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Travis Makes Money
INTERVIEW | Make Money by Thinking Long-Term and Avoiding the Market Timing Trap with Jim Lebenthal
00:30:56
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- [00:00]
Rachel
Hi, diva. It's Rachel and Jordan. Yeah, hi. Quick question. Why are you not spending your Venmo balance? Yeah, we're concerned you can, like, buy stuff with it.
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Jimmy Lebenthal
Ugh.
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Rachel
You love buying stuff and earn cash back on eligible purchases. Mm. You love purchasing eligible things. So the money your friend sent you yesterday, that's today's ramen or rideshare or eye patches. The skincare kind, not the pyro kind. Spend with Venmo, then you can earn cash back with Venmo Stash. Venmo Stash bundle terms and exclusions apply. That's $100 cash back per month. See terms at Venmo Me Terms, Idaho. Verification required to use a Venmo balance.
- [00:30]
Travis
You're listening to the Travis Makes Money podcast, presented by GoHighLevel.com for a free 30 day trial of the best all in one digital marketing software tool on the planet, just go to gohighlevel.com travis. What is going on, everybody? Welcome back to the Travis Makes Money podcast, where it's a mission to help you make more money on this episode of the show. I have a new friend. His name is Jim Lebenthal. He is Serity Partners chief market strategist. Serity Partners is a registered investment advisory firm with financial 40,000 clients, over 1700 colleagues, and $180 billion in assets under management. He's a. He has over 25 years of experience managing investment portfolios and is a regular contributor on cnbc. Prior to his career in wealth management, Jimmy was a submarine officer in the U.S. navy, and he's recently authored a book, how to Ride the Subway Getting around on Wall street and in Life, which combines his passion for New York City's subway system with lessons on investing and life. Jimmy, what's up, man? Welcome to the show.
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Jimmy Lebenthal
Hey, glad to be here. Thanks for having me on, Travis.
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Travis
So you clearly have had a. A thirst for knowledge when it comes to the financial markets that's brought you to an incredible career and being the chief market strategist for a firm that has $180 billion in assets under management. But I want to know where this started for you, Jimmy. Tell me. Tell me. Like, back in the day. Bring me all the way back to, like, the first time that you ever made a dollar, that you were just shocked or surprised by something that you were like, I cannot believe this actually worked. Like, somebody paid me money or I money on this investment for, like, this is crazy.
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Jimmy Lebenthal
That's a good question. You know, it goes way back, way back to when I was 12 years old. I actually grew up, Travis, in a family of financiers. My grandparents started a municipal bond broker dealer back in the 1920s. Wow. And so for the 20th century, that was a great business. My dad was the CEO and he was also the marketer extraordinaire, doing all sorts of radio, TV and print ads here in the greater New York City area. So I grew up sort of in this family thinking about the financial markets. But even coming from a family of municipal bond aficionados, I realized that an earlier age it was possible to make more money in the equity markets. I have nothing against municipal bonds or fixed income of any kind. That was in my DNA. But really, at the age of 12, I said, wait a second, there's this stock market and I can open up the newspaper. Travis, you can't believe this, and your viewers may not even believe this, but 40, 40 years ago, or however long it was ago, you opened the newspaper the next day to find out how your stocks did. It wasn't like you had the Internet check the prices right then and there. But I would do that and say, why are these, these things going up and down by an eighth or a quarter and all these sorts of things. And I just had the bug of figuring out what it is that made a stock go up or down. Now at the age of 12, I had no idea what I was doing. I can't even remember. It must have been my dad who got me to my first two stocks. US Shoe, back to that in a second. And Texaco, which is now part of Chevron. Texaco. But US Shoe was the, was the stock that really sort of, to answer your question, I started to say, whoa, this is how this looks. It was a stock that kept going up and up. It was, it was a growth company back in the 1980s. Now what it did, I'm going to tell you, doesn't sound growthy or sexy at all. It made shoemaking equipment. That's all it did. But somehow that was a growth industry in the, in the 1980s. And the stock kept going higher and higher. They gave me dividends, and then they did this crazy thing where they split the shares. And so I'd be coming home from like seventh grade classes and I'd get these dividend checks in the mail, or I would get this Notice that your 20 shares are now 40 shares and your 40 shares are now 80 shares. And that was just eye opening to me, that if you do this right, you can make wealth over a long period of time.
