We Study Billionaires - The Investor’s Podcast Network - TIP242: Billionaire Jack Dorsey - Lessons From Twitter and Square (Business Podcast)

Episode Date: May 12, 2019

On today's show, we cover important questions that were recently asked of billionaire Jack Dorsey. IN THIS EPISODE YOU’LL LEARN: How and why Twitter and Square was founded How Jack thinks about t...he future of payment processing with Square Why you should invest in megatrends, and which mega trend to follow if you invest in consumer internet  The two main lessons Jack learned from founding twitter Ask The Investors: Do you invest your monthly cash flow or do you invest a few times per year?   BOOKS AND RESOURCES Join the exclusive TIP Mastermind Community to engage in meaningful stock investing discussions with Stig, Clay, and the other community members. One of Steve Jobs' favorite books, Inside the Tornado. NEW TO THE SHOW? Check out our We Study Billionaires Starter Packs. Browse through all our episodes (complete with transcripts) here. Try our tool for picking stock winners and managing our portfolios: TIP Finance Tool. Enjoy exclusive perks from our favorite Apps and Services. Stay up-to-date on financial markets and investing strategies through our daily newsletter, We Study Markets. Learn how to better start, manage, and grow your business with the best business podcasts.  SPONSORS Support our free podcast by supporting our sponsors: SimpleMining Hardblock AnchorWatch Human Rights Foundation Unchained Vanta Shopify Onramp HELP US OUT! Help us reach new listeners by leaving us a rating and review on Apple Podcasts! It takes less than 30 seconds, and really helps our show grow, which allows us to bring on even better guests for you all! Thank you – we really appreciate it! Support our show by becoming a premium member! https://theinvestorspodcastnetwork.supportingcast.fm Support our show by becoming a premium member! https://theinvestorspodcastnetwork.supportingcast.fm Support our show by becoming a premium member! https://theinvestorspodcastnetwork.supportingcast.fm Support our show by becoming a premium member! https://theinvestorspodcastnetwork.supportingcast.fm Support our show by becoming a premium member! https://theinvestorspodcastnetwork.supportingcast.fm Support our show by becoming a premium member! https://theinvestorspodcastnetwork.supportingcast.fm Support our show by becoming a premium member! https://theinvestorspodcastnetwork.supportingcast.fm Support our show by becoming a premium member! https://theinvestorspodcastnetwork.supportingcast.fm Support our show by becoming a premium member! https://theinvestorspodcastnetwork.supportingcast.fm Support our show by becoming a premium member! https://theinvestorspodcastnetwork.supportingcast.fm Support our show by becoming a premium member! https://theinvestorspodcastnetwork.supportingcast.fm Support our show by becoming a premium member! https://theinvestorspodcastnetwork.supportingcast.fm Support our show by becoming a premium member! https://theinvestorspodcastnetwork.supportingcast.fm Support our show by becoming a premium member! https://theinvestorspodcastnetwork.supportingcast.fm Support our show by becoming a premium member! https://theinvestorspodcastnetwork.supportingcast.fm Support our show by becoming a premium member! https://theinvestorspodcastnetwork.supportingcast.fm Support our show by becoming a premium member! https://theinvestorspodcastnetwork.supportingcast.fm Support our show by becoming a premium member! https://theinvestorspodcastnetwork.supportingcast.fm Support our show by becoming a premium member! https://theinvestorspodcastnetwork.supportingcast.fm Support our show by becoming a premium member! https://theinvestorspodcastnetwork.supportingcast.fm Support our show by becoming a premium member! https://theinvestorspodcastnetwork.supportingcast.fm Support our show by becoming a premium member! https://theinvestorspodcastnetwork.supportingcast.fm Support our show by becoming a premium member! https://theinvestorspodcastnetwork.supportingcast.fm Support our show by becoming a premium member! https://theinvestorspodcastnetwork.supportingcast.fm Learn more about your ad choices. Visit megaphone.fm/adchoices Support our show by becoming a premium member! https://theinvestorspodcastnetwork.supportingcast.fm

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Starting point is 00:00:00 You're listening to TIP. On today's show, we cover some questions and answers from Silicon Valley billionaire Jack Dorsey. As many know, Jack is the founder of Twitter and also Square, and his personal net worth is in excess of $5 billion. Jack has been at the forefront of modern technology developments and is only 42 years old. During today's show, we cover Jack's thoughts on mobile payments in the future, his main lessons learned from starting Twitter, and much, much more. So without further delay, here's our episode on the thoughtful Jack Dorsey. You are listening to The Investors Podcast, where we study the financial markets and read the books that influence self-made billionaires the most. We keep you informed and prepared for the unexpected.
