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Written by Motley Fool Staff for The Motley Fool
In this episode of Motley Fool Rule Breaker Investing, Motley Fool co-founder David Gardner is challenged by five ChatGPT-derived questions designed to challenge assumptions, expose blind spots, summon a few strange hypotheticals, and more.
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This podcast was recorded on Sept. 16, 2026.
David Gardner: This week, for the first time in more than a year, ChatGPT is back on the mound. I'm back in the batter's box. Five pitches coming my way this week. Five questions I've asked AI to dream up, each designed to make me think, challenge a Rule Breaker assumption, find a blind spot, or send us all somewhere that none of us quite expected. ChatGPT asks David Answers, five questions, five swings. Volume 4. Play ball. Only on this week's Rule Breaker Investing.
Welcome back to Rule Breaker Investing. Welcome back, Wednesday, Sept. 16, to the one-year anniversary to the day of the launch of my book, Rule Breaker Investing. I want to start this week by thanking every one of you who's ever read a page of the book, maybe read a chapter, maybe even read the book or listened to the audiobook. Of course, that means so much to me. I loved writing my final stock market book. I hope it stands the test of time. I hope more people will buy it over the next five years than did in the first year, although I'm very happy with first-year sales and very proud to have international editions already out in the Korean language, in the German language, and more coming. I couldn't be more excited about Rule Breaker Investing. I especially want to thank fellow Fools Matt Hard and Andrew Gibson for doing a wonderful job speaking to the book and its merits on social media. Matt Hard at 307Fool on Twitter X. You're running a contest this week to give away a few free copies. Andrew, you're pitching in for anybody who replies to your post on Twitter X.
Anyway, that is such an above-and-beyond gesture. I just wanted to call it out. But thank you to everybody who's part of Rule Breaker Investing, which is a book, of course, and will shortly outlive this podcast. Yet, it's also a podcast, too. Thank you for joining me on this week's edition of Rule Breaker Investing. One thing we do four times a year on this podcast is we do a game show, and next week we're going to do the next rendition, the Market Cap Game Show, coming to you next week. I'm excited for you to play along, especially if you're a new listener, a new viewer. Get ready to get your market cap on starting next week.
If you don't exactly know what that means right now, we'll explain it all and play a game with you on this podcast seven days from now. I also want to mention last week's podcast, which I had so much fun doing. Thank you again to Rick Munarriz for joining me. It was 10 years later. That's right. We revisited five stock picks I made on this podcast exactly 10 years before. We review the winners, the losers, we draw the key lessons. That's really the point of 10 years later. Although another key point of 10 years later is to outperform the S&P 500. It's not going to happen with every one of our 35 stock samplers, and surely it hasn't. I've had some real dogs, too, but it was a pleasure to show off the five stock picks last week and review how they've done. If you miss 10 years later, I hope you'll listen in, and by the way, every 10 weeks on this podcast, we do the next one. I'm already counting down the weeks to five stocks to put under the tree, which were done in December of 2016.
Speaking to other highlights of this podcast, I would be remiss if I didn't mention that two weeks from today, we'll be doing our Rule Breaker Investing mailbag. Our email address is rbi@fool.com, and as a few of you have discovered, we're not just taking emails these days, although we always will. We're also taking audio mailbag. If you'd like to have your voice shared with others here on Rule Breaker Investing during one of our mailbag monthlies, I'd love to have you join me. Just drop an audio file. My talented producer, Bart Shannon, will receive that through an email, just as well as any texts that get sent our way. It's really fun to respond to audio mailbags, so I'm playing that up here a couple of weeks in advance.
This episodic series, ChatGPT Asks, David Answers. This episodic series began back on June 5th of 2024 when I asked ChatGPT to come up with five of the most beautiful, challenging, inventive, valuable, provocative, and/or Foolish questions it could ask me about Rule Breaker Investing. Well, ChatGPT asked, and David answered. That was two and a half years ago. We had enough fun. We learned enough together that I brought it back later that year, and ChatGPT Asks, David Answers became an episodic series.
By Volume 3, which was in April 2025, we turned the questions into baseball pitches. ChatGPT takes the mound. I step into the batter's box, and we see what happens. The point, by the way, isn't to quiz me on things that I already know. It's certainly not for ChatGPT to lob me five softballs. The point is to use AI as a provocateur to ask questions that might uncover a blind spot or challenge an assumption, reverse something I normally believe, or simply send us all somewhere, as I mentioned at the top, nobody was expecting us to go. Sometimes it's a hardball, sometimes a curve, sometimes something downright screwy. There are knuckleballs from time to time that could flutter just about anywhere. Five pitches, five swings, and I hope a few thoughts worth taking home from the ballpark.
