Investing Unscripted Podcast 122. How We Invest 2024: Portfolio Checkup

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​Jason Hall: Hey, everybody. Welcome back to Investing Unscripted, where we ask and answer the hard questions about investing. I am Jason Hall. He is Jeff Santoro. That's the voice of the [00:01:00] people. He's my good friend. And he's on the upswing, right, Jeff? How are you today? 

Jeff Santoro: I'm, uh, I'm doing well. As you can probably tell from my voice, I'm getting over a little illness, but I, uh, I feel better than I sound.

So things are looking up. You look exactly the same. That's all I can say. I always look good. There you go. Or like this. 

Jason Hall: I have nothing to add. 

Jeff Santoro: Whatever this is. 

Jason Hall: I don't want to offend anybody. I mean, I'm happy to offend you, but yeah, let's save that for later. All right. So we've got a fun show lined up this week.

It's titled how we invest 2024 portfolio checkup. 

Jeff Santoro: Yeah, because we've been talking a lot the last couple episodes about all these changes that, that you've been making in your portfolio, getting a little bit more into bonds because you are so close to senior citizenship. And it got me thinking, we haven't really.

in a while talked about kind of the current state of our portfolios. And I think that's always a good thing to do. I think people find that interesting, but also [00:02:00] I think we should talk about where we think it's going to go because the whole directional kind of reason that you were making all those changes in your portfolio is because you are on your way to being able to retire at some point, right?

As everybody is just at different points. And I think it's probably a good idea for investors to not only Take account of what they have going on in their portfolios at the moment, but then thinking about like, well, what will this look like next year? What will this look like in five years? What will this look like in 10 years?

Like that kind of a thing. So thought it'd be a fun, fun, retrospective slash, you know, prospective look at each of our portfolios. I like 

Jason Hall: the way you frame that. I want to build on that just a little bit, because I think it's really important. As investors, as stock pickers. I think we're regularly looking at our portfolio and trying to optimize it, trying to improve it, trying to make better stock picks, trying to move away from bad stock picks.

And a lot of times we're just kind of reacting to what's going on reacting to stock prices in a lot of case chasing hot tips [00:03:00] sometimes. And while we're doing that, we're not focusing on what you were talking about. The thing that is changing is where we are in relation to our financial goals.

Jeff Santoro: yeah, that's exactly it. Cause I, I, I think I was thinking earlier today, like I spend so much time worrying about like, what is this stock doing in my portfolio right now? And, and I think as I do think long term in the sense that I'm not trading in and out of positions and I'm thinking about, I think this could be a big winner over the long term and I'm investing in that way, but I'm not.

I've never really asked myself the question of like, where do I expect this to all be down the road in terms of the portfolio composition and how many stocks and my allocation of stocks versus bonds versus other things. And I don't know that I have answers to that, but I have directionally where I think I want to be.

And since you're so much older than me, you have a little bit more of a, you know, of a fine tuned idea where you want to go. So I think that'll be fun to kind of talk through. 

Jason Hall: There, there it is. I was, I was thinking that I would compliment you for not really hitting me on the age earlier. 

Jeff Santoro: I did hit you [00:04:00] earlier.

I 

Jason Hall: said you were almost a senior citizen. Oh, fair enough. Fair enough. But I'm hard of hearing. So I missed that apparently. Well, you don't really pay attention when I talk. 

Jeff Santoro: What was that? I wasn't listening. Yeah. Hilarious. No one saw that joke coming. All right. So maybe we should start by taking stock of where we are now in terms of our current portfolio. So you used to be basically a hundred percent stocks. Have you looked like where do you stand now in terms of that allocation to stocks versus bonds versus whatever else you got going on? 

Jason Hall: Yeah. So for those that have missed the, the, over the past month, The transition I've started to make from being 100 percent stocks, you know, I'm at a point my wife and I, we do fairly regularly sit down, talk about our finance, our financial situation.

A lot of it's just like the daily operating life of running the business of a family, right? Paying bills and how much is in savings and, uh, you know, Saving for vacations and all that kind of thing. But we do try, you know, a few times a year to talk about our, our big picture, uh, retirement [00:05:00] savings, college savings all that sort of thing.

And I started doing some kind of back of the napkin math and I made a Google sheet. I actually, I shared it with Jeff and I was talking through it and I, the realization hit me that here I am in my, in my late forties, which for most people is still 15 plus years from retirement, give or take a little bit.

And I'm, we're at this position where to reach our financial goals, to reach like the number is the income number that we want to have, like for the quality of life that we want to have in retirement, we need around 5 percent a year average returns from the market. You combine that with our expected contributions.

Obviously there's always something that can derail you along the way. But the, the. Point is that my wife and I had this realization that the returns that we need from the market over the next decade or so are significantly lower than just in my head. I had thought that they would be. And at the end of the day was the realization is with, [00:06:00] with my stocks that I own generally over the long term, if I'm buying individual stocks, I want to do better than the market.

But we still have these kind of round number returns that we want to try to get. And I've realized that I've reached this point. That I need to be less focused on trying to outperform the s and p and really just need to be able to deliver on the levels of return that I need to get where I need to get.

And that brings me to this point where I've started to make this transition away from just stocks and cash to stocks, cash and, uh, fixed income. 

Jeff Santoro: Yeah, I've, I've actually started to reach out to a couple different fee only financial advisors. 'cause I wanna sit down with a professional. To sort of have that conversation, like I want to figure out at what point do I need to either Dial back contributions, right?

Like that could be like one way this could go Yeah, or at what point? Is it advisable for me, if it even is, to find some more, find a different allocation? I may be well [00:07:00] enough diversified because of how much of our portfolio is in index funds and ETFs, which we'll talk about when we get to my stuff. But also I don't know what that number necessarily is for us.

Like, I don't know what the dollar amount would be. I'm so much older than you, Jeff. I know. I have so much more time Really, um, to get there. But the other part of it too is I've talked about this before, but like, I have a pension, so Yeah. That's a calculus that, you know, I have to kind of take into consideration too, so, yeah.

