[00:02:46] Patrick Donley: So for our listeners that don’t know, these are the guys behind We Study Markets, our newsletter.

[00:02:52] Patrick Donley: I admire both of you quite a bit. I wrote for the newsletter for a little bit, six months or so, and writing is extremely difficult and I just really want to say right off the bat, like, I really admire you guys for producing the amount of content that you do on a daily basis that’s high quality and really well done.

[00:03:09] Patrick Donley: So I first want to start off with you, Shawn, just, I want to talk a little bit about you, both your backgrounds. Talk to me about just college, post college experiences, and then your transition to TIP and getting into the financial markets and writing. 

[00:03:23] Shawn O’Malley: I mean, well, for me, my financial markets and investing origin story, I guess, starts probably around middle school, high school.

[00:03:30] Shawn O’Malley: I used to, I’m kind of embarrassed to say it now. I used to be a frequent watcher of. Jim Kramer’s mad money. And so that’s where my story begins is just seeing that show on TV weeknights. And I remember in the evenings rushing home to watch it. And that was when I first, I think the first stock I traded, I tried to do the IPO of Fitbit.

[00:03:49] Shawn O’Malley: I had no idea what I was doing, but I love the energy of it. I love the complexity of financial markets. And so I was intrigued and I guess, you know, flash forward a few years and. I’m at college and I’m officially studying finance. And then all of a sudden the world is upended by the COVID 19 pandemic.

[00:04:04] Shawn O’Malley: And so, you know, I’m sent home and I’m, I’ve been home for like two weeks now. And I’m already being driven crazy by boredom. You can’t go out and do anything. You can’t see any friends. You go from this like environment where you’re with your friends 24 seven. And all of a sudden now you’re just in isolation with your parents and your family.

[00:04:19] Shawn O’Malley: And so I was looking for some kind of outlet, I guess. And I remember just being out on a walk and literally being in the woods and searching on my phone, you know, I should listen to something productive. That’s going to make me better. And so I typed investing podcasts into my Spotify search feed and the investors podcast network popped up.

[00:04:37] Shawn O’Malley: And so that was literally how I started. From that moment, I started listening to Preston and Sig’s We Study Billionaires episodes, and I tried to get through as many as I could. I probably went through dozens or hundreds before I ended up going back to school that fall. And yeah, and ever since then, I’ve been, you know, I was a weekly listener of TIP for another, you know, two years after that.

[00:04:56] Shawn O’Malley: And I just started my first job in the real world and was trying my hand at being an adult. Going down a very conventional financial track and studying to be, you know, to earn a CFA license. And to, you know, like I said, try to work very traditional kinds of Wall Street jobs. And I saw a job posting to work at TIP and I gave it a shot.

[00:05:16] Shawn O’Malley: I saw a shot over an email. And I think, you know, maybe what stood out. And my application was that I had highlighted all the books I read. I made a point of listing every book I’d read in the last two or three years. And I think it stood out to the stick who reviewed my application because they’d all been books.

[00:05:30] Shawn O’Malley: He recommended the podcast, basically every time he or Preston recommended a book, I went out and bought it and read it. And so that was enough to give me my first interview with the company. And it actually took me a few rounds of interviews and some convincing, but you know, eventually stick gave me a chance and I was brought on to bring the newsletter to life, which.

[00:05:47] Shawn O’Malley: I know you had an early hand in Patrick and it was fun to kind of jointly launch it together. 

[00:05:52] Patrick Donley: That’s awesome. I want to get into those books here a little later and the transition into TIP and your experience at TIP. But Matthew, I wanted to hear too, first about your background, school and kind of post college transition out of college.

[00:06:06] Matthew Gutierrez: Sure. So I grew up right outside of Princeton, New Jersey, went to Syracuse, studied journalism and finance, but was probably skewed towards 80 percent journalism and writing. Kind of just did what I had to do at the business school, basically to get by. And then similar story during 2020, like a lot of people just became infatuated with markets part of that, surely because seemingly everything was going upward, but also because I really just enjoyed learning about companies, learning about their stories, origin stories, founder stories, and what makes great investing, what makes great companies that drive our economy.

[00:06:39] Matthew Gutierrez: And, you know, in some ways drive our world, right. And jobs can be, you know, a calling, but jobs are also a livelihood. Right. We spend so much time working and trying to earn money so that we can live the lives that we want to live. So that just became really interesting for me. And the time I was working at the athletic as a sports writer, really nothing to do with financial markets, but evenings, mornings, you know, during breaks on weekends, I would just be listening to Shawn, the investors, podcasts, other podcasts, watching YouTube videos.

[00:07:07] Matthew Gutierrez: CNBC was on in the background for better or for worse. And just trying to learn and pick up information, learn some of the lingo tickers and just get acclimated with the whole space and then quickly zooming sort of out financially investing. I did not do much at all, but I will say 1 of the biggest influences was my mom started a small account for me when I was growing up to help fund a very expensive college tuition at a private school.

[00:07:33] Matthew Gutierrez: And Syracuse, but it also, she bought just a small amount of apple stock when I was little on its gigantic amount, but it was turned into a much bigger amount. And what she had invested initially, and I was just amazed that I didn’t do anything. She didn’t do anything outside of the, you know, the initial foresight and investment.

[00:07:50] Matthew Gutierrez: And we didn’t, you know, we didn’t monitor headlines, news and all the bearish calls the last 15 years on Apple and other Mecca cap stocks, all the road through the 2008 financial crisis, 2016, a little dip 2018, the dip at the end of the year. Obviously, 2020, I think it, you know, has shed huge value. And ever since then, it’s just continued to, you know, drive upward despite headlines.

[00:08:12] Matthew Gutierrez: And again, didn’t read any annual reports. Didn’t listen to Tim Cook on any calls, but just kind of. 

[00:08:20] Patrick Donley: That’s awesome. I think that’s such a great experience to just have that. First of all, that your mom did that and to just the whole buy and hold and just sit through it through the ups and downs and not pay attention to too much noise that can really shake people out.

[00:08:32] Patrick Donley: I think, Shawn, I wanted to get back to you and the investing books that you read that Stig had recommended. What were some of the ones that you really did make an impact on you? 

[00:08:41] Shawn O’Malley: Yeah. I mean, there were so many great ones. One that really stood out, and I don’t remember if it was Sig or Preston who recommended it, or where the recommendation came from, but one of the most impactful that’s changed the way I think about the world is Nassim Taleb’s insert to his series of books, Fold by Randomness, Black Swan, and Anti Fragile.

[00:08:59] Shawn O’Malley: I’ve actually only read Black Swan and Anti Fragile, so I can’t speak as much on Fold by Randomness, but those books are just, talk about a contrarian mindset, and a willingness to think differently. That’s really the vibe I get from this into 11. You know, he’s controversial. Some people don’t like his work.

[00:09:14] Shawn O’Malley: Some people don’t like his personality, but you know, just kind of isolating the work for what it is. It’s incredible to think about the kind of the many different biases and the very common ones that people think about are, you know, like overconfidence biases and confirmation biases and those sort of things.

[00:09:28] Shawn O’Malley: But. The more subtle biases of, you know, I think he uses in that book, an example of whenever something goes wrong, for example, we all fixate on the event that happened. And so, for example, when a plane crashes, everybody fixates on the tragedy and you know, what could have been avoided, but every time something or a system in place works the way it’s supposed to, and prevents a plane from crashing or your car from crashing or some other tragedy.

[00:09:53] Shawn O’Malley: Those events don’t get headlines because we just take them for granted. You know, everything worked as it was supposed to do, and it’s not just magic that things work the way they’re supposed to do it. You know, systems are designed to be robust, and that for me was one of the really interesting takeaways from both anti fragile and black swan of thinking about, you know, from the black swan aspect of it, you can have these Crises that seemingly come out of nowhere that in hindsight were predictable using like COVID, for example, nobody in January, 2020 that I was interacting with was expecting, you know, a global pandemic that was going to derail the global economy for two years, but it came.

