Day: November 6, 2025

The first time I saw that ICE was investing up to $2 billion in Polymarket, I did a double take. What do the immigration police want to do with a prediction market? I quickly realized the ICE in question was actually Intercontinental Exchange, the parent company of the New York Stock Exchange. That makes more sense, I thought — but also, only slightly? I thought the stock exchange guys were supposed to be the serious ones in the room, helping companies grow and people save for retirement, not teaming up with the guys who let you guess when the US government will admit aliens exist. But thus is reality in the year of our Lord 2025: Americans have a growing appetite for leaving their fortunes to the fates, and businesses are eager to capitalize.

“When people are given the means to bet, they’re going to bet,” says Jordan Bender, an equity research analyst at Citizens JMP.

The modern explosion of gambling in America began with the Supreme Court’s 2018 decision to strike down a federal law prohibiting sports betting, leading to its proliferation across dozens of states. Now, much of the conversation is being dominated by another type of wagering: prediction markets. These platforms, which allow people to put money on a wide range of outcomes, from election results to natural disasters, have long been limited in the US. But recently, they’ve taken advantage of lax federal regulators and what they say are legal loopholes to offer their services in a growing number of states.

“It definitely looks, smells, and feels like gambling,” says Steve Ruddock, a gambling-industry analyst and consultant and the author of Straight to the Point, a newsletter about the sector.

So do a lot of things these days. The lines between gambling and investing are increasingly blurred, from the crypto market to the stock market to sports, and, increasingly, everyday events. Arguments that this type of activity is beneficial because it shows us something about the wisdom of crowds, market inefficiencies, price discovery, or capital allocation are becoming harder and harder to buy. And businesses, even stodgy incumbents and unexpected players, are increasingly willing to capitalize on Americans’ urge to risk their hard-earned cash. Everything’s casino, and you’re either getting in on the action or getting left behind.

I think a lot about a conversation I had a few years ago with Chris Grove, a sports-gambling-industry investor at Acies Investments, about the growth of sports betting apps such as DraftKings and FanDuel. He made a point that I discounted at the time: Once people get a taste for betting on one thing, they’ll bet on a lot of things. This kind of gateway gambling represented a major opportunity not only for sportsbooks but also for investing apps and cryptocurrency platforms. When I relayed this to people, it felt like I was wearing a paranoid little tinfoil hat, but that case has quite clearly borne out in reality.

The recent hotspot has been prediction markets, most notably Kalshi and Polymarket, which match users willing to wager on either side of a discrete event. Kalshi has made a major push into sports, including in states such as California and Texas, where traditional sports betting is illegal. And as part of its push to become a “financial super app,” investing platform Robinhood has started branching into betting markets in partnership with Kalshi. ICE has invested in Polymarket and will distribute the prediction market’s data to investing customers trying to gauge sentiment on issues such as politics, business developments, and current events. Polymarket, once blocked for users in the US, is on the verge of becoming available nationwide. The NHL has signed licensing agreements with both Kalshi and Polymarket.

More traditional sportsbooks, which set the odds and against which gamblers bet, aren’t only expanding their offerings with things like online casino apps, they’re also taking a page out of their new competitors’ book, too. FanDuel is partnering with CME Group, a derivatives marketplace, to build an events contracts platform in the US that will let customers put money on where the price of gold and oil are headed, as well as economic indicators such as GDP and inflation. DraftKings has acquired the predictions platform Railbird.

It’s tricky investing a lot of money in this space right now, because it might completely go away.

When reached for comment, a FanDuel spokesperson pointed to a press release about the CME deal. DraftKings pointed to comments its CEO, Jason Robins, made at a gaming conference in October, downplaying concerns about competition from prediction markets, saying that sports betting apps are a “vastly superior experience.” Polymarket didn’t respond to a request for comment.