Let's get started. I realize not everybody is, but especially for baseball fans, I asked ChatGPT to pick its pitch type and name that pitch before it throws me the question. Pitch No. 1, ChatGPT has chosen a change-up. Here we go. It asks, what advantage did 30-year-old David Gardner have as an investor that 60-year-old David Gardner no longer has? What advantage does 60-year-old David have that 30-year-old David couldn't possibly have had? That is pitch No. 1 and the change-up. I want to first of all say thank you for the question. I appreciate the question. It was fun to think about a change-up because I think we're playing with time here and changing speeds. This is a good opener. It's investing-focused.
As I think of the first half of the question, what advantage did 30-year-old me, or you, have as an investor that 60-year-old me or us no longer has? The obvious first answer that comes to mind is time. That 30-year-old had 30 more years to compound his returns than I do today at the age of 60. Now, I'm hoping to hit at least 90, which means I'm still looking 30-plus ahead, and I'm invested that way, fully invested in stocks as I always have been. Every time the market rages upward, it's taking all my money with it, and every time the market gets cut in half, and that's happened. My money gets cut in half right along with it. I usually do worse than the market in bear market periods. That's something that's been true of me my whole life, long since I started investing at the age of 18.
Now 42 years later, with all the ups and all the downs, I couldn't be more delighted to see where I am today. Yet, I have to admit, I don't have as much time as I once did. Time, of course, equals compounding, which equals bigger and bigger numbers. As we go, the more years you have to invest, the more time you have to let that money let that oak tree, grow. It's worth pointing out then to all my younger listeners or to all my older listeners who are connected to younger people, which pretty much means all of us, the earlier you can get anyone in your life started, truly investing. I would say not trading, the opposite of investing. I would say truly investing. The better off they'll be, and the happier and more fulfilled you'll be, whether it was you or someone who gave that advice or an opening $1,000 to their account to the happier the world is, the more of us invest, the earlier that we start, so 30-year-old David Gardner had a 30-year head start on me, and the good news is, it was I.
Therefore, I have been invested all the way through, and yet, I have to admit I simply don't have as much time left to compound my returns. I think there was a second advantage that 30-year-old had, and I would say that 30-year-old, relative to me today, was more avidly following not just the markets, although he was, but also the world itself. Technology, the gains, the changes. The Internet was just upon us 30 years ago. We're talking about the mid-1990s. That 30-year-old version of me was an entrepreneur who was a real believer in the new medium, and certainly not everybody was. There were a lot of skeptics who doubted that the Internet would ever really scale or become something. I realize to younger ears, that may sound really silly today, and yet, that was the case. I was avidly following how technology was being reshaped, what it meant for our culture, and therefore what stocks you and I would want to be invested in, and what companies we'd want to be part owners of going forward.
That's just as true today, in the sense that I care just as much about how technology is shaping the future, and I care just as much about my investments today as I did back then. But back then, I was constantly on the hunt for the next stock. Since I no longer pick stocks on a regular basis, formally at The Motley Fool, that simply is not true of me as much anymore. I think it's a great advantage to be always on the hunt. I know many of you listening to me today are actively on the hunt, and I hope we're still delivering in a way that you value as a weekly listen Rule Breaker Investing, whether you catch us on the weekends jogging or listen to us religiously, as this podcast comes out pretty much every noon Eastern every Wednesday.
Yet, I have to admit I'm not following as actively. I'm not needing to make my next stock pick or my next three picks, which is what I was doing every month. Three individual stock picks every month for the Motley Fool. In addition, 10 Best Buys Now, five for Stock Advisor, five for Rule Breakers. There is no substitute for being actively in the game. While I'll always be in the game, I'm not as active and avid as I was as a 30-year-old. That's ChatGPT. That's another advantage that 30-year-old David Gardner has that 60-year-old David Gardner no longer has quite so much.
Now, the second part of the question reverses it. What advantage does 60-year-old me or you have that 30-year-old us couldn't possibly have had? I would say, first and foremost, what comes to mind is that when I was 30, I was imagining what might work. I was believing that six traits would serve me well, the six traits that I was writing about 30 years ago on our site in the 1998 book, which is 28 years ago now, Rule Breakers, Rule Makers, where I first laid out the very six same traits that I'm using today as a stock picker that I wrote about in Rule Breaker Investing when it came out a year ago. Today, I'm still using those exact same six traits, and yet back then, I didn't have results. I had some early results. I had some intuition, but it's impossible to have results at the start of a journey, 60-year-old me can now look back and see what worked and what didn't. Of course, I'm happy to say the reason I'm sitting in front of you today talking is it's worked more often than it hasn't. Otherwise, I'd be the first to encourage you not to listen to this podcast or show up at Fool.com.