[00:10:28] Shawn O’Malley: And now in hindsight, we can say, Oh, well, you know, in 2018 or 2019, the world health organization warned about the possibility you can imagine a pandemic is not an unpredictable event. But it still took the world by shock. And so for me, the kind of takeaway that I internalized from that, and also from his book, anti fragile is how can you build your portfolio to not just prepare for these kinds of catastrophic risks and that, that you can’t necessarily anticipate, but also, you know, one of the concepts that Nasim Taleb talks about an anti fragile is well, literally anti fragility and it’s not just robustness, it’s not an ability to, you know, handle stress, but It’s actually getting stronger from stressors.

[00:11:08] Shawn O’Malley: And so it’s almost like, I think the example used in that book is, you know, exercise. Whenever you lift weights, run, you’re putting stress on your body. You’re putting a strain on your body, but now your body is getting stronger. And so it’s reacting in an anti fragile way. You’re making your body less fragile by strengthening it.

[00:11:24] Shawn O’Malley: And I’m certainly not an expert on option strategies and volatility and those sorts of things, but it was really compelling to me. They’re not just thinking more intentionally about the risks that we’re taking the world and the systems that are designed to mitigate those risks, but also within our portfolios, for example, how can you make your portfolio antifragile and instead of being short volatility most portfolios are maybe constructed to be long volatility.

[00:11:45] Shawn O’Malley: And so you can actually fracture your portfolio can have an asymmetric gain when there’s a market crash. Those are the kind of things that flip my paradigm upside down. You know, you don’t learn that in your traditional business school class to think about those kinds of catastrophic risks and how you can actually, you know, become antifragile to them.

[00:12:01] Shawn O’Malley: But for me, that was a very eye opening type of book to read. And I continued to enjoy keeping up with his work over the years. 

[00:12:09] Patrick Donley: Yeah, those are good points. Great books. I think Clay just did a review of one of Nassim’s books. Isn’t that how he structured his portfolio when he was managing money is like 90 percent pretty conservative.

[00:12:20] Patrick Donley: And then the remaining 10%, like you said, taking asymmetric bets, then if the black Swan hits, then it’s like, you know, really juices the returns. 

[00:12:28] Shawn O’Malley: Yeah. I think he called it the barbell approach. And the idea is you have, you know, maybe 90 percent of your portfolio and Treasury bonds or the S and P 500, you know, whatever your preferred strategy is there with the bulk of your portfolio.

[00:12:41] Shawn O’Malley: And then 10 percent of it is, you know, deep out of the money options that give you that asymmetric kind of long volatility return sequence in those. You know, volatility mostly works in one way. You don’t have, we don’t usually have days where the stock market gaps higher by 50%, but we do have weeks where the stock market has fallen by 50%.

[00:13:01] Shawn O’Malley: And so there is like, you know, volatility technically can go both ways, but realistically, it’s, you’re preparing your portfolio to benefit from downsides. And so, you know, the typical advice is to have a 60, 40. Bond portfolio, but sophisticated enough, and I don’t necessarily claim to be. I know that there are some strategies to do it.

[00:13:18] Shawn O’Malley: And that’s one of the things that NISM’s web is known for. 

[00:13:22] Patrick Donley: I wanted to get into your portfolios here shortly, but Matthew, I know that you read really broadly, not just finance books, more philosophy. Spirituality, all kinds of stuff, which I really appreciate. I’m the same way. What are some of the books that have made a big impact recently that you’ve been reading or it could be investment books or really just however you want to take it in terms of books that have made a big impact on you?

[00:13:46] Matthew Gutierrez: Yeah. So it’s a great question. Always reading a variety. Like, so I’ll have financial books on the nightstand and then, you know, by the couch, I’ll have a meditation book and on my bookshelf, I’ll just pull off a biography. Or a memoir from an investor or a writer or an athlete. So I try to mix it up. Part of that is to keep things fresh, keep topics fresh, different writing styles, fresh, and just, and getting acclimated with how different people write, tell stories and see the world.

[00:14:11] Matthew Gutierrez: So I try to not be, you know, read all equities or all, you know, the coin books, there are a few big ones out there now that are all Zen and. Mindfulness books because I think you can overdo it yet on that end as well on the sort of self help spirituality and so 100 percent just keeping it a balance is really key as far as specific names, you know, I think the big ones like psychology of money same as ever from house like I don’t end up returning to those more than a lot of others love choice of compounding.

[00:14:37] Matthew Gutierrez: Snowball Warren Buffett was something I haven’t read. Every page is a big book. I’ve revisited that quite often. Quite a few other mindfulness books as well. Meditation, wherever you go, there you are on my nightstand. And then a couple others like the almanac of the ball, the almanac of which I know Patrick, you’ve discussed and you’ve had Eric on the podcast.

[00:14:56] Matthew Gutierrez: Those are terrific books. I think they are microcosm of what I try to read, which is They touch on financial markets, but they also touch on health, lifestyle, technology, all those things and how they’re intertwined and, you know, it makes us whole, makes us human, you know, making sure that we’re complete.

[00:15:12] Matthew Gutierrez: So that’s, those are the ones that come to mind recently and then just. Briefly on the value of reading it’s incredible and TIP totally encourages this. And it’s a beautiful thing. Just when you look at any great investor, they are just reading. I think it was an oak tree, not Howard marks, but someone there who has said, I might’ve been on one of our podcasts that it basically looks like a library to visitors at their office.

[00:15:34] Matthew Gutierrez: And I just thought that was a perfect visual. Most of the time it looks like you’re not working, but really you’re just probably doing the most productive thing you could be doing as an investor. 

[00:15:44] Patrick Donley: I’ve seen interviews with Monish Pabrai and Guy Spear and a number of different investors. And it’s the same thing.

[00:15:51] Patrick Donley: It’s like hanging out in a library and that’s, like you said, they spend most of their time reading, which is such a wonderful life just to be able to read and learn and study and hopefully make money while you’re doing it. I wanted to get a little bit into Shawn, some of you’ve covered and studied so much just with the newsletter.

[00:16:10] Patrick Donley: I want to talk a little bit deeper about some of your investment heroes, whether it was a podcast, you know, that you listened to, or a book, or just some of the investors that you really look up to. 

[00:16:21] Shawn O’Malley: Yeah, it was a great question. And there’s definitely a lot of ways you could take it. For me, I’ve always appreciated the simplicity of Joel Greenblatt’s message.

[00:16:29] Shawn O’Malley: And he wrote the, literally the little book that beats the market. And, you know, it’s a simple premise, focus on companies with high earnings yields and high returns in capital, and you’re going to do pretty well. And he devised this, you know, quote, unquote, magic formula for investing. And I remember hearing that and just all my red flags shot up.

[00:16:47] Shawn O’Malley: And I was like, okay, this, Sounds like a scam. This is too good to be true. Because, you know, usually when you hear things in markets, it’s not too good to be true. Like a magic formula, you should definitely be pretty, pretty skeptical. But his data has his returns and his strategy has been thoroughly back tested and over multiple decades has, you know, continuously outperform the market.

[00:17:06] Shawn O’Malley: It’s not really because of any magic, obviously, really, the magic is just investing and owning great companies with, you know, an intermediate to long term perspective. And And holding onto those investments, especially when those stocks are beating down and, you know, really just enduring the emotional side of investing and not necessarily falling into the trap of buying the sexiest stocks that have gone up the most, or have the most innovative new product that also trade at the highest price earnings multiples.

