Investing Unscripted Podcast 103: Imposter or Investor?

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Jason Hall: Hey, everybody. Welcome back to Investing Unscripted where we ask and answer the hard questions about investing. This is Jason Hall coming to you live from my hospital bed. Not really.

I'm in my office. I'm looking at the voice of the people, Jeff Santoro, my very, very good friend. Hey, buddy. 

Jeff Santoro: Hey. Yeah. You, you sound a little bit better, but not, not still a hundred percent yet. 

Jason Hall: Yeah. So you'll be hearing this episode about a week after we recorded it. We recorded two episodes close together.

I am making progress. That's true. Aren't we all Jeff?

Jeff Santoro: Foreshadowing, um, yes, we are all making progress. Yes. Both. In terms of our investing journeys and in your case, your health. We have a fun episode, a fun conversation today before we tentatively, 

Jason Hall: We're tentatively calling this one [00:02:00] Investor or imposter? Toolbox 2.0. But what you actually read on your podcast app might be completely different, right? 

Jeff Santoro: Yeah. We don't have to decide on the title for like another week. So, uh, So we're not gonna, we're not going to, you can ignore everything we just said. Let's, let's do some housekeeping Jason, before we have our little conversation here.

As always remember to reach out to us with comments or questions about the show, especially questions. Cause we hold onto them for when we do mailbags and you can do that in any way that is easiest for you. You can find us on Twitter, you can email us, you can go to our YouTube channel, you can subscribe to our newsletter at

One thing I learned, Jason, is on Spotify, there's a question and answer thing, and people occasionally leave us comments or questions. I've yet to find a way to respond to them and we have We'll just 

Jason Hall: respond to them in our, in our mailbags once a month. 

Jeff Santoro: Well, no, it was, well, I can do it right now, because it's very quick.

Someone asked us a question on, on one of our previous episodes, when we referred to, A position in our portfolios [00:03:00] by a percentage. If we're talking about that specific account or our entire portfolio. So I think that's when we can answer really quick right now. Yeah, if I, if I say a percentage of my portfolio, I'm talking about the cost basis of my entire invested wealth.

Every single investment I have other than my kids, college funds, cause I don't. I don't count that that's spent money, I'm not counting on that. Um, right. And I think you do the same thing, right? You're talking about cost basis. So for me, 

Jason Hall: if I just say a number, if I say like, here's an example, uh, Mercado Libre is a little over 5 percent of, of my portfolio, it's 5 percent position.

That means that the, the market value today is about 5 percent of my entire invested wealth. That's my family's invested wealth. That's across all of my accounts, retirement, taxable, all that kind of stuff. And that's the market value today. Occasionally, I will specify something a little bit different.

If I say cost basis, then it's the percentage of dollars that I've actually invested, right? Not the market value, but what I've actually spent to [00:04:00] acquire shares as a percentage of all of the dollars I've spent to acquire. All of the shares in all of 

Jeff Santoro: my 

Jason Hall: portfolios. 

Jeff Santoro: Yeah. Same with me. I think most of the time I talk about position sizing, it's about deciding how much to invest.

I don't talk too much about the current market value of anything that I've invested because honestly I don't have anything much to brag about. So at least in terms of dollar amounts, I have some impressive percentage returns. Like my NVIDIA position is up, I don't know, 360%, but it's. It's like, I don't know, a total of 1, 000.

It's something very, very ridiculous. Well, Jeff, 

Jason Hall: you're like a lot of other people that are, you know, similar age or just getting started. The vast majority of your wealth is still in your retirement accounts. Right. Yeah, that's why. And that kind of stuff, 

Jeff Santoro: right? Yeah. But it's, so with me, I'm usually talking about position sizing in terms of how much to invest.

So anyway, I wanted to answer that real quick. People can still feel free to leave us comments on Spotify, um, and we'll try to answer them live. I don't, unless they. [00:05:00] Put some function in to respond to them. One last thing, make this a 

Jason Hall: semi recurring segment called Jeff's question corner, 

Jeff Santoro: but we're not going to, we're not going to last thing.

If you listen to last week's episode, you heard us talk about a new thing we're doing on where we have a portfolio that we bought some stocks in and we're going to be adding to it each month. Uh, you can go back to last week's episode to hear more about it. I'm not going to rehash it all here.

But there's, we're going to have 

Jason Hall: something by the time you hear this, we'll, we'll have a, something on the newsletter too, just to write up about if you want more information. So 

Jeff Santoro: yeah, the link is in the show notes if you want to just click on it and check it out. All right. So Jason, here, here's what I, here's what we're going to talk about today.

This started with me bringing a conundrum to you and I think it'll be a fun conversation for us to have. So, and, and, and before I go into this, I'll explain it briefly, but before I do, I would really like anyone listening to share with us if they've had a similar experience, because I'm curious if this is unique to me and the way that my damaged brain works [00:06:00] or if other people feel this way too.

So I'm not going to call out any specific people or any names. But I listened to a lot of podcasts about investing and I find myself when I listen to people who are very much in the camp of you can learn to do this yourself and you should do this yourself and you can beat the market doing this yourself.

I come away from hearing those conversations very energized and excited and motivated to be the investor that I am. Someone who researches stocks and buy stocks and likes to talk about it and likes it enough to do a podcast about it. And then when I listened to. Interviews with people who are professional, like fund managers who their whole, you know, their business is to take money from wealthy investors and invest it for them and they take a fee.

And they explain their very you know, complicated sounding and in depth processes and you know, all the work and time and multiple dozens of hours a week that go into the [00:07:00] research and all that. I come away feeling like there's no way I can do this. And I know that that's not true, but it actually does it.


Jason Hall: you, you can't do what they do. It's they're, they're correct. 

Jeff Santoro: Well, I can't, they have actual certifications and degrees and experience and knowledge. Have time and experience. Yeah. So, and again, I don't come away from those conversations that saying to myself, I should stop doing what I'm doing, but it impacts me enough that it gives me pause and makes me think.

And then I start to say to myself. Well, is that just because that's the incentive structure, right? These, these fund managers, their incentive structure is this needs to sound like it's serious and professional because we want to entice people who have large amounts of money to invest it with us. We need to sound reputable, like we're working hard.

And then the people on the other side of the conversation might have incentives to make people think that they can do this themselves. And maybe they're offering a free newsletter or some sort of product for a subscription that you can, [00:08:00] you know. Pay for it to get the information that would help you do it yourself.