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Travis
So was that was that initially what your idea was to pursue as a career.
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Jimmy Lebenthal
Then at that time, you know, another great question. So I, I went to school and I graduated college in 1990. And I have to say that of my graduating class, probably half of the graduates went to Wall Street. Having grown up in Wall street, that really wasn't where I wanted to go. I kind of knew it already. And I had an engineer's mindset. So I actually joined the Navy right after college. I went to officer candidacy school. I was accepted into the Navy's nuclear propulsion program, which is a very well regarded engineering program. And I drove nuclear submarines for the first seven years of my life. Had just an absolute blast. I look back, Travis, I can't believe the things I was allowed to do at 24, 25 years old. You know, I'm on top of a submarine driving, the submarine captain's asleep. I wouldn't trust a 25 year old today to do that. But they let me do it. So that was my first career. But the Cold war ended. The Cold War came to an end. Submarines were clearly a Cold war vehicle. I had been investing the whole time. So think about, you know, I, I pick a stock and then I go underwater, literally underwater for, you know, weeks at a time. And I can't follow that stock. So I have to be it, it taught me to be more of a long term value oriented investor. Yeah. Price that I paid and the ability of the business to do well over long periods of time really mattered to me because I couldn't trade in and out racket it. Yeah.
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Travis
What a blessing in disguise, huh?
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Jimmy Lebenthal
It was. It definitely was. And then by the way, so when I came out, Cold War ended, went to business school and it just became clear to me that it was time to blend my passion for investing again from the age of 12 with making a career out of it. Goldman Sachs was kind enough to interview me and accept me into their private wealth management business, which I did for about five years.
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Travis
Okay.
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Jimmy Lebenthal
Growing a business with clients, taking care of them across many asset classes, not just equities, but really understanding how to interact with clients. And there's very much a psychological aspect to that. It is not just the numbers and sense, it is making sure. I think honestly the most important thing that I do is hold clients hands. When there's a downturn in the market, when there's a war with Iran or, or there's liberation day in tariffs and the markets go down 10%, people start to really worry that the world is unalterably changing. I remind them it's not the first time the world has unalterably changed. The markets do tend to recover and absolutely go higher over time.
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Travis
Yeah, I love that insight because it's good to hear it from somebody who's operating in the financial markets in the 80s 90s timeframe. Because I think it's even probably more important now with the volume of software and AI that can do the work of a financial advisor to some degree, like can give you some insights and things that you would have had to, you know, put in hours and hours and hours and hours of research, you know, 20, 30 years ago. Now you can get it in, you know, an hour and a half while you leave your desk and come back in. Your AI platform just researched everything. But the thing that you can't outsource to AI is the relationship to the client and the ability to communicate effectively with other human beings. Where would you rate that in terms of skill sets, in your opinion, for young people to acquire?
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Jimmy Lebenthal
I think the personality skill set that you most have to have is earnestness and empathy.
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Travis
Earnestness and empathy.
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Jimmy Lebenthal
If you do those two things, it will create trust. Travis. Trust is the currency of the financial advisory world. Yes, performance matters. Of course performance matters. And yes, access to really cool investments. You know, maybe private.
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Travis
You could say that again.
- [09:08]
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Travis
Now we party.
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Rachel
This is incredible.
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Disney Plus Announcer
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Travis
I am clearing the rest of the day.
- [09:23]
Disney Plus Announcer
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Jimmy Lebenthal
But investments matters. But nothing matters more than your clients trusting. And you do that by being earnest by being honest and identifying with what their feelings are. I like the way you phrased that question and it it shameless plug here. It reminds me of a chapter in the book that I talk about because I'm drawing these comparisons between what I've seen in the New York City subway system and the world of investing yeah. And I loved the subways as a kid, but this was in the 70s when the subways were almost completely, completely held together by the graffiti paintball. You know, now I go into the subways and these, these subway cars have digital displays of how long it's going to take to get to the next station. Or even when you're waiting for the subway, there's a display that says how long it will take for the train to come. The world evolves. And so the way you set up that question was bringing artificial intelligence into the picture and. Exactly. The world has, has evolved so that artificial intelligence can do a lot of the grunt work and free me and other advisors to do the things that I just described, which is that more social skill set, that personality skill set to really take care of your clients. I think, I think AI is going to be great.
