Rick Rosner On, 7: Online Gambling, Prediction Markets, and the Risks Facing Young Americans
Author(s): Scott Douglas Jacobsen
Publication (Outlet/Website): Personal SubStack
Publication Date (yyyy/mm/dd): 2026/06/30
Scott Douglas Jacobsen interviews Rick Rosner about two troubling social trends: the spread of attention-driven online platforms and the rapid growth of app-based gambling. Rosner argues that gambling companies rely on statistical advantage and promotional incentives to encourage continued betting, while he personally experiments with cautious, low-stakes strategies on prediction markets such as Polymarket US. Despite occasional small gains, he concludes that gambling is ultimately a poor use of time and poses significant long-term risks for most participants.
Scott Douglas Jacobsen: What is new in your world?
Rick Rosner: I do have one topic. Actually, two. They are not quite related. AI is chewing up parts of the world of work, right? Plus, there are Americans’ own tendencies. There are two semi-related trends: unverified viral claims have suggested that 10 to 14 percent of American women aged 18 to 24 have posted on OnlyFans, but reliable public data does not substantiate that figure.
Similarly, young American men appear to be at elevated risk for gambling problems, especially through online sports betting and app-based gambling. You have two corrosive trends affecting different groups in different ways.
Jacobsen: Attention for one and gambling for another.
Rosner: Yeah. You cannot beat the house in gambling, statistically. I do not like gambling, but I will do it.
I do not like it because I am good at math, but I will gingerly gamble if I think I can find situations where the payoff is greater than the odds against me. Sometimes I am right, and sometimes I am wrong. Because I am mathy and maybe not addictive in that way, it has not cost me very much.
I deposited 100 bucks with an online bookie six years ago, and I am only down to 60 bucks. I got down to seven bucks, but I grew my stake back up to 60 without having to give them any additional money. They give me money every month.
Gambling is bad for you. Gambling companies give gamblers free money or credits because they expect this to increase gambling activity and, over time, recover more than they give away. This online bookie gives me about $10 a month in free money, which I can use to improve my odds.
If I am betting 15 bucks at normal shitty odds, but I am getting 10 bucks back, then I am really only gambling five bucks. That makes the odds more reasonable. I just joined Polymarket US, the regulated U.S. version of Polymarket, which is separate from the international platform and operates through a CFTC-regulated designated contract market. You cannot necessarily bet on everything that an international Polymarket user can bet on.
I put down 20 bucks. That was my stake. They gave me 50 bucks. Then they gave me another 10 bucks and another 25 bucks. With very cautious gambling, I have won about $1.80, but my stake has gone from 20 bucks to $105 because platforms like this expect many users who receive promotional money to trade or gamble it away and more.
As I said, you generally cannot win at gambling in a life-changing way without taking a significant risk with your assets, and it is not worth it. You are more likely to fuck yourself up than to improve your position.
I think some of the money that Polymarket US has given me may be related to glitches that temporarily took the site down or limited trading activity. As an apology for doing that, some of these extra little transfers of money may be meant to make up for the trouble.
“I am sorry for your trouble. Here is some money.” They can do that because they expect to get that money back. Statistically, or at least based on their tracking of past behavior, they can expect many people to gamble or trade more than they are given.
There you go. I have found one way not to beat the crappy odds, but to lower their impact.
On platforms like Polymarket, where you are trading on the outcome of an event, you can get into and out of a position somewhat like the stock market. Usually, when you bet on an event through a standard bookie, you have to wait for the outcome to see whether you win or lose. With Polymarket, you can enter at a certain implied probability before the outcome is determined.
The market has decided the percentage odds of that event happening. Then the platform’s fees, spread, or trading mechanics can add to your effective cost. You can also sell before the event occurs, or before the event becomes fully determined.
For example, if you bet on a sporting event before it starts, and your team has a two-thirds chance of winning according to the market, then maybe you pay 68 cents to win a dollar potentially. Then, in a soccer game, your team goes up by one. You can maybe sell at 80 cents because the odds that your team will win have gone up. Or maybe your team goes down by one, and you sell at 40 cents.
You do not have to wait to lose all your money or win at the conclusion of the event. You can limit your losses or protect your gains. You can also protect yourself a little bit against the crappy odds because, if you sell before the game is over, you are selling at the market price, minus fees or spread, rather than being locked into the original wager.
So, if you are getting crappy odds before the game, you can sell halfway through the game at something like those same market-driven rates. I do not know how much of a discount that creates against the extra cost you are paying to do this, but it can make a slight difference.
What I am doing, and I do not know if this works or not, is that earlier today I bet a dollar on Canada making it to the next round.
So I bet a dollar on Canada, and at halftime, the score was tied. The odds of Canada winning had declined. When I sold out at halftime to avoid risking my money if Canada did not win, I got 97 cents back.
I will wait for you to come back, or I will not. I will just keep going.
So I wagered a dollar, then I chickened out, and I got 97 cents back. I lost three cents. What I am hoping is that there was some kind of glitch during my day of gambling, losing three cents here and making 11 cents there, that somehow Polymarket US will decide a glitch prevented me from trading as much as I wanted.
Then they might give me 10 bucks to say, “Sorry that your trading experience was not as fluid as you may have wanted.” By losing three cents and making 11 cents, and by making these piddly little wagers, I might be gambling that Polymarket US will have some kind of issue that causes them to give me 10 bucks or 25 bucks in apology credits.
All this is really a waste of my time. Really, I should not be fucking around with this. That is a bigger cost than my bullshit little gambling.
Jacobsen: Thank you very much for the opportunity and your time, Rick.
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