But it got me thinking about how that can make you feel unsettled, how it's just another layer of mindset and. temperament that I think we all deal with, whether it's what I'm talking about or whether it's how you're feeling about the market itself. So anyway, I just, I thought it was an interesting thing to kind of a different way of thinking about temperament and mindset.

I thought it'd be fun to talk through. 

Jason Hall: Well, and that's what, you know, kind of put that working title of investor or imposter in my, in my head, because, you know, I feel like what, one of the things that happens to a lot of individual investors. We get really interested in it, right? We figure we'll give it a try.

We get really interested. We maybe, we have a little bit of early success or we get, we start doing it and really kind of fall in love with it. And then we do exactly what you talked about. Start listening to podcasts, reading newsletters, reading the annual letter of, of all of the big investing pros out there.[00:09:00] 

And at some point along the way, You, you just feel like, what the hell am I even doing? Right? Particularly if that little bit of early success ends and you start to maybe struggle a little bit, then maybe the market goes down. You have a couple of bad investments that don't go well. And you do start to question yourself, right?

And we know imposter syndrome is real. It's normal. Everybody goes through it. No matter how qualified you are to do something, it's pretty normal. When you start doing something new, you, you get past that initial excitement and you, Start to have to work at a little bit harder and, and you start to question if what you're doing is real.

I'll say this too, kind of about a couple of things before we kind of get into the meat of it, because Jeff, what you and I wanted to focus on is really kind of getting back to some of the basics, right? Talk about. Our own investing history is how we've evolved a little bit. We're going to ask each other some questions there, but we're also going to talk about the importance of setting goals and like really understanding what you're actually trying to do.

What are you trying to solve for? What are your aspirations? And because aspirations aren't [00:10:00] goals, right? Then to start thinking about Applying all of those things to yourself to optimize for who you are, right. And how you think and how you operate and leverage all the tools available to you. But before we talk about that, what I wanted to point out is a couple of things about like the differences between the investing pros out there and your average individual investor and some important advantages that we have.

And we'll talk about it more as we go through the show. But number one, I think you're absolutely right. If you're somebody running a website helping retail individual investors pick stocks. Your incentives are to show people the easy way to be successful, right? And you want it, you want to promote that.

It's just you're wired to, it's your incentive, right? I encourage people to go back and listen to our goals and incentives episode that we did pretty early in in, in, in our, in our run. It talks about the difference between how incentives can affect you. And you get, you think about an investing [00:11:00] professional.

Number one, they do things that are very complicated and difficult and challenging. So they're not lying when they say what we do is sophisticated and in depth and challenging, but their incentive is to make sure that people like you said that have lots of money. Want to give that money to them to invest, right?

So naturally they're going to do everything they can to make it seem like that. They're pride proprietary Whatever, you know, they're doing is worth paying for and you need to pay us to do it, right? That's very very true, but they're also being honest, right? I think there's more to it too. And that's what they might be doing what they might be trying to achieve You Might have absolutely nothing to do with what Jeff Santoro or Jason Hall, the individual investor is trying to do to, to try and to accomplish, right?

Our goal is right now we're trying to create wealth while managing [00:12:00] through the market's volatility and not creating too much risk of permanent loss. When you have people with very large amounts of money, Sometimes they're just trying to do simple things like keep as much of that money and minimize their tax exposure as they can.

And they're not trying to beat the S and P 500 or whatever, right? They have very different goals around their money. Then, then you or I might have, and they're playing a different game, right? They are absolutely playing a different game. I was teasing you when I said you definitely couldn't do what they do.

But the beauty Jeff is we don't have to, right? 

Jeff Santoro: And I think that's, I think that's where I've come down for myself. When I hear interviews with people like that, I try to. Listen to it with a specific lens of, let me see if there's anything in here that I can pick up on, even if it's just, you know, like a little strategy or like a, where, where this guy looks for, or this person looks for ideas or something like that.

But I have to kind of remind myself, like, I don't need to replicate. This 80 hour work week where this [00:13:00] person is reading eight hours a day. I don't need to replicate that to do what I need to do. I think that's the distinction I have to, I've kind of forced myself to make. You know, it gets back to, it's another idea I've had maybe for another show about like, we're all just a conglomeration of all the things we've heard other people.

Say so I, I try to just listen to those types of interviews and podcasts and things and take what I can to make it helpful for me. And I think that's kind of what we're going to talk about here. The other thing that got me thinking was. And I think, you know, I, I'd like to, I'd like for us to dive in to like our origin stories a little bit differently than we have in the past, like not so much the elevator pitch of how we got here, but more like what were our earliest understandings of investing?

Because I was thinking about mine and I, I think the, cause here's something I think I tried, I think about a lot. Why did I at age 40 over the course of six months. Go from literally [00:14:00] having never given a second thought to investing to being absolutely a thousand percent obsessed with it to the point where like when I would like run into people or if I see people now who haven't talked to in five or six years and I, you know, how you doing?

What are you up to? And this comes up. They're like, they have, they're like, they have no idea like what, how to even respond. 

Jason Hall: It's like you converted to a weird religion. 

Jeff Santoro: Yes, yes. It's all, it's that weird, right? Yeah. And I think part of it is that, cause I, you know, It makes sense in one way, because I've always been very OCD and anal retentive about, like, my personal finances.

Like, I was, I, like, was using Quicken when I was, like, eight, nineteen. In college, I was like balancing my checkbook to the penny, right? What a weirdo. 

Jason Hall: Right? I cannot, I cannot relate to like, what is the inverse of relating to something? That's what I'm, 

Jeff Santoro: but it's just, it's that, so like I do have it in me to like care about that stuff.

Jason Hall: Yeah. 

Jeff Santoro: I think as I think about it, I think the reason it took me so long to sort of make that switch [00:15:00] over into investing is because it was 2020. And it's a, it's the world of internet and Twitter exists and websites like the Motley Fool exist, and people have free newsletters and podcasts. When I was When I was 19 or 20 years old, I would get, you know, the statement for my, whatever Franklin Templeton fund that my mom had started for me with some inheritance money.

