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Again, that's longangle.com. Hello, and welcome to another episode of All The Hacks, a show about upgrading your life, money, and travel. I'm Chris Hutchins, and I am excited you're here today to talk about investing. And we're joined by none other than Brian Faraldi. He's a financial educator and author of a new book called Why Does the Stock Market Go Up?

Everything You Should Have Been Taught About Investing in School, but Weren't. It comes out April 5th, but I got an advanced copy and I really enjoyed it. Brian has also written more than 3,000 articles on stocks, investing, and personal finance for The Motley Fool. But I got to know his content through the detailed investing checklists he publishes and follows for all his new investments.

In our conversation, we'll talk about current market volatility, Brian's counterintuitive investing philosophy, making an investor checklist, evaluating risk, figuring out when to sell, taking asymmetric bets, and a lot more. That is so much to cover. So let's jump in. Chris Hutchins works at Wealthfront. All opinions expressed by Chris and his guests are solely their own opinions and do not reflect the opinion of Wealthfront.

This podcast is for informational purposes only and should not be relied upon for investment decisions. Brian, thanks for being here. Chris, awesome to be here. I'm pretty sure I'm a day one listener to this podcast, so it's cool to be on it. That is awesome. Thank you for your support and for everyone else here listening.

So you've got a book coming out in a few weeks. Why does the stock market go up? And I was thinking about that this morning. And for anyone listening, we're recording on Wednesday, March 9th. I was like, gosh, in the last month, the market's down about 7%, but somehow today we're up two and a half percent, which seems like some wild volatility.

You wrote the book. How do you make sense of all this? Yeah, the last two years have been fascinating to watch as an investor. It was February and March of 2020 when COVID was taking over. We saw the fastest bear market in stock market history, where over the course of a month, didn't matter what you did, whatever stock or fund that you held, it was going down and it was going down hard.

And then immediately after that, with everything changing in the world, I would have predicted that it was going to be a terrible year for the market, a terrible year for investors. In fact, we saw the exact opposite, where stocks just shot up to the moon. And it was almost like the higher risk the stock, the better the stock did.

I mean, the numbers were off the charts. Good. And then over the last year, we've seen kind of reversal of that. What a lot of the stocks that were left behind in 2020 have since caught up, things like energy stocks and real estate stocks and stocks that were the go-go stocks of 2020.

Things like Zoom and Roku and Peloton have just been train wrecks from an investing perspective. But that's just how investing works over the short term. What determines the value of any given stock or any given indice is just the collective emotions of all market participants, how investors feel about the markets.

And that is always so hard to predict and so hard to read. So I view the stock market, what it's done over the last couple of years as fascinating, but entirely normal. OK, and how do you think about calm times, volatile times? Are we in one of them? Are they all one in the same and you should just prepare for them at any moment?

Yeah. When you're investing in the stock market, you never know what you're going to get over any short period of time. That's why the stock market is a great place to put capital that you don't need for at least three to five years. But it's a really poor place to put money that you're going to need in any shorter period of time.

So if you need money in the next three years for college or for a house or for a car or anything like that, there's a reason why people say don't put it in the market, because no matter how good times see right now, that doesn't mean that the market's going to perform well.

The inverse is also true. It looks pretty dark out there right now. We have a war going on. We have inflation going on. We have interest rates that are rising. Lots of high-growth stocks have been pulverized and are down huge. But there's still no telling what the near-term returns of the stock market are going to be.

So it's really important that if you're going to invest in the market, which I think everybody should be doing with their long-term capital, you have to do so in a way that allows you to endure short periods of extreme volatility, because that is the norm for the market. What advice do you have for people who are just today thinking about, "Wow, we are in this very volatile time.

Should they be investing right now? Is now a good time to get in the market?" or how do you feel about trying to time things like this? I never try and time things myself, because again, if you were to ask me what's going to happen in 2020, I would have said the market's going down.

If you asked me what's going to happen in 2021, I would have said the market's going up. And I would have been wrong, essentially, on both accounts. So my own history with trying to time the market shows how poor I am at it. For that reason, I just say, ignore the timing and when to get in.

Instead, just focus on being in the market and being a continual buyer of the market. It's just called dollar-cost averaging. If you can dollar-cost average for a long period of time, the timing of your buys becomes irrelevant. Do you think there's at least some argument to, if the market is down and you're able to see that that's the case, to get in now, like people who invested after the crash in 2020?

Oh, absolutely. The best time to buy the market is when it's on sale. However, predicting when those sales are going to be is always an endeavor that isn't really worth the time or even that hard to do. However, if you are the type of person that has cash on the sidelines, saving it for a time when the market does fall, I think right now is a great time to put extra capital in if you have that ability.

With the foresight being that you don't know what's going to happen next. I think we're down 20% from the highs last year, which is officially in bear market territory. But that doesn't mean that stocks can't continue to fall further. If you're in that fortunate position of having cash that you've been waiting to invest and you're looking to do so, one trick that I like to tell people to do is come up with a schedule for investing that capital.

Let's say you have, to make things easy, $5,000 and you want to invest $1,000 a month over the next five months. You don't know what's going to happen to the market over that time, but you just create a schedule for yourself. Well, if by chance you invest $1,000 on the first day, and then the next week the stock market falls 5% or 10%, then accelerate your next purchase early.

That way, you can take advantage of that temporary dip and then just stick to the schedule thereafter. But if the stock market stays flat or goes up, you just stick to your regular investing schedule. So that's one way that you can deploy capital more efficiently if you want to take advantage of dips.

That makes sense. And we haven't really talked about what to invest in. So before we get there, how do you think about building your own investment portfolio? I know there's a massive world of investments out there, and we've had on some folks like Andy Ratcliffe and Ben Carlson, and we've talked about passive investing and index funds and that kind of stuff.