But the good news is now I've seen that things that I intuited 30 years ago were right. I especially think of those six traits of the Rule Breaker stock, again, first written about 30 years ago, right around right now. Now I can look back and say, overvalued trait number 6 was absolutely right. Amazon.com, AOL back in the day, Netflix, later on Tesla, Nvidia. The list goes on. Intuitive Surgical, companies that were called outrageously overvalued. Still true today, Palantir called outrageously overvalued. Yet I was saying, I actually think that's a buy signal if you see the other five traits of Rule Breaker stocks present. Of course, there are some stocks that are genuinely overvalued stocks I would never want to own anyway. But when you find true blue Rule Breakers, you see those five traits that I've written about and talked about ad infinitum on this podcast, etc., over the years. When you see those first five traits, and then the whole world, or at least a lot of financial commentators, are telling you that stock is either A, overvalued, or B, so overvalued, priced for perfection. The list goes on of those catchphrases you'll hear people use. That actually 30 years ago, I was saying, I think that's actually a buy signal.
Now I can look back and say, that's true. I can also look back over 30 years now and say how many short-term players there are in the market. They are not investors. They are traders. The vast majority of institutional money moving on our markets every minute, not just every day or week, but that, too, every minute is driven by incredible short-termism. You're seeing people using zigs and zags on stock charts. They don't actually care what the company is that they're briefly invested in briefly, being the keyword. They're just in it for a much shorter time period than I think I hope you and I are. I now know that we have huge advantages as long-game players as Rule Breakers. I couldn't have known 30 years ago just how many people were playing that game.
By the way, just as many short-game players are in the market today. I'm sure there are other things I could observe that I now know with confidence at the age of 60 that I couldn't have known with confidence at 30, maybe I'll throw in one more for now, and that is that I would say people generally underestimate just how tall the best trees that we plant can grow. The best investments that we buy earlier stage, when possible, people have a hard time recognizing just how many times those companies can grow in value. I've now picked for Motley Fool members two 1,000-baggers, both Amazon and Nvidia, both of which I happen to have the coincidental cost basis of $0.16. For each, at the time, I would have had no idea that there would be 10 baggers, let alone 100-baggers, but now I know that you can make 1,000 times your money. If you find the right stocks and have the so-called buy discipline that I hope you'll have in a world where everybody else is talking about sell discipline. If you care more about what you're buying than when you sell, I think you're positioning yourself well. you have to find the great companies of your time. It's not that hard when you look around.
Even more important, you have to hold those stocks. You will never get a 100-bagger unless you're willing to hold through probably at least a few drawdowns of 50% or more. That means your stock is going to get cut in half more than once on your way to stock market glory, and by the way, you can do better than 100 times your money. I wouldn't have been bold enough to have said that 30 years ago, but now I know. Now I can see, and I don't think the next 30 years will be any different in that regard. We'll see. I'll know more at 90 than I know at 60, but thank you for pitch No. 1, ChatGPT, the changer.
On to pitch No. 2. I'm sorry to say, ChatGPT is throwing me a little chin music with pitch No. 2. It is entitled This Pitch, The Brushback. For people who don't follow baseball, what that means is ChatGPT is throwing me a pitch pretty much right at my chin. Brushing me back off the plate. I'm probably dropping my bat and diving out of the way because this is a brushback pitch. Here it is, pitch No. 2. ChatGPT asks, which Rule Breaker Investing principle of yours are you most worried could become less true over the next 20 years, and why? Again, this is a brushback pitch. It's encouraged me to interrogate my own philosophy. There are lots of possibilities because over any 20-year period, surely, things can change. While it's increasingly difficult in my mind to predict the world two years ahead of where we are right now, let alone 20, nevertheless, it's worth asking ourselves, you and me, what principles do we hold dearly today that could be compromised or become less true over the next 20 years. Now, let me review each of the six traits of the Rule Breaker stocks, which I've earlier foreshadowed. I'm going to go through each right now and briefly think about whether I'm worried about that for the next 20 years.