- [10:42]
Travis
Yeah, Yeah. A lot of it's. It's just another tool, you know what I mean? It's going to be a tool that some people use for terrible things, but it's also going to be a tool that some people use to, you know, save the planet, almost literally in some instances. So tell me, tell me how you forge a career like the one that you've had. Jimmy, like, obviously, coming from the Navy, it already seems counterintuitive to, like, start your career not being in the financial industry and then to end up where you are now. What, what do you owe or what do you attribute a lot of that to? Is it more about relationships and people and communication? Is it more about knowledge and competence and the ability to perform? What have you found to be the cocktail of personality traits that's, that's allowed you to get to the position that you hold now.
- [11:30]
Jimmy Lebenthal
Yeah. So let me add on to the earlier point I was making about earnestness and empathy. You have to have a certain level of intelligence. I'm not calling myself smart. That's not what I mean. What I mean by that is you have to have the drive and the discipline to learn this craft.
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Travis
Yeah.
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Jimmy Lebenthal
And that means a voracious amount of reading. It means reading newspapers or, you know, websites from both sides of the political aisle, not finding yourself being down a rabbit hole. Whether it's social media or traditional media that has a just one editorial bent. It means understanding finding out what industry trends are going on right now. By the way, it helps for me to be at a firm like Saturday Partners. You were so kind to talk about the, the size of the firm. And that size of the firm allows us to see a lot of what's going on in the industry. And I'm every day learning something new in this industry. So you have to have that drive, that discipline and that openness to new ideas. But I'll tell you one thing, and maybe this will disappoint some of your listeners. I don't know. I do think experience matters. Now, I don't want to discourage Somebody who's 25 years younger than me. I just said I started 27 years ago. Right, Right. So I remember a prospect once saying, you're too young. And I thought, well, that kind of hurts. I mean, don't you want to give me a chance? You know, it's. Now that I'm older, I've seen a thing or two. I really realize more experientially the importance of staying in the markets for long periods of time. I realize that market timing is really a fool's errand. And I, I, I hope I don't irritate any of your viewers, but that's what I so strongly believe.
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Travis
Irritate away, Jimmy. Irritate away. Don't, don't apologize for that.
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Jimmy Lebenthal
I will, Travis, because I've gotten feedback on this before. You know, there's a famous chart looking at the S P500 over the last 30 years, and it says if you just stayed in the market during the last 30 years, my number may be off a little bit, but you earned something like 9% per annum over the last 30 years. If you tried to market time and you missed the best 20 days out of those 30 days. So not even the best, you know, one day a year, your return, your annual return goes down by more than half.
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Travis
That's insane.
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Jimmy Lebenthal
And it's, I'm, I'm sorry. I'm going to shamelessly plug my book again. The book with a chart that shows it. Here's two things to think about. One, somebody out there is going to be listening to this and saying, yeah, okay, smart guy. Well, what if you missed the worst days of the year? It's by market time. Okay? Of course your, your returns would be higher. But think about that 9% per annum return that far and away strips out. It surpasses inflation. Even with what we've seen over the past few years, your purchasing power goes up a lot, by 9%. And I also have to add this very important point. When we talk about the best days of the market and missing those 20 best days, those best days almost always happen right on the heels of the worst days in the market. So it's actually easy to say hey, the market's high. I want to get out. That's easy. But you have to get back in when every fiber of your instinct says don't get back in because it's a bloodbath out there. Yeah, you know, we saw it last year on April 9, when we'd had four bad days, really bad days in a row after the Liberation Day tariff announcement. And then snap of a fingers, we go higher and it's off to the races. The best days tend to be clustered right next to the worst days. And you don't want to take the chance of missing those 20 best days out of 30 years.