But I, I'm in the same boat. Like, I wanna start knowing that number and knowing kind of what I'm shooting for now that I'm, it's with, it's, it's within reach, I guess, is a way to kind of think of it. 

Jason Hall: Yeah, no, that, that makes sense. So, so I've started this process and at this point we're up to around 3 percent bonds and I insist this is all, this is all, uh, bond index funds.

I want to be clear with that. It's all bonded index funds. And these are all treasury treasuries and T bills. So T bills are short term. Uh, treasuries [00:08:00] are the longer dated ones, just so everybody knows the parlance, parlance. How do you say that word? 

Jeff Santoro: Parlance. I think. don't know. You say a lot of words weird.

I just assume it's because you're from Georgia. No, it's, I read a lot. Which is not because I'm from Georgia. Children's books don't count. Can't your son read by now? 

Jason Hall: He can. He can read better than me. But that word, parlance, is not in my vocabulary. 

Jeff Santoro: Most of your books just have pictures. Anyway, there you 

Jason Hall: go.

Now we're the circle is complete. So, again, the, the idea here with this specific, uh, trench of the portfolio. So I'm using all the financing words today. I'm, I'm really doing well. 

Jeff Santoro: See, I always say at this tranche. I don't know what's correct. 

Jason Hall: Bougie bougie words. Yeah. 

Jeff Santoro: Is that a good band name? Bougie words.

Oh, it's not bad. It's better than the ones you normally come up with. 

Jason Hall: Okay. I'm not gonna, I'm not gonna argue that. The point is, is that I'm starting to build out that part of, of our portfolio. At this point, it's just focusing on the treasuries. And honestly, it's just what I found is that I've had to do less research to identify good funds to own [00:09:00] ETFs that invest in treasuries.

Cause when you start getting into corporate debt, there's lots of different flavors of corporate debt. And treasuries of course, are the safest thing to on earth you can buy in terms of, of, of debt. So I've started that process. We also have around 1 percent in some long dated CDs, uh, fidelity. I'm going to hat tip to fidelity here.

I'm sure other brokers have it as well, but one of the things that fidelity has in its research tool for fixed income is CDs. A lot of banks, smaller banks, you know, they'll, they'll put their CDs out on these different platforms. So they have a larger capital base than just their current depositors.

And I found a five year and 10 year, five year CDs yielding 4.5 percent and 10 year CDs yielding 4.55%. And it just made sense because it's a CD. So it's FDIC insured. I don't have to worry about the quality of these banks, even though I did go on the FDIC's [00:10:00] website and do some research into these banks, because even small banks have to report a lot of financial data to regulators that most private businesses don't.

So I was able to do a little bit of due diligence and the quality of the business, the banks. But honestly, 10 years from now, it won't matter what they're reporting the FDIC now, but the point is it's their FDIC insured and it's cash. And I still think about that as cash in my portfolio and not bonds because bonds gain and lose value, right?

Which can affect bond ETFs as interest rates go up or down, bond prices move in inverse correlation with that. Uh, but CDs are cash. It's a deposit. There's requirements about how long you have to keep it there. And if you want to buy it out, you have to pay penalties and that sort of thing. So I'm still thinking about it as cash because it's, it's, it is a cash 

Jeff Santoro: investment.

Yeah. It's interesting. I, I don't want to go down the bonds rabbit hole again, because, uh, we probably put our listeners to sleep on the last episode about that, but I did click on the, the bonds part of the fidelity website after you told me about that. And I got to tell you, like, as someone [00:11:00] who's never, ever looked at bonds before.

I immediately clicked away. It's a lot, right? It was so overwhelming. Just trying to figure out like all the different terminology. It's it reminded me of like, when I very, when I was a very, very new stock investor a couple of years ago. And I was like, what is, what are all these numbers and, and ratios?

And what does P slash E mean? Like it was like that kind of a thing. 

Jason Hall: Very overwhelming. It can be so yeah, you have to be really careful because you can go into rabbit holes really really quick So 

Jeff Santoro: yeah, but let me ask you this then so you've started out by the the fixed income you've you've purchased over the past several weeks has been treasuries and Bond index funds.

Do you anticipate? Expanding the type of fixed income into into some of those other areas over time and maybe after you have some time to Learn, you know, research about it a little more, or do you think you'll stick in, you'll stick to this area of fixed income? 

Jason Hall: Yeah, no, I, I'm definitely gonna own, own corporate debt as well.

Number one, you can get a higher yield. One of the great things about [00:12:00] ETFs, Uh, is you can diversify easily same thing as with, uh, like an ETF for stock and index fund, right? You can diversify really well and remove that single party, single company risk in the same way, uh, because the challenge with bonds is it's not like with stocks where you can, if you want to buy 50 of a stock, So many brokers now you can buy fractional shares, right?

And if you have 500 to invest this month and you want to spread it across 10 companies, you can you can't do that with bonds. If you're buying individual bonds, it's typically, it's, you gotta pay, you know, it's, you gotta buy a thousand dollars worth of bonds, right? That's like the, it gets a little bit different when you're buying on the secondary market, but the point is you're not making small two digit, small three digit purchase amounts.

So it can make it really, really hard. Unless you have a really large portfolio, it can make it really hard to diversify that single company risk. And even though bonds generally are safe bonds can still be [00:13:00] risky, especially like you talk about, you click on that fidelity thing and the rabbit hole people can fall down as like, they click on the high yield stuff and that's the risky stuff, right?

And that's the things that are more likely to default. And you can walk right into, uh, right into risk and a category that you think is safe just because you don't know what you're doing. 

Jeff Santoro: We kind of talked about the state of your portfolio now and where it's going to go in, I would say the medium term, right?

Medium term, because your plan is to continue down this path of converting some of your equity into fixed income as you approach death. So let's, let's talk about where my portfolio sits. So I haven't actually looked at this in a while, like to figure out like the percentage of everything. So according to the latest calculations I just did here, I am about 15 or 16 percent stocks.