But for you personally, how do you think about your portfolio? I'm a massive fan of index funds. Always have been, always will be. I think that index funds plus dollar cost averaging, as those gentlemen pointed out, is just a wonderful formula for building wealth over long periods of time.

And that's what I personally do with all of my retirement funds. I set it up once to drip into index funds, and that's what I do. But with my capital in my regular brokerage account, I love analyzing businesses, studying businesses, and buying individual stocks. I've been doing that personally for about 15-plus years now.

So, any capital that I have beyond my retirement funds, that's where I deploy it. So, at any given time over the course of a month, I typically buy a handful of stocks myself. And to do so, I just created a list of companies that I'm interested in, according to a checklist that I created, and prices are changing dynamically all the time.

And what's so fascinating about, if you invest in the individual company level, what's happening at an individual company can be wildly different than what's happening with the market in general. When the market is down, there can be companies that are up. And when the market's up, there can be companies that are down.

But when I'm deploying capital in my investment portfolio and trying to invest in individual businesses, what I'm trying to do is optimize, at any given time, for the best combination of high-quality businesses, according to criteria that I selected, times the highest long-term potential, times the companies that are trading at the most attractive valuation at any given time.

So, it's really the combination of those things that I look to deploy my capital into at any given month. So, I want to get into those three things. But before that, how do you think about risk-taking? Do you think of your single stock investing more a portfolio approach, where you can diversify amongst stocks and it's actually not quite as risky?

Or I think if you talk to most passive investors, they would say, "Gosh, if you go buy a stock, that's really risky. You don't want to do that. You want to bet on the market." So, your type of stock investing fits into general investing risk? Yeah. I think that they're actually two of the same.

And it really depends on how you are investing. When most people think about investing in individual stocks or businesses, what they're really trying to think about is timing the market and trading stocks, trying to buy them when they're low and sell them when they're high. And I have no interest in trading stocks myself.

I view the portfolio, the investments that I'm making outside of my retirement funds, as essentially building my own index fund. So, my style of investing is, I look for high-quality businesses that I think can grow for many, many, many years. I buy those companies and I try and hold them as long as they remain great businesses.

So, I'm not trying to trade in and trade out of companies. I move my portfolio very, very slowly. So, what I'm trying to do is handpick, essentially, my own index fund and let those businesses grow for long periods of time. I know you're a fan of the investment policy statement.

How have you used that concept, and for anyone who isn't familiar, maybe walk through what it is to guide your investing decisions? I think this is something that so many people overlook when they start investing. They don't really sit and write down why they're investing in the first place.

They just think, "I have some money. This stock thing sounds interesting. I'm just going to do that." But I think it's really important to take a step back and ask yourself, "What is the purpose of this capital? Why am I choosing to invest it in any given way?" One tool that you can use to do that is just called an investor policy statement.

It's just a very simple set of rules that you set up for yourself before you start investing, and you can use it to guide your decision-making over time. For example, my long-term investing goal is to grow my capital for as long as possible at as high of a rate as possible, while simultaneously assuming as little business risk as possible.

Now, "business risk" means that the companies that I'm investing in, I actually think, are low-risk businesses. That doesn't mean that their stocks aren't high-risk and very volatile, but the underlying businesses that I invest in are actually fairly low-risk businesses. All capital that I put into the market, I don't plan on touching for at least five years, and all of my short-term capital needs are funded by cash that I have on hand and then income from mine and my wife's jobs.

Because of that, we actually take a very conservative approach to our personal finances. We have a large emergency fund. We have a high savings rate. We have multiple sources of income. We have no debt of any kind. So, our personal finances are very conservative. That allows us to, essentially, with our investment portfolio, be 100% stocks and 0% bonds.

That, in and of itself, means that my portfolio is going to be far more volatile than the average portfolio that has a mix of cash or a mix of bonds in there. However, I'm perfectly fine with that volatility because I know that any money that I put into there, I don't need to touch for a period of years.

But I think that people could do so much better for themselves if they just sat down and asked themselves, "Money that I'm going to put into the markets, what's its purpose? What are my investing goals? And how long can I keep it in there?" I like that. Is there a place to get some examples, maybe your book or your website, of those policy statements and how to start thinking about writing one?

Yeah. Now that you're saying that, I missed a big opportunity by not putting it into my book. But if you just Google the terms "investor policy statement", there's lots of examples online that you can use as a guide. Cool. Okay. And so, you've got your policy statement. And now, let's move on to this process of finding something to invest in, to start building out that portfolio.

You're pretty well-known for creating an investing checklist. So, where did that come from and how has it evolved? And talk a little bit more about it. Sure. If you're new to investing, as I am, it's not hard to find companies to invest in once you know what to look for.

There's so many places that you can get investing ideas, whether it's following some big famous investors like Warren Buffett or Cathie Wood, reading free articles that are online, cracking open exchange-traded funds, looking at your own life and seeing what products or services do I use or does my company use?

It's like the list of potential investments that you can make is huge. There's thousands of publicly traded companies for anybody to invest in. When I first started out, I quickly became overwhelmed with choice, and I was essentially trying to think in my own head, "Well, this business, I really like because it's run by its founder and it has a great balance sheet.

But this other business has great margins, high long-term potential, and there are all these factors that I was trying to keep in my head to weigh investments against each other." Turns out, that's a really poor way to do it because our brains are not built that way. Finally, I got smart enough to say, "Maybe I should write this down and create some rules for myself that I can use to guide my decision making." I would suggest that everybody that invests in anything beyond index funds goes through this very process themselves.

First, write down all of the attributes that would make any investment, a stock investment for example, attractive to you. I did that, and I came up with things like, "I want the management team to have a high ownership percentage. I wanted the revenue to be growing at a very high rate.

I wanted revenue to be recurring in nature. I wanted it to be profitable. I wanted the company's balance sheet, how much cash it has, to far outweigh how much debt that it has," etc., etc., etc. I made a list of 30 things that I really wanted in any investment that I made.

