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B
It is Monday and you know what happens on Monday? Normally I say let's raise our glasses and salute our troops. But guys, I feel naked. I don't have a glass. Well, what do you do when you need to salute the troops and you don't have a glass?
C
You have to do thousand burpees.
B
Or I can go get a glass.
D
Would that be.
C
That was burpees.
B
Look at the time.
D
Miss your opportunity, soldier.
B
Yeah, I think we just put our hand in the air and go. Hey, troops. On behalf of the men and women making podcast in mom's basement and all those stackers out there trying to do their thing, thank you for keeping us safe all weekend. Let's go stack some Benjamins.
C
Stack them. Stack them. Let's get some stacking going.
D
Live from Joe's mom's basement, it's the Stacking Benjamin Show. I'm Joe's mom's neighbor, Doug, and I've got 3 to 1 odds that you're gonna love today's episode. Today we tackle betting with your money and how to turn those bets into powerful money moves. We'll start out with a recent piece from the Wall Street Journal about a huge uptick in aggressive investing and prognosticate. That's a big word on where that might end up. But we'll also look at other assets and talk about betting on those. How would those work in your portfolio? But that's not all. We'll also share a TikTok minute featuring motivational speaker Tony Horsemouth Robbins. And then I'll motivate you with some of my incredible trivia. And now, two guys who were motivated enough to put pants on this morning. It's Joe and O. Ja ja, ja.
E
Ja, G.
B
You know I'm motivated when I'm even wearing pants. Everybody happy? Welcome back to the Stack of Benjamin Show. Sit back, relax. You found us. Grab your favorite beverage and your favorite place to take notes because we're diving into your investments today. It seems like some people are investing, well, maybe a little differently than we would recommend. We'll get into that in a minute. But first we're going to get into introducing you to the gentleman across the card table from me. Mr. OG is here. How are you, dude?
C
I'm in the middle of trying to transfer one iPhone to another iPhone, but otherwise I'm doing great to do that.
B
Do you go in the transfer portal? Do you have like the iPhone transfer.
C
Portal in the transfer portal right now?
B
Yeah.
C
They're negotiating for starting positions at a D3 school.
D
I'll be taking my talents to an iPhone 17.
C
Yes.
B
Did you see I was listening to a podcast the other day and sports fans, this is actually about money. Even if you're not a sports fan, this is about money. And I didn't know we were going to talk about this, but on the Rich Eisen show, they were talking about how there are still 1200 kids in the portal, 1,200 athletes in the portal. The reason they went in the portal was because some well meaning adult was like, dude, you need to get paid. You need to get more money. There are maybe, one of this analyst said there may be seven or 800 college athletes that ended their career.
D
Yeah, that decision, it's not like they can. They don't get picked up and. Well, I'll just go back to my old team.
B
Yeah, you're done.
D
Good chance they're like, now we found somebody better.
B
Yeah, you are done. So the money, the money train, as it were, might not be as flowing with cash for everybody as people originally.
D
One way to learn a lesson in college.
B
It is a tough, tough lesson. The grass, believe it or not, is not always greener. We're going to actually talk about that today. When it comes to investments, about investing in your portfolio, what you choose to invest in to some degree, even if it's an investment that makes sense, we call it an investment when the odds are so stacked in your favor that we think it's worth putting your hard earned money toward. We call it a bet when it's based on our gut. However, even an investment to a very, very tiny degree is just a well researched, well reasoned bet. So we're going to talk about recent Wall Street Journal piece that talks about that today. Before we get to that though, I got to tell you what was really cool. When I went into our new product, the Vault, I immediately put my phone number in and it told me that my phone number was on the dark web starting in August of 2024. So all these people that are writing me, Doug going, hey, you coming over for lunch? Hey, are we still getting together later that I'm answering because I'm all excited because I have all these friends that I didn't even know that I had. Well, turns out that those weren't really friends of mine and they were just trying to rip me off. Who knew? Who knew?
D
Back to reality. You've still got one and a half friends.
C
Yes, plus the person from Firehouse and.
B
The person from Firehouse Subs. That's a story we may tell you about later because sadly my phone thinks.
C
I live at Firehouse Subs So does your waistline.
D
Siri give me directions to my house.
B
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C
Hello, darlings. And now it's time for your favorite part of the show, our Stacking Benjamin's Headlines.
B
Our headline today. Okay, how many times have we said this line comes to us from Jason's week? I think we've said that three or four times.
D
Is he on staff here?
B
And he's going to demand royalty checks pretty soon? We are fans of Jason's. Of course we're fans of a lot of the people at the Journal, and we seem to have a few writers that just. Man, they do a great job. And Jason in this one, in his column the Intelligent Investor from a couple weeks ago, his headline is when All Bets are off, All Bets are on. He writes, fellow investors, financial markets work best when everyone knows the rules and we can generally trust other people to follow them. That doesn't mean we know what's about to happen, but we do like to tell ourselves it means we understand what is happening. That's why investors hate uncertainty is one of Wall Street's most common cliches. But what's funny is Jason writes OG he writes uncertainty isn't a rarity in markets. It's the norm. And it's funny because we tell ourselves all these stories that on a daily basis that we know it's, oh, the market went down 100 points today because of XYZ. We have no idea if that's actually why the market went down. But we love a good story. We love telling ourselves that this is exactly why the market, quote market on a daily basis did what it did.
C
As chat GPT would say, volatility or uncertainty is a feature, not a bug. When it comes to investing.