Which is kind of funny to say because I was 0 percent stocks four years ago. So I've, I've put a dent in that. I shouldn't say 0%. I always had my [00:14:00] wife's stock in her company that has been in her account. I just kind of didn't pay attention to it until I did. So that's where I'm now and the rest of our invested wealth is in either index funds or ETFs.

So I think that's why I'm curious, when you say 

Jason Hall: index funds, you mean mutual funds that are index funds, like mutual 

Jeff Santoro: funds in inside of a 401k, 4 0 4 3 B, that kind of four three B. Right, right. Um, and then I, we have a big chunk of ETFs in a. In a rollover IRA that I have in my wife's account that from like an old job, we took her old 401k and rolled it into an IRA and I bought a bunch of ETFs.

So, right. So we're, and, and within, so this was where it ties to the bond conversation within her big bucket of ETFs. She's got some bond ETFs in hers and I have bond mutual funds in my four or three B retirement account too. So I've not gone and looked at like what percentage of. My portfolio is currently in bonds, but it's not zero.

So that's why I'm very curious when I do. You know, sit down with that actual [00:15:00] professional, not you. I'm curious if they say you're fine in terms of bonds right now, or if they might even say like, you're too much in bonds for someone as young and handsome as you. So that'll be interesting for me to see.

I think to me it's, it's weird. Like I know I'm not that much younger than you, despite all of my jokes. So I feel like part of me needs to start thinking about the same things you are, but on the other hand, because I've only been buying stocks for four years, that's all I think I'm going to do over the next.

Five years, just right. Keep buying stocks. 

Jason Hall: Well, and that's, that's where I was, you know, even a year ago and here on the show, I was talking about, you know, sometime in the next four to five years, making the transition that I've started now. And the difference is simply looking at our nest egg, looking at the accumulated wealth we have now.

And one of the things that I've become hyper aware of is. Being aware of like how unique and fortunate the past 15 years have been like in terms of the markets returns, we're looking at, you [00:16:00] know, roughly 15 percent a year average returns. That is so much better than the markets. That's 50 percent better than the market's long term returns, which are closer to 10, right?

It's not 5 percent better. It's 50 percent better, right? It's exceptionally, exceptionally good. And again, getting to that point where I'm seeing the finish line and knowing where we need to be. Behaviorally, it's certain, certainly affected me more than I thought it would. And I'm, the reason I'm doing what I'm doing is, is, is really twofold, Jeff.

It's not just to make sure that I'm like protecting the floor and starting to build out that gear and more, more guaranteed with the treasuries. It's pretty guaranteed with the corporate debt. It's not going to be completely guaranteed, but it'll still be, it'll still be very safe, uh, as I'm building that out.

But it's also one of the things we talk about, and I talk about this a lot is when it comes to managing a portfolio, I think it's managing yourself. Is more than managing what you own, right? Behavioral modification, so to speak, and that's a big part of what I'm doing is it's it's steps that I think can help me avoid [00:17:00] avoid making big forced errors in the future, trying to capture return.

Or in a worst case scenario, trying to make up for losses that I was, didn't anticipate. 

Jeff Santoro: There is a psychological aspect to all this too, like I, the only, the example I have in my own portfolio is, I mentioned this before, but we inherited some money a few years ago and with my son at the time only two and a half, three years away from college, my, my older one, I just took a chunk of cash and just left it in cash.

Like I left it in a high yield savings account and some CDs. And it was weird to just, like, have a bunch of cash not being invested. And even though I made that decision 18 months ago at this point it feels like I've had this. big thing of cash forever, you know, and it's just this mental thing of and again, part of that's because two years ago, cash would have gotten me almost no interest, right?

And now it actually gets me something. So, but I can see how just like that has impacted me psychologically, I just have to kind of think about it. And So I can [00:18:00] imagine like starting to shift away from stocks into fixed income might kind of feel the same way. And I can see why people either delay doing it or change strategies midstream.

So yeah, I think that's something people need to think about too. Well, 

Jason Hall: just to put some round numbers on it, basically, basically where I am right now, if you look at the, the bond, the bond exposure, the CDs and cash, we're roughly 80, I'm roughly 80 percent stocks. And 20 percent cash bonds and long dated CDs right now.

Um, that is certainly the lowest percentage of my portfolio that was directly invested in stocks that I think it's ever, ever been. So it's definitely an interesting different place. 

Jeff Santoro: Yeah. And I've, this is absolutely not financial advice, but I've, I've read on like discussion boards and stuff. I people who are, who are retired basically say, because I keep five years of living expenses in [00:19:00] cash at all times, or short, you know, Easily maybe not cash cash, but like short term cds or something.

Well building like a cd ladder right now But basically they say because I have five years worth of expenses in cash. I'm 100 stocks. Otherwise. Yeah And right that's for them. That's the hedge they need right, you know, and and Exactly. That, that could be also making like social security income or something like that.

Or maybe these people have pension, 

Jason Hall: well, that's a smart mental edge because if you think about it, because one of the, you know, we've heard Peter Lynch in the past, David Gardner, uh, in the past have talked to have talked about being a hundred percent invested in stocks and typically staying a hundred percent invested in stocks.

Now with Peter Lynch, we know he's worth. Massive amount of money. David Gardner has done pretty well too. So there's a little bit of a hedge built in when you've already built up a large amount of wealth, you can stay a hundred percent invested in stocks. Your portfolio can get halved and you still have a lot of wealth, right?

That's just not where most people are, but you can create a mental edge by having that same mindset where you [00:20:00] have. short term needs in cash and you're a hundred percent long term needs invested in stocks. So you can still operate kind of from that same mental framework. And I think it can be a healthy way to manage yourself while you're also managing your finances.