Simultaneously, I made another list, which is, "What are all the things that I don't want to see in an investment that I make?" For me, that's things like, "I don't like it when a company gets the majority of its revenue from just a handful of customers." That's called customer concentration.

"I don't like it when a company is operating in an industry that I think is actively being disrupted, like the oil and gas industry right now. I think it's primed for disruption over the next 10 or 20 years. I don't want to make any investments in that." "I don't like it when a company's stock-based compensation, the amount of options that they hand out to employees, is such a high rate that the dilution rate is high," etc., etc.

So, I have my list of things that I'm looking for. I have my list of things that I don't want to see. And then I rank them in order of most important to least important. That's a tricky exercise to do when you really have to force yourself to rank things against each other, but it's so useful to do so.

Finally, I have both of those things in place. And I just applied a very simple scoring system to weigh my criteria based on the factors that are most important to me. And the same goes for the factors that I'm not looking for. I just came up with a simple 100-point scoring system where I doled out 100 points in total based on the factors that I just listed.

From there, I now have my criteria built out, so I can take any company that I come across, I can research it, and as I'm researching it, I'm filling out this checklist. And at the end, when this process is all done, I get to know whether a company is a match for what I'm looking for in investment or not.

I've done this now hundreds of times. I have a list of companies that are very attractive to me as an investor. And simultaneously, I have another group of companies that there's just no way I'm going to invest in. So, the process of creating a checklist for myself, ranking it, and scoring it has helped to clarify my decision-making so much.

I have so many follow-up questions right now. I'm like trying to take notes to organize them. So, a few things. One, you make this checklist of your own available on your website, correct? Yep. You can make it freely downloadable. Yep. So, we'll make sure we link to that in the show notes.

But as you were walking through your criteria, it made me think, I'm not sure even I have an opinion on these things. So, is this something that takes years of playing in the stock market to build? Do I care about whether there are a lot of options granted to employees?

These seem like things that the average person might not have an opinion on. Where do you suggest people get started? Or is it best to use someone else's list? Or is there a way to educate yourself on why you may or may not care about some of these things?

The checklist as it exists today is a constantly evolving process. And what it is today is through trial, error, and most importantly, feedback that I've gotten from other smart investors that I respect. By studying the styles of great investors that I deeply respect, I find out what really matters to them.

And then I took that and evolved it into what matters to me. But I don't claim that the version that I have right now is "perfect". It's just the best version that I've come up with so far. But to your point, all of these things do take time to research.

If you want to go through the process of researching a stock, there's a lot that you have to learn. You have to learn accounting, you have to learn how to read SEC filings, you have to learn how to think about competitive advantages, studying the competition, thinking through the business model, studying potential risks.

There's a lot to evaluating individual stocks. This is a big reason why so many people say, "Forget all that and just stick with index funds." Right? It's so much easier to do that. So this process, I think, is a good process if you're in that 1% or 2% of the population that is really fascinated by business the way that I am and is really interested in studying the subject.

That's why I created this. I absolutely love everything about investing in research companies, but I'm right there with you. This is a time-consuming process and it turns off a lot of people. If there are specific companies that people listening to this are thinking about, I've actually gone and... Brian has a YouTube page where you actually break down going through your checklist for different companies.

So I'll just give that a shout out because I thought that was really fun to go and look at a couple companies. I think Peloton is a great example. You did one and then you came back and did a recheck in because it had been an interesting adventure for that company.

We got that one wrong. Yeah. That's why you're making more than one bet. But what you said about it taking a lot of time, if someone listening to this is like, "Index fund investing is fine, but there's some companies that I like. Is there a place for trying to invest in those stocks that whether you like them or you think they're exciting or the company has potential that doesn't need to take this much time?

Or is your general advice, if you're not going to take the time, you probably shouldn't do it?" The best advice that I can give there would be always think about your overall asset allocation. Some people say that stock picking is a complete waste of time. They're not interested in it.

Fine. Just stick with 100% index funds and call it a day. But I think there's room for a happy medium in the middle. There are some people that I think should put, say, 90% or 95% of their assets into index funds, but if they have a hunkering, or there's some businesses that they're really interested in or they want to research, I see nothing wrong with taking a few percent of your overall portfolio and putting it into investments that you pick out.

So, if you can pick, say, five companies or something like that that you're really passionate about and put 1% or 2% of your portfolio in it, even if you're wrong, even if the process that you go through, or if you don't want to do the research, you just want to make an investment in those companies, even if you're wrong about them, well, 90% of your net worth is perfectly fine in the market.

If you don't want to go through the research process and you just want to put a little bit of capital in, I think that's fine so long as you size it appropriately. As I walk through what you're saying, I'm realizing that you're presenting us all with an option for building a part of your long-term diversified portfolio on your own with stocks.

So, I think some people listening might think it's okay to take some bets with 5% of your portfolio, but be safe with 95%. And you echoed that sentiment, but you've said, "Look, if you take the 95%, there's a different way than index funds that you could invest that 95%." And for you, it sounds like some of it is index funds, but some of it is building a portfolio of a lot of stocks that you spend time and research on.

And if you're interested in that time and energy to do that research, you could treat your index fund portfolio, and you could split it apart and do two different things without having to feel like you're taking a significant amount of risk on your stock investing. Do you think that the type of investing you're doing is passive investing, or is it more like wild bets people often say they're taking with stocks?

And I ask that because it feels like it actually is more like passive investing. Yeah, if you crack open the S&P 500, you might naturally think that you're diversified equally across 500 companies. That's actually not the case. The S&P 500 is weighed by market capitalization, meaning, the larger the company, the bigger a portion of the S&P 500 that is.

Now, there's still 500 companies in there, but if you look at the giant companies that are in there -- Apple, Microsoft, Amazon, etc. -- they take up a pretty sizable portion of the portfolio. The last time I looked, they were at least 3% or 4%. If you're investing in the S&P 500, you have a higher concentration of your funds in those businesses just by the nature of investing in an index fund.