B
It is 100% a feature. Jason says he wrote in 2008, investors hate uncertainty in quotes. Well, that's just tough uncertainties. All investors have ever gotten or ever will get, from the moment barley and sesame first began trading in ancient Mesopotamia to the last trade that we'll ever take on planet Earth, if tomorrow ever knowable with absolute certainty, who would take the other side of a trade today? I mean, this is really the key. Even when you're investing, is there somebody who thinks it's going to go up? And there's got to be somebody who thinks it's going to go down. Which really means what? For you to decide which side of that trade you take, you actually begin doing some research and you start looking into, okay, what's the probability that this thing is going to happen? And I'll give you an example. What's the probability that your checking account is going to go down in value tomorrow? 0% chance. What is the chance that your checking account is going to keep up with inflation between now and 10 years from now? Also 0% chance that that's going to happen. So we begin looking at, at the bets here. Here's the scary thing though, OG about betting is. So we look at January and the stock market. Treasury yields rose and U.S. stocks fell on January 20 because President Trump threatened to impose tariffs on Europe and didn't rule out using military force to annex Greenland. And then you saw on the glimmers of this vague plan for a greater US Presence in Greenland, prices bounce right back. You get all kinds of volatile things that happened in January. And yet we look at a double leverage. Rare Earth etf, which hypothetically might benefit, Jason writes, from economic development. Greenland, it went up 63% in a day and a hundred percent in a week. Stocks in Denmark at the time when we're calling Denmark, our, our leaders are calling Denmark names, you would think, oh, Denmark sucks. Denmark ETF source goes through the roof, does better than the S&P 500 over that same time frame. Canada, of course, the President saying that Prime Minister Carney booted out of his peace plan. Canada stocks go up in January more than the S P500 does, even though we think that it couldn't. And in fact, when you think, okay, well, this is a Trump problem. Anything that said truth, social or was related to Trump, those things all went up more, more than the S P500 went up. This is all in Jason's piece. A new study of speculative financial behavior over more than two centuries finds exactly what anyone with common sense would have predicted. People take more risk when stocks go up and the economy is booming. And it can last surprisingly long. So there is this thing. What's the point here, OG Is that the stock market's been going up. Generally, it's had its nicks and its cuts, but it's generally had this nice long run of going up. And the more it goes up, the more people speculate and the more wild it gets. Like, why are we betting on Denmark? Why am I betting on a Trump etf? Why am I betting on. On what? What was it? Rare Earth Metals, 2x leverage. The betting escalates the longer the stock market goes up because we start feeling more and more we. We feel more and more confident over time.
C
Is it that or is it because people have more margin of safety? And they're like, yesterday I had a hundred thousand dollars and today I have a million dollars. So betting the house is money I can invest. Bet 100k right now, and I'm still. If I lose it, I'm still good.
D
I assume that's what Joe meant when he said have more confidence. Yeah, maybe equals more money. More cushion for the push.
B
Well, yeah, I mean, it definitely makes us feel. I hadn't thought of that, though, guys. That having more money would make me more confident because I'm So far ahead of the game, I can afford to take the bet. But on the other side too, I've been winning so much lately. Like, there's been so much winning going out of my portfolio.
D
Really good at this.
B
Yeah. The chance of me losing. Okay, does anybody lose at this stuff? We've warned people about this a couple times OG in the past couple years. And in fact, about a month ago we did a similar headline talking about gambling and about how scary this can be, this gambling mentality that people have. These prediction markets that we talked about at the beginning of January that were coming online and becoming more and more popular. And now I see, by the way, my social media feed non stop where you can bet on where markets are headed. You can bet like anything. Like it's DraftKings. So you're not just betting on the NFL.
C
You can bet on any sort of thing that's in existence right now.
B
The boom in these markets. Zwig writes, I knew that these markets are booming. I didn't realize it was by this much. You can play short term bets in just about anything. And these markets, Kalshee and Poly Markets alone, just two platforms. How much money you think they're doing right now in weekly trading?
C
Oh, I would bet individually or together?
B
No, together.
C
It's got to be a million dollars, $10 million, $20 million. It's crazy.
D
It's more like 500 million. Come on. I see these ads like every time I finish playing a hand of Euchre.
B
On my phone, it's a billion dollars. A billion dollars a week. Just think about this. So this isn't even, quote, investing.
C
Well, none of that's investing at all.
B
Exactly.
C
No, no.
B
Yes.
C
And I don't want to call investing in Denmark betting. I don't want to call investing, you know, in precious metals betting. If you are doing it from a trading standpoint. If you're saying, I think a great example, I saw this thing on Twitter or Instagram or something the other day. An investor, you know, it was like on unusual Whales or something, an Investor had bet $30 million, levered 5 to 1 that the silver market was going to go down. Pretty big number.
B
Pretty big bet, Pretty big bet. Yes.
C
Now that person, and this is, you know, alleged. I don't know anybody who did it. It was just online, so it must be true. But I saw it the day before the nomination for the next Fed chair came out. And that day that the nomination came out, Silver was down 27%. So this person bet on the silver market going down five to One levered and then the next day the silver market went down 27%. Okay, I'm no expert, but that's shady AF, right? That's not betting or investing. That is just pure manipulation. But if you're looking at something and you're saying, I think this company's gonna do X, Y and Z because of a, B and C, and I'm gonna make a short term investment, I'm gonna make a short term purchase of that stock or a short term sale of that stock because of this news, that's a bet. That's 100% a bet. But if you're saying I need to be diversified and part of my diversification is to include smaller countries that I don't generally have in my portfolio because I have all my money in the S and P and I want to have some international companies and because of that I have a 2% position in Denmark. That's investing.
B
Sure.
C
A 2x levered ETF on rare earth metals the day before, the day after this press conference of, you know, whatever. Okay, That's a bet. And you may win or you may lose. But don't confuse that for investing.