Jeff Santoro: Yeah. And it also, you know, to use that example of people who are. You know, five years of cash and then all stocks, you also don't know like what all stocks means because they, they could be, they could have dividend paying stocks that kick off what some percentage of the cash they need every year. Right?

right there, they're always kind of building back that cash cushion without having to actually sell the stocks in our portfolio. 

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 , all right, so let me ask you these questions, right? Where do you think, where do you see yourself professionally in terms of work and your portfolio on the following time horizons?

Three years, five years and 10 years. 

Jason Hall: Okay. So I'm going to start, I'm going to do this backwards and do the 10 years first. Fair enough. Because 10 years from now is, really kind of transitional point in my entire family's life. A decade from now, my son will be a senior in high [00:23:00] school. And there's a lot of changes in a family's life that come along with that.

And that will also be the financial point. Based on the math that we're looking at is that my wife and I both could be very seriously considering retiring. I doubt either one of us will want to, because we both love what we do. And my wife probably would not want to spend that much time around me.

If we're being, if we're being honest who would, well, fair enough. I mean, I don't like being around me as much as I am. That's why, that's why I take naps. 

Jeff Santoro: That's the reason we can only do one episode a week. I don't, I don't like it either. 

Jason Hall: Fair enough. But no, but seriously, it's the, so there's two, it's twofold.

Number one, I don't expect that we will want to walk away from the thing, our professional uh, pursuits. And if we did the, the things that we would want to do cost money. And I don't know that we would have the amount of money to do all of the things that we would want to do. So we will definitely be at a point where we'll be making some decisions [00:24:00] about really the next three to five years.

You know, a lot of parents that even if you get to that point, you know, you want to keep working while your kid's in college to kind of be there to backstop. And maybe their insurance is through you and you need to be employed to have insurance. Like all of those things kind of come into play, right?

Your costs can go up a lot. Uh, when you retire early, you're too young for Medicare, you know, again, kid, child dependence, all those sorts of things. So that's 10 years from now, we'll be really starting to really focus hard on what is our, what is our long term life plan. Based on our, our, our, our kid, like a lot of people kind of go through that sort of thing.

Jeff five years from now, my guess is that things will look a lot more like they do now than they will in 10 years. because there are still going to be a substantial amount of, of, of my investing decisions are going to be based around finding businesses that I can own for 20 or 30 years that are going to grow.

And create value, um, and add to my wealth. And I've already made such a [00:25:00] transition to trying to find dividends and dividend growth stocks already as like part of my strategy, the barbell. But I do think five years from now that I will have probably. Started increasing the amount of my current contributions that go into to fixed income investments.

All right. What about three 

Jeff Santoro: years? 

Jason Hall: You think it'll just sort of be similar to now? I don't know. I don't know. I don't know if it's going to look more like it does now. Or more like it will in five years. In other words, I don't know. You know what I think, I guess the best way to answer it is I think the market's going to probably inform that.

If we go through a period of time where I see one of the things that's happened over the past four or five years is I've become more and more of. Making the contributions, making the contributions, and then making investments all at one time. I don't buy stocks every month anymore. I buy stocks a few times a year where I invest a lot of the capital at a time.

I keep more cash looking for market sell offs to add again. I don't only buy dips, but [00:26:00] I like to be prepared to do it when the market gives me those opportunities. So I think the market's going to determine like what is my portfolio going to look like? And what is the mix? I would be. Super happy if the mix of stocks was similar to what it is now, that means that the market did really, really well if, if that's the case 

Jeff Santoro: now, your, your turn now, well, I will, I'll do that, but I was just going to add on to what you said I do, I think I asked you this on the episode when you talked about you were going to buy bonds, but I, I do wonder if, if we had had that Yeah.

If the, if the market right now was like, it wasn't 2022, if you would have been doing the same thing at the same time I wonder if we were in a bear market, if you'd be like, you know what, I'm going to do this bond thing, but maybe not right now, because there's too many compelling stock options that are options for stocks out there.

Yeah, 

Jason Hall: no, that's, that's exactly right. I think that's, that's a good way to put it. I really wish I had made this decision in say, October of 2021. Right. For those who don't know, that's roughly when the NASDAQ 100 [00:27:00] peaked. Yeah. Before the tech stock crash. 

Jeff Santoro: All right. So for me, 10 years this is funny. Like we're going to be in very different places.

10 years. Oh, away from me. My kids will be 22 and 26. So I will be a grandpa. I will be. Oh God, my God. I guess theoretically I could I will be done paying for college, God willing. I will be pretty close to having our mortgage paid off, assuming there's no other refinancing decisions I make over the next 10 years.

And I will be old enough to retire and collect my pension. So, I, I don't know what I will do in terms of, Work at that point. I don't I'm excited to get to the point where I can you want to hold the option That's it Like I'm like you like I will not I can't not do something like I'm not the kind of person who could retire especially at 55 which is where I'll be in 10 years.

Yeah, and then just like golf three times a week Like that's not I couldn't do that And it would be [00:28:00] a crime to the sport of golf if I played three times a week. You could, you could golf three times a week. You couldn't only golf three times a week. Yeah, fair enough. Right. But that's what I mean. I couldn't just, you know, if I was 85 and retiring, I could probably just sit around, you know, but not at 55.

Um, so I will do something for the next 10, 15 years. However, until I really do want to, do want to just kind of, Stop and travel and relax and stuff. Folks, folks, we're never going to quit this podcast. I want to be clear. No, no, no, no. 

Jason Hall: The last episode will be at the funeral service of the one of us of the first one to go. Yeah, exactly. Exactly. 

Jeff Santoro: I, I think we should do, let's get morbid for a second here. I think whoever goes first, we have to make an agreement with the other one will show up with a laptop and a podcasting mic. 

Jason Hall: We'll live stream the funeral. 

Jeff Santoro: All right. Moving on. I want, well, no. All right. Well, one more thing about dying.

I want the rough cuts theme song playing at my. And my funeral, 

Jason Hall: if, if I have to say anything with the boombox from [00:29:00] outside the funeral home I will do it.