To your point, with the vast majority of my capital, especially capital that's outside of retirement funds, I don't think that I'm taking on a huge amount of risk because I own a collection of a few dozen stocks, but the top 20 stocks that I have have earned their spot in my portfolio.

Meaning, I bought these companies a long time ago, and I just got them right, that they just happen to be great companies that grew and grew. For that reason, when a company does very, very well on the markets, it's typically because the business underneath it is succeeding. One of my top holdings is Google, which I bought, oh, jeez, 13 years ago.

It's grown into a top holding for me, not because I set out to make it a top holding, but I just bought it many years ago and have just held onto it. If you look at Google's business alphabet, as it's called Google's business today, it's an extremely reliable blue-chip company.

The company has hundreds of billions of dollars that come in. It generates huge profitability. It has a war chest balance sheet, and it's still growing to this day. If you're invested in the S&P 500 index fund or total stock market index fund, it's a top holding for you, too.

I don't think what I'm doing with my portfolio, since I'm diversified, since I'm buying good businesses and since I'm holding them for long periods of time, is all that drastically different than people that just invest in index funds. It's just more time-intensive, and that's OK with me. We talked a lot about different types of stock buying, but one thing I noticed you never mentioned you cared about, or at least I didn't hear, was what's the price of the stock right now?

Is that even a factor when you make a decision? That is such a confusing thing about investing. In fact, when I first started investing, I had no clue about the relationship between price and market cap. Like so many people, I thought that the success in individual investing was looking for companies that trade at a very low share price.

A lot of my first investments -- my investments in air quotes, because I had no idea what I was doing -- was in penny stocks. It turns out that penny stocks have the reputation they have because they're typically places that you can go to destroy capital. So many of my first forays into the market were buying awful businesses solely because their share price was really low.

The way that prices work in the stock market is so different than the way prices work in every other consumer good that we buy that it's naturally very confusing. If you were to go in the market and find a company that was trading at $500 per share, and you found another one that was trading at $5 per share, and say, "Which one is more expensive?" Only in investing can you say, "Not enough information." The stock that's trading at $500 per share might be less expensive, a better bargain price than the stock that's trading at $5 per share.

The reason for that is, the equity of a company is two things. One, the dollar price of a share, which is the number that's quoted everywhere that you look. You go on Google, you open the stocks app on your phone, what do you see? You see the price of one share.

However, what you don't often see is the market capitalization of the company. That's the dollar value of the company's total equity. To find that number, you have to look at how many shares exist at a company. Here's something that not many people know. The number of shares that exist at a company is a totally arbitrary number that the company chose.

A company can go out there and say, "I want to have a million shares of stock," or that same company could say, "I want to have a billion shares." What we look at when we're looking at the price isn't enough information to tell us if that company is trading at an attractive number, or if it's cheap, or if it's expensive.

However, that's such a counterintuitive thing that so many people assume the dollar price of a stock will tell you what you need to know about the company. Two follow-ups. One is, the valuation of the company or the market cap is something that you do pay attention to when deciding to invest.

Is that what I'm hearing? Yes. I care much more about the market capitalization of a company than they do about the dollar price of one share. If I'm analyzing a company, one of the first things I look at is the market cap. That will give you a rough size about the total value of the business.

The reason I focus on that is, when I'm looking to make an investment in a company, I typically want to buy companies or add companies to my portfolio that I think I can at least earn a 5X return on, or better yet, a 10X return on. The size of a business is going to show me how hard that is for that company to do that.

For example, if I come across a company and it's trading at a $1 billion valuation, that's the size of the market cap, for me to earn a 10X return on that company, that company would have to grow into a $10 billion valuation. There's lots of companies out there that are currently worth $10 billion, $50 billion, $100 billion, or more.

It doesn't take a huge amount of imagination to believe that a company can grow from $1 billion to $10 billion. Conversely, if you come across a company like Apple, for example, Apple's market capitalization is currently enormous. The company is currently trading at $2.7 trillion. For Apple to grow five times in value from here, it would have to be essentially an $11 or $12 trillion company.

That is such a gargantuanly huge number that I personally have a really hard time seeing Apple ever do that. I'm not going to say it's never going to happen, but holy cow, is that a lot of market capitalization that has to be added onto Apple for its stock to 5X from here.

That's why I'm really focused on the market capitalization of a company, not the dollar price of one share. How does that change over time? You mentioned one of your investments early on was Google. Now, even though it's clear that in the last 13 years, Google probably did 5X the business, but now let's say you're looking at it and you think, "Gosh, now it's a lot harder.

It might be for Apple." Does that mean you have to get out? How do you think about exiting positions that you've made? When I first made an investment in Google, it was far, far, far smaller than it was today. The market capitalization was well under $100 billion when I started buying it.

Today, I'm quite happy to continue holding Google, and I do not expect Google to 5X really in any period of time. Google is a $1.7 trillion company, so for it to 5X, it would have to be a $9 trillion company. I'd be very happy with that outcome, but I don't think that it's going to happen.

Instead, I view Google as a part of my portfolio that is more of a bedrock anchor, something that I think can grow at a low double-digit rate, but I don't expect the company to deliver a 5X return from here. So, in general, while I'm very happy as a Google shareholder, I wouldn't approach it from a "I'm interested in buying this company today," I would be more interested and likely to sell it to fund purchases of other companies that I think have higher growth potential.

But, I'm not going to sell a company solely because it's huge if I've owned that company for a long period of time, and I'm still happy to own it. It seems like with every business, you get to a certain size and the cracks start to emerge. Things that you used to do in a day are taking a week, and you have too many manual processes, and there's no one source of truth.

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So check them out today at allthehacks.com/peak, P-I-Q-U-E. So when do you decide to sell? Whether it was a pick that didn't work out or a company that's worked out and now doesn't have that potential, I can tell people listening that I have some random stocks I've invested over the years, and I personally am struggling, like, when do you exit?