I think it was just a mutual fund in there. I had, I would just, it was just gobbledygook on a piece of paper with some numbers. I had no idea what it meant. And there was nowhere to go to get that information. Like there wasn't even really. A good internet, like that 

Jason Hall: weird channel with the numbers that ran across the bottom that you like went past as quickly as you could to get to the sports channel.

Right? Right. 

Jeff Santoro: Yeah. I feel like if I had been born 20 years later, I probably would have been. really into investing when I was like 19. And I think that's the, the reason I bring that up [00:16:00] is I think that's a microcosm. That's like an example of, I didn't have any choice back then. It was like, all that was out there was the super, you know, you know, the, the suit wearing wall street You know, you must have a lot of money and you must give it to me and I'll tell you what to do, you know?

They're the whole thing. Like I got a guy, you know that whole thing, right? And now there's obviously way more options Because like I had no I had no idea about any of that and I think it was hard to go get that information So, I don't know. I'm curious if you I you know We've told the story about how you would were really bad with your money in your 20s and stuff But I'm curious when I 

Jason Hall: encourage people to episode 10.

Yeah You That was our original origin stories. It's like a 20 minute episode too. It's pretty quick. People want to get here more about how Jeff and Jason became who we are now. But I'll say this, you know, you and I've had this conversation, um, offline a lot of times and talked about our history and one thing I want to talk, of course, I'm going to describe you like I always do this with people.

It's [00:17:00] weird. You're an educator and a musician. And you grew up in a family of musicians and educators, right? So you, you, we've talked about it. Like you, you, you, Didn't grow up with people that were working in commercial enterprises and businesses that might've been more exposed to that and then exposed you to it.

And the interesting thing to me about that, Jeff, is that that's actually kind of similar to a lot of my background. So my mom on a picture framing shop when I was a kid, um, and you think, well, Hey, there's a entrepreneurial. driven person. It was true, but it was one of those really small businesses where basically she just owned a job sort of thing.

So there was no time to really do anything. And I just saw her struggle, right? I just saw that, that struggle to manage costs and still pay the bills. Uh, my folks split up when I was young. I was like five. My dad was largely a civil servant. Most of, most of my life that I remember, he worked as a carpenter in the early eighties when the economy was terrible.

And then he got into the civil service and [00:18:00] was a postman. He retired from the post office. His wife, my still my step mom, she's been part of my life for almost 40 years at this point. She's a teacher. So similar background, the people that I was around, my, you know, the parents, my parents my grandparents were both civil servants too.

So same thing. I never really got that exposure. It's funny. We were talking about it. Yesterday I remember the, I think it was in sophomore year, the economics class where they did the stock picking thing where everybody picks a stock. I remember picking IBM. That's all I remember. I don't remember anything else from that.

But then where you and I, like our paths kind of diverge, you stayed in education. I went into kind of more business world, started getting more exposure to people who were investing and buying stocks and that kind of thing and kind of got that more natural exposure to it earlier than you did. But while you were Super well organized and smart about managing your [00:19:00] financial life.

I was an utter and complete disaster with money. Money is feelings for so many people. And I just felt like spending my money as soon as I got it. I was terrible at managing my money was so incredibly fortunate that my wife was with me for so much of those years before we, um, even got married and helped me kind of grow up.

And it was in, you know, it was in my thirties, early thirties that it was right around the time I turned 30 that I realized I have nothing. I have to get it together. And found socks. So we've talked about my experience. 

Jeff Santoro: Well, so let me ask about that because it, I'm curious if your experience. In your thirties, because now that's, you know, I just keep, I keep anchoring to like my late teens, early twenties, right?

When I was like getting towards the end of college, graduating college, starting working at as like my, cause you know, you, you, you only think about money as like a early teenager in terms of like, I have a summer job so that I can spend money. Like that's, I think that most kids think about it. Right. So the point [00:20:00] I was making about like, you know, early two thousands being overwhelmed by.

Like the intimidation factor of like understanding investing. Did you feel that it was any different? Cause you were like a decade ahead of me as you like started to maybe pay closer attention, even if it was a different, in a different way than I was when I was in my twenties, like that decade of difference might've made it easier for you to find the, you can do it yourself path, if that makes any sense.

Jason Hall: Oh, there's no doubt about that. I think there's a couple parts of it. One part was The, the, the last job that I did my career, I was in outside sales before I began full time investing and writing and all of, all of those things related to investing. I was mostly dealing with a lot of business owners directly or people that reported to the owner of a company.

So I dealt with a lot of people that had like a business ownership mindset. And I think that really set me up incredibly well when it came to like investing [00:21:00] in stocks, like to have that mentality that you're becoming a part owner of the business. And I just tried to keep things really simple. Of course, I was lucky to find the Motley Fool too at the time that it was like, let's, they're doing a ton of pre vetting work to like, help me, help me avoid stupid stuff.

And really fed into like the way I was already kind of leaning the way I was wired. But I never felt overwhelmed or challenged from that perspective. I just felt like I could do anything. Fast forward two years into my investing career and yeah, I felt like an absolute loser. Went through the double dip recession.

The market didn't do very well. It seemed like every stock I bought fell. And a lot of things we're about to talk about, kind of the core part of the conversation, like really getting back to basics, focusing on goals, building frameworks and thinking about managing yourself. Luckily, I found a lot of those things then or else, you know, I could have [00:22:00] compounded what felt like mistakes by actually making 

Jeff Santoro: mistakes.

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So that's, That's a question I have for you. Like what we talk a lot on the podcast about having tools in your toolbox. And hopefully if we're doing our job, we're helping other people, you know, add to their toolbox as, as we talk about things, I'm curious, did you have anything in your toolbox when you.

Like, let's forget your twenties, we know you had your toolbox is empty in your twenties. But when you, when you first, it was just 

Jason Hall: one giant tool and it was 

Jeff Santoro: me,

you said it, not me. But like using the point where you said, all right, I got to get my act together as like your. You're, you know, right. Jason took around zero, right? What what tools did you have initially? Like, was there anything you didn't have to go learn? Like, were you wired with any or you given any tools innately that you felt like you could use when you first started investing?

Jason Hall: So it gets back to my professional experience and training. The, the job that I was doing was primarily studying businesses. [00:24:00] Trying to understand what they're, what they're trying to solve or what was the opportunity that they were trying to pursue, help them to develop process, acquire the technology, integrate it, operate it to achieve whatever their financial goals were.