B
If we just lay down something definitionally to agree on og, which is that even though you don't like the term bet and I don't like the term bet in a very, very broad way, everything we do is a bet. We're betting that the thing that I had for lunch is going to be cooked. Right. I'm betting that it's going to taste good. So I feel like there's these degrees of bets and I love the definition. No, no, no. This is investing, this is betting. I totally get that. But even when we look at the s and P500 over a long time or, you know, take what you said earlier, Denmark. I'm betting on the fact that Denmark is going to be around. I'm betting that the historical stuff that's happened with Denmark that I could use to make my decision will help me grok how this is going to help my portfolio in the future, I am betting that the instrument that I'm using is either diversified enough or to do whatever it's going to do in the portfolio based on a hell of a ton of information. So it doesn't have to be a huge leap. But I do feel like, like an investment in a single economy is still much more of a bet than an investment in the total stock market index as an example. Like an investment in the banking sector is more of a bet. Even if I'm doing it from an investing standpoint, it still is more of a bet, I believe, than a broadly diversified across many sectors investment. And so I kind of see this. On one end I've got DraftKings and the Poly market and all this craziness. And on the other end I'm betting some economy somewhere is going to continue. So I do vtsax, right? So I do the Vanguard Total Stock Market Index. I'm just going to buy everything because I'm betting that something's going to continue.
C
I don't like the word, but I'm not going to argue anymore about it with you. I think it boils down to time frame more than anything.
B
The reason that's important is because if somebody is new to investing and they're listening to us, you really want to do some calculations around probability, around risk management. You know, Annie Duke said this, the poker player when she was on the the show about thinking in bets. I want to think about probability and the difference in probability with a dollar when you invest in the S&P 500 versus a dollar down at the liquor store, at the Powerball or the Mega Millions. There's a huge difference in those bets.
D
Some of my best investing happens at the liquor store. I don't think I like where you're going with this.
C
It's not even the same thing. I don't think those are comparable in any way, shape or form.
B
It's going to be use of a dollar. Well, no, they're not. You know why they're not? Because the probability of success is so incredibly different. Zweig writes. How should investors as opposed to traders approach these markets where you can bet on everything? I like his next line. OG with a 10 foot pole and a hazmat suit, it's fine to do a little bit of speculative trading, he says, for fun in a Mad Money account. But never, and I mean never, mingle that with your long term accounts. Isolate your speculation a separate account on a trading app. Use only for that purpose. Give the account a nickname like Play Money to remind yourself this is the only place you'll speculate, measure your gains and losses accurately. So you don't kid yourself about whether you're good at it. But I think this is important and the reason I love this piece is because for you, og, it's clearly two different things. But that's because you're trained in this to somebody who is brand new to investing and they go, oh, I could just bet them where The S&P 500 goes up and down today. Why Would I not just bet on it one day versus betting on it long term? Like why would I keep my money around every day? That just doesn't seem to. Well, it's because we know. We know how it works. We know how the probability game plays. But a brand new investor doesn't realize the huge difference in probability. This is why when we answer your question, Stackers, when someone says, well, should I get in front of this and put more money into AI stocks? OG will go, that's stupid.
C
Don't play that game. Don't do this.
B
And that's because your probability of success is so much lower and the juice not really worth the squeeze.
C
It's never worth it.
D
He says that about everything though.
B
Don't do that. Link to this piece on our Show Notes page@stacking benjamin.com after the break. What we are going to look at is your different probabilities of success based on different investments that you may make. And some of these may be surprising if you're a new investor. So we're going to look at not things as obvious as the Powerball versus the S&P 500, but all the nuance when you look down that whole scale. That's coming up next. But right now I think, Doug, you've got something that happened on today's date in history, right?
D
Sure do, Joe. Hey there Stackers. I'm Joe's mom's neighbor, Doug. And today we say happy birthday. Happy birthday to an actor who's earned tons of Benjamins while starring in some of your favorite films like Creed, Black Panther and Fruitvale Station. Who is this birthday boy? I'll be back right after I see if I can score an audition for the next Black Panther movie. I could play his brother by another mother.
F
You didn't start a business just to keep the lights on. You're here to sell more today than yesterday. You're here to win. Lucky for you, Shopify built the best converting checkout on the planet. Like the just one tapping ridiculously fast acting, sky high sales stacking champion of checkouts. That's the good stuff right there. So if your business is in it to win it, win with Shopify. Start your free trial today@shopify.com win.
E
Most people don't realize how much their personal information is being bought and sold every day. Data brokers are making billions pulling details about you from public records and the Internet, then packaging and selling it, usually without your consent. That's how your information lands in the hands of scammers, spammers, even stalkers. It's why you get endless robocalls and why ads seem to follow you everywhere. That's where Aura comes in. Aura actively removes your data from broker sites and keeps it off. They also instantly alert you if your information shows up in a breach or on the dark web. But Aura goes beyond data protection. With one app, you get a vpn, antivirus, password manager, spam call protection, dark web monitoring, and even up to $5 million in identity theft insurance. All backed by 247 US based fraud support. Other companies might just sell credit monitoring or just a vpn. Aura gives you all of it together at the same price. Competitors charge for just one service. Start your free trial today at aura.com Secure. Protect yourself now at aura.com Secure.
G
Most people don't realize how much of their personal information is being bought and sold every day. Data brokers are making billions pulling details about you from public records and the Internet. Then packaging and sell selling it, usually without your consent. That's how your information lands in the hands of scammers, spammers, even stalkers. It's why you get endless robocalls and why ads seem to follow you everywhere. That's where Aura comes in. Aura actively removes your data from broker sites and keeps it off. They also instantly alert you if your information shows up in a breach or on the dark web. But Aura goes beyond data protection. With one app, you get a vpn, antivirus, password manager, spam, call protection, dark web monitoring, and even up to $5 million in identity theft insurance. All backed by 24 and US based fraud support. Other companies might just sell credit monitoring or just a vpn. Aura gives you all of it together at the same price. Competitors charge for just one service. Start your free trial today at aura.com secure. Protect yourself now at aura.com secure.
D
Hey there stackers. I'm budding actor and guy who whose Hollywood dreams have been crushed because Joe's mom won't let me use the phone. Joe's mom's neighbor Doug. I already told you, Ma, I used up all my minutes calling Ms. Cleo.
B
Jeez.
D
Joe's mom ruins all my great ideas. But that's okay. That means I'm still here to deliver today's trivia answer to the question, who is today's birthday boy who starred in many of your favorite films like Creed, Fruit, Bale Stadium Station and Black Panther? The answer, of course, it's a guy who's a big fan of the show. Michael B. Jordan. Happy birthday, Mike. And now back to the money. Superheroes at the microphones Well, I mean, at least they enjoy wearing tights. Joe and OG.