[00:17:32] Shawn O’Malley: And so there’s a simple. And kind of an elegant message to what he does. And I really appreciate the, he set up this forum called the value investors club that I’ve tried my hand at to submit a few stock pitches to that, that haven’t been selected, but you know, there’s a certain, very high caliber of investor that he has into that forum.

[00:17:51] Shawn O’Malley: And the really interesting thing to me is that, you know, he set this up and it’s kind of a, It’s just an opportunity for anybody, anybody, where in the world to, who’s very sophisticated with stock investing and knows what they’re doing to submit a pitch. And then there’s, you know, I don’t know if he personally, I think he has a team of people that review the best stock pitches that are sent in every single month.

[00:18:10] Shawn O’Malley: And then you basically get added as a member and then you can see all the most recent picks. But it’s not something that you can buy into, you know, there’s no price tag on the membership. You have to, it’s merit based, you have to earn your way in. So, you know, I don’t know how many years I’ll have to keep trying my hand at trying to earn my way in, but it’s pretty cool that club that he’s put in.

[00:18:28] Shawn O’Malley: And I know that just through trying to, my hand at trying to be accepted into it, I’ve garnered a lot of respect for the process. And really his career in general with Joel Greenblatt. 

[00:18:40] Patrick Donley: It’s interesting. You said that I interviewed a guy that you probably both are familiar value stock geeks on Twitter, and he also recommended Joel Greenblatt’s book as probably a good one for, well, whether beginner, intermediate or advanced investors too, to check out.

[00:18:56] Patrick Donley: It’s like you said, you can’t argue with the returns that he’s had. I guess the challenge for most people is to hold during the downturns that are likely to happen, you know, to, to stay with it and stick with the strategy. I think that’s the challenge is making sure you pick a strategy and stick with it.

[00:19:11] Patrick Donley: Matthew, what about you? What are some of your investment heroes? You mentioned Buffett, obviously in snowball, but any others 

[00:19:17] Patrick Donley: that 

[00:19:17] Patrick Donley: come to mind? 

[00:19:18] Matthew Gutierrez: Yeah, well, quickly on that, Patrick, I think just the other day, it was four years to the day since some just massive sell off right when COVID was beginning and someone threw the chart up of all the, the sea of red that day.

[00:19:29] Matthew Gutierrez: And I think, you know, big mega cap tech firms were down 10, 12 percent in a day and someone posted their prices at that time. And here we are 4 years later. So to both of your points, to be able to ride out those downturns, it’s really where people separate themselves and that doesn’t feel like it at the time, but that’s really where the returns are being made in a lot of ways.

[00:19:46] Matthew Gutierrez: Yeah. It’s pretty boring as far as the mentors, like definitely Buffett monger. Monash, who’s a, you know, TIP family household, those guys come back to over and over the almanac of Charlie Munger and the snowball, which going back to my mom, I think right around 2009, right after the financial crisis, I think that book came out in 08, I want to say or 07, correct me if I’m wrong.

[00:20:06] Matthew Gutierrez: Which is, you know, interesting timing there in itself, probably a coincidence, but that book was on my mom’s nightstand. And then I just remember being a young kid, I probably could not comprehend most of it, but just being enamored by that and seeing, Hmm, that’s interesting. I wonder who that guy is. And just sort of keeping him in the back of my mind.

[00:20:22] Matthew Gutierrez: We did have, you know, a small allocation to Rooster Hathaway as well. Yeah. I always stick to the Buffet monger approach, or at least I’m saying I am, you know, we’ll see the next downturn. Hopefully I do. But for the long term. Long only, you know, mostly fundamental analysis and just really looking at what masterpieces I want to own in the portfolio for hopefully the rest of my life and or pass on to, you know, my children or grandchildren over time.

[00:20:45] Matthew Gutierrez: So. That’s how I’m thinking about it. I really don’t sell or trade at all. I don’t try to look for new tickers every month or every year just to keep busy, you know, let the flowers grow, so to speak, and just let the wonders of compounding work their magic. That’s really what I’ve learned the most. And I guess the last thing is on Buffett.

[00:21:02] Matthew Gutierrez: I think his 20 slot metaphor has really resonated with me and just. You know, I’m probably around 20, if not higher than that by now, but it’s just a great metaphor for thinking about investment decisions. And if I think, okay, I only get 20 of these in a lifetime, I better make sure that this is something I really want to stick to.

[00:21:19] Matthew Gutierrez: And just entering every decision with that framework is really powerful. 

[00:21:24] Patrick Donley: It sounds like your mom has made a big impact with, you know, the book on her nightstand and buying an app early on. I think it’s great to have a parental influence, Shawn. I’m curious, were your family, were they investors? And did you guys talk about investments around the dinner table?

[00:21:38] Patrick Donley: Did you have that kind of influence growing up? 

[00:21:41] Shawn O’Malley: No, I, I wouldn’t say quite the same way. And my dad has always been very supportive of my journey with investing and wanting to learn about it. And he certainly did everything he could to, I guess, kind of feed my appetite and make sure of that. You know, I was learning and growing productively.

[00:21:57] Shawn O’Malley: And, you know, he did do some things like when I was in high school, he gave me some, a little bit of my college fund to try my hand at investing with. For me, I do remember, you know, I, I had an uncle who was a banker and I remember that he would sit around and he’d read the wall street journal in the morning and drink his coffee and then he’d watch CNBC.

[00:22:16] Shawn O’Malley: And so I remember almost looking up to the success he’d had in life and wanting to mimic some of them. His daily habits. And so I thought, yeah, let me just start reading about the markets in the mornings and let me watch CNBC and I’ll have a successful life as well. So I certainly had a number of positive influences in my life that allowed me to have those early touch points with investing in finance and approach it honestly, and just being allowed to learn and make mistakes and fail, which is the most important part.

[00:22:42] Shawn O’Malley: I think, unfortunately, a lot of people don’t have those positive role models. In a financial capacity to look up to sometimes. And so you’re not always allowed to fail. And all of a sudden investing becomes this overwhelming and kind of scary thing that, you know, again, people are afraid to, you’re afraid to make mistakes.

[00:22:57] Shawn O’Malley: Like what if I invest in the wrong thing or, you know, I don’t know what I’m going to be doing. And then you almost get it. Paralyzed by paralysis by analysis, right? And you get paralyzed and there’s an element of inaction that comes into it, or even just a fear of, you know, rebalancing your portfolio and checking back up on it.

[00:23:12] Shawn O’Malley: Cause it’s like, Oh, well I put everything together and let me just leave it. I don’t want to mess with it anymore. 

[00:23:17] Patrick Donley: One of my favorite chapters, Matthew, you mentioned the psychology of money. My favorite chapter. And I’ve said this before on previous episodes is the last chapter called confessions, where he just kind of takes a look under the hood of how he manages his own money.

[00:23:30] Patrick Donley: Yeah. So I kind of wanted to talk a little further about that, Matthew, you touched on it to some degree, but I really wanted to talk about money moves that you specifically have made coming out of college. What you’re doing now, you mentioned the 20 punch ticket kind of theory that I really like a lot, but talk to me more about some money moves that you’re making that you think somebody that is just starting out that’s listening to this and investing would be 

[00:23:57] Patrick Donley: smart 

[00:23:57] Patrick Donley: to consider.

[00:23:59] Matthew Gutierrez: Yeah, well, I’m certainly no expert and I’m always open to learning new things, but from what I’ve learned, both from mistakes and some successes here and there is, you know, I guess to start simple with living below your means and trying to invest the difference as silly as that sounds, it’s amazing. My mom’s influence was a blessing, but also on the other end of the token, had I not had that.