If your head is spinning at all of this, it’s understandable — this is all fast-moving and precarious. For one thing, it appears to be a reversal of previous regulatory approaches. Gambling has historically been regulated by states in the US, and at the heart of the matter now is whether prediction markets are considered gambling and, therefore, whether states should regulate them. Prediction markets say they’re OK because they’re simply offering contracts on the outcomes of future events and aren’t on the other side of the trade. Since these are futures contracts, like those offered for gold or oil, the theory — and current reality — is that prediction markets should be federally regulated by the Commodity Futures Trading Commission, not by individual states. The CFTC may be going along with this for the time being, but there’s a lot of gray area. Basically, an 18-year-old in California can bet on a Dodgers game on Kalshi now, if it’s considered a federally-regulated event contract. If it’s sports gambling, that’s illegal in California, and even if it were allowed, most states put the age limit at 21. Sportsbooks have state tax obligations that prediction markets avoid. Winnings are taxed differently, too.

“The vast majority of people that I deal with in this industry look at this and say, ‘This is gambling, it’s insane that we’re having this conversation,'” Citizens JMP’s Bender says.

Multiple states, including Massachusetts and Nevada, have sued or sent cease-and-desist letters to prediction markets, alleging they’re offering illegal sports gambling. Native American tribes that operate casinos and sports betting operations in certain states have made similar claims. The answer to, “Hey, is all of this activity on prediction markets kosher?” seems to be ¯_(ツ)_/¯.

“The big question is, do these contracts violate all of the sports betting regulations? And that’s kind of where things are right now,” says Chad Beynon, an equity analyst at Macquarie. “It’s tricky investing a lot of money in this space right now, because it might completely go away.”

In an emailed statement, a Kalshi spokesperson told me the company is “confident” in its legal standing. “Federal and state turf wars over commodities markets have been going on for decades in America, and the law is clear — Kalshi exists under the sole jurisdiction of the CFTC.” they said.

All the trickiness hasn’t stopped some major players from getting involved. Peter Thiel’s Founders Fund has invested in Polymarket. Donald Trump Jr. is involved with both Kalshi and Polymarket. The president’s social media company, Trump Media, is planning to allow its Truth Social users to jump into prediction markets.

“You look at the money that is lined up behind these two names, and that’s not money that has historically been involved with regulated gambling,” Grove says.

To be sure, what counts as gambling has always been hazy to define, says Peter Malyshev, a partner in the financial services group at Cadwalader, Wickersham & Taft. What constitutes a legitimate commodity futures contract is something regulators and courts battled over in the 19th and early 20th centuries, and when they arrived at their current definition, they couldn’t have envisioned a world of sports betting taking place on mobile phones.

“The whole notion of what gambling is, what is not, is very, very loosey goosey and it’s arbitrary,” he says.

It’s almost astounding to think about how commonplace speculation has become across the economy. A survey by the American Gaming Association found that 55% of US adults gambled in 2024, and Americans bet almost $150 billion on sports alone. That doesn’t include activities that very much resemble gambling, such as exotic stock options, crypto, and prediction markets. I recently discovered members of my family are crossing the Wisconsin-Illinois border to place sports bets on NFL Sundays, as gambling is legal in the latter state but not the former. And I have not been immune to the allure. On a recent trip to Chicago, I stopped at a DraftKings bar outside Wrigley Field, where I could place bets. During a pre-season Bulls game, I checked out a FanDuel lounge to catch some contemporaneous baseball and hockey games and placed a few small bets from my phone. This is all stuff that would have been unimaginable five years ago.

“Once upon a time, you had to know a bookie or a broker or go to a casino, that’s a lot more steps, and now it’s just a few taps away,” Parker Bach, a Ph.D. student at the University of North Carolina-Chapel Hill, who is studying digital political culture and prediction markets.

The less-than-ideal possible outcomes of gambling’s expansion were put on full display in recent days with the NBA betting scandal. Federal prosecutors allege that current and former basketball players, as well as people in their orbit, passed along insider information about players ahead of games to place bets on them. Sportsbooks are the victims of the alleged crimes — they’re the ones that were defrauded. However, the case has made clear opportunities for funny businesses that widespread gambling affords.

I mean, if we’re just being completely honest, it’s all gambling.