B
Oh, geez. Big fan of wearing tights. And Michael B. Jordan. Happy birthday, man. Happy, happy birthday. Doug, you are a big fan. Do you see Fruitvale Station?
D
That's been on my list for a while because I know that is very well reviewed, well regarded, and I have not, I've not seen it.
B
You and I disagree on several movies. We won't disagree on that one. You will really like that movie.
D
Okay, yeah, I got a powerful movie, good stuff. Gonna get that one to float to the top of the list again.
B
Yeah, but that list is always just so long, isn't it? It's like, yeah, 50, 000 things I need to see. The enemy is time. Speaking of time, let's do a tick tock minute. This is the time in the show where we shine a light on a TikTok creator who is either doing something brilliant or air quotes brilliant. Our theme today is probabilities and whether you're making good investments or bad investments. And what I love about this topic, OG is even. Even people you think should be really good investors share bad moments. This is a voice that many of you have heard before. A motivational speaker named Tony Robbins talking about an investment he made that might not have been as great as he thought it could have been in your worst investment.
H
When I was like 17, this woman pulled up in a brand new Rolls Royce cornice convertible. I was dumb enough to think I had a moment with this lady, right? So I talked to her a little bit and I said, wow, what's your business? She calls, well, my husband's business. I was like, okay, yeah, he's in penny stocks and everything else. I said, really? I said, well, dumbest thing you can ever ask. Got any tips? She goes, actually, we do. And I took $10,000, which at that time was a huge amount of money for me. I poured it all in this stupid speculation and sure enough, it went up for about two months and then it went through the floor and I lost all of it. And that's what told me, you don't speculate. You learn to become an intelligent investor.
B
When you hear Tony Robbins say that, you're like, yeah, not a great idea. But it's the exact same line that we just heard Jason Swigg say in his piece. Yep, I am not going to speculate. I'm going to learn to play a longer game. And I think what we do, OG is we look at these different asset classes. As an example, early on I talked about how Your checking account a phenomenally safe place for one day. But over 10 years, you're going to lose your butt to inflation. Right? The S P500. Our friends over at Ritholtz Wealth Management, of course, both Josh Brown and Barry Ritholtz been on the show on a daily basis. Buying into The S P500 is a bet because you win. According to Ritholtz, this is since 1950. You win 54 of the time. So, oh gee, in a given day, if you're going to put your money in the S P500, you might as well go to Vegas because it's pretty Damn close to 50 50.
C
I mean, Vegas isn't 50 50.
D
So I was going to say that's still better than Vegas.
B
But you are 5% better than the roulette wheel there, right? 49 chance of winning on the roulette wheel if you just play red or black. If you leave it in though, for a month, right, that bet, which is 54%, becomes 64%. But if you leave it in the stock market for a month, you now have a 64 chance of that investment winning. If you invest for a year, what was 54 for one day now becomes 79 chance that you're going to win. And that's in one year. And oh, gee, I know you well enough to know, you know, if somebody says a one year goal, you're still not going to tell them to put money in the stock market. But if we're thinking in bets, I got a 79 chance that I will win that bet, right? That's still pretty damn good odds. But look at why we call this investing. We call investing in stocks a good idea when you get past five years. Because at five years, historically since 1950, any five year period, you came out ahead 93% of the time. Over 10 years, the bet goes to 97% of the time you came out ahead. And get this, there was never a 20 year time frame between 1950 and now. Take any series of days you want where you didn't come out ahead a hundred percent of the time you came out ahead. This to me is the point of what Zweig's talking about. Why the hell am I putting my money in these predictive markets, gambling, when I could put a dollar in something where if I don't need the money for 20 years, I'm going to very easily make money. And I think a lot of new investors don't realize what a layup the stock market is over these long periods of time. And they're thinking, I gotta get rich tomorrow. Oh, gee, I gotta make this happen now.
C
Well, that's really the biggest issue is recognizing that the benefit of investing is the compounding that happens over long periods of time. And the problem is that it's very difficult to see in real time that happening. Even to the extent that you have something that's a little bit more fixed or guaranteed, like a high Yield savings account, 29 of the 30 days, you don't get any notification that you're going to get interest. It's just the one day a month where they go, we deposited $19 into your account for interest. You're like, oh, wow, sweet. And then you forget that the other 29 days it's earning it. You just don't manifest it until that 30th day. You don't get to experience it until then. When you extrapolate that out and say, now you have something that you know you're going to put in your thousand dollars or your, you know, your investment number, whatever it is, and if you happen to pay attention to it every single day, eat these wild swings of emotions. From today it's worth 990 bucks, and I lost $10. To tomorrow it's worth 1100, and I made 100, and then I'm back down to 1,050, and I lost 50, and now I'm back to 1100. And it's not as good as the first time I got to 1100, but it's still cool. And now I'm back down to 990, and that hurts worse than the first time I was at 990, because the first time I only lost $10, but now I lost $110. You get these wide range of emotions on a daily basis. And the best you can hope for is that that thousand bucks or the average I should say that you hope for is that that thousand bucks at the end of all of that chaos, 365 days later is worth 1100 bucks, and you go, la de da. I made a hundred frigging dollars with all of that chaos for an entire year just to have one year's return of a hundred bucks. But it's really not that. It's the stacking of those hundred dollars. It's the stacking of the thousand dollars. It's the stacking and compounding of it over time, which is the other reason when you do your financial plan and you put it in an Excel worksheet and you say, okay, I'm gonna say, I'm gonna Invest you know, 401 maximum is 24,500. I am 26 years old, so I can max it out. I'm gonna retire when I'm 66. That's 40 years. I'm gonna say the market grows at 8% a year, but I have $7 million. And you go, nah, that's not right. But wait, it gets better. That's putting 24, 5 in every single year for, you know, for 40 years. But what happens when you're 66 and you have $7 million in your bank account or in your investment account, right? And you don't touch it for the next 30 years. So for whatever reason, you don't need that money. You have other money, you have Social Security, whatever, your 401k money, you just let sit. You retire at 66 with 7 million in the bank. Without thinking about it, guys, how much money do you have 30 years later?
