Alibaba was a great business, it was taking an approach to growth that just wasn't optimal for creating shareholder value. In my view. I could have come to that conclusion a lot earlier had I allowed myself to adjust my conviction levels rather than stubbornly holding on to them as I did with Alibaba. Now, Anthony Bolton warns us that beliefs can really calcify when new uncertainties appear. And this directly explains what I think happened to me with my Alibaba investment The calcification of beliefs and conviction is a very perilous thing. And if you allow thoughts in your heads to calcify just too much, you rapidly increase the risk of making bad decisions because you become blinded by new facts that counter your existing beliefs. But this year I came across a quote that profoundly changed just how I view conviction, and that was simply strong convictions weakly held. This is where the flexible part of flexible conviction comes into play. You can think of this as kind of a way to test the calcification of your ideas. There are a few ways that I do this now, so the first is to use what I call conviction ranking. This is a journal entry that I make pretty much every month in which I determine whether any new information that I've learned is either strengthening or weakening my conviction. And you can really do this however you want. You can give it a letter grade, you can have a number, a percent. I personally use percentages, but it really makes no difference. The reason this is so effective is that it shows whether you are gaining or losing conviction in your ideas. In my last entry from November 24th of 2025, I noticed a few highlights. I had one business where my conviction levels dropped a little more compared to some of my others, and then I had a few positions that gained a few more than others. Now I'm not going to name either of these positions, but I can tell you that for one of the businesses where my conviction actually kind of decreased a little bit, there were a couple of reasons here that I can share. So the first is that the last two quarters have been pretty ho hum. Had I known the business would probably slow down as much as it has, I would have delayed buying it since this is kind of one of my inflection point businesses. But I still actually have enough conviction in the position that a lot of the new spending that's causing this contraction in margins, et cetera, is going into money that can probably improve the business over the short to medium term. So that's money that's going into things like SGNA and research and development, which I think will probably end up helping the company. So my plan here is just to kind of wait and see what happens over the next year or so. There are some specific contracts to do with this business that are completely outside of their control and once they get awarded to their customers, then their customers will begin shopping with businesses that the company I'm discussing sells. So there are specific contracts that are completely outside of their control that should actually end up helping this company once they're Announced. Now, as for the position where my conviction went up, my conviction simply increased because the business has been going through some of these temporary headwinds. And this quarter really showed to me that a lot of these tailwinds that the market was very, very fearful of. And I wasn't very, very fearful. You know, I held my position and even added to it, but it was a position where I felt like I wanted to see how they were going to deal with them. And again, that's kind of a short term problem. But I felt that they deal with them very, very well. And now that those problems are mainly behind them, there's probably going to be a re acceleration to its growth and intrinsic value. And so the next few quarters should further reinforce my conviction that things are moving in the direction that I'm hoping for, which is to continue moving up. So one key to this test is to ensure that your conviction in an idea is coming from the fundamentals of a business and not from your emotional about a company's share price movement. So when I look at where I increase conviction, I see stocks that have actually fallen in price. For instance, Lumine and Topicus have both decreased substantially in price, but my conviction in them just really hasn't faltered at all. This helps determine my actions, as I then know that they're very good candidates for me to probably add capital to and increase my position size. So this conviction ranking really helps me be more decisive, but maybe less delusional. If there's a business where my conviction levels have dropped, you know, in half, there's probably a really good chance that I shouldn't be adding to that position, even if there's a corresponding drop in the share price. Just because a stock's price drops doesn't mean that that's a valid opportunity to invest in it. You need to look at things like the fundamentals of the business and decide if the market is correct or incorrect on its current perception. And my conviction ranking helps me make that independent decision that are not tied to the market. Now, it's essential to never get married to an idea or fall in love with one. As I've said, conviction is really just a test. And the businesses that stay in my portfolio will tend to be the ones where my conviction levels are improving over time. These improvements generally come from very strong fundamentals, such as higher growth metrics, higher margins, greater capital efficiency, or maybe even more robust validation of capital allocation decisions. Now, I know that I've constantly tried to test myself to see where I could be wrong. And while this can obviously hurt the ego. A degree of humility in investing is much, much more valuable than having a high iq. Another way a business can improve its fundamentals is through a less discussed strategy, which is strengthening