[00:24:18] Matthew Gutierrez: I don’t know where I would be investing wise because it’s not taught in public school, at least where I was, and really in business school, I don’t know if anyone really even threw up like a basic compounding chart of just like, you know, SMP the last 100 years, like that was not part of the repertoire of the coursework.

[00:24:34] Matthew Gutierrez: So that’s just to have. You know, to both of her points to have those role models is in a way unfair. Cause you know, it’s just kind of luck and who you’re surrounded by when you’re growing up. But the biggest thing is just surrounding myself around those people. And that was her motto as well.

[00:24:46] Matthew Gutierrez: It’s just, you know, anytime she got a bonus or a little bit of extra money, it was invested. It was not. It was not, here’s a new car. Let’s go to the Bahamas. It was, you know, let’s just put a little bit away and let compounding work. It’s magic. And that’s the biggest thing. Like we can get into allocation 

[00:25:00] Matthew Gutierrez: and everything, but 

[00:25:01] Patrick Donley: yeah, I kind of was curious.

[00:25:02] Patrick Donley: Do you strictly, are you more of an active investor or do you siphon off funds into index funds? I kind of wanted to talk about passive versus active investing. What you personally do. 

[00:25:13] Matthew Gutierrez: So personally, I have a small allocation to, you know, S and P 500 and the Q’s basically, but most of it is, like I said, Apple.

[00:25:21] Matthew Gutierrez: Yeah. Microsoft, Amazon are my biggest players, which, you know, kind of boring, but that’s what I’ve stuck to and incredible companies. And then the last probably three plus years, dollar cost averaging into Bitcoin. Part of that is, you know, Preston to blame, read his insights and just still have a lot to learn on Bitcoin.

[00:25:38] Matthew Gutierrez: But the technology is fascinating and. Thankfully, the dollar cost average approach has worked for people in the last, you know, call it 10, 15 years, really excited to follow it as well. So Apple used to be a sizable part of the overall portfolio and slowly Bitcoin is making up a much larger part of that, both by appreciation and then just by adding a little bit.

[00:25:57] Matthew Gutierrez: Every month, so I think it’s somewhere around almost 50 percent right now. Bitcoin pretty strongly feels that way. It used to be under 20 percent and we’ll see where it goes from here, but I’m just going to keep adding no matter, you know, rises 30 percent tomorrow or drops 30 percent 

[00:26:12] Patrick Donley: the dollar cost.

[00:26:13] Patrick Donley: Averaging is really a great way to go. And I don’t, I think I was listening to a podcast this morning. There’s not too many people that are sitting in a loss on Bitcoin at this point. It’s worked out pretty well. And the whole Michael Saylor micro strategy strategy that he’s pulled off is pretty remarkable to watch and what’s been going on.

[00:26:30] Patrick Donley: And I know Preston’s a big fan of what he’s been doing in the last, well, last four years or so that he’s been in Bitcoin. But Shawn, what about you? I want to take a look under the hood. How do you, what do you personally recommend and some of the moves that you’re doing in your own portfolio? 

[00:26:44] Shawn O’Malley: Yeah. Well, you know, just echo Matthew a little bit too.

[00:26:47] Shawn O’Malley: I mean, It is so easy to get lost in, like, the individual stock picks. And for some people, that’s where they start with their personal finances. And so I would just say, generally, what’s gonna be most important for most people is make sure you have an emergency savings fund. Are you matching out your 401k up to your employer match?

[00:27:01] Shawn O’Malley: Are you taking advantage of IRAs, Roth or traditional? Do you have health insurance, you know, those are kind of basic questions. And then, you know, once you set those basic standards and you’re not, you’re, you figure out how to budget, you figure out that you’re allocating to your retirement. And then the question is with this 20, 30, 40%, whatever it is, what fraction of my income that I’m going to be investing with, what decisions am I going to make with it?

[00:27:23] Shawn O’Malley: And you generally, this is something I’ve talked about before, but you know, there’s an illusion of passive and active. And I guess in the traditional sense, I would call myself A blend of, of passive and active, but I would also push back on that and say, you know, there’s in a way, there’s no such thing as passive investing.

[00:27:38] Shawn O’Malley: There’s really just, you know, are you aware of the decisions and trade offs you’re making, or are you not aware of the decisions and trade offs, right? Right. For example, you know, people will say passive investing is buying the S and P 500. Well, the S and P 500 is an index that’s formulated by S and P global, right?

[00:27:53] Shawn O’Malley: And so there are active decisions as to what companies get included and cut from that. And then you say, well, I buy, you know, the entire market. And then I would say, okay, well, you know, how is that index listing every publicly traded sock? Is that equally weighted? Is that market cap weighted? So for me, one of the things that’s just been over the last couple of years is learning about those trade offs and not just saying, I’m going to be a passive investor.

[00:28:14] Shawn O’Malley: I’m an active investor and I only pick, you know, Warren Buffett status stocks. It’s just at every step of the road, trying to understand the trade offs that I’m making with my finances and why those might be important. And then, you know, another point I want to make too is connecting back to anti fragile and something that SMELLED talks about is this concept of via negativa.

[00:28:31] Shawn O’Malley: And so, you know, we often when we think about whether it’s with our health, the relationships with our money, we think about, you know, how can we add more and somehow we’re going to add something that’s going to help us. And it’s going to be something new. Supplement or some vitamin, or, you know, we’re going to add more exercise into our routine, or we’re going to add this stock to our portfolio, and it’s going to dramatically improve things.

[00:28:51] Shawn O’Malley: And, you know, the principle of negative is, you know, first, let’s focus on what we should avoid. What should we not do? And so, you know, maybe with health, it’s like, okay, well, rather than trying to trade to run a marathon, let’s start with cutting out the junk food or, you know, whatever it is. And literally the negative and just removing the things that are weighing on you or killing you or whatever it is.

[00:29:09] Shawn O’Malley: And instantly you could have an order of magnitude improvement and the structure of your portfolio or your health or whatever it is. So, you know, in my portfolio for me, and my question often is that quote unquote, passive tilt where I try to own most of the market generally, and, you know, various ETFs. And then I think a lot about what I want to avoid?

[00:29:28] Shawn O’Malley: And so for me, that’s why I don’t invest in Chinese stocks. You can say that, you know, I’m missing out on the world’s 2nd biggest economy that I’m missing out on, you know, perhaps. Some of the best tech companies in the world, but for me personally, it’s not a place that I’ve thought through a lot of, I don’t feel comfortable with the ownership rights there, the governance, the tensions of being a U.

[00:29:51] Shawn O’Malley: S. citizen and trying to invest in a place like that. There’s just trade offs that I don’t want to make with my money there. And it’s a place that I avoid. And so I only invest in, for example, emerging market ETFs that don’t include at all or greatly minimize their exposure to Chinese and Taiwanese equity.

[00:30:09] Shawn O’Malley: For me, to some extent, it’s a question of that via negativa with my portfolio, where I start with the premise of let’s own everything and then let’s cut out the things I don’t want to own. And of course, there are times where I see opportunities to zoom in on specific things and kind of tilt my portfolio weights in favor of things like Bitcoin or.

[00:30:26] Shawn O’Malley: You know, for example commercial real estate has been beaten down a lot over the last two years. And I wouldn’t necessarily say anybody go out and buy a commercial real estate ETF or buy VNQ or, you know, whatever it is, just because again, there’s a lot of nuance out of these different strategies that we’re trying to use in commercial real estate.

[00:30:42] Shawn O’Malley: Are we talking about warehouses? Are we talking about office buildings and what are we talking about? You know, what type of office buildings like grade A or grade C, right? So there’s just a lot of nuance. These types of things, but again, that’s an example of where I have a few different ETFs with large commercial real estate exposure that I’ve been looking at and probably trying to tilt my portfolio towards what’s a pretty beaten down section of the market.