B
Oh, goodness.
C
When you're 96 years old, first number.
D
In 30 years, it's going to double six times.
C
I said first guess.
D
Okay, fine. First guess I'm going to say is 94 million.
C
Okay, pretty close. Like $80 million. It's inconceivable that you can tell a 26 year old, hey, if you guys put $24,000 away in your 401k for the next 40 years and then you retire and when you die when you're 100, you're going to give your family $100 million or $80 million or $75 million or $92 million like that doesn't that. We can't make those numbers check in our brains, you know, because 24, five a year for 40 years, you know, 800 grand, 900,000, whatever the number is. That's the power of compounding. It's the back end number. That's why Warren Buffett was worth $60 million when he was 50 years old. A hell of a lot of money, by the way, and now is worth 100 billion at 90. That's the difference. 60 million is insane amounts of money. 100 billion is incomprehensible. You know what I mean? Can't even fathom how much money that really is. But that's the compounding.
B
That's why the first thousand bucks is harder than the second thousand bucks. Why the first a hundred thousand bucks is harder than the second hundred thousand. That's why everybody says the first million, right? Millionaires like, oh yeah, the first million was hard. Then the second million just took off. It was like bam. All of a sudden it's there people going from 10 million to 100 million, yada, yada, yada. I want to take a look at these odds that we're talking about for stocks because you and I have seen OG people going, you know what, I'm not going to do that. I'm going to invest in a business because a business gives me a much bigger chance of success or a much, much bigger win. But again, we take a look at owning a business the same way I just looked at stocks. We can look at probability of success survival the first two years. 70% of business owners, their business lasts two years. So your goal, OG when you start off is to have a business plan and have a business that's going to be in that 70%, 30% of you are going to fail, but 70% of you are going to win. When we get to five years out though, instead of going up like the stock market, where it gets better the longer you keep your money in five years in a business, 50% of businesses survive longer than five years. And then we take a look at long term success. If you survive that first five years, 69.5% again, nearly 70% of those will last 10 years. If you can last five years, which is only one in two, then you have a 70 chance among those people of making it to 10. And by the way, if you make it 10, 76.5% of those people will last 15 years or more. So there's this, there is this clear delineation that you can see if you're going to own a business. If you're thinking in terms of bets, there's a much better chance that you're going to lose that bet. If you win, you, you can win. However, what do you see? In the stock market, we have to spend zero time working inside that business. But for the average business owner, you're going to spend a ton of time. And based on these odds those first five years, OG I want to be in the trench because if I can make it five years, I've got a much better chance of making it to 15 years. But the only way that I'm going to make it five years is to spend a ton of time doing it. So this probability that owning a business is going to be a better bet than stocks, I think it depends on what you're, what you're actually solving for. If you're solving for more life, it's going to be difficult. And also the chance of success, not nearly as much as in the stock.
C
Market, which is why the returns better.
B
Yeah. It can be better. But how many business owners do you know that are just barely making it? You know, but you're right. I want to ask you about a few strategies because you were talking about all that volatility. You know, there are some strategies that investors use sometimes to make the probability of success maybe higher. Dollar cost averaging, is that one of them?
C
No.
B
Dollar cost averaging doesn't make your chance of success higher.
D
Nope.
C
Statistically, putting the money in as fast as you can makes. Makes your probability higher.
B
Yeah. Dollar cost averaging just evens out your return stackers.
C
Well, it's just more realistic. It's like, what's better, investing 24,000 in your 401 a year for the next 40 years or putting in a million dollars today? Well, yeah, putting in the million today is better, but we aren't given the million on our 26th birthday. Okay, here's your choices. You put the million in today and get it at 60, or you can do 24,000 a year for the next 40 years. What do you want to do? It's like, well, yeah, I mean, given the opportunity, I would put it in. You know, if you have the choice to put the 7,000 in your Roth or it's 7,500, I guess this year. If you do 7,500 in your Roth on January 2, or should I do whatever that is, 600, 500 and some odd dollars a month. If you can do the 7500, do the 7500, which, by the way, is still dollar cost averaging. You're just dollar cost averaging annually instead of monthly. If your cash flow doesn't allow that and you can only do it weekly, then do it weekly. The goal is to get the money in. Not to be too precise about it. Yeah.
B
I think the lesson there, og is just don't hold on to cash. Waiting for a better day. Right. Do it as soon as you can.
C
Hear people that'll, you know, people say, oh, I'm changing jobs and I'm rolling over my 401k to my IRA or rolling my 401k to my other 401k, you know, because I changed jobs, maybe I'll wait to invest it. Like, why would you do that? Like you said, you got a 50, 50 shot. It's higher tomorrow anyway. And a 70% chance is higher in a year. There's some chance is not going to be. And by the way, it was probably invested yesterday when you had it in your old 401k anyway, so why wouldn't you keep it invested?
B
Basically but to your point, early on, this does not increase your chance of success because the underlying investment goes under. It still goes under. I mean, you're not going to win or lose based on that. What about using options?
C
Options are binary outcomes. You either are successful or are not. Options in the sense of trading them for purposes of making money. You lose more than you make for sure.
B
Yeah, I think 100% options can be.
C
Used very conservatively statistically using options on the upside. Because you're worried about. Well, if you're worried about the downside of, of a stock and using an option to protect the downside there more times than not the volatility will, you know, get you out and then you miss potential upside, you know, future upside returns because you're out of the market. So.
B
Well, that was my next thing, which is some people try to use stop losses. Right. And stop losses, these triggers that you set below the price that the stock's trading at now to try to prevent catastrophe. But so often people will set a stop loss og to your point and the stock goes down to the stop loss and the exchange traded fund goes down to the stop loss. You sell immediately, which by the way, it's all programmed in so you don't have to sit and watch it. It's a put into a computer on your behalf and then you're out of the position. And then, and then it works back.