Jeff Santoro: Back on track here. So I, I think 10 years for me, like I'll be in a different place than you will in terms of like my life cycle with my kids and all that kind of stuff.

But yeah, I, I want the optionality, like I want to be able to go just do something different if I want to like not stop working. So in terms of my portfolio. I honestly think it could end up looking a lot like it does now, except not 16 percent stocks. I actually think my stock allocation 10 years, 10 years from now could be higher.

Jason Hall: Not, I absolutely think it will not 

Jeff Santoro: up to 80 like you, like I, there's, I had, Too much of a headstart in my other accounts, I think to catch up that much, but I could see it getting, I don't know, I'm bad at math. So I could see it being a lot bigger of a chunk of my overall portfolio than it is now. Not to 

Jason Hall: give away too much of your personal financial situation, but I know one of the things that we've talked about is.

And you talked about it too. It's like when you meet with a CFP, one of the things that you might learn [00:30:00] is it's time to pull back on retirement contributions. We've actually done that a little bit to focus more on like money for the now stuff. 

Jeff Santoro: Yeah. 

Jason Hall: And you don't have to live as frugally and you can enjoy more things now and have that.

That's like one of the things that we've done, but I could see you being in the situation because of your pension where you can dedicate more of your cashflow from income to stock investing between that. And the fact that I really believe you're a pretty decent stock picker between making good stock decisions and the kind of the weight of the, the bond aspect of, of some of your, your other portfolios that could reduce the returns.

If we get a good bull market period, I mean, I think just the higher contributions and the outperformance of your stock picks versus the rest of your portfolio. Yeah. I, I definitely think your stock portfolio is going to make up a bigger portion of your wealth. 

Jeff Santoro: Yeah. Because I, they could, I could sit down with someone and they could say basically like keep doing what you're doing, which is [00:31:00] essentially buying stocks a lot.

Right. Which would just increase, you know, cause one of the things I've done over, over the last couple of years is as I've gotten raises, I've not, I've not upped my four or three B contribution. Like I used to every year in terms of a 

Jason Hall: percentage as your, as your income has gone up, it's increased the contributions organically, but you're not taking a larger percentage, correct?

Jeff Santoro: Right. And then I've taken the increase I would have made in the old days. And I, that's what I use to buy stocks with. So every year I'm more, more, a higher percentage of my. Invested income is going towards stock. So yeah, unless I'm told by a professional, I'm doing a very wrong thing. I could see it being a lot more stocks in 10 years, five years from now, I absolutely think it'll be almost exactly like it will 10 years.

I think my trajectory is not going to be very, very different, honestly, over from now to the 10. I could see a scenario where it's just sort of like a steady, Like up until the right in terms of stock allocation, up until I get to the point where [00:32:00] I'm no longer contributing at all. Just because I've had such a head start before I started buying individual, individual stocks.

And I was just gonna say the same thing with my wife too, like she's been all in mutual funds in her retirement account forever. So we just have such a massive head start with that part of it. So yeah, I think that's where I'll end up being. I have a, I have a question for you. That's not 

Jason Hall: on the outline that just came to me.

And maybe we don't answer on the show, but what's the, what's the worst case scenario in say 10 years?

 Like what's the most likely downside scenario? 

Jeff Santoro: Speaking just financially, like assuming there's no catastrophic life event that changes, 

Jason Hall: exactly. Yeah. You're, you're still earning, you're still making the same, similar contributions, right? 

Jeff Santoro: So, so I, I think honestly, I think. The answer to that question is also what could make me change my plan is if, you know, you mentioned we've had such a blessed 15 year run in the stock market where the average returns have been above the longer historical average.

I [00:33:00] think if it was the opposite like there have been periods of time if you go back through market history where there's been multi year chunks of time where the market went sideways. Or just down a little, right? The 

Jason Hall: seventies were a lost decade. 

Jeff Santoro: So I guess that, so there's your answer. If there was a lost decade in terms of just the market, and that was this coming decade I think that would probably be the worst case scenario.

And you may end up being a little more protected from that if you're, you know, getting into fixed income a little bit more over that time. Yeah, I, I guess that would be it. I mean, Unless we want to go down the road again of like catastrophic events like nuclear war or you know, someone gets really sick or one of us loses our jobs permanently, like that kind of stuff.

Jason Hall: Yeah. And honestly, I think a lot of what I'm doing now is, is, is based on that potential reality. You know, cause one of the things I've always talked about when you look at say 2000 to 2007, you know, the market did a round trip, um, and then the financial crisis happened and really from that 2000 high.

Through the financial crisis, it [00:34:00] was like 13 years, right? Cause the market was back to an all time high and above those levels for a few months before the global financial crisis happened. And then you look at the 1970s. And the easy response for me has always been, well, I'm just going to be contributing all the way through the low point, right?

So it's an opportunity for me. And I'm looking at my portfolio today and thinking about where we want to be. And I'm still thinking for four to 5 percent average returns a year. So we're talking about still seeing over a decade. We're still talking about the existing portfolio today being 60 to 70 percent larger before the contributions that I would, we would be making over the next decade.

Grow. So I will tell you simply if we see a big market sell off in the next few years and it takes multiple, multiple years to recover, It, it could absolutely upend those, you know, 10 years from now being at the [00:35:00] financial point where we're ready to retire scenario, hence me starting to really be more mindful about protecting more and more of the downside of my portfolio.

Jeff Santoro: Yeah, no, that all makes sense. I mean, I, with whatever projections I ended up using to kind of figure out That the number, so to speak, that I need to get to, I would like to calculate that using below average market returns just to be conservative. I don't know how, how below market I'd like to see a bunch of scenarios.

I guess like, that's kind of what I'm hoping to get out of meeting with a financial advisor is like, what does it look like if the market, you know, Average over the next 10 years is 3%. Yeah. And what does it look like at five? And what does it look like at 10? Right. Like the long term average just to kind of map out, you know, or maybe even a worse scenario than, 

Jason Hall: than those.