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Travis
Yeah, no kidding. And like, my thing is that you have people like you, and you have people like the Buffets of the world, and you have the Ray Dalios of the world who have dedicated, they're like decades of their professional career to learning this game, and they still don't know how to time the market completely. And you think sitting in your spare bedroom in a bathrobe, in a bag of, you know, halfway down a bag of Doritos, you think you're going to be able to out earn all of the smartest investors the world has ever seen. Like, it just doesn't make any sense to me. And it's so like you're doing so much more work to make less money. Just, just trust that the, the economy's probably going to go up and to the right time and let time be on your side and just put the money in the things that you believe in as well as a bunch of different funds, and then you're probably going to be pretty, pretty good.
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Jimmy Lebenthal
Right? You know, Travis, this part of the conversations takes us to a phenomenon that's happening today where there is a gambler's mentality in the markets. Now, I'm not being judgmental. I. That sounds judgmental, but it's really what I see. So if I look at, for instance, the explosion in stock option volume, the trading volume, stock options, that's highly speculative, that's rolling the dice. And a lot of those stock options are zte or zero time to expiration options, meaning somebody's buying them today, they expire at the end of the day. I got news for you. That's a roll of the dice. How a stock will end up the trading day from the beginning of the day, that's just a roll of the dice.
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Travis
Yeah.
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Jimmy Lebenthal
Or Things like levered ETFs, exchange traded funds that use futures to augment, in some case triple the returns of an underlying stock or sector that is not investing, that's speculating. Now I mean it when I say I'm not being judgmental. If people can make money doing that, great. Here's my experience. And again, experience matters. The number of people who actually are able to make money doing that is a tiny fraction of the number of people who think they can make money doing that. I, I just, I offer that as a cautionary tale. It's a good way to lose money. Trading rapidly is a good way to lose money. To me, this actually started in the late 1990s. The digital age came Internet 1.0. And you, you saw the advent of day trading and it was really cool at the time. I remember these merit trade commercials with Stuart or these E Trade commercials that were promoting taking over your finances, taking over your stock portfolio from your old school broker, and it promoted rapid trading. Rapid trading tends to lead to worse performance, not better performance.
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Travis
Yeah, I read a stat recently that was like 98% of day traders end up losing money if they do it for longer than one year or something like that. You get, you get like the first hit and then you, you just automatically go, well, I'm a genius. And then you start taking bigger and bigger bets and bigger and bigger swings and then the inevitable downfall happens at some point because you let your emotion like we're, we're just, we're too, I, I, I personally feel like I'm just too emotional of a human being. And, and this is coming from somebody that would, I would try to think that I'm more logical, but ultimately nobody's actually logical. We all make decisions based on emotion and we try to justify it logically. And, and there's no way to justify those types of moves logically. And to me it's like, especially with like some of the newer vehicles that you were referencing, I look at it a lot like going to the casino where it's like if you go sit down, you can play blackjack, which is a game that's been around for decades and decades and decades. And then there's 30 other tables on the casino floor that are doing like these new fangled versions of blackjack or they have this new concept of a game. And every time I see those, I'm just like, yeah, I don't think the casino is knowingly inventing games that are going to give them worse odds than the ones that have been around for decades on end. You know what I mean? Like, it's probably is something that's built to benefit the person that's telling you to do it more than it is to benefit you. And it seems to me that in that investment world on Wall street that a lot of those newer products are very similar to what casinos are doing.
- [19:29]
Jimmy Lebenthal
I love the analogy because I love playing blackjack. Coincidentally, right now in my stock portfolio, I happen to own shares of Wynn Resort, so it's a casino as well. So. Yeah, look, I've seen exactly what you're talking about. I don't go gambling that much, but I go to Vegas once in a while. And you go to a blackjack table and you see these side bets. Yep. Most of the time I can't figure them out, but what they do is they play on your emotions because they put on there some cockamamie combination of cards that if it comes up, you're going to get like a 10,000 to 1 payoff. But you nailed it, Travis. The only reason Wynn Resorts or any other casino is putting those out there is because it's a faster way to strip you from your money.
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Rachel
Yeah.