[00:31:04] Shawn O’Malley: So it goes both ways, but like I said, I start with this premise of trying to own everything, figuring out what I want to cut out and don’t want to own short term treasury bonds. I don’t want to own Chinese stocks and also figure out where I want to tilt in favor of it. There’s a big sell off in a certain sector of the market I might load up there.

[00:31:20] Shawn O’Malley: And that’s kind of my general framework that I operate from.

[00:31:23] Patrick Donley: I like that idea of via negativa and what to avoid. I remember you sharing with me this idea of political risk. You had invested, I think, in like a Russian ETF. Maybe right before the Russian Ukraine conflict. Can you share a little bit about that?

[00:31:40] Shawn O’Malley: Yeah, no, it’s a lesson I learned the hard way. This is, you know, applying via negativa for my portfolio is unfortunately not something that I was born intrinsically with the inclination to do right. This is something that I’ve learned from experience. And so. You know, I think in 2020, 2021, I was looking around at what actually caught my attention, specifically this headline that oil prices had gone below zero and how could they be negative?

[00:32:04] Shawn O’Malley: And I didn’t think I understood anything about the oil market and Jesus trading and COVID was a crazy time. And we were, you know, a few months in a lockdown, whatever it was, but I knew enough about finance and economics that oil prices are not going to be negative. Forever, and this seems like a pretty good time where you could buy in and they’re certainly not going to get more negative over the next 6 months or a year.

[00:32:24] Shawn O’Malley: This is a good time to buy in and look for the upside. So that initial train of thought, I started looking at buying individual oil and gas stocks and ETFs. And then I came across, you know, these gazprom and some of these, you know, Russian oil and gas companies that were trading at peaks of like 5 to 10, even back in 2020, 2021.

[00:32:44] Shawn O’Malley: And they would have, you know, massive dividend yields, massive earnings yields, and also all the upside of the potential price appreciation of, you know, whenever we do recover from the, from this kind of COVID induced recession, and we have more global demand for energy and gas and energy, oil and gas prices surge again.

[00:33:03] Shawn O’Malley: They’re going to have that bonus upside. And, you know, there are some other dynamics I was looking at or where the interest rate differential between, between the rates that would be paid on the Russian ruble versus the interest rates in the U S were at zero. There were a lot of attractive elements in theory about why one should invest in Russia, right?

[00:33:21] Shawn O’Malley: I mean, ever, brainers to me. And it sounds You know, I’m almost embarrassed to say now that I made those investments, but in 2020, it seemed like there were a lot of upsides in my favor. And obviously I’ve held onto those into 2022, where you, when you had the Russian invasion of Ukraine, it essentially became illegal to own any stocks and bonds in Russia.

[00:33:43] Shawn O’Malley: And so, you know, I was only 22 or 23 at the time. And so the amount of money that I was investing is ultimately inconsequential, but it was still, you know, a fraction of my network that essentially just went to zero immediately. You know, when they’re, when you read John Bogle and Vanguard and the kind of passive investing and ETF approach to investing, you don’t ever expect that you could just truly go to zero.

[00:34:04] Shawn O’Malley: That was not an idea. You’re always sold. Oh, well, the S and P 500 has fallen 80 percent or 50 percent and it’s fully bounced back. And the NASDAQ, you know, you always eventually bounce back in this case. I don’t want to say because of a technicality, but because of political risk and geopolitical tensions, you know, regardless of whether those companies are good to own and the fact that I own them in an ETF, right?

[00:34:25] Shawn O’Malley: It wasn’t like I picked two or three stocks. I owned like 30 or 50 Russian oil and gas companies in this ETF. Unfortunately, yeah, because of that war, the geopolitical risk completely outweighed any of the upsides that I had thought were so attractive. And so I certainly didn’t have an understanding of the geopolitical risks that I was taking, the nuances to owning international equities, and even the fact that in theory, sometimes you can be right.

[00:34:50] Shawn O’Malley: Objectively, I was right. Betting on oil and gas at that time was the right thing to do. And Russian oil and gas stocks were the cheapest ones to bet on. But, you know, there’s a clash between Theory and reality. And so having appreciation for political risk, it’s just something that I’ve come to think a lot more about over the last couple of years.

[00:35:10] Shawn O’Malley: And so, for example, like I said, when I look at China, you know, I’m not necessarily saying that I think there will be an equivalent fallout in relations between the U. S. And China. But when you’re talking about the chance of your portfolio 30 percent right? Most emerging market ETFs. It’s dropped now because Chinese equities are down a good bit.

[00:35:27] Shawn O’Malley: You know, the average emerging market fund, the M. S. C. I. Index is like 30 or 40 percent Chinese plus Taiwanese stocks. And so. If you’re putting a substantial chunk of your network into that, there’s a chance that could get zeroed out for similar reasons. And so those are the kinds of concerns. And that’s where I say, this is just something that’s, it’s a too difficult pile, as they say, that it’s just not worth the downside risk of owning.

[00:35:50] Shawn O’Malley: And also the stress of trying to constantly monitor and think about how those risks are evolving over time. 

[00:35:56] Patrick Donley: And I think it’s such a good learning lesson to have this experience at a pretty young age in your investing career. I mean, this is a lesson that you’ll never forget, right? That you’ll carry forward for the rest of your life.

[00:36:10] Patrick Donley: It’s really a pretty good lesson. Matthew, I wanted to kind of segue a little bit into Your experience at T. I. P. You were, you said you were listening to we study billionaires and some of the podcasts, but I wanted to hear a little bit more about how you found out about T. I. P. And the newsletter and the process of applying and then coming on board to T. I. P. And just what the experience has been 

[00:36:31] Patrick Donley: like for you. 

[00:36:32] Matthew Gutierrez: Sure. Yeah. I don’t remember the exact specifics of how I came across the job posting. I think I had just been a big listener and ended up going to the site and I’m going to say I just saw one of the postings and. Submitted the application.

[00:36:45] Matthew Gutierrez: I believe the, the sample S sample writing piece was a, was reflections on a Warren Buffett interview on one of the podcasts might’ve been a Robert Hagstrom interview who wrote the, you know, he wrote the Warren Buffett way and probably should have mentioned that as informative book. Love how he talks about quotes in there where Warren says, Robert, we’re just focused investors.

[00:37:04] Matthew Gutierrez: And I just, that was like. It’s really well articulated so much of what Warren’s about in that mentality. So that was the application and ended up speaking with, you know, former podcast hosts Robert and then Shawn and stick as part of the interview process. Was challenged during that process, I think a couple of times and they asked really great questions.

[00:37:22] Matthew Gutierrez: It was not a breeze hiring process by any means. Fortunately, they brought me on, which I’m so grateful for. This has been by far the most exciting education filled peaceful, happy work environment that I’ve been a part of. And I’m not just saying that it’s really been as sticks as optimizing for happiness and seeing that.

[00:37:41] Matthew Gutierrez: Yeah. This is not a work around the clock environment. This is, for the most part, work when you want and how you want, and really just putting us in the driver’s seat, sort of giving the, you know, the point guard of the team, sort of the reins to run the offense the way they want to. So I love that we can just get up every day and look at that blank newsletter, Shawn and I, you know, 7, 8, 9 a.

[00:38:02] Matthew Gutierrez: m. and try to make a, you know, work with that blank canvas and just make something that will resonate with people. In such a clickbait headline crowded media space overall, right? And I’m just speaking generally with newsletters as part of the media and really just trying to differentiate ourselves, educate readers, inform them.

[00:38:19] Matthew Gutierrez: And as Shawn and stick have sort of laid it out in some of our emails every day, we’re getting feedback from stick. And I think 1 of the lines that stood out was we’re taking care of the reader and I really like that. That phrasing and just sort of serving the reader and just trying to walk them through a scenario and explain a financial concept beyond just to start moving up or down or.