customer loyalty. This is another area that I've spent more and more time thinking about after researching my episode on the book Hidden Monopolies. Instead of focusing purely on traditional competitive advantages that businesses have, such as being a low cost provider, economies of scale, network effects and IP moats, I started to look more and more at the relationships that a business has with its customers. If a company is, you know, top of mind in their customers minds and customers just can't see a reason to switch to a different business, then you have a business that has a very, very strong moat. So yes, you can think of hidden monopolies as a type of switching costs. But as I outlined in that episode, there are many, many ways that a business can improve its customer loyalty and it doesn't have to be explicitly tied to monetary reasons. My favorite case study from the book showed how a business with very obvious scale economies could still actually end up losing to a competitor who was able to improve customer loyalty. The story highlighted Nokia, which was once the absolute king of mobile devices, and it had exceptional scale benefits as well, which seemed to be indisruptable by newcomers such as Apple. But Apple built more and more customer loyalty over time, which eventually led to Nokia's loss of its mobile device dominance. Now the beautiful part about customer loyalty is that it combines fundamentals such as intangibles with tangible results. For instance, if consumers spend a small amount of money on a product, they might not see any reason to switch as they satisfy the satisficing heuristic. This is an advantage that you generally won't see on a business's public presentations. But when you dig a little deeper and look at the thought processes that a customer makes in relation to a product, you will see these types of relationships and businesses that have these relationships, such as, you know, a Netflix saw substantial increases in their intrinsic value specifically because customers didn't see a need to jump to a competitor. Now as a quick side note here, I actually don't believe Netflix's score in this area is going to increase over time. It's probably going to decrease over time, but five to 10 years ago it was a very, very significant advantage for them. Now, when you have customer loyalty, you don't need to spend as much time on customer acquisition. You can simply enrich the customer experience and keep customers happy who will continue doing business with you that saves a ton of money on things such as customer acquisition costs, which can then be diverted elsewhere. The other bonus of having high scores and customer loyalty is that the business becomes much, much more predictable. If a business has to fight, you know, tooth and nail to get every single new customer, it's going to have to spend a lot of money and you have limited certainty whether those customers will actually stick and stay inside of that business. If you know a business already has a very sticky customer base, then chances are it'll have the same customers five to ten years from now with greater certainty. This is why software businesses with switching moats trade at such high valuations. Investors tend to have high confidence that these businesses will increase their annual recurring revenue. And those are highly valuable. So what I like to look for are the hidden monopolies. This is where businesses have maybe improved their customer relationships, but the market doesn't quite understand how those relationships have improved. In those cases, you can truly get some incredible returns because once the market finds out, there's a great chance that you'll get a RE rating in that business's multiple. Now, similar to conviction testing, I like to audit my businesses to observe their customer loyalty metrics. I try to do this now on probably a yearly basis, so I can see if there's any large scale changes that I need to focus on. Additionally, I can look at what other companies are doing and see whether my business is maybe cloning some of their best practices to help improve customer loyalty, or if they're just getting miles and miles further ahead in their own abilities to improve customer loyalty. So one business that I can talk freely about here is Aritzia. I've done my customer loyalty analysis on the business and I concluded that they just don't have a very high customer loyalty grade. And that's actually okay. I think most retail businesses will not get the highest grade using this exact framework. But it was still valuable to really go through each one of these 20 line items to see where Ritzia scored somewhat strongly. Now, I didn't score it very highly in any one area, but it had some medium scores and things like satisficing personal relationship costs and exclusivity. Now I can see whether these metrics move up or down as the business continues to scale, which will help me determine whether they are improving customer loyalty. Now, finding customer loyalty is great, especially when you decide to sleuth a business. I covered sleuthing in a lot more detail, and I've already mentioned that hidden monopolies often requires quite a Bit of digging just to find the hidden monopoly and some of the aspects that I covered regarding sleuthing can become very, very helpful. So the problem with some businesses that I know I own is that I'm not a personal consumer of that business. So if I was to analyze a business such as Apple, it's pretty easy. You know, my house is littered with Apple products. I'm writing this episode on a MacBook Pro. I'm listening to podcasts on my iPhone. I got an Apple TV right next to me when I want to watch a show. But there are many businesses that are in my portfolio that I have zero ability to put myself in the customer's shoes simply because they just serve markets or have products that I'm not going to shop for and nor will I probably ever