The first one, trait No. 1 of Rule Breaker stocks, is top dogs and first movers in important emerging industries, and I really don't think that that's going to change meaningfully. I think it's very important to be focused on the leaders. If you're not the lead husky, the old line goes, your view never changes. I love the lead huskies. The sled dogs out there that are leading us, leading our sleds, leading our portfolios into amazing, unpredictable places because they are in the lead position of the dominant, world-changing technologies of our time, and there are now many. Not about AI, as much as we may hear about AI these days. There are so many different technologies that are on the bleeding edge. I don't think it's going to change at all over the next 20 years that that is a principle we should be following.
The second one is having a sustainable competitive advantage, and that will be as true 20 years from now as it is today. The third trait, number 3 of Rule Breaker stocks, is stellar past price appreciation. I'm very convinced that, in contrast to most people looking to buy low and sell high, if you and I, as Rule Breaker stock pickers, are instead looking to buy high, that means buy the so-called expensive stocks that have actually, ironically, done very well before we buy them. Not a great feeling sometimes to be researching a stock as it goes up 30-40%. In the few months leading up to you buying it, a lot of people think, at that point, wait, it's already up 33% since I started researching it a few months ago. I should wait. I've missed it. I'm never going to buy that stock, a lot of people conclude.
Yet, trait number 3 reminds us for Rule Breakers, that is a great buy signal. Very contrary, I think that'll be as true 20 years from today. I'm confident that one trait number 4, of Rule Breaker stocks is that we're looking for excellent people. It's the human capital. It's the CEOs or founders. It's the backers, the VCs. It's the people. Stupid, I sometimes say, not so much the stock chart that people are looking at, or even the products or services or industry dynamics. It's the people that make the decisions that run the companies. Into the ground in the worst cases and up to the moon in the best.
I think it's going to be as true 20 years from today. Now, I will say that a lot of the decision-making over the next 20 years may well be taken over in part or, in some cases, in whole by artificial intelligence. If I were to think of these six traits and which one is most possibly likely to change in some way, it's not a way that worries me, by the way, ChatGPT, since you said, what am I most worried could become less true? But I think of these six, that's the one most likely to be different. We're going to want to ask who is making the decisions, and are decisions being made well. It will be as competitive a world, possibly, and even more competitive world 20 years from today. I expect it probably will be even more competitive then. Thinking about who's making the decisions is going to matter a lot.
Now, when I say that, a lot of us might be thinking, you know, CEO like decisions and strategy decisions, but that's one small part of running a company. A big part of running a company is having a winning culture, creating a place that people want to work at, that people feel energized to work there. It's not about the product launches or competitive decisions made against a competitor. A lot of it is managing the internals. I'm not sure that AI will do any better of a job there than the best humans, people full of heart and empathy. It'll be interesting to see how AI evolves. I wouldn't ever gainsay that AI can acquire those things and be really good. But I think those human traits and that human dynamic, emotional creatures that we are, I think that's going to count for a lot still 20 years from now. But some of the decision-making and some of that human capital that I think about with trait number 4 of the Rule Breaker stock may morph. It's worth pointing that out.
The last two, I don't think, are going to change either. I think we're still going to care deeply trait number 5, about strong consumer appeal. That is to say, brands are going to matter as much, I think, 20 years from now as they do today, as they did 20 years ago. Of course, that concept of Rule Breakers being overvalued, I feel very confident that that will be as true 20 years from now as it is today. ChatGPT, you were asking me which Rule Breaker Investing principle of mine am I most worried could become less true. I felt like I wanted to run through the six traits of Rule Breaker stocks. But I do notice you wrote principle. If you really know my work, ChatGPT, then you know that when I use the word principle, I'm thinking not about stocks or truisms or truths. I'm specifically thinking about portfolio management principles.
That's the context under which I use principles in my work and in my book. Just to give a quick answer, then to the brushback pitch here, I'm not going to review those, but I would say of the six portfolio management principles that I put out there, the one I'm most worried could become less true might be portfolio principle number 6. That is to review quarterly. I tell all investors, as I try to do myself, to review quarterly and manage accordingly. I will say that I think the world is speeding up. I think faster decisions are needing to be made in part because technologies themselves are being dreamed up and discovered faster. They're being deployed faster, and they matter faster than ever before. The speed feels not quite breathtaking yet, but it feels stressful to me. In some ways, that could mean that the degree of attention that serious investors need to pay to our portfolios could be sped up.