Starting point is 00:00:49 All right, welcome to the Investors podcast. I'm your host, Preston Pish, and as always, I'm accompanied by my co-host Stig Broderson. And like we said in the introduction, we're covering Jack Dorsey today. and let's just jump right into the first question that we want to cover. So this might sound surprising to some folks, but Jack actually got his inspiration for Twitter by studying the way taxi drivers communicated. When he was asked about this idea, this is how he responded.
Starting point is 00:01:24 Yeah, yeah, I really missed the boat on creating Uber, but I was huge into dispatch. I'm from San Luis, Missouri. And so in the 40s, 50s, and 60s, a lot of people left the city and moved out to the suburbs. And my parents always stood by the city. You know, for me it developed this obsession and fascination of cities as well. And the way that really manifested for me were maps.
Starting point is 00:01:48 I was just obsessed with maps, and I would get lost in them constantly just wondering what was happening at, what was down this street, whatnot. And I had tons of maps of St. Louis and tons of maps of my other favorite city that I had never been to, which is New York City. My parents also had a police scanner, always in a CB radio. And I would always listen to the trucks and the police and the fire trucks and the ambulances. And eventually my parents got an IBM PC Jr. and a Macintosh.
Starting point is 00:02:24 And I would actually take the information from the police scanner and plot it out on my paper map so I could actually watch the police cars move because there was reporting where they are and where they're going, what they're doing. But little by little, the computer became this thing that was amazing because I could actually build a map on it. And I could put dots on that map and I can make those dots move. And I taught myself just enough programming to make that happen. And that's always been my approach in my life is I've never really had a desire to become an engineer.
Starting point is 00:03:02 I never had a desire to become a CEO or start a company or be an entrepreneur. I learned whatever it took to move me to the next step to unblock whatever I wanted to do. And for me, I wanted to see the city in a new way, and the computer was the way to get there. So little by little found public databases that were accessible on the internet of historical movements that I could program in. And then I learned when I was about 17 or 18 that this whole thing that I was doing had a name. and it was called Dispatch. So I found the biggest dispatch firm in the world, which happened to be in New York City.
Starting point is 00:03:39 And it was called DMS. And I found their website, but they had no contact information, no way to get in. So I was pretty good at computers at this time. And St. Louis had a pretty strong underground hacking culture. And I learned a lot from it. And I figured out a hole in their website.
Starting point is 00:04:00 and I found their corporate email list. And I found the name of the CEO and the email of the CEO and the chairman, and I sent them an email saying, your website has a hole in it. Here's how you fix it. And by the way, I write dispatch software. And they flew me out, and I joined DMS. And suddenly I was working on dispatch for all of New York City.
Starting point is 00:04:24 It was amazing because the thing about dispatch for me is you could actually see how the city. city is working, living, breathing, how it moves. But unfortunately, in that case, it's from a very vertical standpoint in terms of city services. And Twitter really was born out of a desire to see it from a personal level. If an individual could report what they're doing and where they're going and what they're doing next, and we could see that all in real time, what would that look like? Most of my fascination and career really started in dispatch was just high transactional, always available, low latency systems that were deep, deep, deep, deep in the background.
Starting point is 00:05:10 Very interesting response. Not so much the point about how to hack a future employer to get a job, but more the concept Jack Dorsey is working under by starting with the end in mind and then work backwards. In this situation, it was living in the city and working with dispatching. This is a very powerful concept that many, many successful and effective people are using. And it's also a concept that it's relatively simple and we can all utilize. So this is all about starting things with a clear idea of your destination, so that the steps you take are always in the right direction. Or said another way, if you have to be busy, at least you should always be doing what's
Starting point is 00:05:51 important to you. And this is more like a subconscious trick really that you're doing. because the principle tells us that things are created twice. The first creation is your mind and the second is the physical reality. So aside from very successful business people, this is also a very common use in elite sports. So what coaches would tell the athletes is to imagine the successful result of an event before they start competing because not only will they use all the conscious energy but also all the unconscious energy toward that goal.