I want to, I want to throw a number out here cause I think it's, this is one of the things that's got me thinking about the, the down, the downside of things is, yeah, we've gone through this wonderful period and generally it's been pretty good. It was one, we have one 20 percent drawdown in the late 20 [00:36:00] teens.

And then we had the pandemic where we saw that 30 percent drawdown in barely a month. And it was like nine months for the market to round trip back to where it was. And then we saw the selloff from the beginning of 2021 where I guess the market bottoms at some point in 2022, I guess, before we started to really fully recover.

But what I wanted to talk about is like the impact of interest rates over the long term. And if you look at from January 4th of 2021, which I think was the peak, that was the most recent peak before the bear market that we've fully recovered from now, through now, through, through to date and that was really when interest rates were started to go up was in 2021.

The market is, is up on a total basis. the market's up 25 percent. On an annualized basis. That's 8.4%. So we have seen the impact of higher interest rates on stock market returns already. So 

Jeff Santoro: yeah, look, I'll take [00:37:00] 8.4 percent annualized for the next decade. Yes. Yes, please sign me up.

That's fine. 

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Jeff Santoro: I, you know, I, I worry that, you know, like, all right, here's your point. You mentioned over that 15 year span earlier in the episode, the market has been basically 50 percent better than it had over the long term. So like if you think about reverting to the mean do we get another 10 or 15 year span where it's 50 percent lower than the long term average?

Yeah. 

Jason Hall: You know, well that's, I'm not, I'm not expecting that. I'm not either, but I'm not, not expecting it. 

Jeff Santoro: Yeah. I don't it's what's the expression right like, uh, plan like invest like an optimist plan like a pessimist or whatever, like, um, Yeah, to kind of try at least be thinking about the, the bad scenarios.

All right. So I want to shift the conversation a little bit because one of the things that we wanted to talk about, and I've been thinking about more recently is selling because I, uh, infamously declared on this podcast earlier in the year, I was going to try to go the whole year [00:39:00] without selling anything.

And I failed miserably at that. But I also think, and I'll probably look back on this and make fun of myself in the future, but I think I'm selling more smartly now. I will, I will join you in the making fun of you. I appreciate that. That's, that's what, that's what I, that's what you're here for. I'm here to support you, 

Jason Hall: Jeff, 

Jeff Santoro: but this is the question I want to ask you.

So you've been doing a lot of active selling in order to buy bonds. I'm curious how you have approached the decision around what to sell and, and how much and why and all that kind of stuff. 

Jason Hall: So it's, interestingly enough, so far. So far, all I've done is deploy cash into, into bond funds and into the, those CDs.

I actually have yet to, and I've talked to you about a lot of different ones, but I have yet to actually sell anything to generate that cash to, to invest in fixed income. And, and part of it is because I have the extra cash. And it was the smarter move because we've talked about this. One of the things that I [00:40:00] will do, and this is, I'm not alone in this is come up with BS reasons to, to sell a perfectly good investment.

Jeff Santoro: Oh, this is, I mean, that's why I wanted to ask the question. This is a tailor made. I'm going to find an excuse to sell a stock. That's not a real good reason to sell a stock because, Hey, I got to buy bonds. I, this is, this is part of my plan. I got to do it. What was I going to do? I had to do, you know what I mean?

Like it's, it's, that's why I've been pushing your thinking on it. And I'm, I didn't know you hadn't sold any yet. I didn't know. I haven't yet. 

Jason Hall: No, I haven't yet. So I will say, and I want to, I want to, I want to talk about this one right now, because this is one that you and I discussed that, that, and I'm, I'm 90 percent sure that I'm going to and that's, that's NVIDIA.

I do think I am probably going to either trim, probably by half and possibly completely exit my NVIDIA stake. And you brought up a good point. Do you want to, do you want to say it again or you, you, you share it, you share up the good point that you brought with me. 

Jeff Santoro: All right. So I threw so many points at you mostly just to mess with you.

I actually don't know what point you, 

Jason Hall: what was the [00:41:00] main, what was the main reason why selling Nvidia would be a mistake? 

Jeff Santoro: Because we had this exact conversation a year and a half ago when it was a mistake to sell Nvidia, 

Jason Hall: right? So you can go back in our archives of the show and find the episode where we talked about it.

And we both trimmed, I sold half. I can't remember what you decided to do. 

Jeff Santoro: I sold like 80 worth, I think. Yeah. Yeah. No, I said it at the time and I'll say it again. I did it because I wanted to say I turned a position. Yeah, that's right. That's entirely why I did it. Exactly right. Yeah. Cause I, it was such a, all my positions are so baby, baby size right now that it was one of those things.

I think what I did was I had bought, I had a, whatever the percentage of the, the amount I had was mostly in my brokerage account, I think. And I had a little bit in my IRA and I just sold the IRA piece. Just so I could say, 

Jason Hall: I have, I have Nvidia shares that I paid split adjusted. You know, a couple dollars a piece for this has been a wonderful long term winner for me.

And when I sold half my position [00:42:00] a year and a half ago, admittedly part of it was an ignorance. I simply didn't fully understand the scale of AI, particularly at this point, still generative AI. The, the spending that was going to happen that continues to happen and the opportunity that that presented for Nvidia, who has been so far ahead of everybody else.

So, so in hindsight, I should have, uh, traded less and learn more. To, to steal your, your phrase, Jeff over the past year and a half, I've steeped myself in so much more about the semiconductor industry, AI, the spending that's going on, the opportunity, the challenges and the risks, and also kind of rolling all of that in together with where I am, uh, in my financial life and thinking about my long term goals and thinking about what Nvidia has done for me at this point.

And then the most important part is looking forward. I [00:43:00] think, I think Nvidia is going to be a lot bigger in a decade. I don't know what's going to happen over the next five years. I keep seeing deals like Microsoft signing a big enough contract with constellation energy for them to restart Three Mile Island.