If that were the case, that would worry me a little bit. I hope that won't be the case. I like to think some of my favorite members at the Motley Fool check in a few times a year with their portfolio. I've always said, and I say to you now, I check in every day with my portfolio. The same way I check in every day with my favorite baseball team or sports teams. I love to follow the game of sports. I love to follow the game of the markets. I don't trade every day. In fact, there are whole years that go by where I don't make a single trade, so I'm always fully invested, never particularly active there, but I follow every day. I don't become tempted to take actions just because I personally follow every day.
I realize that's not true of all of us. I certainly hear from members, both on this podcast and mailbags. I meet people in person. I've encountered so many people over the years who worry that if they were to follow their portfolio more actively, they would be more active in their management of it. I'd be the first to say that can be a mistake, and try not to make that mistake. But if I were to worry about any of my six portfolio principles, that might be the one that I would think about. I myself will resist the inclination to feel like I need to be much more active following the markets more so than I am today or more active in the management of my own portfolio. There's my answer to the brushback pitch. Let's move on to pitch number 3.
David Gardner: Now, for those of you who really know baseball, you know what an eephus pitch is. When I say ChatGPT has selected an eephus for pitch number 3, you know exactly where I'm headed. But for the majority of us who probably don't know what that word means, we're referring to a pitch where a pitcher throws the ball very slowly, very high up in the air in order to get it all the way from his hand to the catcher's mitt. An eephus pitch is a comically high, slow pitch, typically thrown by people who are not professional pitchers. If you ever see a ball thrown to open up the game, let's say, during a pregame ceremony, they have some noteworthy stand on the mound and throw out the ceremonial opening pitch. Those are eephus pitches, most of the time. Sometimes pitchers try to surprise hitters with an eephus pitch, but usually not. Now, does this eephus pitch surprise me? Does it surprise you? Let's see. Here we go.
Pitch number 3. ChatGPT asks you may learn the exact December 31st, 2046 stock price of one company. But you're forbidden from ever owning it. Which company do you choose? What are you hoping its price tells you about the future? Eephus pitch. Love it. Basically, 20 years from now. What one stock price would I love to know, but I'm not allowed to own it, but it would tell me something really helpful and important about the future? This is probably the one I thought about longest when I saw the five pitches, and even though it's the eephus pitch, it's the one that I find the most interesting and challenging. My gut answer, I realized, is invalid because my gut answer was going to be that I pick ticker symbol SPY. That would be the S&P 500 ETF, basically the index fund that tells me how the stock market has done. That would be really interesting, 20 or so years from this week, to know exactly where the market was.
But first of all, that's not valid because ChatGPT, your question was, what is the stock price of one company? ETFs are not companies, and the standard PR is 500 is composed of 500 companies. I realized that's an invalid answer. Not only that, but as I thought about it some more, I expect the market to be up somewhere 7, 8, 9, 10, 11% annualized over the course of the next 20 years. It's not even that important or interesting an answer for me. Then the next thought I had, my second thought, was, what's going to be an amazing Rule Breaker? I'd love to know what the price of a dynamic Rule Breaker would be, until I thought that I'm probably asking about companies that barely even exist today.
After all, most of the great Rule Breakers show up as smaller, earlier-stage companies. Some of them are inking their first capital raise probably this week at a very small valuation. I can't even name the great Rule Breaker 20 years from now today. There's no company name I can put on it that would really give me a great answer. Plus, if I did find an amazing Rule Breaker that's 20 years from now, ChatGPT, you already pointed out, I couldn't even own it. That's the one I'm not allowed to own. It can't be a company that doesn't exist yet. If it's a great stock, I wouldn't want to spoil it by making it the answer to this question. I did then think about Tesla because Tesla is such a dynamic company, and over the course of the next 20 years, who knows what Tesla might become? I could imagine it merging with some other Elon Musk companies. I could imagine it going out on its own beyond robotaxis, the so-called Tesla cybercabs. It's very obvious that Tesla is focused on robots and the Optimus robot. It would be really helpful to know where Tesla stock was 20 years from this year. But then again, I thought, I want to keep owning the stock. I've already owned it for 15 years. It's been a 100-plus bagger. While it's been a rocky ride, and I'm not always a big fan of everything that Elon Musk does, I do think he's one of the greatest entrepreneurs of all time.
I don't think there's ever been anybody more innovative on planet Earth. I'm dead serious about that at scale than Elon Musk. Whatever you might think of him, and I'm generally a fan, but not a fanboy, I think it has been worth clearly it has been worth owning. I'm going to keep owning it, which means, ChatGPT, I can't answer it because you're forbidding me from owning the stock that we come down with.