Starting point is 00:06:27 also mean they won't second guess themselves or be nervous, but they're more just going through the motions, doing what they're trained to do to reach the end goal. All right, so for Jack's next response, he was asked this question. How do you see Square working with things like Apple Pay and the introduction of NFC chips on smartphones? Additionally, how do you see cryptocurrencies like Bitcoin working on the Square platform?
Starting point is 00:06:53 I think our philosophy has always been, And we're building this register, right? And we need to empower our sellers to accept every form of payment that comes across a counter. And whether that's cash, check, EMV, NFC, Bitcoin, any other digital currency that comes their way, our sellers should never have to think about that. They should only think about making the sale. And buyers should just have the freedom to use whatever they want to use. So if they want to use Bitcoin, they should be able to use Bitcoin.
Starting point is 00:07:25 and the seller should not have to think about what currency or what payment method they're using. So we started in the U.S. We opened in Canada and Japan, and NFC has just never been large in those markets. And I know that seems a counter to what you all experienced because NFC is growing quite quickly in the rest of the world. But I always found that U.S. is really behind in technology adoption, mass technology adoption. Like even with Twitter, it took us 10 years to really adopt SMS in mass. You all had it for 10 years prior to the United States. And we didn't really get it until 2005-2006.
Starting point is 00:08:13 And the reason why is it was the first time when you could send a message between the two largest carriers, a text message between the two largest carriers, which were Verizon and singular because they both had different technologies. SMS, as you know, is a GSM technology and Verizon is CDMA. So we never really invested in building an NFC reader because we're in markets that had no buyer adoption whatsoever
Starting point is 00:08:41 of NFC. So Apple could change that, but what they've done is they've created a convenience which is a chip that proxies, a physical card and allows it to be read by an NFC terminal. So we certainly don't see it as competition in any way because we're not building a phone and we're not building a payment device. We're building a register that accepts payments.
Starting point is 00:09:06 And what that means is we need to build an NFC terminal that accepts it. And back to that philosophy of making sure that our sellers can accept every form payment, something we have to do. We have a product called Square Market that allows anyone who's using the register to flip a switch on any of the items in the register and it builds a webpage for them that they can tweet out or put on Facebook or put it on their own their webpage and people can actually buyers can actually use Bitcoin to pay with that so if if they've turned on the e-commerce side for any of those items
Starting point is 00:09:41 Bitcoin is an option for a buyer and we get a small amount of orders from that but it was important for us to make sure that we're constantly testing, testing these new technologies. And, you know, our sellers are paying us to do that work and to be ahead of it. Let's take a quick break and hear from today's sponsors. All right. I want you guys to imagine spending three days in Oslo at the height of the summer. You've got long days of daylight, incredible food, floating saunas on the Oslo Fjord. And every conversation you have is with people who are actually shaping the future. That's what the Oslo Freedom Forum is. From June 1st through the 3rd, 2026, the Oslo Freedom Forum is entering its 18th year bringing together activists, technologists, journalists, investors, and builders from all
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Starting point is 00:14:11 context behind Jack's response here. Let's talk the tech piece a little bit so people understand some of the terminology that he was using there. He said NFC chip and what that stands for is near field communication. So if you were paying, say you went to Target or you went to any type of store and you were paying for something and you've seen the new credit card readers and how they have like a little logo on them for maybe smartphone use or if you're able to bring your credit card kind of close to the device and it'll read it, that's using a near field communication chip. And all that is is it's radio waves and they're within a 10 centimeter distance, you are able to establish a line of communication using radio frequency waves in order to conduct a purchase.
Starting point is 00:15:03 And so that's what Jack was addressing in the discussion there. There's also not to geek out on people, there's another thing called RFID technology. This is a read only where the NFC, the near field communication is a two way back and forth between the two devices. But long story short, the reason that I want to talk about this is because I think it really highlights Jack's hyper focus on the customer and the demands, the current demands of the customer and not trying to build too much into the types of products that he's delivering to the marketplace, too far in advance of the demand. And so when you're looking at this technology, this NFC technology, you're seeing it in wide
Starting point is 00:15:47 use in other parts of the world, but here in the United States, customers aren't demanding it and customers aren't using it at a high rate. So I find it really interesting that a lot of the devices that he has put out there into the marketplace weren't already equipped with this technology. Now, in the future, it sounds like they're, they're, they're. moving in that way. But this wasn't something that he immediately built in. Instead of he was just focused on what is it the people need right now. Let me service that. Let me not try to build in too much technology too early and then ship this stuff way late and lose market share.