Right. So like I was actually doing business analysis before I really fully understood what it was. And that turned out to be incredibly valuable when it comes to studying companies, right. Stocks, reading filings and that kind of stuff. Now, where it was different is. My goal was to sell something to somebody.

Right. So I was looking for those things from the perspective of trying to find a way to present whatever it was I was offering in a way that was going to appeal to whatever their fear and greed was. So those, those again, find, figure out what their incentives are and appeal to those things. And that's, and that, and what I hadn't really fully understood was like, Inverting that and thinking about it within like, uh, the, the, the context of the decisions I was going to be making to buy and sell [00:25:00] stocks.

How was, how was my internal wiring? How was I going to react to what that stock did based on that buyer sell? So I didn't have. Like besides the basic tools of understanding that you're buying businesses and the focus is owning them for the long term. And then having at least at that point, the realization that I'm 30 years away from needing to touch any of this money, making it easier to kind of hold.

You know, I didn't really have a whole lot of tools at that point besides that 

Jeff Santoro: so one of the things. I know we wanted to talk about in this episode and that we've talked about a lot previously is the idea of having goals. We did a whole, like you mentioned it earlier, a whole episode on goals versus incentives.

And I'm curious when you started investing, did you really have a goal, a longterm goal or was it more, it was the only goal just basically like I'm a mess and I need to figure this out. Like, I'm curious when it occurred to you that you need to, you know, you do need to set like a specific longterm goal, whatever it is like, okay, I want to be able to retire at.[00:26:00] 

65 and live comfortably like did that form early on or was that something that came? And I think that's something a lot of people probably struggle with. I know for me, like, I guess I subconsciously had a goal when I was in my early twenties and I set up my retirement account. Like I, I knew what that was for.

It's called a retirement account for God's sakes. But I don't know that I, Ever gave it much more thought than that. 

Jason Hall: Oh, it was buy stocks that go up. I mean, that was, that's where I was. Yeah. Also you got to remember during that period of time, interest rates were so low and then would stay low for the next decade is that I was very bond averse.

Like a lot of people kind of still are because the lack of yield and just very much married to the idea that stocks are it, this is it invest in. So you want to create wealth as an buy stocks, right? That's the way to do it. Which frankly is not healthy and it's very limiting because you're limiting the number of tools that like, so besides you have the skills, right?

We talked about a little bit of tools, but [00:27:00] also the actual tools, stocks, bonds, real estate, cash, all that stuff, right? I was immediately limiting the, the things that I could use to try to create and preserve wealth from the very, very beginning. So 

Jeff Santoro: what's your, what is your take on having more than one goal?

Here's why I'm asking this question. So one of the things, one of the things I did when I was new, like new to investing in like 2020 and figuring all this out, I didn't even have a brokerage account. So I was opening accounts and figuring things out and I was intrigued by the robo investors. So I actually had an account at betterment.

Okay. And it was cool. Like I actually liked it. I think it's a good product. I think for certain people, it could actually be a really good option, especially for getting started. But one of the things I noticed was you could set up just a regular old, you know, you're, you could set a goal when you create the account and you could set the goal of retirement, right?

And you would put in your age and all that kind of stuff. But you could also make a goal for a whole bunch of other stuff, buying a car, buying a house, going on a vacation. [00:28:00] And I know I was late to investing, but I was not. naive, and I understood that if you're going to put a whole bunch of money into stocks, and it was all ETFs, but still it's stocks and have a goal of like next summer's vacation, that probably isn't smart because there's no guarantee that the market's going to not crash between now and next summer's vacation.

But exactly. But I also have heard You know, very successful investors who I admire say things like, Oh, I sold some of my Apple stock so I could pay for college for my kids because they've owned Apple for 35 years. And there's probably a big chunk of money, right? I'm curious if you have or had or what you think about having multiple goals, like, so the very long term goal of investing for retirement, but then also not near term goals like next summer's vacation, the goal of 10 years from now, I want to take a really nice vacation or 15 years from now, I want to buy a.

beach house. Like what's your take on multiple, multiple goals? 

Jason Hall: So I think it's yes. But because [00:29:00] it's the sort of thing that you have to, I think for most people, you have to be careful to not make it too complicated by having so many different goals that you're trying to manage too. But at the same time, you The goal itself, like the thing, like the payoff, retirement, the boat, the kids college, and the payoff there is they're out of your house.

Um, by the way, if anybody was wondering but no, it's, it's, that's, that, that doesn't matter. I mean, it's a goal, right? It's a thing. It's the flag on the green at the golf course. Right. So it's, It gives you some incentive, right? It helps keep you kind of focused on it. But I don't really think about goals so much as the, what is the win?

Because that's where you can actually use it to make sure you're applying the right tools and you're not for me. So I don't perform self forced errors, right? Uh, so for example my son is still in early, early elementary school for his college savings. It's still enough time that exposure to stocks is [00:30:00] not risk.

Right. It's, it's the best way to generate wealth to, to grow the value of that assets. But sometime in the next five years, five to seven years. That's going to change where the risk of a financial crisis pandemic, those are extreme risks, but even just the, the bear market of 2022, right. That we saw is substantial enough that all of a sudden you could lose a year of college money if you're a hundred percent in stocks and the market won't recover in time to cover it.

And then you make that second error, which is you double down, right. To try to ride it back up. It doesn't come back up or whatever. Right. So the, the, the, the win is so important because it makes sure that you apply the right tools and start de-risking based on volatility, risk and single company risk and like all of that kind of thing when it comes to stocks.

So yeah, I, I definitely use it, but not in [00:31:00] like, I, I don't cut it into a hundred different pieces. It's like, what's more than 10 years from now? What's less than five years from now? What's kind of in between? So, so, and I think for most people, something like that probably makes sense. Now for somebody like you, I could see you being incredibly nuanced 

Jeff Santoro: with this.

Yeah, but I'm not, I mean, I have, I have my kids retirement. I mean, sorry, I have my kids college funds. I have five 29s for them, but those are just in target date funds. So I don't really have to worry about the de risking part. That'll do it for you. Yeah. I think if I were going back in time and, or if I could, you know, go talk to 20 year old me, 

Jason Hall: yeah, 

Jeff Santoro: I might.

