Betting Against Ourselves

The rise of prediction markets isn't just a financial story, it's a cultural one.

Last month I wrote about something that had been building in my mind for years: the realization that active trading was doing more harm than good in my life.

I wrote about how I had finally put systems in place to turn my trading and account management over to trusted parties who are far better and more disciplined at it than I am. I had to separate the fact that I feel great about often being an accurate prognosticator on my blog about market trends, but that executing the corresponding trades was simply something I wasn’t good at.

Now, thirty days since my last trade, I couldn’t be happier that I made the decision. Admittedly, it hasn’t been incredibly easy, especially because I can’t remove all of my triggers and simply ignore the news, world and current events. I’ve been chugging coffee, reading headlines and trading every morning for the last 20 years. So I don’t expect it to be an easy habit to break.

But it’s getting easier, and I’m stepping away from reading every headline, every day, toward putting the phone down and living in the present moment once my work is done and my column is written each morning.

And I can’t imagine a better time to undertake this exercise. “The market” was once a symbol of integrity and serious business run by old fucks in bowties and suits, like the Duke brothers.

Now it has become less a mechanism for allocating capital and more a 24-hour Las Vegas freak show carnival of increasingly exotic wagers. Our market has become the pro boxing equivalent of when Screech from Saved by the Bell fought Horshack on Celebrity Boxing.

Back in year like 1980, a company had stock. Simple enough. Today you can trade options on the stock, leveraged ETFs tracking the stock, tokenized versions of the stock at 2 a.m., and prediction-market contracts on whether or not Joe Kernen is wearing a toupee when he reports on the stock.

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Wall Street and Las Vegas used to be different places. Those days are over. And new reporting from The Wall Street Journal confirms it. They reported this week that Charles Schwab is preparing to enter the prediction market business through a partnership with Cboe. According to the report, Schwab customers will soon be able to trade binary-style contracts tied to the performance of the S&P 500. The contracts function much like prediction market wagers: traders make a yes-or-no bet on whether an index finishes above or below a certain level and receive either a fixed payout or nothing at all.

In other words, one of the largest and most respected brokerages in America is moving further down the path of turning market outcomes into wager-like products.

To be clear, this is not simply a Schwab story, it is a sign of where the entire financial industry is heading. The distinction between investing and gambling is becoming harder and harder to identify.

Prediction markets have exploded over the last several years. Sports betting has become ubiquitous. Options volumes continue to reach extraordinary levels. Crypto exchanges offer leverage that would have seemed insane a decade ago. Every event, every opinion, every outcome increasingly becomes something that can be traded. Sometimes it’s tough to remember there’s actual company equity at the bottom of the pile of all this speculative shit somewhere.

Last month I wrote: “Every event is now a market. Every opinion is now a wager. Every moment of boredom can be monetized by putting money at risk on your phone.”

If anything, I understated the trend. The financial industry sees demand and it is responding exactly the way industries always do: by supplying more product. The problem is that the costs aren’t limited to individual traders. Most discussions about gambling focus on personal responsibility, addiction, and financial hardship. Those concerns are real. We already see rising stories of people using credit cards, personal loans, margin debt, and other borrowed money to fund speculative activity. The American consumer is tapped out, as I detailed a couple week ago.

Source: Zero Hedge

We’ve seen countless examples in crypto, options, sports betting, and meme stocks where people become trapped in cycles of chasing losses and doubling down on increasingly risky positions. But the risks do not stop at the individual level.

When enough leverage accumulates inside a system, personal mistakes become market problems. Speculation funded by borrowed money creates fragility. Fragility creates forced selling. Forced selling creates liquidity events. Liquidity events create contagion. The history of financial markets is filled with examples of this dynamic.

And as savings dwindles, margin debt as a percentage of GDP is consistently rising. In other words, we’re taking more risk. Gambling more. Investing less.

But leverage doesn’t look dangerous during a boom. It looks efficient. It looks sophisticated. It looks profitable.

Then something breaks, and when everyone is crowded into the same trades using borrowed money, small problems become trapdoors. And when market dynamics create multi-trillion dolllar trapdoors that are force fed into the indices, mutual funds and the average American’s retirement fund right before this happens, that’s when questions about systemic issues arise.

Crypto has already provided multiple examples of this on a relatively small scale. We have watched cascades of liquidations wipe out billions of dollars in value within hours. We have watched exchanges fail, lenders collapse, and leveraged traders evaporate seemingly overnight. This can, and will, happen in equity markets, prediction markets and option markets going forward.

And the world we are heading towards is one where prediction markets, binary options, leveraged crypto products, sports betting, and traditional brokerage accounts increasingly overlap and compete for the same attention.

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I don’t think we fully appreciate the psychological consequences of where we are heading. Twenty-four-hour prediction markets are inherently unhealthy for many people. Human beings were not designed to live inside a perpetual casino. Anyone who has ever been to Vegas for more than 2 days understands this. You arrive healthy, in shape, sober, excited to see friends and maybe place a couple bets on the NFL game, and you leave destitute, broke, 10 pounds heavier, smelling like cigarette smoke and trying to figure out which stripper stole your credit card number (this is a purely hypothetical example, I swear).

These platforms don’t just compete for your money. They compete for your attention, your focus, your relationships, your sleep, your peace of mind, and your ability to be present. They monetize uncertainty itself. They thrive off of your loneliness and boredom.