Starting point is 00:16:25 I just found that really quite fascinating that that wasn't something that was built into his product originally, even though that that technology was out there. And I think it was all based on his real strong understanding of what the demand signal was here in the United States for that specific piece of technology. There's a really fascinating book. We've mentioned it a couple times on the show. And the name of the book is Inside the Tornado. This was one of Steve Jobs' favorite books.
Starting point is 00:16:54 If you're in the tech sector and you're trying to understand where and when and how you need to fill certain pieces of technology into the marketplace, I think that this is just, a premium book for a person to read to kind of understand the thought process and the methodology. And when you look at a company like Apple and companies like Square, you can see that these founders and these leaders that are putting these products into the marketplace that truly cannibalize themselves use a lot of the fundamentals that are talked about in that book. So I just want to put that book out there and kind of this idea of properly inserting technology into the marketplace at the right time and really kind of mastering that optimization.
Starting point is 00:17:39 The other piece here that was interesting in the conversation was this idea of crypto. What's interesting is the point that I just made that I thought that Jack did really well, which was not putting that into the marketplace too soon. You see him being way out in front of cryptocurrency. And so I have to ask myself, why is he so early on this? because how many people are going to the store trying to buy something with Bitcoin, let's say. And I think one of the reasons that he has done this, and I might be completely wrong. So if you have a better narrative, hit us up on Twitter, let us know what you think.
Starting point is 00:18:16 But I think one of the reasons he's doing this is I think, first of all, it's really good for marketing. A lot of the people in the cryptocurrency space are heavily involved on Twitter. and he's probably seeing a lot of that traffic. I think it's got a lot of his attention and I think he's realized that, hey, if I can implement something and it's not a lot of work for me to do onto my platform, then, hey, that might be some really good marketing for Square. And when you look at what's required for him to do to implement Bitcoin payments, I don't really think that it's too difficult for him to receive those types of payments because at the
Starting point is 00:18:58 end of the day, it's kind of a barcode scan that's required in order for a crypto purchased, or at least a Bitcoin purchase to take place. And if he can kind of work with some type of exchange that just immediately converts it into U.S. dollars before his company receives their cut of the payment, it should be relatively straightforward. Now, I'm sure I'm oversimplifying the software piece to this, but in general, compared to implement. a chip when you get into like the NFC stuff that we were talking about earlier, this would probably be a lot easier technical solution. And again, if I'm oversimplifying this, be sure to let us know on Twitter and we'll try to make a correction. But it's just an interesting dynamic as he
Starting point is 00:19:45 was talking about these various technologies and you look at the timing of how he inserted it versus not inserting it. So that's pretty much all my thoughts on that clip. And we'll go ahead and move on to the next question. For the next clip, we're going to play. Jack Dorsey is giving a talk about how Square is made commerce easier. And Jim, who is referring to here in the clip, that is Jim McHelvey. And Jim McHelvey is a friend of Jack, and he co-founded Square on the time he had a small shop where he was a glass artist. I went back to St. Louis in 2008 for Christmas, and we wanted to work together.
Starting point is 00:20:21 We wanted to do something together. We didn't really know what. We didn't know what to do together. So he had an idea of like, let's build an electronic car. And I said, okay, I have no idea how to do that, but I'd really love to work with you on figuring it out. And then we kept coming up with ideas and nothing was really sticking. And then he called me in frustration one day and saying, Jack, I just lost a sale because I couldn't accept a credit card. And, you know, we both had these phones next to our ears, these iPhones and supercomputers that could do anything right next to our ears.
Starting point is 00:20:51 And we wondered, like, why was that so difficult? Why was it so difficult for Jim to accept a credit card? And we took a month and we figured it out. That month was the answer to that question, why? And that month was the beginning of Square. Since then, we've realized what we're actually doing, making commerce easy. So with Twitter, we made communication easy. We simplified it down to its base essence.
Starting point is 00:21:16 With Square, we want to make commerce just as easy. And the interesting thing about communication and commerce is I don't really see a very large difference between the two. We were actually trading goods as a civilization before we were using language to speak with one another. Commerce actually was occurring before communication was occurring. And communication has always been worked on to be more efficient and more free and more frictionless, easier, simpler. And you see that with Twitter and Instagram and Facebook and Vine today. But commerce, for whatever reason, became more complicated. and more abstract and more expensive.