And it's like. This AI thing, this data center part of the universe probably still has some legs, but it does steadily move more and more into the two hard pile. The stock still trades for more than 70 times earnings, and you know, it's a two plus billion dollar, trillion dollar company. And I, I just, I don't want to, I don't think this is gonna be a GE or a Microsoft in 2000 situation, but I don't know that it's not.

And I do know what my financial goals are. And that's why I think this is a good one for me to think about at least harvesting some of and and use to fund some of that fixed income. 

Jeff Santoro: I mean, it's this is one of the things that I have. This is like a shift in my thinking that [00:44:00] I have to make because You know, I went 40 years of, well, I shouldn't say 40 years of life because I went 20 years of being an adult, um, you know, from when I got out of college to when I bought my first individual stock, never being in a position where I could use an investment for anything other than retirement.

And yeah. And we talk a lot about how that's the primary reason most people invest is to have enough money to live on when they can no longer know when they physically can't or don't no longer want to keep working. And ideally it's it's ideally it's a situation where you get to choose. I know plenty of people.

You know, and sometimes the story is like, Oh, I wasn't like, I'll use, uh, I'll use Matt Frankel as an example, because I think he's told this story publicly. I don't think I'm giving anything away here, but I'd, I forget, honestly forget what stock it was, but I think I told him, I've heard him tell the story of the biggest stock, you know, sell mistake you've ever made, you know, he sold something to me.

Yeah. in order to pay for his wedding that ended up, I don't know, 10 [00:45:00] X ing in the time since he sold it. Right. It was like a Netflix or something like that. Yeah. Yeah. But it also paid for his wedding. Right. So like I, I. I get married to a 

Jason Hall: lovely, wonderful woman and they have a family together, 

Jeff Santoro: but I think about that a lot.

Like now that, now that's actually an option for me. You know, if I'm good enough chooser of stocks and I give it enough time you know, even my stupid little Nvidia position that I started with like 900 worth. And by the way, that was built up over. a long time. I didn't, I didn't just buy 900 worth of it.

I didn't have that kind of money when I started buying stocks. You know, just because it's up, it's been, I just had good timing and it's up, I don't know, 500 percent since then. I'm like, Oh, I could sell that and go on vacation, you know, or like whatever, pay off my car, you know, whatever the thing is.

So I think, you know, to your, to your point about whether or not to sell In video, which is a position that you said you have a cost basis of a couple of dollars on a stock that's trades for a hundred something. Right? Isn't that why you do this? Right? Like, [00:46:00] that's kind of the exactly. So I, I, I, I, even though I was pushing back at you on it and I will absolutely bust your chops when it 10 X is from here.

I, I get why that's maybe top of top of your list. Cause like, that's, so here's what I, I've been thinking about a lot. I'm down to 40 stocks and I was above 100 kind of in the first year that I started doing all this. So it's still actually easy for me sometimes to like justify selling a stock because it was one I never really picked for myself or had conviction in because I bought it.

three and a half years ago for no actual good reason. So the cells that I've made this year have been maybe one or two of those kind where I, it's just like, I didn't really pick this. Yeah, but I did sell a couple that were actually winners, but I talked about this on, on an episode. I realized I actually went and did the math on how much of those stocks I actually owned.

In my index funds too. So like I saw, I can talk about it now. Cause I think [00:47:00] when we recorded that episode, I couldn't yet. Like I sold Microsoft because I own a lot of Microsoft between all of the index funds and mutual funds and ETFs across my wife and I's investing portfolio. And I sold, uh, Apple for the same reason.

And I love Apple. Like I didn't want to sell that stock, but it allowed me to take some of that cash and then buy Some of the smaller companies that are not as well represented in my, in my ETFs and index funds and things like that. But I'm going to get to that and you know, and I'm trying to have less stock.

I'm trying to be more concentrated because this with, with a stock portfolio, that's only 15 percent of my overall portfolio. It almost doesn't make sense to have 40 stocks in it, but I'm going to have less weeds to pull. If I get down to like 20, you know, like it's not like, Oh, I'm going to sell this thing.

It's a couple of hundred bucks. I bought it three years ago off of a recommendation and never had conviction and I'll eventually get to the point where they're all mine and I can't use, this wasn't ever my pick as like my excuse. right. So that's why I wanted to bring it up because it, I've been thinking [00:48:00] differently about how and why I sell.

And I also wanted to just share this cause I don't know if I've told you this yet either, but what I've been doing lately. The last two quarters I did this is after results come out for all the companies in my portfolio. I do my spreadsheet and like I've talked about that a bazillion times, but I've actually been listening to the earnings calls rather than reading them.

And I listened to him on like, you know, 1.5 speed. So I just try to get through them, but it's been very interesting to me, giving me vibes, I guess is the best way to put it. Like I'm processing the data and the information. There's a little bit of a different BS filter you can put on when you hear.

People's voices. Um, and I think it takes 

Jason Hall: a few quarters to, to kind of get to know, because honestly, some, some executives are just, they're really good at it. Well, some are not. 

Jeff Santoro: that's actually a question I asked, um, a very well known investor who I won't call out right now. I asked that question. I had a chance [00:49:00] to talk to him and I said, how do you hone your BS meter when you talk or hear CEOs talk?

Because the reason they're a CEO is because they're really good at talking about their, their Why their company is great. But so using that same logic, one of the companies I sold, I just got a very, I didn't get that vibe. And my takeaway was either this guy really isn't good at his job because he's not selling me or things really aren't good.

So anyway, I've just tried to be a little bit more. Judicious and like have a reason for selling versus, you know, some of the more arbitrary reasons I 

Jason Hall: having a reason versus coming up with a reason. 

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

Jason Hall: All right, let's talk. We got a few minutes left here. Let's talk top end of our portfolio and bottom end of our holdings. 

Jeff Santoro: All right. You go first. 