shop for. This is where speaking with other people about their experience is so valuable, as well as why getting, you know, kind of boots on the ground is so important. If you have people like family, friends, or acquaintances who work in industries that use products of the businesses that you're looking at, that can be a highly, highly important person to talk to. And in that case, you definitely should try and find out more about the relationship between that customer and the company because you can unveil some incredible insights. For instance, I don't have a ton of experience with, you know, vertical market software businesses, so I have to go and depend on information from others who do use these types of products. So, for instance, my stepdad works at a post office in Canada and they recently switched to a new software for processing payment. And he said it was an absolute pain in the ass to learn. He had to spend weeks learning the latest software and teaching it to others at his location. So he didn't decide whether Canada Post would switch. I think if it had been up to him, he would probably have decided that he did not want to switch because he knew that there would be a lot of time and energy that would be spent in learning this new piece of software. So this, you know, little piece of information really helps me understand the switching costs that are involved with a lot of these vertical market software businesses I own, such as Topicus and Lumine. Now, one of the favorite episodes I did in 2025 was on the psychology of human misjudgment that was outlined by Charlie Munger. So making that episode was great for me personally because I can more closely examine the psychological biases that I personally have succumbed to in the past. And if you asked me when I started investing, what's the greatest Risk to investing. I probably would have said things such as leverage, maybe lack of a moat, or poor capital allocation. It would have been something that seemed clean and rational. But the honest answer to that, which I didn't really start to understand until I gained more and more experience, is probably a lot messier and irrational, and that's that the biggest risk in investing is myself. There are two investments that I made from two completely different worlds that I think have helped me understand this at a much deeper level. So for the first trade, we need to go back to 2017. So Bitcoin had shot up from 3,000 and 20,000 in just a few months. And every altcoin with, you know, a website seemed to double nearly in a couple of hours. It was an environment that was really easy to fool yourself into thinking that you were smart. I quadrupled my capital months and I felt like I had found something that was truly special and life changing. So I built what many temporary successful people do. I built my edge. Looking back, there wasn't much science about it, but it felt scientific to me at the time. I looked at things like ichimoku clouds and other indicators that I didn't really understand all that well. I took screenshots and I focused on trends and specifically on the short term. But when the market rapidly turned against me, I didn't really adjust or take any time to step back and look a little more closely at what I was doing. Instead, I just doubled down and told myself things would probably go up, but I need to just wait it out. Much like Isaac Newton, who added to his South Sea company bet once it popped. I made the mistake of thinking my crypto wouldn't go down for too much longer. So this mistake showed me that my system was more or less built around a narrative that justified a lot of the emotional biases that I was exhibiting. And as Spinoza said, emotion makes us pursue the worse while seeing the better. A few months later, 97% of my crypto net worth completely evaporated. And that didn't happen because, you know, bitcoin was a scam, but because I fell victim to things such as a loving tendency, reward super response tendency, and doubt avoidance. It was unfortunately, the perfect storm of misjudgments, a negative lollapalooza effect. The second trade took place recently, in the last quarter of 2024. I'd evolved a lot since my days as a crypto speculator. I thought I had a much better framework and structures in place to help protect my downside. But the danger of Emotional reasoning is always around the corner. When I first bought a business called Simply Solventless, a Canadian cannabis company, I did quite a bit of work. I did scuttlebutt, management interviews, due diligence. I spoke with other investors and people involved in the cannabis industry. And I liked the industry consolidation story that Simply Sovernless was a part of. And you know, I like the price, I like the upside, and maybe I liked it a little too much, which was probably the beginning of my mistake. When you like something too much, it's like putting on beer goggles. You're looking at an unclear picture, but it appears to you to be in 4K when a significant acquisition they made fell through. The stock dropped very sharply. But looking back, my first instinct wasn't caution, which it maybe should have been. It was excitement and a view towards opportunity. I wrote in my journal after buying more shares that quote, this might be a mistake. I like the price drop, but there's a lot of uncertainty in the idea because of the unknowns with the material adverse conditions. Now after that event came things like accounting changes. Then there are revenue recognition adjustments, and these added more and more to the uncertainty with the business. But then a switch kind of changed in my mind. What if I've been wrong on this business the entire time and I was simply just allowing my emotions to cloud my judgment? I promptly sold the whole position at unfortunately a considerable loss, the largest percentage loss that I've ever had. Let's take a quick break and hear from today's sponsors.