Starting point is 00:21:55 And it departed from communication. But when you really think about what commerce is, it's not payments. It's a simple activity between buyer and seller. It's a simple exchange of value. Exchange of value is just communication. So our mission at Square is to make commerce as free as communication, to make sure that it goes back to its natural state,
Starting point is 00:22:18 to make sure it goes back to something social, something that is conversational. And the way we started is we looked at the social, system, and we realized that, hey, everyone in the world is paying with plastic now. Everyone is paying with credit cards. They're not paying with cash anymore. They're not carrying their checkbooks around. So you have all these people using these cards, but you barely have anyone who can accept them. No one can accept them for whatever reason. We didn't really know what the reasons were, but we found out. We saw that people were not only charged for the hardware, they were charged monthly, they were
Starting point is 00:22:51 charged a PCI fee. They were charged a fee for the transaction. They were charged a percentage fee, which is called the interchange, which is just this giant guessing game of things that you have to do. And it took anywhere from a week to four weeks to even start accepting credit cards. So if the economy is moving to plastic and you can't participate as a small business, as a medium-sized business or even as a large business, then how do you build your business up? How do you remain relevant. The answer is you can't. So that's the problem that we wanted to solve immediately because Jim had that problem, because we wanted him to be able to accept credit cards. That was the picture initially, and it was something that we could achieve. We decided that we wanted to get it
Starting point is 00:23:36 down to such simplicity that someone could download an app and in under a minute start accepting credit cards, download an app, put in their name, put in their mailing address. We would send them a free credit card reader, and they were in business. And we actually, were able to do that. We actually were able to build the hardware. We're able to build the software. And we did that in one month. And this was the best company to pitch and demo in the world, because I would go around to all my friends and to all these investors and say, do you want to see my new product? And they would say, yes. And I would say, well, give me your credit card. And they would say, no. And I would say, well, I'll show someone else then. And I would say, okay. And I would take
Starting point is 00:24:16 anywhere from $5 to $500, depending on who it was. Some people would give me a black amex, and you know exactly what I would do with that. So we ate very, very well in the early days of the company. But the thing is, like, when people saw that, when people saw that swipe, they said, wow. And the second time they said, wow, was when they signed on the screen with her finger.
Starting point is 00:24:39 And it seems very simple now. It seems very obvious now. But at the time, it was seen as a superpower. You just took money off my card. And I said, yeah, check your statement. It'll say Jack Dorsey, $500. Just an amazing feeling. And then I would say, see ya.
Starting point is 00:24:57 I really found this clip very interesting because I listened to this interview not too long ago with Jeff Bezos when he talked about how important it was to invest in megatrends. And I think Square is a part of a megatrend. One megatrend that is evident using Amazon, perhaps as the best example, is the value of matching the buyer and the seller
Starting point is 00:25:19 much faster and much better targeted than we ever seen before. And this is simply a result of consumer internet taking over commerce. I just don't see that stop anytime soon. You know, Square is a good example, Amazon is another, but we can look at other companies who have grown really, really fast due to the same megatrend. LinkedIn is matching buyers and sales of labor much smarter than before. Airbnb, matching vacant rooms and guests looking for a place to stay, Uber, vacant cars with a traveler. And you just see that so many places right now and so many successful businesses because of that principle. I think that we as business people and the stock investors should factor this mega trend in whenever we're making our business decisions and our investment
Starting point is 00:26:08 decisions. It's definitely not a buy recommendation for Square. I was really tempted in the research of doing this episode and I think Square is an amazing business. It seems like the market also realized that has priced it really, really expensive. But I think that we need to factor in the companies who really mastered this matching efficiently. They can sustain revenue growth rates that are much higher and perhaps also for longer than we previously have seen. Let's take a quick break and hear from today's sponsors. No, it's not your imagination. Risk and regulation are ramping up, and customers now expect proof of security just to do business. That's why VANTA is a game changer. VANTA automates your compliance process and brings compliance, risk, and customer trust together on one
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Starting point is 00:30:19 And this is how he responded. There were many. I you know again I really had no aspiration to be a CEO or to be a leader in a company or even create a company I just wanted
Starting point is 00:30:33 I wanted to to build and use this thing and I was so excited about that and and really you just learn whatever you have to you learn whatever you have to learn to make that work and right now a company is just a great vehicle
Starting point is 00:30:48 to spread an idea around the world and it allows an idea to thrive. But the idea and the purpose of our work always leads, not the company. The company is support, and the business is oxygen to that idea. So I think when you are tasked with then creating a company, you kind of want to, or at least I did,
Starting point is 00:31:16 you grow up a little bit too fast sometimes, and you try to put too much structure in place or the wrong structure in place and that distracts you from you know really the work that you absolutely need to do and one of the interesting thing two big lessons from from that time number one was the power of instrumentation
Starting point is 00:31:38 the power of knowing exactly what's happening within the system and the power of transparency within the system but also within the company so we would go down a lot in the early days of the company because we just had no instrumentation at all. It's like driving a car, flying a plane, and not having any sense of how fast you're going, right? It's extremely dangerous.