Here's where I'm settling, then, on this one. It's not going to be a be-all, end-all. This is an angled answer, but I'm going to say the one company whose stock price I'd like to know on December 31st of 2046, I can't own the stock, and by the way, I don't right now. It's a mega-cap company, and I don't find it that interesting to own at such a massive market cap, but I would say SpaceX. I think it would be really helpful for me to know the price of SpaceX on December 31st, 2046, and I say that in part because the industry itself is fascinating and, clearly, hugely Rule Breaking and very interesting, the commercialization of outer space.
We've started, of course, with satellites. There will be other technologies coming. It is utterly fascinating to me. I was always a Trekkie since being a little kid and watching Star Trek and reruns of the few seasons they did. I think I saw all those episodes. Captain Kirk three times over before I was 15. But my whole life long, I loved space. I remember, as an undergraduate at the University of North Carolina at Chapel Hill, reading my Astronomy textbook. I took an astronomy course, and I remember saying, and this is a sign of the times back then. This is mid-1980s. I remember that textbook saying, again, to an undergraduate student, it said, "We cannot prove the existence of planets outside our solar system because we have never yet detected one." That's a sign that I'm older. These days, it's now patently obvious that there are planets outside our little solar system. By the way, people say about life today, life in outer space, what they once said about planets, which is we can't prove that there is life outside of our solar system. Yet, for the longest time now, I have thought maybe you too, that it's so obvious that life is spread throughout the universe at a scale you and I cannot even imagine. Space has always been interesting to me.
Star Trek, Star Wars, etc. There are a lot of space fans listening to me right now, and people who work at NASA, which I never have or will, but people who are deeply invested already in this industry professionally and perhaps financially as well. When SpaceX came out as a stock, I was just like, It's not that interesting to me because it's such a massive market cap. I'd much rather find smaller-cap companies in this space. I mentioned this before in this podcast, I have. I've invested in Rocket Lab a few years ago. It's been a multi-bagger for me, and I think that's a good example of a Rule Breaker that also lives at a much smaller scale in that same industry. I'm not here to pound the table for Rocket Lab, which has certainly lost a substantial amount of its own value in just the last few months. Doesn't daunt me as a Rule Breaker investor.
But it would be awfully helpful to know for several reasons. Where SpaceX stock is year-end 2046, I think in a lot of ways that would help me understand where my Rocket Lab and other companies that both exist today and don't exist yet are headed. There's a chance I'm overrating how big space could be. Sometimes we can see stuff, but our timing is off. For example, I once thought nanotechnology would clearly be widely deployed by now. I've written about this in the and nanotechnology is always a 20-year overnight story waiting to happen. That could end up being true with outer space companies, and yet I doubt that's going to be the case. That is my best swing at your fast pitch, ChatGPT. Thank you for pitch Number 3. We're through three pitches. Two more to go.
Pitch Number 4. ChatGPT is labeled the splitter. That means this is a fairly aggressive, fairly straight pitch designed to throw a strike and probably try to put it by me. Here we go. ChatGPT asks. Two companies look equally Rule Breakery today. Company A, ChatGPT goes on is already a $1 trillion global leader. Profitable and dominant. Company B, is worth $10 billion. It's losing money. It's future is far fuzzier. But if it works, its runway looks enormous. You may buy only one. Which way do you instinctively lean and has that answer changed over your investing lifetime? I think part of the wordplay that I now see from our AI friend is, well, when you call it a splitter, you're splitting things so I can only go one direction or the other.
Of course, my answer in most cases, with questions like these, is that’s the wrong question because it’s not a trade-off. You can own them both. In fact, I would look to own both of these companies in my portfolio, and I do. Maybe you do, too, dear listener; there is never any need to only own one company and not the other if you like both. I think it’s great to have a mix of big-cap or mega-cap companies right alongside small-cap companies and a lot of other types of companies in between. I would start by saying it's the wrong question, but since you've phrased it this way and you've made it a splitter, then I'm going to rest on a couple of my key concepts, which I've certainly talked about over the years, and Rule Breaker Investing fans should expect me to say.
The first one that comes to mind is habit Number 6 for the Rule Breaker Investor, and that's aim for 60% accuracy. To start to answer the question, I generally want to feel like when I pick a new stock, whatever it's market cap, I want to feel like six times out of 10, we're going to beat the market with this stock. I want to feel confident. Now, I realize some of my greatest stock picks we found really early, and it would have been hard to be confident about those companies when we first found them. Netflix, for example, was just a DVD-by-mail company, and it was much smaller than Blockbuster Video back in the day when we picked it. Certainly, we don't always and can't always have 60% accuracy in mind that this company will likely beat the market. Yet, that is the default that I go with. I'm already leaning toward that $1 trillion company because it feels much more likely you already said, ChatGPT, it's profitable. It's dominant. It's a global leader. I feel much more 60% accuracy about that one than our $10 billion small cap that's losing money and has a far fuzzier future.