How do you help people think about when's the time to either cut your losses if it's down or take your gains off the table? Yes. First off, let's acknowledge something. Knowing when to buy a stock is much easier than knowing when to sell. It's much more fun for me to research and think about companies that can grow in value than it is to be on the other side of the transaction.

However, there are some reasons that I think a stock should be sold. First and foremost, the No. 1 reason that I sell a stock, and it's the most common, is I was wrong. So, I came up with a thesis for a company. I thought that the company was going to grow to take advantage of a blank market opportunity, and I thought the company had an advantage over its rivals.

If that proves to be incorrect, if the company is clearly struggling to execute that and I am proven wrong, I have no problem saying, "I got that one wrong," and selling to be to play in my capital. Two, if I'm right about a company and it grows to be too large a position in my portfolio and I'm too concentrated in that company, that is a situation where I'm also happy to trim that company.

More recently, I personally trimmed a little bit off of my position in Tesla, not because I don't think Tesla is a great company with a bright future ahead, but Tesla has grown to be my No. 1 position by far, simply because of how well that company has done, and I've been trimming my position surely for risk management purposes.

That's a happy reason to sell it. No. 3, if you have a better use for that capital, if you're no longer interested in following a company or own a company, and it might be a lukewarm investment, but you find another investment that you're more interested in, I see nothing wrong with selling the one that you're not interested in to buy more of the one that you are interested in.

And the best reason of all to sell is that you need the money for your personal life. The whole reason we invest in the first place is to grow our capital so that we can live a better life. So, I see nothing wrong with selling a stock if you need to use that money for a purchase.

So I think one takeaway for me out of this is, the best I can remember, I'm going to go through the handful of stocks I own and try to write down why I invested them in the first place. And that'll give me a place to look to decide when it's appropriate to sell because maybe I don't believe in that thing anymore.

One thing that I personally do and I'm a big advocate for, in addition to writing an investor policy statement for yourself, is to keep an investing journal. So every time that I go and I buy a stock, I just write down what stock I'm buying, a few words on why I'm buying it, and also the valuation that I'm paying at the time of my purchase.

It can be time-intensive to do that, but so often, if we buy a stock, it's not all that uncommon for us to change our thesis over time as the business results come in. It's really helpful to have an anchor point to look back and say, "What was I thinking at the time of this purchase?" and to match up the reality that the business is doing against your initial predictions for those businesses.

If those two things are mismatched for the worst, that can be a sign that company is no longer for you and it's time to sell that company. But again, broadly speaking, buying is much more fun than selling and knowing when to sell a stock is very, very hard. So we talked about buying.

We talked about selling. What about adding to a position? Is that something you find yourself doing over time and how do you decide that you want to double down? I don't invest all the capital that I'm going to invest in a company up front. I tend to buy in small chunks over periods of time that are spaced out.

I do so because I know from my own track record that I'm often wrong, right? A company can check a lot of the boxes that I look for in a business, but that business still has to go on and execute against the opportunity that it presents for itself, and sometimes new competition can come along, or the market can change.

It's common for me to be completely wrong about a stock. So when I'm looking to add to a position over time, what I'm attempting to do is two things. First, I'm looking to invest in companies that are winning. That's a very counterintuitive thing. Most people think, "Oh, I bought a stock for $10, it went to $20, I can't buy any more of that stock.

It was at $10 before, now it's at $20." Conversely, they buy a stock at $10, it falls to $5, and that's the one that they're interested in adding to because it's at a lower price. What I've discovered the hard way is that more often than not, it's better to take additional capital and put it into the company that's already doubled for you, as opposed to the one that's already halved.

The reason that companies go up and their stocks tend to do well is because something about the underlying business is succeeding, and Wall Street is recognizing that business is succeeding. Conversely, if a stock is underperforming, that's a sign that the company is having a hard time succeeding, and it's not meeting investors' expectations.

Broadly speaking, winners tend to keep on winning, and losers tend to keep on losing. So when I'm looking to add to companies, I'm typically looking at the companies that are winning in my portfolio first, and those are the ones I'm actually adding to. I think some people might hear that and think, "Wow, that sounds a lot like the opposite of the tried-and-true buy low, sell high.

That sounds like buy high, sell low," which I think everyone says, "That's what you shouldn't do." How do you juxtapose what you just said with what I would say is pretty commonly-believed advice -- maybe you disagree with it -- of buy low, sell high? I think it's helpful to actually look at some studies of investing and how the market actually works, which are hidden from us if you're investing in just index funds.

J.P. Morgan did this wonderful study where they looked at thousands of publicly traded companies over a period of 30 years, and they looked at the returns of those companies. What they found was that if you put your capital into 10 random companies, what you can expect is that four of those companies will suffer a catastrophic loss and stay down permanently.

Three of those companies will go up in value, but they will underperform the market in general. That leaves three other companies. Two of those companies will be modest market beaters, and one of those companies will deliver multi-bagger returns. What actually drives the market forward over time is a very small minority of companies.

It's really about the top 10% of companies that are literally responsible for 90% of the market's returns over long periods of time. When I've looked at that and I've studied some investors that have taught me this really counterintuitive lesson, what you actually want to do, it really matters that you get some of your portfolio to include some of those 10% of companies that are the mega-winners.

What do mega-winners have in common? Their stocks have already gone up a lot. If you think back to some of the mega-winners that are today -- Tesla, Google, Apple, Netflix, Chipotle -- if you bought those companies after their stock doubled, tripled, or quadrupled, you then went on to earn a massive return, even after their stocks were up huge.

That's why it can actually be a good sign if a company's stock is going up. That's an indication that the business model is working and that Wall Street is recognizing that the business model is working. Conversely, if you want to buy a stock that has lost badly to the market, underperformed the market, history shows that the chances are pretty good it's in that seven out of 10 stocks that is going to permanently underperform the market.