I might say to myself, like, okay, I'm going to put some money into some stocks and for a down payment on a house, you know, whenever I get married and want to buy a house, right? Because if I did that when I was 19, I would have had whatever, 5, years before that was a thing. I don't know, I would still probably have been worried that like, Right before I [00:32:00] want to put that down payment on the market crashes and I lose 20 percent of my down payment money Right, and I'm at the point now where the only like long term financial goals I have are really just to pay for my kids college and to retire like I don't want to buy a boat I don't need a beach house So like now I'm sort of the way I look at it is I'm investing for retirement in a combination of my retirement accounts, you know, and my IRA and the things I can't access till I'm 59 and a half and also some in my brokerage.

And I'm kind of just looking at my brokerage account as who knows if I'm lucky to be at a point at, at, at some moment in time where There's an option to sell some of those stocks to pay for a big thing. Cool. Like icing on the cake, you know, like maybe it's 

Jason Hall: excess wealth, right? I can pay for a little 

Jeff Santoro: more college and take out a little less debt or something like that, you know, like, but I think 

Jason Hall: if there was a single sentence, Jeff, that, that I've, that I use for this and I've heard it from other people and really it kind of talks about risk, [00:33:00] but I think it's a perfect way to think about defining your goals.

And that is a goal is something that. Prevents you from risking something you can't afford to lose to gain something that you don't need. 

Jeff Santoro: Yeah, that's a good way to put it.

Hey everybody, we'll be right back, but first, a word from our sponsors. Earlier in the show, you heard us talk about investing platform That's where you can trade options with no commissions or per contract fees, and you get a rebate of up to 18 cents per contract traded. NerdWallet recently gave Public five out of five stars for options trading.

If you want to see why, go to and start getting a rebate of up to 18 cents per contract traded. Paid for by Public Investing, options not suitable for all investors and carry significant risk. Full disclosures and podcast description, US members only. All right, so pulling it back to the whole like imposter or investor kind of framework. I think, I think one of the biggest things you can do for yourself to beat the imposter syndrome is sort of the same thing you can do.[00:34:00] 

To fight all of the other mindset things as it relates to individual stocks, right? So I think a challenging thing is a stock you own drops 30%, right? That's a challenging thing. You have to figure out why you have to decide if it's just the market being crazy or if it's an actual fundamental flaw with the business.

And I think you can have that same sort of feeling of the market dropping 30 percent when you start to question your own ability as, as an investor, um, as a stock picker specifically. So I'm curious, I want to have a conversation about temperament mindset and how, how that has evolved for you over time.

Like what's something that you've gotten much better at as it pertains to that. And maybe what's something that you still have a lot of work to do with mindset. 

Jason Hall: I've talked about my rule around cash before and how that's evolved and that's certainly applied to it. I think to me when it comes to temperament, this is who you are, right?

And over time, this is something that we, I think we can improve as an investors just because with anything is you gain [00:35:00] skill and experience and you understand it more, you're, you don't change your temperament, but you, your temperament. doesn't drive you anymore. Again, it gets back to fear and greed, right?

If you're the kind of person that's very risk averse when it comes to loss and you're just starting out as an investor and maybe you've read that, you know, stocks fall 10 percent once a year, 20 percent every five years and every, you know, 15 years or so, we'll get a 30 percent sell off. Like you've read that before, intellectually, you understand it, but it's a very different thing to go through it.

Right. And if you're very, very risk averse, even though you might know that then going through it, your ability to actually operate through that without screwing yourself by locking in those losses by selling is a completely different thing. And so my, I don't think my temperament has really changed, but because I've become so much more experienced as an investor and I inoculate a lot of the fear through [00:36:00] understanding what I own, the puts and takes of the markets those companies operate in, the risks the companies face, their competitors, like all of those parts of like understanding what you own, that has helped me more when it comes to like.

Pushing back against the, the, the bad things about the way I'm wired than anything else. And it's helped me have a better mindset, right? Because of that. The other part of it though, is again, because I am wired that like when the market sells, I've never really been like, uh, I'm going to sell because the stock has fallen and I'm afraid it's going to fall more.

But what I will do is I'll sell half my best stock because this other stock has fallen 30 percent and I see a great opportunity to buy more of that one, right? So I'm going to, I'm going to trim the flowers to what are the weeds. So I've, I've, that's one of the things like with building up cash and holding that's helped me to like deal with that part of my temperament because it gives me money.

To put to work to not mess with my investments, right? And [00:37:00] harm and commit self harm. So I think that's probably the biggest thing that I've evolved is, uh, something that kind of keep me from committing self harm, um, in my own portfolio. And that's really the core of my holy cash. What about you? 

Jeff Santoro: Well, I was going to, I'll, I'll answer that in a second, but it, what you just said reminds me of, it's kind of related to note, being able to know yourself both as a person, but also as an investor.

And I think you bring up a really good point. It's impossible to ignore the feelings you have. About the market and about individual stocks like and I don't think you should pretend like you you know you don't feel the things but reacting to the things is is different and that comes with experience and knowledge and Honestly having people to like either listen to or talk to about it.

So you don't feel like you're on an island and so I think Yeah, I, I think for me, being a contrarian by nature has helped. I, I like to think that I'm pretty resilient to, like, falling for someone's [00:38:00] B. S. Um, you know, I, I'm a believer of the, if things are too good to be true, they probably are, and that there's always a catch, and I like to, I like to have, like, fun, hard, you know, lighthearted arguments with people where I just, you know, Take the other side of the argument for like intellectual enjoyment, I'm a little bit predisposition like that when now that's how I am now it at age 44 when I was 24 I was just stubborn and bull and bullheaded and thought I knew more than I did and was probably a little bit of a jerk And I bet you 

Jason Hall: were insufferable.

Jeff Santoro: Maybe I might still be. If you ask, if you ask certain people like those who live with me. But I think so for me again, it's not like, I think the thing that I've changed is almost similar to you is like, how do I harness those things I just described to help me? Help, help me prevent myself from hurting myself.

You know, it's like the thing I've said before, I, you know, everyone's an idiot as sort of just like a filter. So you don't get caught up in FOMO and, [00:39:00] you know, I have to have this thing because everyone else has this thing. Now, again, I feel all those feelings. And, and I am impulsive at certain times. In fact, I was very impulsive in certain ways with my money when I was younger, too.