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Jimmy Lebenthal
And it absolutely applies as an analogy to the stock market. I want to say something encouraging about this, though. There's no lesson quite like losing money. There's no lesson like that you lose money. Look, I'm emotional. You can see, you can hear me, the way I talk. Right. And when I get behind a stock like a Wynn Resorts or any stock, you know, I. I really. I like the business model. I like the company. I like the management. And, And I. I think it is. I hear a lot. Hey, Jimmy, you shouldn't be so emotional. You should be more disciplined or more stoic. I get it. I should be. But I'm not. I'm me. And you know what? It's those emotional decisions that sometimes go awry. And you build up this repertoire, this history of the things that work, the things that don't work. And then you can recognize that pattern, albeit from your emotions. You can recognize when something reminds you of a winning trade or a losing investment and you either go in it or you stay out of it.
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Travis
Yeah. Something you mentioned at the top of this, before we hit the record button, that I'd like to spend a little bit of time on before we say goodbye is the. The rebounding of the markets currently in a. In a economy where it seems like a lot of other things are on fire is something that you've been asked about recently. Can you kind of talk about that for a second?
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Jimmy Lebenthal
Yeah. Well, you know, we. We see right now as. As we're talking that the s and P500, I think it was just yesterday set a new record high. And yet we've got the Strait of Hormuz closed. We have kinetic warfare continuing on between the US And Iran. You know, Kuwait's airport was bombed yesterday and somebody died. I mean, that's not good stuff. That's bad stuff. We've got inflation going through the roof. I mean, if I buy a cup of coffee, I'm stunned, let alone, you know, filling up your gas tank. $5 plus gas. There's the potential that the Federal Reserve may raise rates by the end of the year. That's not a good thing. A lot of political disagreement. So we get a lot of inquiries from clients or comments basically saying, how on earth can the markets be higher, equity markets be higher, with all this bad news going on? Or by the way, not just equities. How can bonds, how can Treasuries be so stable? And they are, in light of everything that's going on, more debt and deficit financing. And the answer is basically three things. One, the economy is doing quite well. Now, I know there are people out there who are suffering, and I'm not making light of that at all. But the economy is growing nicely also. Second thing, profits are growing. Profits are growing really rapidly. So that helps the financial markets. Lastly, and this is more sociological, this is more to every man. The labor market is actually improving. For most of 2025, we were quite worried about the labor market. We were worried that jobs were starting to get shedded from companies, particularly companies worried about margins as tariffs were instituted. But we're seeing jobs being created. We're seeing very little in the way of firing. So those three things together, economic growth, profit growth, and an improving labor market, are the reason why the financial markets are doing well.
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Travis
When you are, are there, are there hints or are there, is there evidence to you that that is going to be something that is a short Runway like that. It might shift at some point. Or are there things that you can watch out for or the average investor can watch out for?
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Jimmy Lebenthal
Yeah, I mean, the things that I mentioned as worries, particularly the Strait of Hormuz inflation, those are real worries. Those are like things to actually categorize as risks. So I mentioned also that the Fed may raise rates in response to this inflation. So I'd really like to see some resolution coming out of the Persian Gulf whereby the Strait of Hormuz gets open. Otherwise, if the Fed raises rates, number one, I don't think it's going to do anything to cure the straight of hormones. And number two, on the margin, it may hurt the labor market, which I just said is an important part of the three legged stool that I mentioned. So that, that really does worry me. We need to get, we need to get the straight of our moves open.
- [24:19]
Travis
Yeah, I want to touch on this before we, before we take off here. I know it's something that people ask you about a lot, but I do think that it's in, it's in the news a bunch right now and I'm curious to hear your insights on this. And really there's two or three major IPOs besides just SpaceX. I think anthropic is another one. There's a couple like, you know, big ones that people are really keeping their eyes on. What are your thoughts on a couple of these major IPOs?