So, I think the phrase "buy low, sell high" sounds really good in theory, but when you actually get into the practicality of investments, some of the best investments that I've ever made was buying stocks that were already up big and were at all-time highs. My conversation with Andy Ratcliffe was that some of the best investors are quite contrarian.

I like that you're taking a different approach, and I'm glad we got to dig into some of the data about it. We talked a lot about ways to invest, but I want to ask what platform you're doing this on and if it makes any of the things you're doing easier.

You mentioned buying a stock, maybe you want to deploy over time. But gosh, let's say you wanted to put $500 into Google today. There's not an easy way to say, "I want to put $500 over the next 5 months and then stop." At least I'm not familiar with one.

Is there an investing site that you like or recommend that makes some of those kinds of things easy? I'm pretty sure that M1 Finance has done many of those things with, you can create a pie for your portfolio, and as you put capital into it, it automatically allocates, and you don't have to worry about things like buying exactly one share.

You can buy fractional shares. We as investors are extremely lucky because there's lots of platforms out there that allow you to buy fractional shares of stocks. To answer your question, though, the broker that I use is called Interactive Brokers. I signed up with them 9 years ago, and what I liked about them is it's a hassle to use their system.

It is a pain in the butt to log in, and once you're in, buying and selling is easy, just like it is on any other platform. But I actually like that there's friction to the platform. I don't use any app on my phone because the easier it is to buy or sell, the more tempted I would be to do it when I'm feeling emotional.

If I owned a stock and that stock was down big or up big in response to whatever the news of the day, my decision-making skills would be compromised because of what I was seeing on the screen. I also use Interactive Brokers, and it's funny, it's one of the few products that I've probably never even mentioned I use on this show because I think most people would hate it.

I agree. The interface is difficult. I'm often unsure of how to find things and have to read long manuals. But for me, the other big perk of Interactive Brokers is that if you need to borrow against your portfolio, the amount of interest many institutions charge is very high. So Interactive Brokers is quite low.

At Wealthfront, we have a portfolio line of credit that's also low for index funds. And everywhere else I've seen is like 5%, 6%, 7%. So that's another plus on Interactive Brokers. But in general, I will say it is a confusing interface. I'm happy to put my referral link in the show notes, but I don't expect a lot of usage of it because of that.

But it's funny, I also use that for my single stock investing. And I'm also not familiar with an easy way to say, "Oh, I want to invest $1,000 in this company. Can I do it over five months?" Because doing it each month manually just invites emotion to change the decision you made in advance.

One other platform technology question I have, so often I see people say, "Gosh, I picked this stock and over the last month, it's down 7%. How should I feel about that?" I'm like, "The entire market is down 7%." So relative to the benchmark of the market, your stock hasn't gone up, hasn't gone down relative to the benchmark.

Is that a way you look at things? Do you look at how a stock's done absolute on its own, or do you try to compare how it's done to the general market to get a sense of relative performance? I always like to compare things to the market. You have to have something to compare it to.

I'm happy just to compare it to the standard benchmark, which is the S&P 500. But yeah, you can't look at stocks in a vacuum. What's even more confusing about investing is that there is a one-to-one relationship between the performance of a business and the performance of a stock over long periods of time.

The reason that companies go up substantially over long periods of time is the underlying business that's underneath them has improved dramatically. Maybe revenue is up a whole lot, margins are better, profits are improving, they've made an acquisition, or whatever the reason is. There's a direct tie between what happens to a business and what happens to the stock over long periods of time.

Over short periods of time, there's almost no connection at all to what a business and a stock are doing. What's happening in the macro environment can often so overwhelm the actual business performance of a company. This can be so confusing to you as an investor, because you can buy a company and you can say, "I think this company is going to become more profitable, its revenue is going to grow, and the stock's going to do well." You could be right about the business.

When they come out with a quarterly report, they could say, "Revenue is up, profits are up, we're hiring more people, we're expanding, hey, we've got this new product that's coming out." And that stock can fall, and that stock can fall really hard. So, in the short term, there isn't always a direct relationship between the performance of the company and the performance of the business.

That's why investing can be so trying on your emotions. However, over long periods of time, the performance of the business always is eventually reflected in the stock price. When I'm judging how my companies are doing, I'm almost never looking at just the stock price. I'm always asking myself, "How did the company do?

What's the general direction of the business?" And I'm focused very heavily on the business itself. In those short-term scenarios where comparing how it's done to the benchmark is really helpful, right? Because you might feel like you got a dud, but really just the market, as you said earlier, it's down almost 20% from highs.

Is there an easy way to do that online for someone who maybe wants to look at their portfolio and say, "Gosh, I invested in Square 12 months ago. How has Square done relative to the market?" Is that an easy calculation anywhere you know? Interactive Brokers gives me an overall portfolio versus the market over various periods of time.

So, that's what I do. But you can use some very simple charting tools, especially ones that are on Yahoo Finance or Google if you want to look up an individual holding over shorter periods of time. Sometimes the smallest changes make the biggest impact, and trade coffee is a great addition to your New Year routine.

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Okay. We went a lot of places and we talked briefly at least a couple of times on asymmetric bets. And I think most people listening might've thought, "Gosh, Brian's this guy that invests in a lot of stocks. All he's doing is making a bunch of high risk asymmetric bets across his whole portfolio." And hopefully if they're still here, they've come to the conclusion that's not the case.

That you're actually trying to do a different type of investing with the bulk of your portfolio. But I'm curious where those asymmetric bets do fit in. And do you take those much higher risk bets in your portfolio and how do they fit into everything? Yeah. The bulk of my individual holdings are in companies that are low risk businesses with strong competitive advantages.

They're growing at an above-average rate. They tend to be profitable, free cash flow positive. They tend to be very high-quality businesses. I don't think I'm taking on a whole lot of risk by investing in those companies. However, with a portion of my portfolio, I also am happy to invest in higher risk situations, knowing full well going in that I'm assuming a whole lot more risk, so I better be compensated for that risk with the potential for higher return.