I also want to mention the snap test. How could I not? The snap test. Let's snap our fingers and make these two companies disappear overnight. Which one would more people notice is gone? Which one would break more hearts when overnight it disappeared from planet Earth. I think the answer is, again, obvious, it would be the $1 trillion global leader profitable and dominant, not the fuzzy future smaller company losing money. Clearly, Company A passes the SNAP test, as well as aligns with my 60% accuracy habit.
Finally, there's something else I favor about swinging at this splitter with Company A. That is this concept. It seems to me, and I've observed this over the years, a lot of people just think it can't go bigger, I being whatever stock they're looking at or the market at large, or just the numbers we put on market caps these days. A lot of people, 30 years ago, would have thought there will never be a $1 trillion market cap company. How could anything ever get that big? It can't go bigger. That's true of a lot of us as we look at companies like Apple. Even today or 10 years ago, or 30 years ago, or Nvidia, 10 years ago, or today or any Microsoft, the list goes on Google Alphabet. It can't go bigger, we think. That's always made me smile because as a Rule Breaker, thinker, and investor, I've always pictured the employees at a company like Google Alphabet. Do you think they walk around 9:00 to 5:00, whether they're working from home or in office? Do you think they walk around going, I don't think we can possibly grow this company from here, how could we? We’re already so big? The answer is nobody thinks that way in Silicon Valley.
Virtually every company out there, at least the growers, the companies with new technologies, leadership, the lead huskies taking their sleds in unpredictable directions. Nobody on that sled, whether the person mushing the dogs or the dogs themselves, nobody's there going, well, why would we even bother? Clearly, we can't get any bigger than we already are. Another reason I favor Company A is that so often people don't they just think, how could it possibly get bigger? The answer is, it will get bigger and bigger than that. We've seen that over the years.
Now at the age of 60, I've seen any number of remarkable companies, many of which we picked, but I wish I had them all. I certainly have it. I've seen amazing growth to heights unparalleled and certainly unexpected. By the way, I expect that to continue. People will be flabbergasted when the first company trips over the $10 trillion scale or $50 trillion scale years hence, that'll just keep happening. It's also true of great companies and their market caps. People think that stock couldn't get any bigger. That to me is a dark cloud I can see through. That to me is misguided thinking that a lot of people have rattling around in their heads. I think you and I benefit. We can take advantage of that by not thinking that way. Pitch Number 4, ChatGPT, you're splitting me here. I've already told you the correct answer to this question is by both Company A and company B. But whether it's because we're aiming for 60% accuracy or because I'm snapping my fingers and making things disappear or because I love to poke holes at conventional wisdom, and it can't go bigger is one of those I love to poke holes at. For all of those reasons, I favor Company A. That gets us to our final pitch this week. It's a delight to have brought back. This is the first time in a year and a half we've done.
ChatGPT Asks. David, Answers. I hope you're having as much fun to your listener as I am with these pitches. ChatGPT, thank you for your effort. As always, thanks for standing on the mound and having the guts to throw these pitches at me. Let's check the knuckleball. Which is how pitch Number 5 is labeled, and here we go. Imagine you're allowed to make one final investment. Not necessarily a stock, ChatGPT asks, and you'll never know how it turns out, but you can invest money, time, reputation, knowledge, love, anything you possess. ChatGPT asks, "What do you invest in what and why?" Well, it's a fun one to close on. It begins sounding like an investing question, but then it quietly becomes something a little bit bigger than that.
There is a particularly nice Rule Breaker resonance here, because the best investments we make may be ones whose returns accrue beyond our own traditional numerical financial scorecards. The first thought that comes to mind when I think about if I'm only allowed to make one final investment, which will certainly be true one day, the first of the three part question, what do you invest in what and why is what do you invest? That one's pretty easy for me because I think my final investment will almost inevitably be financial, because if you're fortunate to have, at the end of your life, something leftover that can be invested, that for a lot of us is going to be our final investment. It's our legacy.