I, I was, I was very likely to like not spend money on anything that normal people would spend money on, but like really, really want a new car every five years. Like that was, that was the way I was with my money. I didn't buy a lot of little things 

Jason Hall: you do to save 2 here and 5 there. You would immediately waste substantially more buying a new car.

Correct. Yeah. Five years. 

Jeff Santoro: And so that's wonderful. I love knowing that about you. Yeah. But, but, but again, like, I've, I've, I think I've gotten better with that as time has gone on. But I, again, I'm getting the point I'm trying to get at is like, those are all things I know about myself now. And I think just being aware of those things has helped me make some maybe mistakes.

with the investing stuff. And also I think has given me to some degree, some confidence [00:40:00] to be a self managing, you know, self managing of my, of my investments and making decisions and things like that. Well, Jeff, 

Jason Hall: there's the, there's the saying that talking about wealth and, and, and booze they don't change who you are.

They, they show who you are, right? And I think that's important when it comes to like knowing yourself is important too, because I don't think we necessarily change. I think we just become more of who we are, right? We kind of distill down. And it's important as an investor that you really internalize that.

And that you build your framework around, I'm, I'm such a firm believer that the framework that we talk about a lot. It's so much more about optimizing for yourself than it is about optimizing for anything else. 

Jeff Santoro: Yeah. And it's, it's funny, like I have, I have this sort of soft rule that I'm trying to force myself to follow this, this year where I'm, I'm trying not to sell anything in 2024.

I've said this on the podcast [00:41:00] several times, I'm going to try to just not sell any stocks for this entire year. And I'm glad I sort of set that benchmark for myself. And this is, this is about me knowing myself because. I will, in the absence of that, I will justify selling something even, even though I probably shouldn't.

And I hesitate to call it a rule because if something comes up where like I really, really. I feel like I should sell something. I'm not going to prevent myself from doing it, but I've already caught myself on several occasions having that like thought and then being like, Nope, don't even waste time on it.

Move on because you're not selling that thing. Um, and it makes me think that like, that's something that I've. learned over the last couple years is how to have, and this is something I learned from you, like the whole idea of like frameworks help you think rules tell you what to do. Like, this is sort of just like a framework I'm trying.

That's kind of how I'm thinking of it. And it feels less oppressive than a rule. But I, I think that's another another kind of trick. To, for people who maybe struggle with some of the temperament and mindset stuff is sort of [00:42:00] set these soft rules or frameworks up and just try to stick to them.

Because even if you, even if you don't stick to it two out of every 10 times, those eight times you did stick to it are learning experiences. That's what I have found. So anyway, just that popped into my head based on what you said. So. All right, so as we kind of wrap the conversation here, and speaking about like frameworks and processes, do you ever think that the frameworks can get in the way?

Like, do you ever feel like it's not a good thing to have a framework or a process in place? Or is that not the right question to ask? Does it depend on? You as a person, 

Jason Hall: I think the framework should get in the way. There's a good chance. If the framework is frustrating you, it's working because you're frustrated for emotional reasons.

And one of the things that a good framework should do is help you get past whatever emotion is affecting you and driving you to make that action and try to find a little more objectivity, right? We're [00:43:00] never truly objective. You can't be right. We have too many biases and too many incentives. Tied to the decisions we're making to really act objectively.

So I think broadly no, but, and the but is there's plenty of, you know, junk in junk out. If your framework is arbitrary and it's based on something you read that you think you should do, or something you heard me or Jeff say that we're doing and you're doing it because we're doing it, not because it necessarily applies to you.

They could certainly be limiting. You know, there's no doubt about that whatsoever. But I think broadly, , if you're operating within a framework that you've built, that's based around helping you more quickly do the things that you're good at and making it harder for you to do the things that can be detrimental. Then you might be frustrated with that process sometimes, but if you look back in five years, it's, it's going to have probably worked out to your advantage.

Jeff Santoro: I agree. And I, even though I'm the one who asked that question, I was answering it in my head while you were talking. And I think I, I agree with what you said, but I would also add this. I think you, you should [00:44:00] also, when you're frustrated by the framework, be thinking about how to change it or tweak it.

Because I think the idea of changing a framework or a process you have in place is a lot more important. intentional and purposeful than just changing your mind about a decision. cause I think about the frameworks and processes that I have in place for what I do and how much they've changed. Just in the past couple years, like I've always had something, but that something was very different in 2020 than it was in 2021 Then it was in 2022 then what it is now and it'll probably be different a year or two from now But every time I've made a change it's been because I've thought about the process and the framework and not just thought about the decision and So I think you're right.

It should if it's frustrating you it's probably working, but I also think It's good to be open minded that it should change over time and you shouldn't try to do what anyone else does. That's one thing I find myself [00:45:00] doing. I hear someone say something like, Oh, this is what I do and blah, blah, blah. And I'm like, Oh, I wish I could be that person.

But then I realized I'm not like I've talked about journaling before, right? The amount of times I've opened a doc with the intention of writing something down about my decisions that I just don't do it. 

Jason Hall: You're not a journal. You're a spreadsheetist.. 

Jeff Santoro: Yeah, I think that is my journaling. Actually, not as I think about it.

Um, I think 

Jason Hall: it serves the same purpose for you and probably better. 

Jeff Santoro: Well, yes, yes, no, yes. And no, because here's what I don't keep track of that. I think actually would be helpful, which is like what my when you act 

Jason Hall: and why and that kind of thing, 

Jeff Santoro: like what my, what my thinking was at the time. Yeah. Right.

Like I, I can, I can say to myself, I remember that I was thinking about buying this stock back in the. Winter. And I didn't. Right. And I might misremember or just not remember the reason why. Sometimes I can recreate it if I go back to the spreadsheet and see, and I'm like, Oh yeah, that's right. I remember it was because of this.

Anyway. All right. Any closing thoughts as we, [00:46:00] uh, wrap the conversation here? 

Jason Hall: Yeah. I just, I think I want to talk about that kind of evolving part again. I, again, I don't think people really change. I just think you become more who you are. You kind of distill down. And I think it's really important. That's just one thing I've learned a ton is like, I've.

I've certainly had to evolve how I invest to a certain degree here. And part of it for me is just my wealth has grown. I've, I've been fortunate enough to be successful and shifting from that, you know, just, just investing new and growing your wealth and really trying to also think about uh, what's the word I'm looking for here?