I know you've talked in the past about making investments in crypto, like Ethereum and Bitcoin. I view those the same way. They're asymmetric opportunities. If you invest, say, $1,000 into a high-risk stock, the wonderful thing about investing is the worst you can do, assuming you use no leverage, is lose $1,000.

You are completely wrong about the company. It goes belly up. You lose your $1,000. However, if you're right about that company, that $1,000 can grow into $2,000, $5,000, $10,000, even $100,000 if you are right about the business. Yes, those companies are extremely rare, but they are out there. So, with a portion of my individual stock portfolio, I'm happy to buy higher risk companies if I believe that I can earn 10x plus returns on them.

When you're thinking about these asymmetric bets, do you try to limit them? Do you try to make them regularly? Do you have a way to come up with ideas for them? How do you find them? Well, I'm a stock market junkie, so one of my favorite things to do is to research companies.

But to answer your question, I'm a contractor for The Motley Fool, so I get access to all of their recommendations, and that's one place that I go to. There's also tons of ways to find investments by looking at high-growth portfolios, high-growth ETFs. The ARK funds, for example, have become very popular with investors, although those things are losing very badly to the market over the last year.

There's lots of asymmetric risk-reward companies that are in there. Finding potential ideas isn't the hard part. The hard part is vetting the ideas and asking yourself, "What kind of risk level am I taking and what are the odds that this company is going to go on to beat the market?" But finding ideas is really easy nowadays.

Is the vetting process for these higher risk, higher return investments, is that a different investing checklist? Or how do you think about making those picks differently than you would others? No, I still take it through my exact same checklist, it's just that the companies typically score very poorly on my checklist for doing so because I value things like free cash flow, I value things like net income, I value competitive advantage, etc.

I still go through the exact same process that I go to, but even after that process is done, if the company scores poorly, but I still believe that the potential is huge, I will go in and make an investment in that case. I just do so going eyes wide open that this is a high-risk, high-reward bet that I'm making, and I just size it appropriately in my portfolio.

Cool. This is a question that I'm not sure I was going to ask. And I feel like I'll probably get some emails from listeners if I don't ask it, but I'll probably also get some if I do. But are there any companies right now that you're particularly excited about?

And to be clear, this is not an investment recommendation from Brian or an endorsement by me. But if someone's sourcing ideas, are there any you want to seed out there right now? Sure. As part of the show notes, you asked me to come up with the 5 stocks that I like.

I like stepping up to the plate and swinging, but to your point, I own four of these stocks. I don't own one of them, and I'll tell you which one I don't own. But I have confidence that all these stocks will beat the market from here. But going back to the percentages we talked about earlier, history shows that when I make 10 investments, I'm wrong about half the time.

But that's OK, because the half of the time that I'm right, I do so well on just a few of them that the losses that I have and the ones that I'm wrong on are dwarfed by the gains that you get than the ones that you're right on. But to play the game, five stocks that I think are good buys right now are Roku, Pinterest, Zoom.

How's that for contrarian? Fiverr and Upstart is the fifth one. That's one that I don't own, but that is a high growth, profitable company that I'm very interested in. For the second or maybe the third time with the disclosure at the beginning to say, "This is not a recommendation." Brian is not telling anyone here to go buy these stocks, but I love playing the game.

I love hearing what's on top of your mind. Thank you. And what's fun about that is it's not hard to track ourselves. So I'll create a little spreadsheet for us right now on today's recording date. I'll put these companies in there so I actually can see how these companies do over time.

Oh, that's great. Let's make it a Google sheet. Let's make it public. I'll put it in the show notes. And even a few weeks from now when this comes out, you will be able to see how it's been done. These are multi-year investments. These aren't multi-week investments. Oh, sorry.

Sorry. I meant when this episode's out in a few weeks, people will see how it's done. But yes, don't judge them on their short nature returns. Okay, cool. Last thing on investing and then I have a couple totally different questions for you. One is on just books. People listening to this that think, "Gosh, I want to get more educated." I'd love it if you could throw out a few of your favorite resources.

They don't have to be books, they could be online. Both for people who are like, "I need to brush up." And people who are like, "What are the next level books that I should be reading if I've read the basics?" Anyway, that's interested in individual stock investing, there are a couple books I'll throw out there that I think are wonderful resources.

The first is called Warren Buffett and the Interpretation of Financial Statements. This is a book that was written by Warren Buffett's daughter-in-law, Mary Buffett. And it basically takes the three major financial statements, the income statement, the balance sheet, and the cash flow statement, and it goes through them line by line and it shows you how Warren Buffett thinks about those numbers.

So, it's a wonderful book for learning accounting and thinking through how financial statements can be turned into investment decisions. So, that one is a hidden gem. Another one is called The Little Book That Builds Wealth. That one is by Pat Dorsey. Pat Dorsey is the former head of research at Morningstar.

And that book really goes into how to think about competitive advantage in businesses and how to spot investments that have a competitive advantage. That's a very important topic that everybody needs to learn about. And the third one I'll throw out there is a fun book called 100 Baggers by Christopher Meyer.

So, that's a study of public companies that returned over their lifetime, earned investors a 100X return on their investment. It talks through some of the principles that they had in common and what investors can look for. So, those are three under-the-radar books that I think are wonderful. That's great.

Thank you for sharing those. The interesting thing I want to jump to, which has nothing to do with stock investing at all, but what reminded me of it was, I both heard you talk about it on another podcast, and I recently got an email from a listener asking about picking their mortgage.

It'll draw back to investing a little, but they said, "Gosh, if you start from a 30-year fix..." They were like, "I could make a strong argument to try to get a 15-year mortgage to pay it down faster, but I could make an equally strong argument to go for an interest-only mortgage and take all the money that I would have put in the house and invest it, which I believe will outperform the low interest rates I'm facing now." I always fall on the, let's call it, financially rational decision of, "Well, you're going to earn a higher return here, so maybe that's the path.

