At least three Philadelphia businesses — a bakery, a sandwich shop, and a BYOB — got the same unsolicited pitch on Instagram last week: trade on the Eagles beating the Giants, and let the payout cover the cost of a win-day promotion. The Eagles lost anyway.
A Pitch Delivered Straight to the DMs
The prediction-market platform used its verified Instagram account to reach out to Philadelphia businesses ahead of Sunday's home game, according to Inquirer.com. The message floated a specific idea: place a trade on Philly winning, so if the Birds won, the payout would cover the cost of a giveaway tied to that win. A Kalshi spokesperson confirmed the company contacted a number of Philadelphia businesses before Sunday's game, but did not specify how many received messages, how recipients were selected, or whether any of them placed trades.
Rougarou Baking co-owner Paige Wenrick, whose shop sits in Queen Village, described the pitch as lopsided. “So it felt like [Kalshi] was specifically asking small businesses in the Eagle's home city to just give up money,” she said.
'I'm Already Gambling With Enough of My Money'
Chance Anies, who owns Tabachoy, a 28-seat Filipino BYOB in Bella Vista, also did not respond to the message. Anies said of running a small restaurant, “I'm already gambling with enough of my money.” The pitch was especially beside the point for his business: Anies is a San Francisco 49ers fan, and Tabachoy doesn't even have a television to broadcast games.
A third message landed with Liberty Kitchen, which has locations in Olde Kensington and Chestnut Hill. Culinary director Beau Neidhardt described getting the Kalshi message simply as “so weird.”
How Kalshi Frames the Offer
Kalshi calls these small-business trades “hedging,” and a company spokesperson compared the practice to insurance, saying the platform lets businesses take action against risks that affect their operational outcomes. The spokesperson said an Eagles-win trade made sense specifically for a business running a promotion tied to an Eagles win, since a payout would cover giveaway costs in that scenario. Kalshi said its outreach was meant to be educational rather than a direct instruction to hedge. Kalshi itself called the Giants a “clear favorite” in the matchup, which the team lived up to: the Eagles lost to the Giants 19-11 Sunday, extending the team's losing streak to seven games.
Kalshi has solicited small businesses before, too — in June, it asked the owner of New York City bar The Jeffrey to wager on the Knicks winning an NBA Finals game after the bar lost $4,000 in one night covering customer tabs during the Eastern Conference Finals. According to Fortune, The Jeffrey placed a $5,000 bet on that Knicks game, and the trade paid out $13,500 — enough to cover the tabs and leave an $8,500 profit. At the time, per CNBC, Kalshi's spokesperson said The Jeffrey was the platform's first and only small business to hedge with it.
Bigger Bets, Bigger Swings, Elsewhere
Fortune's reporting lays out larger examples of the same strategy. An unnamed Los Angeles hospitality group operating 25 bars traded $60,000 on Kalshi to hedge against the Dodgers missing the World Series; after the Dodgers lost to the Milwaukee Brewers in the NLCS, that position returned almost twice the original bet, helping offset revenue the bars would have earned from additional playoff games. A Los Angeles ice cream shop, meanwhile, reportedly earned nearly half its monthly rent — up to $1,500 — by betting on when cold fronts would arrive, a hedge against slow demand.
Founded in 2018, Kalshi began as a prediction market for trading on yes-or-no outcomes of real-life events and entered professional sports markets two years before publication. Sports now drive most of Kalshi's $30 billion trading volume, according to research from Pew cited in the Inquirer's reporting. Kalshi says it functions more like a stock exchange than a traditional casino or sportsbook, with users wagering against each other rather than against odds set by the house. It is federally regulated by the Commodity Futures Trading Commission and says it can operate in all 50 states.
A Regulatory Fight Still Playing Out
That claim to operate nationwide is contested. The NFL and attorneys general from 39 states, including Pennsylvania and Delaware, filed amicus briefs last month supporting New Jersey's request for Supreme Court review of state authority to regulate prediction markets. Judges in Ohio and Tennessee have already ruled that states can regulate the markets, while a separate ruling gave Nevada the authority to ban Kalshi outright.
For Philly's restaurant owners, the pitch arrived at an already rough stretch for the team. Quarterback Jalen Hurts was placed on injured reserve in mid-October after a blood clot traveled from his legs to his lungs, and the Eagles have now dropped seven straight. None of that history changes the math that gave Wenrick and Anies pause in the first place — a trade that only pays off if a struggling team wins, built around a business that still has to make good on its promotion either way.