Clearly, my answer is my final investment is going to be money. Now, of course, there are a lot of things tied to that things like it took some time to get that money together and put it into an idea that we've thought out. It's not like it's just money. ChatGPT you asked me about reputation. Yes, part of our reputation is tied to our legacy, so that's certainly there as well. You mentioned knowledge. Love, all of these things are baked into that final investment we make. When I say money, that shouldn't sound cold or callous. There's so much loaded up into that, at least for me, and I hope for you, too, my fellow Fools. That's my answer to the first part.
Then the next question is, in what? What guides me there is this notion, I got it from conscious capitalism that we want to create a win. What do winners do? I many times asked on this podcast in my book and in social media, and in my writings, I think you already know the answer. What do winners do? The answer is, of course, winners win. Yet, what I went on to say in Rule Breaker Investing is that real winners win. They win for themselves, they win for others, those that they're connected to, and they also win for their community or the world at large. Winners win, and that's worth remembering when you're adding up to which stocks you're winners, I prefer to add up, not double down. Winners win, but real winners win. We're making a final investment, I think we're thinking, how do we create a win for everyone?
With that money that we're investing, I would say in such a way that builds trust, George Schultz, former Secretary of State, the man lived to just over 100, wrote a wonderful essay called,"Trust is the coin of the realm." I agree with that statement. There are a few things that I can think about that are more powerful than trust. That you trust me, that I trust you, that we're willing to take a risk and trust each other, that we're willing to cooperate, and in some cases that we're willing to love, even strangers. That actually explains most of the advances of the human race, let alone most of our best investments cooperation explains so much of the things that we take for granted in our culture today from domestic circumstances to transportation, it is, in fact, this has been pointed out many times by evolutionary biologists that humans have so far outperformed apes and chimpanzees is because we're able to cooperate at a scale they can't think it's something like if you get 80 chimps together, they start to fight. Any number over 80, they can't get it done.
We are amazing by contrast, which explains a lot as to why we are where we are and they are, God love them, where they are. Cooperation and love explain most of the advances of the human race, and therefore that win that you and I should be looking to invest in to make happen, whether it's today or that final investment we make at the end of our lives. For me, it's all about trust. We need more of that.
People don't trust when they fear. Wherever you find fear in society, it's driving out trust, and any investment we can make toward love and trust scares away fear. Pronoia. I'm not going to define the term. Some of you will remember that. I've talked to it this year, ever since Kevin Kelly introduced it to me earlier this year, pronoia, my friends, optimism. Whether you think you can or whether you think you cannot. Henry Ford was reported to have said, you're right. The world will always be to the people who think, yes, we can, who will take a risk to cooperate, to love and to build trust. I have no particular specific investment, ChatGPT, in swinging at your knuckleball that I'm going to propose. I'm trying to think on behalf of all of us and think about what are the most powerful investments we can make if that final investment we're looking to make one, long, loud statement. I want each of us to be building wins for all of us, and I want us to be investing toward greater and greater trust. For me, a lot of that is tied to optimism.
I think of my friend Bill Burke his podcast, which I was honored to appear on the Blue Sky Podcast, The Optimism Institute. Bill founded and leads that. He has a great line. It's what tips off his podcast every week. It's where it pulls its name. In so many words, Bill says, "There's always blue sky above, but sometimes you just have to get your head up above the clouds. To see it." I would say, ChatGPT, in answer to your knuckleball, we should be investing that final investment using money, in ways that build trust and optimism and bring people together. Why you ask? Because to me, that's the most valuable thing we can do for the human race and for our world at large. That is as specifically, I think, as I would want to swing at your knuckleball. But really, I'm swinging for all of us in a way that I hope lands with enough of us. Well, five pitches, five swings.
We covered some ground this week, looking backward at how an investor changes, looking forward, at a future, none of us can know, testing a few Rule Breaker assumptions and entertaining some improbable hypotheticals along the way. That's what I enjoy about ChatGPT Asks, David answers. Good questions. They make us think sometimes our answers surprise even ourselves once we force ourselves to think about them.
To my fellow Fools, my dear listeners, thanks for thinking along with me and swinging along with me this week. Next week? It's our Market Cap Game Show. Get ready to get your market cap on. Fool on.
David Gardner has positions in Alphabet, Amazon, Intuitive Surgical, Netflix, Palantir Technologies, Rocket Lab, and Tesla. The Motley Fool has positions in and recommends Alphabet, Amazon, Intuitive Surgical, Microsoft, Netflix, Nvidia, Palantir Technologies, Rocket Lab, and Tesla. The Motley Fool recommends the following options: long January 2028 $520 calls on Intuitive Surgical and short January 2028 $530 calls on Intuitive Surgical. The Motley Fool has a disclosure policy.