[00:38:41] Matthew Gutierrez: Or an energy market doing X, Y, Z, or really explaining why and telling the story 

[00:38:46] Matthew Gutierrez: behind it. 

[00:38:48] Patrick Donley: Shawn, how about you talk a little bit more about your experience of coming on? You shared a little bit about early on that you were listening to a lot of podcasts, but I want to talk, you trained me on the newsletter and I learned a ton from you and kind of onboarded me in many ways.

[00:39:01] Patrick Donley: So I want to hear a little bit more about your experience coming on into the TIP. 

[00:39:06] Shawn O’Malley: Yeah, well, you know, it’s funny, I think I joined February, 2022 or March, 2022. And there was this like a three or four month gap, right? We didn’t start to actually start publishing the newsletter until July. But the whole purpose that I was hired for was to write the newsletter, but because of some, you know, advertising arrangements we had in place, we weren’t going to start until July.

[00:39:26] Shawn O’Malley: And so I had almost three or four months of kind of empty time to fill. And so I spent a lot of the time just reading and learning and it’s six guidance to some extent. And then also we kind of thought, you know, Hey, we’ve been looking for a YouTube post, which is actually the job I originally applied for.

[00:39:43] Shawn O’Malley: And I said, you know, why do you have some time to kill? Why don’t we send you a camera and start making some videos? And it was almost full circle. Cause like I said, when I originally applied to work at TIP, I had applied to be a YouTube post. And over the course of several rounds of interviews, they decided that they’d be a better fit to be a newsletter writer.

[00:39:58] Shawn O’Malley: But yeah, so I ended up with cameras and I, I, it was. Quite a process to get everything wouldn’t believe the amount of work that goes into a YouTube video. And also, you know, even just our newsletter each day, just to get everything looking and sounding right. And so I know as a podcast, as Patrick, you can also appreciate that.

[00:40:14] Shawn O’Malley: So I had a several month stint just making basic YouTube videos about finance and book reviews before I sold it full time focusing on our newsletter. We see the markets, and I know I had the privilege of working with you pretty early on. Patrick and one of the kind of lasting messages that one of our colleagues told me of how to think about the newsletter is, you know, let’s create something that’s of the same quality of our flagship podcast.

[00:40:36] Shawn O’Malley: We study billionaires and let’s do it in newsletter form. And so I brought that too. The newsletter very seriously of, of being a longtime fan of TIP and, and wanting to feel like I could recreate the same quality and value and trust with people that had been built up over our podcasts over the years and this new media format, and I’d like to think that we’ve accomplished it, or we put a lot of work into just getting better every single day.

[00:41:02] Shawn O’Malley: And I mean, I know we look back at the early editions of the newsletter day by day, week by week and month by month. I mean, it has just gotten exponentially better and that’s not because we’re brilliant people, but that’s just because we’ve been so humble, every day. We say, what can we do?

[00:41:17] Shawn O’Malley: How can we improve this? Should this be shorter? Should this be longer? Can we do a better job explaining it? You know, would this font look better? Should we bold this? Where should we add in links? And just every day we are willing to change and be flexible and have an open mind for how you can improve things.

[00:41:30] Shawn O’Malley: And so, you know, sometimes I look back at some of the first newsletters I wrote, and that also we wrote jointly together. And I cringe and then I also kind of see the beauty of that progression that we’ve made along the way. And, you know, it’s certainly busy. As Matthew said, you start every day with a blank slate, which is scary to an extent.

[00:41:47] Shawn O’Malley: You know, when you’re focused primarily on writing the newsletter, every day is a new day and it’s not really like any other job. You know, I’ve had other jobs and plenty of friends who work, you know, insurance and banking and regular types of jobs and your work carries on day to day. Right? You might have projects you do for weeks or months, but, you know, with a daily newsletter, it’s kind of something you craft and curate it exists for a single day and you spend all day working on it and then you send it out and then by the next day, it’s already outdated and you’re on to the next one.

[00:42:18] Shawn O’Malley: You know, and there’s not necessarily a continuity of newsletters, right? He said, every day is kind of a new day when you’re trying to provide current market news to keep people informed about what’s happening. So even just that process of starting a new one, every single day has been humbling. Cause you know, sometimes you say, and I want, I wrote a killer newsletter yesterday and then it’s like onto the next.

[00:42:37] Shawn O’Malley: And so it’s very humbling, you know, like your ego can’t latch on to success too much because you’re always turning a new page constantly. 

[00:42:46] Patrick Donley: Yeah. It’s like you’re creating a baby every day and releasing it out into the world and moving on to the next baby. 

[00:42:51] Shawn O’Malley: Right. It’s like the, you know, the, like sand mandalas, I’m not sure what they’re called, these intricate artworks that are drawn in sand, and then they’re just immediately, they’re cleared away as soon as they’re finished.

[00:43:01] Shawn O’Malley: It’s kind of what. Not to compare, you know, our newsletter writing to the beauty of that type of art, but it is the same idea of you, you put so much effort into something and then you just wipe the slate clean. 

[00:43:11] Patrick Donley: It’s a great analogy. It’s really true. There’s so much work that goes into a newsletter.

[00:43:16] Patrick Donley: I don’t know that the average person can really. You know, when they see the finished product, appreciate how much work that actually goes into each day producing that much content. And I remember the early days they were, their newsletter was way longer and like, it was a lot more content to produce. And yeah, it’s interesting to see the evolution for our listeners though.

[00:43:35] Patrick Donley: Those aren’t current subscribers. Matthew, can you talk a little bit about something more in depth about. The newsletter is geared toward what you’re trying to accomplish the mission, that kind of thing. 

[00:43:46] Matthew Gutierrez: Yeah, sure. Well, basically in a nutshell, the biggest stories in financial markets every day, that’s how I think Shawn came up with that tagline.

[00:43:53] Matthew Gutierrez: And that just speaks to what we’re after. We’re not necessarily chasing every stock that’s moving around or what some pundits said on, on TV, but really just what are the big market movers or in some ways, what is the story that’s being overlooked, but we think is substantial, you generally long term, even though it’s a daily newsletter, we’re trying to think about.

[00:44:11] Matthew Gutierrez: Things that are going to have bigger effects down the line. So that’s what we’re after. We also obviously keep track of S&P, Nasdaq, Bitcoin, oil, gold, all that’s in every newsletter. We usually try to sprinkle in a little fun in the intro and some charts as well, which we’ve really doubled down on the last, call it what, maybe a year, Shawn, of really just adding more visuals so that people who, you know, realistically are commuting home or in line at the grocery store on their phone, reading it, they might be skimming or scrolling.

[00:44:38] Matthew Gutierrez: So we do want to have speaking to the mission point, we do want to have something accessible. Something where you don’t need an MBA to understand something that no one on all honesty, probably a college student would be able to understand virtually every word because we’re really spelling it out credit to Shawn for, you know, financial terminology, really just spelling that out for readers, which you don’t always get when you’re reading the wall street journal or Bloomberg, which are great, you know, great platforms.

[00:45:01] Matthew Gutierrez: But we really try to educate and inform and add, add those definitions, add those examples. Add those stories to the headlines. So that’s it. And I’ll show, I’ll have some pop quizzes, some polls for fun as well. And just to sort of put it, put a cherry on top. 

[00:45:15] Patrick Donley: Yeah, it’s good stuff. I look forward to getting it every day.

[00:45:18] Patrick Donley: Shawn, I wanted to hear a little bit more from you about just the newsletter, what do you think about the evolution of it? Like you were there at the very start of it started at, I mean, you’re the founder in many ways. How has it changed over time? Like, how would you say it’s kind of progressed? And. You said it’s gotten a lot better and it has talked to us a little more specifically about that.