C
Now you have, now you have a million dollars of cash and now you have to figure out when to get back in.
B
Yeah. And then it roars back. So options and stop losses I think are ways that you can get rid of the worst case scenario. But you also create a lot of worst case scenarios that would have never happened had you just decided I'm going to stay in this for 20 years. Like the statistics showed. Options, I think options, you know, if I'm using them to protect against my downside and what an option is, I mean this could be guys, an option to sell. So I've got this option to sell the stock market if it goes down. Right. So I can buy that option. But oh gee, when you look at the price of buying that option because it truly is, you're buying an insurance policy against what you have. The drag on that over time. I can't imagine how much money you're going to spend for this downside protection versus just going, you know what, I'm going to be investor for 20 years in the stock.
C
Yeah. Options are trading instruments, they're not investing.
B
Yeah. I've got one more piece on this which comes to us from a private wealth company and I will link to it in the show notes but I found this this piece that was five key probabilities for investment success. Probability number one stocks are likely to be cash over most 20 year horizons. Actually we just talked about over since 1950 over all of those 20 year horizons. Key probability number two, owning the market over trying to be clever is likely to pay off. The less you try to be clever the better you're going to be. It's almost funny. We talked to George Newman OG a couple weeks ago about creativity and he was like people get in trouble with creativity when they try to be clever. People get into trouble with stocks when they try to be clever.
C
Yeah. Don't.
B
Third, key probability number three. Diversification is likely to deliver a better outcome than concentration.
C
I disagree with that.
B
What I think it's going to more often deliver a better outcome than concentration. However, under diversifying can give you bigger cha ching at the cash register if you're right. If you under diversified just don't be wrong.
C
Yeah, yeah, precisely. That'd be right.
B
Yeah. Key probability number four holding sensible exposures to well researched risk factors should pay off.
C
It's a bunch of silly words all put together.
B
Not all equities have the same risks. So having sensible exposures to well research risk factors. In other words, I could buy a single small company stock or I can buy the small cap index. The small cap index is a sensible exposure to well researched risk factor versus just picking five small cap stocks to purchase.
C
Okay.
B
Key probability number five. If I'm looking at two investments to the same the one with a lower cost is much more likely going to give you more money 100 of the time.
C
Literally just say much more likely to give you more money. Is that what they are?
B
Much more likely.
C
No, actually synthesizing that. Okay, I am.
B
I am synthesizing the words.
C
If they are the same investment and one is less costly it will provide 100%.
B
I'll link to these on the show notes at stacking Benjamin stock. I would love to talk more about this either in our comments on Spotify or in our basement Facebook group. And let's talk about thinking in terms of probability. But clearly this betting that's going on. Oh gee, driving me drive me crazy. Just, just a billion dollars.
C
Stop losing and it won't drive you crazy. Be better start winning some of those. That's it's pretty fun.
B
That's probably the point. Doug, let's go out on the back porch because we've had some discussions lately around some of the episodes we've done.
D
Yeah, I can't wait to talk about this in particular because we have uncovered a whole bunch of stackers who are in the Costco love camp with me. We got a lot of people responding to our TikTok minute back on episode 1795 where we talked about Costco or the Tick Tock minute talked about Costco.
B
And that minute, just for people that didn't hear it, was about the Tick tocker. David said that people go into Costco and they think they're going to save money on a pallet of toilet paper, which they will. But there's so many hidden savings to going to Costco that he had never considered.
D
Yeah, right, exactly. And then we got a couple of suggestions from goers on Spotify. Goers says Costco travel is great for hotels, resorts and cruises. I'll check the hotel's website and then Costco's. I normally save substantial money and now you are dealing with Costco's cancellation policies and not the hotels. That's a big point.
B
Well, is it a big point because I don't know Costco's cancellation policy, is it better than the hotel?
D
Most. Yeah, in most cases they are. And that's. It's unusual because a lot of times when you go through a third party, if it's Expedia, right. It's worse and the hotel just like backs away and we're like, sorry, not our problem. Deal with Expedia. Which means you're not getting your money back. But Costco is incredibly strong negotiator for a lot of these things and, and typically have better policies around around those things. Then Costco throws in a Costco digital gift card often if you book through them, you can and use it in the store and online. Last reservation goer says they got 97 gift card back.
B
Wow. Yeah, that's almost the cost of the executive membership is what, 125 bucks?
D
I think they raised it. It's like 135, 145 now. But it's so. I mean, you make that back so fast.
B
Well, one is it just that 97 gift card alone a huge part of the way there.
D
We got a great comment from Hope. Ditto on the travel. Also, the Costco credit card includes travel insurance. And if you have the executive membership, certain rental agencies give you an extra discount. They got an auto program that works with specific dealerships and finding used cars and new cars with less hassle and bigger discounts, you get a gift card there too. Apparently, Hope also added you can get pet insurance and water service and other things. This is just one giant ad for Costco at this point.
B
Well, you've got the 2% executive membership rebate as well for all these expenses. So on top of that, and I.
D
Think I mentioned that back in that episode 1795, we just put every expense we can in our household onto that one Costco card. We get a sizable. I never go to an ATM for the year because I get. I. You don't have to. You can get a direct deposit or you can get a gift card. Well, it's actually, I don't know if they give you the gift card over a certain amount, but I just take cash and I don't go to the ATM pretty much for the rest of the year because who really spends much cash anymore? But it's a great program in my opinion. And then Hope also comments that Costco now has these things called business centers where you don't have to be a member. And they found out in her household that you can get some pretty inexpensive meat, obviously in bulk, but divide it up, however you need to cut it up, get it into a good Ziploc bag or whatever and freeze it. And you've got a big discount just using the business.
B
I think she was saying that as a non business member, you can still go in and buy from the warehouse, which includes like the. A lot of the same Costco stuff.