Starting point is 00:31:59 So we just didn't know what people were doing with it, how the resources were being used, and ultimately it just crashed to a halt multiple times. And little by little, we started instrumenting the system. And we built simple things, would tell us what the system is doing or how people are using it. And these seem, like, of course you build dashboards, and of course you look at the data,
Starting point is 00:32:30 but in the moment when you're creating these things, that's not what you put first. It's often an afterthought. And the biggest thing that that solved was we stopped speculating about what was going on, and we could actually point to what was going on. And then, since we could point to it, we could fix it. And we had a ton of communication issues in the company at that time. Just we wouldn't talk to each other in some cases.
Starting point is 00:33:03 And like engineering, sometimes we wouldn't talk to operations. And when you have those divisions in the company, the people using the service actually see the results of it. So any organizational difficulty actually manifests in the services. self. And that's just ultimately rude and selfish and you're putting your own mess in front of the people that are using your service or the customer. So as we started instrumenting the system, we had a lot healthier communication. This is a funny thing because we're building a communication company and we couldn't communicate internally. So that was number one And the first bit of code I wrote for Square was an admin dashboard
Starting point is 00:33:52 So we could actually see everything that's happening constantly And then number two is just how important it is to To really make sure that you're building the right team dynamic And that means hiring great people who share your you know Who share the purpose and share the vision But it also means that we're parting ways of people who who don't And and we have to had some people in the early days of Twitter who were just, you know, not folks who really
Starting point is 00:34:25 worked well together with others. And this was probably the hardest thing for me to do as a CEO in the early days is I had to fire someone who had the entire system in their head. And when you're faced with that, you're like, well, I can't fire this person because if I fire this person, then the whole system is going down. can never get it back up. And it took me a long time to do it. About six months, and that's, you know, a regret, actually.
Starting point is 00:34:56 But ultimately, when I did it, and I did it, and, you know, when I was, when I was, when we were parting ways, I was crying, and he was crying, and then I went back to tell the company, and we're only about seven people, and I was crying, and the company was crying, and, like, it was at a very emotional period, because we were also under a lot of stress, because we were constantly going down and now we just parted ways with the guy who knew how to bring the system back up. But something really interesting happened immediately after that. All these new leaders in the company emerged. And actually we didn't go down. And we built a lot of great practices to stay up more and more. So I think when you're just getting started, whether it's a company
Starting point is 00:35:36 or organization, you try to get people really quickly, but you don't edit as much and you don't really make sure that there's a great team dynamic. And if you don't, it can be really, really poisonous to the culture and ultimately will block new ideas and new leadership from emerging. So constantly looking at the team and making sure that we have the right team in place is something I applied to square as well. So at this point in time of the show, it's time to play a question from the audience. And this question comes from Kyle. Hi, person in Stig, Carl from South Africa. I just want to ask a question about, about a comment stick made in one of the beginning podcasts was that when he said he bought three
Starting point is 00:36:17 stocks last year and he felt like he was overtrading. I just want to know, how do you guys invest? Do you save up a large capital and then invest that three times, four times a year? Or do you invest monthly with your monthly savings? So then you take your savings and just reinvest in the stocks that you currently own as opposed to one or two large investments every year? Thank you guys, loving the show and keep up the great work. Great question, Kyle. I don't have a fixed rule about my monthly cash flow. If anything, my rule is that I set
Starting point is 00:36:49 aside money every month for investments, but I don't always put it into the market. It's more a question about whether or not I can find a great investment, and if I can, I'll invest in it, and if not, I won't. The comment you referred to is that I felt I was over-trading because I bought two new stocks. I would like to provide some context to that. The reason why I was a lot of you. The reason why I was I said that is that I generally have a very concentrated portfolio, less than 15 stocks. I simply can't watch 100 of stocks. So what I do is I monitor a smaller amount of high quality stocks that I feel I understand and are trading at good prices. And the good businesses do come across, but trading at a great price, that really hasn't happened for a long time.