[00:45:38] Shawn O’Malley: It was one of those things where we truly started with the newsletter with an open canvas. I was just asked to take, we built up this email list over years of doing the podcast, but we weren’t necessarily emailing people and communicating with folks who had signed up to hear from us. And so, you know, the mission was kind of just, Hey, let’s build a daily newsletter.

[00:45:58] Shawn O’Malley: And then Shawn, you let’s figure it out, you can figure out what it should look like, how it should read, how it should sound. And so, you know, it wasn’t this kind of thing where like from day one, I knew. I didn’t even really know who I was writing for, right? Like I was trying, you’re trying to figure out who’s actually going to read this, who is this going to be valuable for, and that’s kind of one starting place.

[00:46:16] Shawn O’Malley: And then from there you have to figure out, okay, you know, how should this actually look? How should it flow? What should the tone be read? Should it be more casual and fun, or should it be very serious and professional? So there’s a lot of different ways we’ve gone out. I would say we’ve pushed in those different directions over time.

[00:46:30] Shawn O’Malley: And I would probably say at the beginning, I thought I almost took it more seriously than I needed to. 

[00:46:36] Patrick Donley: What do you say more about that? Serious in what way? The tone of the writing was more serious. 

[00:46:41] Shawn O’Malley: Like having fun, you know, making jokes, interesting, linking to interesting things, even in pop culture and stuff, you know, but when I first started, I think I thought I needed to have this very strict.

[00:46:52] Shawn O’Malley: Financial markets focus and just talk about numbers and treasuries and stocks and what exactly ‘is happening on a very technical level and over the course of doing it daily for nearly 2 years now, it’s just something Matthew and I have talked about. We just want to have fun with it, right? Like when you’re having fun with what you’re doing, your life is a lot better.

[00:47:10] Shawn O’Malley: And so in some ways, the newsletter is, I would say, becoming more casual. It’s become more fun to write and hopefully to read and hopefully just easier to read too. And so Yeah, and like I said, it’s been a constant work in progress, but you know, we’ve ended up in this place where we realized, like, you know, I used to, when we first started, I think about, you know, okay, I’m writing it for this person, John Smith, 40 years old, who lives in Maryland, or, you know, and you’d have some idea of who you’re writing for, and over the course of time, and it took me a little bit to learn the wisdom of, you know, just Put something out that you want to read and that’s interesting to you.

[00:47:46] Shawn O’Malley: And so that’s ultimately where we’ve leaned into is me think, I think really it’s gone from me thinking about trying to make something that would make other people happy and to just creating, you know, knowing that I’m an investor and somebody very interested in finance myself and just figuring out, you know, what would I enjoy reading?

[00:48:02] Shawn O’Malley: And yeah, that’s where we’ve ended up. And, you know, along the way, we’ve learned some small things that I’ve thought about, like exclusionary life, the languages, finance and business in general. And even you open up CNBC, which is considered the most mainstream and accessible, you know, business and financial media company.

[00:48:18] Shawn O’Malley: And there’s just still so much jargon that’s used. And sometimes people don’t ask the first questions first and the principles of like, what does it actually mean? You know, what is actually inflation and what is an interest rate and why is it important? And so, you know, we don’t always go through it at such a basic level in every single newsletter, but you know, if you’re reading every day, I think you’ll see that we take a lot of those opportunities to just zoom in ways that other people don’t.

[00:48:41] Shawn O’Malley: And answer those principal questions of like, sometimes. You just take for granted that you think you understand something and you have to, you have to have somebody else push you and remind you to question, you know, something you just assumed that you understood about financial markets. And this is why I P.

[00:48:56] Shawn O’Malley: O. S. happen while you do and you take it for granted. That’s what it is. And I think, well, hey, maybe there’s a different way to do an IPO, right? And so just those are a few examples of how we’ve tried to, as Matthew said, try to make things as accessible as possible to people and retain the sophistication of the concepts.

[00:49:10] Shawn O’Malley: Yes. While removing the exclusionary jargon that makes people feel like they’re not qualified to read business and financial news, 

[00:49:18] Patrick Donley: Matthew, I wanted to hear a little more about as you’re going through the process of writing, what are some of your favorite resources that you’re turning towards to craft the newsletter?

[00:49:28] Matthew Gutierrez: Yeah, so certainly mainstream news, like Shawn said, we’re reading just sort of, we probably get, I don’t know, Shawn might get a bunch as well. I probably get at 1. 20 newsletters in my inbox a day. Yeah. And part of that was just sort of seeing what other people are doing. I’ve since unsubscribed and cleaned out the clutter a little bit, but we’re just reading all of those.

[00:49:46] Matthew Gutierrez: You know, scanning CNBC, sometimes I’ll scan CNN and CNN business just to get a pulse. We’re not necessarily writing anything based on those articles, but just to sort of get a feel for what’s going on in the day, both financially and not. I think the main ones, Shawn and I keep coming back to our Bloomberg financial times, wall street journal, occasionally New York times and Washington post.

[00:50:07] Matthew Gutierrez: Those are the, let’s just call it 4 or 5 that we, that I’m reading every single day that we have counts with and we’re reading, you know, the financial market stories, but some of those publications also have more business and tech stories as well that we might sprinkle in the newsletter. Occasionally we’ll throw in a sports story, whether it’s, you know, LeBron James is holding.

[00:50:25] Matthew Gutierrez: Or Michael Jordan being a billionaire, how does he look about markets and, you know, NBA ownership, for example, or brand deals. So we try to have fun with it. Certainly primarily looking to those publications for. You know, traditional market stories that we will branch out a little bit and anything just sort of with the ancillary business and financial stories as well for 

[00:50:46] Matthew Gutierrez: some people, 

[00:50:47] Patrick Donley: Shawn, talk to me a little bit about the vision of where you want the newsletter to go.

[00:50:52] Patrick Donley: Currently, you’re at tell me again with the number of subscribers and just kind of your vision for the future for the newsletter. 

[00:50:58] Shawn O’Malley: Yeah, well, you know, right about 32, 500 subscribers, and I’d like to grow it to hundreds of thousands and millions. And, you know, I was actually looking back at a publication we’ve learned a lot from, and that’s Morning Brew, and I think they’re several million folks who read that, and they just celebrated their 10 year anniversary.

[00:51:16] Shawn O’Malley: And so, you know, sometimes I’m frustrated, I have my head down, and I’m thinking, you know, why are we not getting more people to read this? How can we get it to grow faster? And that stuff. Morning Brew. And then other times I think about, you know, it’s just a long journey to really, truly, I think of it as we’re building a business with the newsletter, it’s a long journey to build trust with people and add enough value to them that they’ll recommend reading it to others.

[00:51:35] Shawn O’Malley: And you just build that sort of following organically. So it’s a work in progress. We’re almost 2 years in, and I’m proud of a lot of what we’ve accomplished. I think there’s plenty of room to, you know, as we’ve been talking about, I think that our message resonates with a lot of people who want to keep on top of the biggest stories in financial markets, and they don’t want the jargon and they want easy to read charts that, you know, be cliche, right?

[00:51:57] Shawn O’Malley: A picture is worth a thousand words, and sometimes you can convey so much more in a simple chart than you can in a thousand word write up. And so we just try to blend as many of those elements as possible by coming up with jargon while also touching on the nuance of financial stories. Because what kills me sometimes too, is when there are plenty of folks who do try to very dumb down what’s happening in the economy or in the stock market.

[00:52:19] Shawn O’Malley: And some of that stuff is just, it’s just hard to read because there’s no appreciation for the nuance and coloring between the lines of, or how complicated some of these stories can be. And unfortunately, the gap that we’re trying to fill is for more of that nuance. Oftentimes you have to go to these legacy financial publications that are very technical and very filled with jargon.