Wealth preservation, you know, things like that. Changes, but I think you also, it's, it's easy to forget. Sometimes it, your tools need to change too and not fall too in love with what works because this is a really, . So Ben Carlson has talked about that, you know, the skills to, Get rich are very different than the skills to stay rich. Right. The stories of people that have [00:47:00] created a fortune and lost it all, created another fortune and lost it all again are more than you would imagine.

So I think it's really important to, to, to remember that and, and, That your process has to evolve more fully than just a framework and just doing what you've done and keep doing it. Yeah. That usually works, but at some point you have to also think about the tools you're using. But I think the point is that, As we reach these goals, not falling in love with just doing what we've done, but be thoughtful about changing our entire process over time to make sure we keep those goals in mind.

But really be mindful and really be mindful of that. 

Jeff Santoro: Yeah, I agree. And I, I think I would say just in closing that the biggest thing that has helped me fight the whole like imposter syndrome thing, is just having other people to listen to if it's a podcast or read about if it's an article or talk to if it's a friend of mine.

And I hope 

Jason Hall: then, and then thinking in your head, they must be an idiot 

Jeff Santoro: because everyone's an idiot, right? [00:48:00] Um, no, but I, and, and I hope that, I mean, this was sort of like a wide ranging conversation that we wanted to be very organic and organic. Not planned, unscripted, if you will but I, I hope that it's a, it's illustrative of the fact that everyone has these thoughts, I think, and it's good to kind of just talk through stuff and make sure that you're staying motivated to, to do the things you need to do to, to reach the goals that you have set.


Jason Hall: hey, Jeff, let's, uh, let's take a little break and then let's. Talk about the portfolio contest. We just finished a month. Let's do it.

Hey, Jeff, it's we're recording this May 1st. So we are, uh, we're due for an update for 2024 Investing Unscripted portfolio contest 

Jeff Santoro: hot off the presses spreadsheet updated this morning before the market opened.

So as a reminder, we're doing just very brief updates every month on the B section of our podcast, we do full wrap ups every quarter. And that's where we talk about [00:49:00] who won and who we give money to for the charity part of this. So I did the spreadsheet this morning and. Once again, 

Jason Hall: can I say this?

Can I say this part? 

Jeff Santoro: Yeah, go ahead. 

Jason Hall: It's Mitch 

Jeff Santoro: Fatale's world. We're just living in it. That's right. For the third month out of the past four stand up comedian Mitch Fatale has, uh, won the month. He had the highest return of his stocks from April 1st to April 30th at 7%, uh, as an average for his six stocks, five stocks.

And. So this will be an interesting one to follow throughout the rest of the year, because it was always interesting because one of his stocks is just a penny stock that we're curious to see where it goes, but it's actually been pretty good for him so far. But what's really interesting is that one of his stocks, Shockwave Medical, is being acquired as long as it goes through regulatory approval by Johnson and Johnson.

So it only was up 3 percent in the month of [00:50:00] April. 

Jason Hall: Cause those, those gains are basically locked in. 

Jeff Santoro: Right. So I would anticipate for as long as it remains a standalone company throughout the rest of this year, it won't be. See much of a dip or pop, right? It'll stay around zero percent. If, if the market feels like this deal is going to go through, then the stock's going to stay around the price of the deal.

Jason Hall: But from the beginning of the year, that stock's up 73%. So I think any of us would take 

Jeff Santoro: yes, 

Jason Hall: a stock if he locks in a seven year, 

Jeff Santoro: right? Right. But, but, but those gains will, will theoretically be locked there. Like, and that's good, but it'll just be interesting to see how that impacts Mitch's, uh, overall performance for the rest of the, for the rest of the year.

So we've never had this happen. So I, I'm assuming that it is, is the first buyout. Yeah. So at whatever month, if it, if it even happens in 2024, I didn't look it up. I don't know when they're expecting it to happen sometimes. Sometimes these things can take longer than you would expect. But anyway, at whatever point it leaves the public markets, as it gets acquired by J and [00:51:00] J, that'll be, it'll just, it'll stay on his scorecard, so to speak, locked in at that Dollar amount.

And then we'll just take it from there. The other, I'm thinking 

Jason Hall: about nobody else that picked shockwave. He was the only person that, 

Jeff Santoro: yeah, he's the only one who has that, that stock. So the market itself, the S and P 500 was down just under 4 percent in the month of April. So as you would imagine, a lot of the stocks in the portfolio, a lot of the portfolios in our little contest here were also down.

I counted, I think 10 or 11 of the portfolios actually still beat the market. Yeah. In April, which was encouraging. But I'm curious if you had any other. wide ranging thoughts as you look through the results here for the month of April. 

Jason Hall: I continue to suck. I'm so glad you said 

Jeff Santoro: it. 

Jason Hall: Right, right. I had to beat you to the punch, but you know what?

Jeff Santoro: I sucked less than you. You did. Yeah, you had a better April than, than I did. You had a better April than some other people did. I think what's interesting to me, When we talked about this after Q1, I believe one of the questions we asked each other was who, whose [00:52:00] portfolio did we think had the best chance of, of winning for the whole year?

And I picked Nick and Casey Rosalillo, which with their semiconductor heavy basket of stocks, but they had a rough April. And interestingly enough, even the, even Nvidia was down 4%. in the month of April. So because their entire portfolio is semiconductor related stocks, and because all of them, with the exception of one, were down for the month.

A question I have for you, Jason is, yeah, is this a blip? Or do you think? The air is coming out of the semiconductor bubble just a little bit. 

Jason Hall: I don't think it is. I mean, maybe a little, but like in thinking about looking at their portfolio, you've besides NVIDIA and TSMC A lot of the other semiconductor stocks they own, they're, they're still, they're not like AI chip companies, right?

So the semiconductor industry is still in a little bit of a cyclical week period. So I think sure, as much as there might be a [00:53:00] couple of theirs that might underperform based on, you know, if AI investment starts to slow in the second half of the year or something like that, I think broadly, no, because the cycle is starting to turn smartphone units are better.

If PC units start to pick up industrial activity starts to pick up, I think this, that portfolio could still do very, very well. I really do. So, 

Jeff Santoro: all right. What about your stocks other than being absolute trash garbage? I'm curious if, if you have any, anything to say about any of the stocks in your, I look, this is just a one month thing.