Jason Hall: So my, my largest, uh, individual holding continues to be Mercado Libre. It's over 6.2 percent of my portfolio. I have no plans to sell. I'm not adding it's 3.3 percent of my cost basis [00:50:00] too. So I believe it's probably my fourth largest on cost basis. And then we've got live Oak bank shares.

It's done really well lately. It's, it's over 4 percent of my portfolio now. And then Maritosh homes. Three point, just about 3.7% of my portfolio. So no Brookfields in that, Jeff? No. Brookfields.

Jeff Santoro: Yeah. That's interesting. I would've, I could've swore there would be a Brookfield up there. 

Jason Hall: If you add up all the Brookfields together, it's around probably 9%. 

Jeff Santoro: I would've said 90, but, alright. No, I'll take nine. 

Jason Hall: On a cost basis. Okay. Brookfield is in here. 3.6 percent Brookfield infrastructure. Live Oak Bank shares 3.47 percent and actually Mercado Libre is number three here. 3.3%. So you see, Often is the case, high conviction ideas earn more of your money and are also big winners like Mercado Libre and Live Oak, uh, Live Oak Bank have done really, really well for me.

So they've earned more of my money. 

Jeff Santoro: All right. So my top, my [00:51:00] top three by market value, right? That was how you sorted yours. Yep. Mercado Libre is number one for me. Don't have the percentage of my, it's actually now 1 percent of my overall portfolio, but I don't have it by my stocks. CrowdStrike is my number two and, uh, Datadog is three, but it's very closely followed by Rhyme and Hospitality properties, which I might have a little bit more conviction in than, than Datadog actually.

But Live Oak for me is really good. Is number, uh, number five. So I have that near my top two. Now if I sort it by cost basis, cause I think, oh, and I'm going to mention this one too, cause I think it'll be funny when I sort by cost basis. Nvidia for me is number eight. So now let me sort by cost basis.

Okay. So this is a little bit misleading because of an options covered call I have, but my number one by cost basis is actually Celsius holdings. But that's just because I have a covered call on it right now. So excluding that, [00:52:00] Mercado Libre is So for those who don't know, um, if you're selling calls, you have to own at least a hundred shares.

Right. So, I have a hundred shares of that that I, I don't really consider to be like part of my core holding, because I could lose them at, at any time. But besides that, Mercado Libre is actually also my number one By cost basis, then Ryman Hospitality, then DataDog. So, and I think that's a product and they've all done very well for me.

They're all market. What? Two out of three of them are actually market beating for me, but that's a, that's, I think the difference between owning stocks for three or less years versus decades like you have. But here's the funny thing. What did I say? In video was eight. On a market value cost basis, it is,

uh, 32nd. 

Jason Hall: There you go. There you go. All right. I'm going to do something different with my bottom. I'm just going to give my bottom 10. I'm not even going to name all the companies. I'm going to give out some numbers, the bottom 10 stocks in my portfolio in terms of the percentage of my portfolio. They are [00:53:00] 0.38% of my portfolio.

So a little more than one third of 1% of my portfolio on cost. Is that based 

Jeff Santoro: on market value or 

Jason Hall: on cost basis? Uh, 3.3%. So on, on average they're down around 85%. Alright, so my bottom 10 you said, so that's my bottom 10. So the key across all of these very small starting positions. And so the largest positions Teladoc health was 0.

6 percent and outset medical was about 1%. So, that, I mean, that tells you right there, those two stocks are basically half of the bottom 10 and cost basis. So this is why I use that method of starting very small with companies that I don't have a lot of conviction in because they've all been terrible losers.

And I've lost 3%. Of my portfolio. 

Jeff Santoro: , my bottom 10 are only if you add them all up, they are.

Like less than a 10th, a [00:54:00] 10th of a percent of my entire right, because again, my stock portfolio is so tiny. I mean, they're meaningless, but I I'll say this, the mistake I've made in, when I look at some of the ones that are near the bottom here is in the overall scheme of my portfolio. They are insignificant, but in my stock only portfolio, I probably went a little too hard, a little too fast with some of these early on, like when I was.

Like if I could go back in time, like for example, like one of the ones that's kind of near the bottom for me is Moderna, which I actually think over the long term will be fine. I, I still have a decent amount of long term conviction in that company, but I was really excited about it when I first started buying it.

Oh, and by the way, that was in like, 2021 when we were all getting vaccines for the first time. Um, in the scheme of my overall portfolio, it's insignificant, but I, I look at that 50 percent loss in my portfolio and I'm like, ah, rookie mistake. You know, that's what I would have been [00:55:00] much more slowly adding to over time.

If I, if I knew that what I know now, 

Jason Hall: all right, Jeff. So, so that's it. We've talked about vibes. We've talked about longer term, more near term stuff, a lot of philosophy here. And, um, I think it's a good chance for us to just kind of publicly talk about our portfolios, hold ourselves accountable, help hold each other accountable as well.

I think we've done about as much damage as we can for one day. 

Jeff Santoro: Yeah, no, this was, this is, this has either been very interesting or very boring. I don't know. 

Jason Hall: Yeah. Give us your feedback though. Give us, uh, send us comments. No, like this, this 

Jeff Santoro: was a different direction for us. . 

Jason Hall: Yeah. Let us, let us know what you think.

You can hit us up on our socials, send us an email. If you're on Spotify, You can comment down there on the bottom of Spotify. It's going to ask a question. You can just give us feedback. You don't have to actually answer the question or whatever it is. 

Jeff Santoro: Yeah. I would love to hear back from you. Feedback though, is to give us a five star review on Apple podcasts and then tell us you didn't like the episode.

Jason Hall: That's perfect. Yeah. Five star, five stars, then we will read it. [00:56:00] That's the, uh, that's the deal. Thank you all. We appreciate everybody for listening. Tell a friend that's always helpful too. And as always. These are our answers. We love giving our answers to these questions, whether they're our questions, whether they're your questions, you got to make your own answers.

You can find your own answers. I believe in you. You can do it. All right, Jeff. We'll see you next time. 

Jeff Santoro: See you next time. 

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