[00:52:38] Shawn O’Malley: And so kind of the opportunity we see with folks is to, you know, go deeper than most mainstream media goes on financial and investing topics. While also not having the same jargon that you would get if you picked up a wall street journal or a Bloomberg. So the message that I hope resonates with a lot of people and I, so far, it seems like we had a chance to meet up with some readers when we were in Omaha last year for the Warren Buffett or to the Berkshire Hathaway shareholder meeting.

[00:53:03] Shawn O’Malley: And so, you know, from what I can tell people, it resonates with them. And also for me, it’s just a message. Is compelling because sometimes I read things and, and there’s so much jargon in it. I’m like, God, I know a lot about finance, but I feel dumb reading this. I have no idea what they’re talking about.

[00:53:17] Shawn O’Malley: And then you look up, you know, the terms and the language that’s being used, and you realize, oh, these are actually very basic concepts that are just being packaged in this way. You know, coming back to that word exclusionary, I think honestly, you know, for a long time, Wall Street money managers have built up a reputation of wanting everything they do to be as esoteric as possible.

[00:53:36] Shawn O’Malley: They don’t want the average person to understand what they’re doing, because if people understood the actual money moves that your average mutual fund or hedge fund manager is doing. You wouldn’t pay them the type of fees that you’re paying them. Right? I mean, they’re the average money manager who is not doing anything extravagant and they’re not some, you know, brilliant Wolf of Wall Street type of person.

[00:53:56] Shawn O’Malley: They’re just making very basic moves for the most part. And they try to use, I think there’s a culture of language that’s been perpetuated over several decades of making yourself sound more important and kind of self flattering. Language of, of just making things very technical and they don’t need to be.

[00:54:13] Shawn O’Malley: So, you know, that, that’s kind of an irate about it, but you know, as I, the more I’ve peeled back the onions of the financial world and each layer I go through, I realized just like, there’s a lot of that element of people wanting to sound like they’re more sophisticated than they are so they can justify charging higher fees.

[00:54:29] Shawn O’Malley: And that’s the unspoken truth. And you know, I’m not going to say that we’re going to peel back every layer of the onion for everybody who reads, we study markets, but we really make an effort to just shine a light. Dynamics like that. And also just to cut through the BS and cut through the jargon and just put things out there plainly.

[00:54:45] Shawn O’Malley: And also just a respect for people in that we don’t need to tell them what to think, right? We think of it as truly like we’re presenting information for people to decide on their own, what they think about, about different matters in the financial markets. 

[00:54:58] Patrick Donley: You guys are doing a great job at it. I know one of the key metrics is open rate.

[00:55:03] Patrick Donley: And the last time I checked, it was over 50 percent open rate, which is just testament to the high quality nature of the newsletter that you know, and the quality content that you guys are putting out every day. I think it’s rare to get that kind of number of over 50 percent. Fairly rare in the newsletter world.

[00:55:20] Patrick Donley: Matthew, I’ve been reading lately about how we study markets pro. So can you talk to me a little bit about that? I’m curious about what the new developments are with the newsletter and we study markets pro. 

[00:55:31] Matthew Gutierrez: Yeah. Well, thank you for the kind words. Patrick is certainly, you know, we’re not about clicks. We’re about information.

[00:55:36] Matthew Gutierrez: And of course we want people to read our work. No doubt. We’re not going for a graphic just for the sake of traffic, right? Really going for the educational component. As Shawn said to me the other day, We’d rather have fewer subscribers who are really engaged. And educated and learning then, you know, a lot bigger, but people aren’t really opening it or they’re just skimming it or not interacting with them.

[00:55:55] Matthew Gutierrez: So there’s a closed loop there. Yeah. As far as we study market pro, we’re excited to roll that out. It’s $67 a month and you get 1 weekly strategy report featuring market charts and historical data to inform and educate investors on their decisions. That’s weekly. We have an occasional signal report as well.

[00:56:15] Matthew Gutierrez: Based on an economic release, like an inflation print, for example, we’ll have something right shortly after those releases. We’ll have quarterly webinars and then we might roll out some other features as well. But everybody gets a free trial to cancel anytime if you don’t like it. And we’d love to have you on board.

[00:56:33] Matthew Gutierrez: We welcome you to a 1 on 1 intro call. And hear about what you’re looking for, how you think about markets, how you like to invest, what you like to read, and that can help shape our product as well. So we’re very much listening and interested. 

[00:56:46] Shawn O’Malley: Yeah. And just to add to that, too, right? You have a daily newsletter that we normally put out.

[00:56:50] Shawn O’Malley: Just studying markets is free for everybody to read and access. And the aim of that, as we’ve talked about the last few minutes, is to educate and inform people. And that certainly doesn’t change at all. But the idea we say markets pro is to go. And take the kind of information that’s being provided, you know, generally keeping people up to date on the markets and we study markets and we say markets pro provide actionable insights and actionable, you know, institutional level hedge fund level data that the professionals are honestly paying big money for to access and we’re taking some of that data and the hope is to distill it and deliver it into, you know, weekly actionable reports for folks that they can actually make decisions off of.

[00:57:31] Patrick Donley: It sounds like good stuff. I mean, one of the great things about TIP is it is super entrepreneurial. I mean, Shawn, you’ve started a newsletter and you guys have run with it, and this is like a new development that will be exciting to see how it unfolds. And I just want to thank you guys. This has been a lot of fun for me, fun to learn more about you and.

[00:57:48] Patrick Donley: Just your insights on things that are really helpful. And Shawn, for people that want to get in touch with you, talk about how they can do that. And a little bit more about how to subscribe to we study markets too. If you could touch on that. 

[00:58:01] Shawn O’Malley: Yeah. Yeah. Well, you can just go to the investors podcast. com.

[00:58:04] Shawn O’Malley: It’s our home based website for all of our podcasts and our newsletter. There should be a few pop ups that you’ll see in different places for you to input your email. You can also go into the academy tab. There’s a drop down that you can click on newsletters. You can see our whole archive of recent newsletters.

[00:58:19] Shawn O’Malley: You can subscribe and you can also check out we’ve city markets pro from there as well. So yeah, I really appreciate you having us on Patrick and we’ll see you next time. You know, if you do have questions about the, about least city markets or we study markets pro, you can just email us a newsletter at the investors podcast.

[00:58:35] Shawn O’Malley: com. And we open every email that comes in there and we make an effort to respond to everybody who writes in. 

[00:58:40] Patrick Donley: Awesome. Matthew, how can people get in touch with you? And if they want to reach out and have questions about, you know, anything, whether it’s market related or we study markets pro, or just a rap about some of the books you mentioned, how can they get in touch with you?

[00:58:53] Matthew Gutierrez: Yeah. Best way is email. Like Shawn said, we read every email. We love sharing from our readers on Matthew at the investors podcast. com. And you can also check us out on Twitter slash X or we study markets there. We post a lot more regularly of late. So check us out there. And we do have some presence, like, like Shawn said, of course, TIP on YouTube generally and Facebook as well.

[00:59:14] Matthew Gutierrez: Awesome. 

[00:59:15] Patrick Donley: Gents, thank you so much. This has been a lot of fun. Okay, folks, that’s all I had for today’s episode. I hope you enjoyed the show and I’ll see you back here real soon.

[00:59:25] Outro: Thank you for listening to TIP. Make sure to follow Millennial Investing on your favorite podcast app and never miss out on our episodes. To access our show notes, transcripts, or courses, go to theinvestorspodcast.com. This show is for entertainment purposes only. Before making any decision, consult a professional. This show is copyrighted by The Investor’s Podcast Network. Written permission must be granted before syndication or rebroadcasting.