The more events become tradable, the more incentive there is to constantly monitor outcomes. The result is a culture where people never disconnect. Every election becomes a market. Every earnings report becomes a wager. Every sporting event becomes an opportunity to speculate. Every idle moment becomes an invitation to check prices, odds, probabilities, and positions. The smartphone becomes both casino and brokerage account.

And the “markets” are not regulated at all and are susceptible to massive corruption. You thought a questionable pass interference penalty at the of a playoff NFL game was bad? How about when Coinbase’s imbecilic CEO ended a company conference call by spouting off random words to cash bets for god-knows-who in the prediction markets? He said live on the call: “I was a little distracted because I was tracking the prediction market about what Coinbase will say on their next earnings call. I just want to add here the words Bitcoin, Ethereum, blockchain, staking, and Web3 — to make sure we get those in before the end of the call.”

As I noted last month, I’ve seen people trading crypto between rounds at the gym. I’ve seen friends checking futures markets during dinner. I’ve seen twenty-somethings betting every pitch of a baseball game while sitting at a bar. And I’ve been all of those people myself.

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When I step back and look at the bigger picture, I can’t help but wonder whether all of this is symptomatic of something much larger. A society doesn’t become stronger by turning every aspect of life into a wager.

A society becomes stronger by rewarding patience, discipline, craftsmanship, productivity, delayed gratification, and long-term thinking. Those are the traits that build companies, families, institutions, communities, and civilizations.

What worries me is that we’ve spent years moving in the opposite direction.

We have normalized endless money printing and financial engineering instead of productive growth. We have rewarded speculation over investment. We have encouraged debt over savings. We have elevated influencers over experts, virality over wisdom, and instant gratification over patience. We’ve built social media platforms designed to monetize outrage, political systems incapable of long-term planning, and financial products that increasingly resemble casino games.

And now we’re building twenty-four-hour prediction markets on top of all of it. It’s bad enough bullshit shows like Flavor of Love and The Golden Bachelor exist. It’s toxicity squared when we can bet on the outcome. At some point you have to ask whether we’re creating anything of lasting value or simply inventing new ways to distract ourselves.

The frightening part is that every one of these products is marketed as empowerment, democratization and opportunity…but many of them are really just mechanisms for harvesting attention.

And the commodity being extracted isn’t just money, it’s your time, focus, peace of mind and energy. To quote Morpheus from The Matrix, it is “…a computer generated dream world, built to keep us under control in order to change a human being into this.”

The irony is that the technology that promised to make us smarter often seems to be making us less capable of sitting still, thinking independently, or focusing on what actually matters.

That is precisely why I’m grateful for the decision I made last month to stop trading. It was about recognizing that the environment is becoming increasingly engineered to encourage constant participation. And I want no part of it.

As I said then, the older I get, the less interested I become in chasing every opportunity and the more interested I become in protecting my time, my health, my relationships, and my peace of mind. The irony is that the more speculation becomes available, the more valuable restraint becomes.

The easier it becomes to trade, gamble, wager, predict, hedge, leverage, and speculate on everything, the more important it becomes to simply step back. Because if the trajectory we’re on continues, speculation won’t be confined to casinos, crypto exchanges, or niche prediction market platforms. It’s going to be everywhere.

And that’s exactly why I’m thankful I already started walking away.

QTR’s Disclaimer: Please read my full legal disclaimer on my About page here. This post represents my opinions only. In addition, please understand I am an idiot and often get things wrong and lose money. I may own or transact in any names mentioned in this piece at any time without warning. Contributor posts and aggregated posts have been hand selected by me, have not been fact checked and are the opinions of their authors. They are either submitted to QTR by their author, reprinted under a Creative Commons license with my best effort to uphold what the license asks, or with the permission of the author.

This is not a recommendation to buy or sell any stocks or securities, just my opinions. I often lose money on positions I trade/invest in. I may add any name mentioned in this article and sell any name mentioned in this piece at any time, without further warning. None of this is a solicitation to buy or sell securities. I may or may not own names I write about and are watching. Sometimes I’m bullish without owning things, sometimes I’m bearish and do own things. Just assume my positions could be exactly the opposite of what you think they are just in case. If I’m long I could quickly be short and vice versa. I won’t update my positions.

As of May 20, 2026 I personally no longer actively trade (read my story here). My investing/saving is done by recurring contributions mostly to sector ETFs and a few select equities, trusted third parties who oversee my accounts, and advisors. Such advisors or funds, through individual equities, options, index funds, mutual funds, ETFs, or other securities, may have positions in, exposure to, or holdings of names mentioned herein that I know nothing about. Basically, via index funds, ETFs and individual equities it is possible I could own, have exposure to, or not own anything at any point. As of the same date, May 20, 2026, in an attempt to lead a healthier lifestyle, I’ve also excluded myself from fantasy sports, sports betting, online and in-person casinos and prediction markets.

And all positions can change immediately as soon as I publish this, with or without notice and at any point I can be long, short or neutral on any position. You are on your own. Do not make decisions based on my blog. I exist on the fringe. If you see numbers and calculations of any sort, assume they are wrong and double check them. I failed Algebra in 8th grade and topped off my high school math accolades by getting a D- in remedial Calculus my senior year, before becoming an English major in college so I could bullshit my way through things easier.

The publisher does not guarantee the accuracy or completeness of the information provided in this page. These are not the opinions of any of my employers, partners, or associates. I did my best to be honest about my disclosures but can’t guarantee I am right; I write these posts after a couple beers sometimes. I edit after my posts are published because I’m impatient and lazy, so if you see a typo, check back in a half hour. Also, I just straight up get shit wrong a lot. I mention it twice because it’s that important.