So you don't need to go too crazy, but, um, this is also, I should say one more thing. This is also a month where. almost none of these companies had any substantial news. Right. You know, 

Jason Hall: there's a little before earnings, little before earnings 

Jeff Santoro: and, and after the last quarter, obviously. So, 

Jason Hall: Yeah, I mean, probably I talked about this a little bit when we did the quarterly thing, but I think the big thing for me is thinking about renewables with, you know, TPI composites and in phase.

When the cycle turns there, [00:54:00] those two could just be huge winners at the second half of the year and we started to see a little bit of a bottom with solar from what in phase reported with. Their units and expectations for their next quarter. And TPI, I think was actually set was second best for me stock.

Cause outset, as we mentioned last week's episode, got an upgrade. So that stock went up but TPI. Okay. Things are happening there. I mean, that's really it. It's just, to me, it's just so much bottom feeding, waiting for things to turn for these companies. Last point, this is more than you wanted me to say, but that's what I do.

It does. So far, I'm just, I'm. Absolutely befuddled with SoFi. Sure, their guidance wasn't super perfect, but like all their financial results were better than they said. And they raised some of their expectations around profitability. And the market has absolutely punished that stock so much over the past, you know, few market days since they reported earnings.

Jeff Santoro: I don't know so far very [00:55:00] well, but my assumption would be, and you can tell me if I'm wrong about that. Is it one of those situations where it's priced to perfection? So any kind of little blip or is it actually not? No. 

Jason Hall: Okay. No. It's like at this point you're talking like probably, I don't know, 12 times next year's earnings.

Jeff Santoro: Well, so the thing I wonder about end phase, just going back to that for a second is, is You know, one of the things that did happen this month was, and I think it's what drove the market's bad performance for the whole month, was a realization that maybe interest rates don't come down as soon as we thought they were, you know, the, the forecasts have gone from six rate cuts in 2024 to like maybe two and a company like Enphase, which is pretty struggling because with higher interest rates, customers who would have financed solar roofs are now not doing that.

I wonder if some of what they're struggling through is just market sentiment, like delay, a delay versus a right. The cycle is not going to turn soon. Right. Yeah. 

Jason Hall: No, I think probably so. Now I [00:56:00] will say this too, their results were a lot worse than expected. So that was part of it too. I mean, still generating free, free cashflow, but, so I think it was a little bit of both.

And I think the, the latter. Amplify the former. In other words, the fact that the results were worse than expected, amplified concerns that higher interest rates are going to keep the cycle negative before it starts to improve longer than a lot of people are thinking. But again, I say in phase in phase management's saying something a little different.

They're saying that this is probably the trough and that results are going to start to get better. So what about your portfolio? 

Jeff Santoro: All right. So as much as I keep telling myself, I'm going to stop talking about outset medical I'm going to say two things about it, and then I'm going to move on one. I still think it's going to be a winner.

I'm going to, I'm going to go on record and say that over the long run, this is going to be a winning stock. I have confidence in what they're doing, but what the second thing is, it's just been wild just this year, down 44 percent in January, [00:57:00] up 4 percent in February. Down 30 percent in March up 22 percent in April.

That's how much this stock moves around. Now that has added up to, for me, a position that's down, I don't know, 96 percent from where I bought it. 

Jason Hall: I bought it, but so far this year, now this includes today. And I haven't looked at today, but because of the way Up, down, up, down, math actually works. It's down 48 percent here today.

Jeff Santoro: Wow. Yeah. Yeah. So, yeah, that's it. I mean, everything, there's nothing else that really, again, because I think it was like a slow news month, like I don't think anything substantial happened with any of these companies in April. 

Jason Hall: Yeah. 

Jeff Santoro: In terms of news or anything like that. So may will be a much more interesting conversation cause we should have.

Almost all of the results in by that a couple, a couple of early June ones. We won't, but, uh, 

Jason Hall: I have a, I have one question for you before we wrap it up, looking in your portfolio. Now, the stocks that you picked, what's, this is a two part question. , what's the first stock you would [00:58:00] buy?

And then the other question is, what's the stock that you really wish you hadn't have hadn't have put in the portfolio? 

Jeff Santoro: So the one I would buy right now,

 I'm going to give two answers because it would be for different reasons. I would buy EPR because I think it's undervalued for its potential, but I would buy CrowdStrike because I, that falls into a bucket for me of, A stock, I would want to buy it almost any price that tell that's how much conviction I have in them.

so like if I was trying to like maximize returns from here, I'd pick EPR. But if I was like building a portfolio from scratch for the next 20 years, 30 years, I'd probably start with CrowdStrike out of the ones I have. If I was going to go back in time and not pick one of these for the contest, I picked health peak properties because I wanted to force myself to learn more about it.

Um, and I don't still don't want to, it just, it bores me. I'm not [00:59:00] interested in it. So I wish I hadn't picked that. What about you? What would you bail on? And what would you buy? 

Jason Hall: So, I would probably bail on TPI composites. I'm hopeful they get it together, but my concern is it's just too much of a commoditized business and the, the way the cycle has turned and the trouble they got themselves in with, with debt.

that it was just bottom feeding and not focusing enough on a good quality business. So probably TPI. Stock I'd absolutely buy right now. So far, definitely. So far it's, I just can't wrap my head around the markets. I think maybe the concern is a little bit of like the, the, the out, the, um, upstart concern with the kind of loans that they make so much of their loans are unsecured personal loans and, and refinance student loans that there's just concern that these are high interest debt and the risk of default may be [01:00:00] higher, particularly with the personal loans, not so much with the student loans.

That the market's just afraid the credit quality is not as good as it's been. And that if we do see an economic downturn, that they're just absolutely going to get slaughtered with credit losses. So, so we'll find out eventually the market's going to do, the economy is going to get bad. So we'll find out.

I think the market's wrong. I think they're doing a good job with their lending.

Hey, Jeff. I think we're done, buddy. I think we did it. We did it. Words about things, stuff about stocks. All right. As always, we'd love to give our answers to these questions about investing and personal finance and talk about our journeys. Every man walks alone. Every woman walks alone.

Even the children out there. You're on your own kids. Our answers are not your answers, but you know what? You can find your answers. I believe in you. You can do it. Jeff, you can do it too, buddy. 

Jeff Santoro: Thanks, man. 

Jason Hall: I'll see you next time. 

Jeff Santoro: See you next [01:01:00] time. 

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