Starting point is 00:37:35 Now, that being said, I don't want to have much cash in my portfolio, as the opportunity cost is high since cash has no yield, and it's a balance since the opportunity cost of being invested in an overvalued market is also high since you're taking a high risk of losing your principle. So the approach I use is that I invest in high quality stocks, even at fair prices. That way I feel I get the best of both worlds, or perhaps I should say the least bad given the current mild conditions. I still get a return and my risk of losing my principal is limited. This can actually actually be a bit harder mentally than what it sounds like. Since investing in your winners, for instance, Berkshire Holloway, for a much higher nominal price than what you bought it for in
Starting point is 00:38:21 the first place, is difficult because it increases your average price of the stock. For instance, if you bought Berksie Halloway at, say, $50, and now you're adding to that position at a stock price of $200, you feel like you're taking a risk. It doesn't feel good to have a new higher average price you bought in at. I would actually argue the opposite. Investing in the winners that you have followed for years, understand, and if it's trading at an okay price, I think that's a great placeholder for most of your cash, giving the current mind conditions. So, Kyle, similar to Stig, I don't have any fixed rule for buying and selling, but I will say this. In general, I try to keep my portfolio under 15 stocks or ETFs and more than 10.
Starting point is 00:39:13 So that's kind of where I'm trying to have ownership in that range. I personally think that anything above 15, it gets really kind of hard to keep track of all the information and research and knowledge that you really need to have under your belt in order to actually own something. And then I think anything under 10, you're just kind of getting too focused in your portfolio. And there's been a lot of research done on the specific number of 15 and the statistics behind how exposed you become, assuming that you kind of have an equal weighting if you have 15 picks. But that's just the general rule that I have for how many. As far as the way that I invest, I'm heavily reliant on the ideas of deep value investing.
Starting point is 00:39:58 A lot of the things that Toby Carlisle writes about as far as using filtering mechanisms in order to find the right picks. And then what I do is each month, as I look at the free cash flow that my business or that I've generated personally, that I am looking to invest non-operationally, I look at that cash flow and whatever that amount is that I'm looking to invest, I'll look how the picks that I currently own have changed, whether there's new picks that have showed up on some of the filtering mechanisms that I use through like deep value fundamentals and see if something else looks like it's a better value. or producing a higher yield, then maybe I'll bring that into my mix. A lot of the times I reallocate capital into companies that I already have in my portfolio. So it really depends on what changes have occurred over the last month. But typically my buying and selling happens on a once per month kind of basis. I would tell you that I don't really trade much more than that. And it all comes down to the yields that I'm expecting. So I don't know. know if that helps you understand, but that's just kind of the way I personally do. It doesn't mean
Starting point is 00:41:09 that that's right or wrong. It's just the method that I use. So, Kyle, as a token of our appreciation for leaving your question, we're going to give you access to one of our free courses on the TIP Academy page on our website. The course that we're going to give you is our intrinsic value course, and our intrinsic value course teaches people how to determine the value of an individual stock. It also teaches you how to think about the market cycle and when you're buying your stock. And it also teaches you some stuff about options trading. So we're really excited to give you this course. If anybody else out there wants to check out the course, you can go to tipintrinsicvalue.com.
Starting point is 00:41:45 Or you can just go to our website and click on Academy, link at the top of the page and courses right there. So if anyone else wants to leave a question on the show, go to Ask the Investors.com. And if your question gets played on the show, you'll get a free course. All right, guys. That was all that Preston and I had for this week's episode of The Investors Podcast. We see each other again next week. Thanks for listening to TIP.
Starting point is 00:42:06 To access the show notes, courses or forums, go to theinvestorspodcast.com. To get your questions played on the show, go to Asktheinvestors.com and win a free subscription to any of our courses on TIP Academy. This show is for entertainment purposes only. Before making investment decisions, consult a professional. This show is copyrighted by the TIP. The IP network. Written permission must be granted before syndication or rebroadcasting.

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