D
Yeah. So a lot of. Lot of ways to save money. And people initially bristle at that membership fee, but, man, you make that back so fast because there's so many other things besides just buying a gallon and a half of mayonnaise. And everybody makes that joke. But there's so many other ways.
B
I saw a piece this morning of Warren Buffett being interviewed, and he was talking about Kraft and all of the different products that Kraft has. You know, just think of Kraft and also how old they are, how in the zeitgeist they are, how many advertisements Kraft has had. They've been around forever. And Kirkland brand has been around for 20, I think 23, 24 years. Is that all what's incredible about Kirkland brand stuff in the same categories where they compete against craft, they're beating them like 2 to 1. I don't remember the exact number, but it was close to 2 to 1. They're doubling the amount of business. Kirkland on private label, where Kraft spends all this money on name recognition. Kirkland throws name recognition out the window and is out selling craft pretty Pretty incredible.
D
Agree. Why are we have. We're having this major love fest for Costco, which is.
B
I don't know.
D
It feels too good to be true.
B
I usually get stackers run all over it. The stackers. Stackers were all over it. What else we got?
D
Yeah. Also on Spotify, Joe Christian made a comment about our discussion about NASCAR driver Kyle Busch and his spouse Samantha. We did it. You might remember. I don't know if you do if you're paying attention, Joe. We did a story about them back in episode 1792. I've got this eidetic memory for everything.
B
Oh, gee, wasn't here for that one. And our friend Dana Ansbach took us through kind of how these IUL policies work so that we could look inside of them. But yeah, Kyle Busch and his spouse.
D
Samantha, they're suing Pacific Life, calling Life the life insurance that they bought retirement fund a scam. Christian says Iuls should be illegal or at least treated like private investments and restricted to accredited investors. Christian went on to also agree with me about how ridiculous their kids names are. Brexton and Lennox.
B
I don't remember this part at all.
D
He just sent that to me directly. Yeah, Christian just sent that to me directly. But he was like, Doug, dude, nailed it. Brexton and Lennox, ridiculous kids names. I think collectively they're called Brexit maybe.
B
What do you think? That's where the whole Brexit comes from. We just combine the kids names. Og what do you think about that idea that I. I mean, Iuls being illegal, that's one thing that's like, okay, but Iuls for accredited investors only. There's a piece of me that goes, you know what? These are complicated investments. When you look at the modified endowment contract rules, you look at how the inner workings of how you actually make money on these, how they work, it's so smoke and mirrorsy. It certainly seems to me that it's convoluted enough that accredited investor rules maybe should apply to iul.
C
They're not investments, they're insurance contracts. So you're never going to get. It's like asking the DMV to regulate the airspace of NASA. It's like a different thing altogether.
B
And that's exactly the kicker, because the story that Dana and I covered was how it was sold to NASCAR driver Kyle Busch and his spouse as an investment, as a retirement investment.
C
Well, yeah, but didn't they also not do their part of it, which was to put all the money into it like they're supposed to?
B
No, they did they were told that they needed to.
C
I read the countersuit from Pacific, and to be clear, I'm not saying that they didn't get screwed on this.
B
Sure.
C
But Pacific Life is countersuing them, saying, first of all, you can. Can't talk trash about us. You signed all this paperwork. You can't claim ignorance. Not only did you sign all this stuff, we also gave you 30 days to review it and then change your mind, which you clearly did not. And they're saying, again, I didn't dig into this at all, so I don't have any idea. But they're saying, hey, this thing was illustrated. As if you were going to put. I'm making the number up a million dollars a year into it for 30 years. You did a million twice and called it good. And then it blew up.
B
They did it five times or whatever. Yeah, yeah, they did it five times. And that was. The Bush discussion, was that they were told they had to put money in it five times. And then when they got the bill for the sixth time, that's when they went, this is not at all the way it was explained to us. Well, and then Dana and I also went on to talk about that. The same stuff Og, that we don't know. We don't know. And it's a complicated thing. And I can see somebody saying, you know what? This is a scam, or their friends telling them that it's a scam when it's just so damn convoluted how it works. And you could also, because you've seen these illustrations, you could have a guy who's telling you something, you got to put this in five times. And having you sign a thing that is showing. I mean, heck, how many disclosures do you sign when you buy a car? Right. We were just at the Volkswagen dealer, and it was amazing how quickly this guy's just shuffling paper. And he was so annoyed when I wanted to look at every page. He was so incredibly annoyed that I wanted to look at all of them. But, man, when you. When you buy these things, there's 50.
C
Million disclosures, waivers, not saying he didn't get screwed. I'm just saying, like, he had an opportunity to read it and review it.
B
Yeah. So to Og's point, Christian, if it truly is a life insurance policy, then it really wouldn't be subject to accredited investor status. The fact that it was marketed, this again, according to the Bushes, not as an insurance, but a investment. Og, that's always what makes insurance problematic. So we start crossing those two things together. Good stuff, Doug. Well, thanks everybody for those comments. We have had great chats on Spotify. We've had great chats in the basement. Our Facebook group. Go to stacky benjamins.com basement for more of those. If you're here specifically not because you want to talk about life insurance or about probabilities of stocks winning or being a business owner or. Or these bet on anything platforms that are bringing in a billion dollars a week. Now you really want to put together a comprehensive financial plan. Oh, G and his team are taking clients. So head to stacking benjamins.com OG and that is the link to their calendar. That's going to do it for today, I think, guys. So, Doug, let's bring this thing home. What should be on our to do list today?