Consumer protection and legal issues aside, it’s worth considering how some of this activity is distorting the economy and blurring the lines between investing and pure speculation. Investing is intended to drive capital allocation in ways that foster good businesses, good services, and good products, and, ultimately, grow the economy. Gambling is entertainment. But when money from the former pot goes into the latter pot, that could become a problem — it’s not capital that’s going toward creating anything, it’s just a transfer of wealth. Tyler Gellasch, the president and CEO of the Healthy Markets Association, a nonprofit focused on increasing transparency for investors, says that the drive to funnel more money into speculative activities isn’t just a concern for individual bettors or investors. “It also takes real money out of the real economy and into essentially side bets,” he tells me.

Proponents of prediction markets say they have real value. They tap into the “wisdom of the crowd” and, in elections, may rival polling in predicting who will come out ahead. They can be used as a hedge against the possibility of different events — you place a little money on something that would hurt you, like your house burning down in a California wildfire, so that if the worst comes to pass, you’ll make money to offset the loss. These arguments can be shaky: Pretty much everyone on prediction markets was wrong about the 2025 papal conclave.

I don’t want to say everything’s casino, but a lot of things are casino.

“I mean, if we’re just being completely honest, it’s all gambling,” Ruddock says.

It speaks to a sort of nihilism within the American public — this idea that the system’s flawed, so you may as well go for it with a gamble. It also says something about just how alluring speculation can be; people do it because it’s exhilarating and fun and, for most, not a problem. We can quibble over legal and regulatory definitions all day, but the demand for speculation is there, and the supply is ever-expanding to meet it.

Emily Stewart is a senior correspondent at Business Insider, writing about business and the economy.

• Duolingo’s CEO highlighted the Duo-themed Halloween costumes that went viral this year.
• He said that the app’s cultural relevance is an “accelerant” to its product.
• Duolingo is famous for its creative and guilt-inducing app notifications and social media posts.

Hundreds of versions of Duolingo’s owl went trick-or-treating this year, and company leadership noticed.

On an earnings call on Wednesday, CEO Luis von Ahn highlighted the stream of funny and unhinged Duolingo-themed costumes people wore for Halloween this year.

“In terms of kind of being culturally relevant, et cetera, we really are seeing a complete pickup on that,” he said. “Throughout the world, certainly, there were thousands of Halloween costumes that were just Duolingo costumes.”

Von Ahn made the comment in response to an analyst’s question about whether the language learning app is focusing more on product or marketing.

“If we have a product that is extremely retentive that also teaches really well, that’s the best thing you can do, and that’s where we spend most of our efforts,” he said. “Yes, the cultural relevance matters. But to me, that’s just an accelerant to something that is where the main dish is the product.”

Duolingo is famous for its creative and guilt-inducing app notifications and social media posts. Marketing experts say the approach works, especially with Gen Z, because the app’s green owl mascot appears authentic and consistent. Whether it’s on TV, in YouTube ads, or on TikTok, where Duolingo has over 16.8 million followers, the company is among the first to tap into viral, often country-specific trends.

In the days leading up to Halloween, people shared their Duolingo-inspired costumes on TikTok, Instagram, and X. Many dressed up as the green owl mascot, while others recreated other animated characters on the app, such as Lily, a sassy, purple-haired teenager.

One costume, shared via a TikTok video, went particularly viral. The video, which has garnered 10.1 million views, featured a shirtless, muscular man in green shorts, green body paint, and a Duolingo owl mask dancing with his skeleton-costumed friend.

The costume racked up thirsty comments from users.

One person wrote: “If this were my Duolingo reminder, I’d suddenly be the most punctual student alive.”

Another TikTok user said: “I forgot to do my Spanish, come kidnap me.”

The company got in on the joke, too.

“Yeah I’ve been working out,” Duolingo wrote in a comment on the TikTok video.

Despite revenue and active user growth this quarter, Duolingo’s shares fell as much as 20% after hours on Wednesday because the fourth quarter estimate missed analyst expectations. The company’s stock is down over 19% this year.