- [24:41]
Jimmy Lebenthal
Right now we're in a really interesting time in the IPO market. So SpaceX is coming imminently, that's next week. And then OpenAI and Anthropic. And the reason that this is interesting is the size of these companies are enormous. We're talking trillion dollar plus valuations, which hasn't ever been seen in IPOs. And the actual dollar values being raised are in the, collectively hundreds of billions of dollars. Oh, by the way, add on to that, add to that that Google Alphabet just raised about $85 billion this week. So that's, there's all of this capital being created. These are big numbers. Exactly. These are wow numbers. I think with the iPodOS though, that specifically we're talking about, I want to add an element of caution here. Now I'm not saying they're going to be bad IPOs, but just be aware that these companies have already had so much wealth created while they're private that there is going to be a number of people, parties, entities that want to exit with that wealth creation, that want to sell. Of course IPOs have lockups to try to mitigate that. But just if you're looking at getting in these IPOs, just be aware there are a lot of people who are going to be looking to exit what you're buying. And they're great companies. I think what SpaceX in particular is doing is awesome. Landing these rockets back on the, the towers that they launch from with those chopsticks. That's incredible. Yeah. And I hope he does launch data centers in space and I hope he does get to interplanetary travel. I'm talking about Elon Musk. Yeah, but the stock's coming at 90 times sales.
- [26:18]
Travis
Yeah, nine. Yeah, I was going to say it's at the low end. SpaceX would trade at 94x sales is the last number I saw, which is, I mean, that's wild. There's a couple of comparisons here. Let's see. When Meta IPO'd, it traded at 28x while growing 88%, which is not the same growth rate. Google IPO'd at 10x revenue while growing 240%. And you have SpaceX, that would be trading at 94.4x sales. If this is what actually comes to fruition, that's. Those are some crazy numbers, man.
- [26:54]
Jimmy Lebenthal
You know, there's a great quote from around the year 2002 and anyone can look it up. Type in Scott McNeely, CEO of Sun Microsystems and valuation, and what he's doing, I forget if it was 2000 or 2002, is he goes back and looks at his own stock a few years earlier at 10 times sales and he goes on a kind of diatribe of how foolish 10 times sales is. It's a, it's a well written piece, it's well known, anybody can find it. And it's worth reading in light of what you just said and, and what I'm saying as well. I think, you know, this is a case of caveat emptor. Buyer beware. Yeah. Yeah.
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Travis
It's not necessarily saying that it's always going to be a bad buy, but maybe, maybe take a beat before you throw some money at that one.
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Disney Plus Announcer
Yeah.
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Travis
Because like you said, like, the future of it seems great. Like you said specifically to me, launching data centers into space. I think, I mean, there's almost no other way to scale with the demand of data centers that AI will require, like the amount of compute power that's needed. It's like, well, we just won't be able, the Earth will not be able to contain the volume of compute power that will be needed. So there are some things that, like in the future that I think are still going to stabilize that company and make it extremely valuable in 5, 10 years from now. But man, 94x is pretty wild. So buyer beware.
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Jimmy Lebenthal
And you know what? Maybe if somebody wants to participate in the ipo, that's fine. Why don't you save a little capital to buy some, you know, a few weeks later after the IPO has been digested.
- [28:32]
Travis
Sure, sure. Well, Jim, I appreciate you taking the time. I know you're a really busy guy. You got a lot of demands on your schedule. So I do not take that time lightly or for granted for those that are tun in you. You know, we have, we have these conversations a lot on the show. But it's rare to have somebody with this volume of experience who has taken all of that wisdom and put it into a book for all of us, all of us normal folks down here on earth to, to. To. To pour through and find ways to operate our own financial portfolios better. So. How to Ride the Subway. Go pick up a copy of Jimmy's new book. I know you will appreciate the. The his wisdom in that format. Jimmy, is there anywhere else that people can go to get more from you and the things that you're talking about?
- [29:10]
Jimmy Lebenthal
You know, I do appear on CNBC quite often, the Halftime Report, about two or three times a week, noon Eastern.
- [29:16]
Travis
Love it. Cnbc. Go catch some of Jimmy's segments over there and then please go pick up a copy of how to Ride the Subway. You will not regret that, Jimmy. Thank you for taking the time. Everybody else tuning in, remember, money only solves your money problems. But it's usually easier to solve the rest of your problems when you got a little bit of money in the bank. So let's solve that one first here on the Travis Makes Money podcast. Thanks for tuning in, guys. Catch you next time. Peace.