But I know you disagree. And so, I want to make sure a contrarian opinion makes it out here because I love giving people both sides to every story." So, what would your response be to a question like that? I love investing. I love stocks. I've earned a decent return since I started investing in the stock market, but I actually made the decision to pay off my mortgage fully aware of the math that goes into it.

So, there is a very strong mathematical argument that you should never pay off your mortgage. You should leverage it as much as possible, and you should take the difference, and you should invest it into the stock market. You'll earn a spread on the return. So, why on earth would I pay off my mortgage if I do believe that?

And it just, to me, gets back to, what's the whole point of money? Why do we invest in the first place? What's the highest use of money? The highest use of money is for us to live the life we want without my money being a financial factor. So, when I made the decision to do so, me and my wife made the decision to do so, what we asked ourselves was, "Does permanently eliminating our largest fixed monthly cost make our lives better?" Yes, it does!

By paying off my mortgage, my future expense rate is permanently lower, literally, for the rest of my life. So, I don't really care that the money would be better spent by putting it into the market. What I cared about was lowering my fixed monthly costs forever. So, that way, the future amount of money that I have to make in any given month, the amount that I need to live on, is permanently lower.

It gets back to what Morgan Housel, I think, said so brilliantly. "My financial goal is to make my finances unbreakable." I want to make myself immune to the economic cycle. I don't want to have to worry about losing my job or my family's life being disrupted at all for financial reasons.

That's why I keep a pretty sizable amount of cash out there, and that's why I also have zero debt to myself. Doing so gives me a level of freedom and allows me to think and act long-term, and really helps me to sleep at night. Knowing full well that the mathematics of that decision is unfavorable.

I would be richer today if I didn't decide to pay off my mortgage, but I would go back and do the exact same thing in a heartbeat. And just for all the credit card nerds listening, a no-debt lifestyle does not mean you don't use credit cards to earn points and cash back and then pay them off each month, correct?

Oh, yeah. I love credit card hacking. I'm a big fan of credit cards. I'm just a bigger fan of living debt-free. So, like people say that are in the travel hacking world, table stakes is no credit card debt. Table stakes is paying them off every month. I think there's a way to use credit cards responsibly to earn higher rewards, like promote.

So, yes, I also do that. I just have to throw it out there because I know there's the Dave Ramsey contingency. No debt means not even using credit cards. I don't want people to think, "Oh, Brian, this guy doesn't even believe in credit card points," because I know you play that game as well.

So, to wrap us up, I want to hear some of your local recommendations for anyone who's taking a trip to Rhode Island. Would love to hear favorite meal or someplace people should go check out to eat, a place to meet up, grab a drink with a friend, and an activity that's not the most obvious thing for anyone to do.

And take your time if you want to... Yeah. We're blessed in Rhode Island to have Providence, which has tons of great restaurants in it, no matter if you're into steak or seafood or sushi or Indian food or that kind of thing. But there's a wonderful restaurant downtown called Hemingway's, which is a perennial popular pick for seafood.

So, I would say that's a great place to get a meal. Great activity to do. Also in Providence, at night over the summer, there's something called Water Fire, which is when they take gondolas and on the little river that's downtown, they do bonfires in the middle of the river up and down them.

And it's right by Rhode Island School of Design, so RISD. So, there's all kinds of paintings and sculptures that are on display at the time. It's just a really nice way to spend the night, especially if it's a nice night out, walking along the river, watching these fires and seeing some kind of artsy things on the side of the road.

Not something that many people know about Rhode Island. And the last one was a... Grab a drink after. Like many parts of the world, we have also seen an explosion of breweries in Rhode Island. So, Rhode Island is a pretty small state and I think there's like 17 breweries in our state.

One of them that I'll give a shout out to is Tilted Barn Brewery in Exeter, Rhode Island. It's just got a wonderful atmosphere and some very tasty beers, if that's your thing. Awesome. Thank you so much for joining us on the show. I think in the last few years, there's been so much conversation about the craziness of meme stock investing and people taking wild risky bets with stock.

So, I feel like it was really a breath of fresh air to talk about stock investing and what I'll call a more civilized and rational approach than just taking crazy bets. So, thank you so much for being here. Where can people find everything you're writing and the content you're creating online?

Sure. The best place to connect with me is on Twitter. That's where I'm the most active. If you're interested in learning how to invest in individual stocks or my checklist, check out my YouTube channel, which is just my name, Brian Feraldi on YouTube. Awesome. Thank you so much for being here.

Chris, thanks so much for having me. I really hope you enjoyed this episode. Thank you so much for listening. If you haven't already left a rating and a review for the show in Apple Podcasts or Spotify, I would really appreciate it. And if you have any feedback on the show, questions for me, or just want to say hi, I'm Chris@allthehacks.com or @hutchins on Twitter.

That's it for this week. I'll see you next week. I want to tell you about another podcast I love that goes deep on all things money. That means everything from money hacks to wealth building to early retirement. It's called The Personal Finance Podcast, and it's much more about building generational wealth and spending your money on the things you value than it is about clipping coupons to save a dollar.

It's hosted by my good friend, Andrew, who truly believes that everyone in this world can build wealth and his passion and excitement are what make this show so entertaining. I know because I was a guest on the show in December, 2022. But recently I listened to an episode where Andrew shared 16 money stats that will blow your mind.

And it was so crazy to learn things like 35% of millennials are not participating in their employer's retirement plan. And that's just one of the many fascinating stats he shared. The Personal Finance Podcast has something for everyone. It's filled with so many tips and tactics and hacks to help you get better with your money and grow your wealth.

So I highly recommend you check it out. Just search for The Personal Finance Podcast on Apple Podcasts, Spotify, or wherever you listen to podcasts and enjoy.