D
That's right, Joe. First, take some advice from our headline betting. At least think about the odds that you'll win with your investment. That process alone would change how you think about your money. Second, if an investment could win big but you aren't sure and still want to invest, well, first, that's probably just a bet. And second, ask yourself if you'll still be okay if that bet goes sideways. But the big lesson, don't give Joe's mom 2 to 1 odds she couldn't guess. Today's trivia question. Who knew she was such a big fan of Michael B. Jordan? I mean, how was I supposed to know that? Happy birthday, Mike. Join us Wednesday when we talk relationships and your money. Douglas and Heather Bonaparte, join us with stories about relationships with your money, money accountability buddies or your partner. You're not going to want to miss it. This show is the property of SP Podcast, LLC, Copyright 2026 and is created by Josal Sehai. You'll find out about our awesome team@stackingbenjamins.com along with the show notes and how you can find us on YouTube and all the usual social media spots. Come say hello and oh yeah, before I do, not only should you not take advice from these nerds, don't take advice from people you don't know. This show is for entertainment purposes only. Before making any financial decisions, speak with a real financial advisor. I'm Joe's mom's neighbor, Doug, and we'll see you next time back here at the Stacking Benjamin Show.
B
As we're recording this, Doug, just before we started recording, you wrote to me that we found out that Catherine o' Hara passed away.
D
We did. We did. That one's a bit of a shocker.
B
She was only 71 and on Schitt's Creek. So funny.
D
Just nothing. She wasn't funny in.
B
There was nothing. She was.
D
Other than maybe Home Alone, where she wasn't really supposed to be that funny, but other than that. Wow.
B
Forget. That's her in Home Alone. Because she was such the mom, you know.
D
Right?
B
Yeah, she played the mom. So, so, so. Well, she was part of the cast of the show that won the Golden Globe that you and I both thought shouldn't have the studio. Seth Rogen show. The studio. She was. Had a big part in that.
D
I mean, she probably deserved it. I saw whatever, two episodes of that. And yeah, she's good in it. She's good in everything. But, you know, in Schitt's Creek or in. Was it the Mighty Wind. A Mighty Wind. The mockumentary and best in show. Best in show.
B
Christopher Gass.
D
She's just a vixen, just a hussy. And everywhere she goes, she's bumping into guys that she slept with her husband just doesn't get it. Oh my God. Just amazing.
B
And it's funny because you can't think of her without thinking of Eugene Levy. Like those two. You just think of, you know, even though they do a lot of stuff separately, those two, just from the beginning of their career coming up through what, SCTV for both of them, I think.
D
That's right. Yeah.
B
Yeah. And for our stackers that haven't seen the old SCTV skits that, that took Saturday Night Live.
D
Pretty much all of them.
B
It took Saturday Night Live to another level. Just. Just a whole nother level.
D
Right. It was on. Was it on like super late on Friday nights? It didn't go head to head with Saturday Night Live?
B
I don't think it did not.
D
But man, I mean, that's where the Bob and Doug McKenzie skit comes from. There's a lot of. Of stuff that made it into. I'll use your word again because you.
B
Were so proud to use Zeitgeist into the Zeitgeist. Yeah. John Candy.
D
Yeah, John Candy. And trying to think who else. It launched some pretty big careers and almost nobody saw it, I don't think. No, I mean that was early 80s Canadian, so early.
B
Not that popular and launched ton of careers, but Catherine o', Hara, man, gone too soon.
Theme:
This episode of The Stacking Benjamins Show—titled “Are You Investing or Just Placing Bets?”—dives into the sometimes-blurry line between investing and gambling, especially in today’s environment of speculative financial products, “prediction markets,” and aggressive trading behavior. Hosts Joe Saul-Sehy and OG use their signature light-hearted style to help everyday listeners understand risk, probability, long-term investing versus speculation, and how to stay grounded with money decisions amidst the current hype.
[10:33] Joe:
“Financial markets work best when everyone knows the rules and we can generally trust other people to follow them. That doesn’t mean we know what’s about to happen, but we do like to tell ourselves it means we understand what is happening... That’s why investors hate uncertainty—but uncertainty isn’t a rarity in markets, it’s the norm.”
[11:57] OG:
“As chatGPT would say, volatility or uncertainty is a feature, not a bug. When it comes to investing.”
[19:34] OG:
“A 2x levered ETF on rare earth metals the day before, the day after this press conference… That’s a bet. And you may win or you may lose. But don’t confuse that for investing.”
[21:39] Joe:
“Even when we look at the S&P500 over a long time… I am betting that the instrument that I’m using is either diversified enough… But an investment in a single economy is still much more of a bet than an investment in the total stock market index.”
[17:36] OG:
“Well, none of that’s investing at all.”
[17:47] Joe:
“This isn’t even ‘investing’… a billion dollars a week.”
[31:09] Joe:
“…if you leave it [money] in the stock market for a month, you now have a 64% chance… for a year, 79%… over ten years, the bet goes to 97%… There was never a 20 year time frame… where you didn’t come out ahead.”
[32:58] OG:
“The benefit of investing is the compounding that happens over long periods of time… it’s the stacking and compounding of it over time.”
[37:00] Joe:
“There is this clear delineation… there’s a much better chance that you’re going to lose that [business] bet. If you win, you can win big… but in the stock market we have to spend zero time working inside that business.”
[41:08] Joe:
“I think the lesson there, OG, is just don’t hold on to cash waiting for a better day. Do it as soon as you can.”
[42:31] Joe:
“Options and stop losses I think are ways that you can get rid of the worst case scenario. But you also create a lot of worst case scenarios that would have never happened had you just decided I’m going to stay in this for 20 years.”
"I took $10,000, which at that time was a huge amount of money for me, I poured it all in this stupid speculation and sure enough, it went up ... then it went through the floor and I lost all of it. And that’s what told me, you don’t speculate. You learn to become an intelligent investor."
[29:43]
"That’s the power of compounding. It’s the back end number… you can’t even fathom how much money that really is…"
[36:00]
“The betting escalates the longer the stock market goes up because we start feeling more and more we… we feel more and more confident over time.”
[15:34]
(from [43:57])
[End-of-Episode Summing Up – [56:17] Doug:]
“Take some advice from our headline: betting. At least think about the odds that you’ll win with your investment. That process alone would change how you think about your money.”
This episode is a big-picture, friendly but wise reminder: If you want to stack Benjamins, don’t confuse gambling for investing, and trust the math—especially time and compounding—over hype or “hot” plays.