1. A Social Experience

For those accustomed to football squares and a smorgasbord of side bets with friends and work acquaintances, Super Bowl LV may feel lackluster compared to big games of previous years. In most states, medium to large social gatherings are strongly discouraged or banned. But when it comes to creating the community wagering experience you’re looking for, surprise, surprise, there’s an app. Betcha markets itself as the four-way love child of “sports betting, fantasy, Twitter and esports.” For those watching the Super Bowl alone, you can use this mobile app to make player predictions, challenge friends, follow others and participate in friendly smack talk. “Certainly with Betcha, part of their core mission is targeting that competitive streak,” Lloyd Danzig, a Betcha adviser and the founder and managing partner at Sharp Alpha Advisors, tells OZY. “People like me, who grew up playing video games, rooting on sports, betting with our friends in March Madness pools, that’s who they want to speak to.”

Last month, Circa Sports signed an exclusive deal with DeckPrism Sports, which will provide Circa’s mobile sportsbook in Colorado with advanced in-play betting technology. DeckPrism is advertised as a way to remove clunky waiting periods before an in-game bet is accepted while also providing players with better prices. Thus far, the sports gambling community has praised the company’s efforts. But responsible gaming concerns surrounding live betting remain. “One concern surrounding AI-powered in-play markets generally pertains to the rise of ‘microbetting,’ where the conversion of every sports ‘micro-moment’ into a betting opportunity could lead to consumer protection issues,” says Danzig.

3. Sports Gambling Still Illegal in Your State?

In addition to Betcha, there are several other fantasy sports companies that offer betting-like functionality, including PrizePicks, ThriveFantasy and Underdog Fantasy. These apps are designated as paid fantasy sports, which allows them to operate in many states where sports betting has yet to be legalized. Additionally, in most jurisdictions, customers over the age of 18 are eligible to play paid fantasy sports, whereas the legal minimum age for sports betting is 21 in all but six states.

4. Industry Appeal

In the future, this could make those innovative fantasy startups especially appealing to larger gaming companies hoping to keep up with FanDuel and DraftKings. Both sportsbooks began as daily fantasy companies and thus are able to acquire a customer base in states still on the brink of legalization. For this reason, last week the casino operator Bally’s purchased the emerging paid fantasy sports brand Monkey Knife Fight for $90 million. Even in the press release announcing the deal, Bally’s president and CEO, George Papanier, highlighted the appeal of leveraging MFK’s “collection of depositing players.”

5. Gamifying Fandom

Not every gaming startup will choose the gambling route. FlashPlays Live, another company Danzig advises, started in 2019 as an app where fans could make predictions and even win prizes. Since then, the company has streamlined its business model and designed the Dolphins GameTime app for the Miami-based NFL franchise, using the same innovative technology. Now fans can make real-time predictions while watching Miami games with the highest-performing fans taking home Dolphins-related prizes. Rush Sports has provided similar gamification services to last year’s Super Bowl runner-up, the San Francisco 49ers, as well as the Chicago Bulls and New York Islanders.

After witnessing sharp (aka professional) bettors go big on the Tampa Bay Buccaneers through the first three rounds of the NFL playoffs, the SuperBook at Westgate Las Vegas was the first to post its betting line for the Super Bowl. The Kansas City Chiefs opened at 3.5-point favorites, which turned out to be slightly higher than average. “There seemed to be not much interest on either side,” SuperBook’s Rex Beyers tells OZY. “Nobody was rushing to take out numbers that seemed to be off like they’ll try to do in other games or have in another year.” Since then, the SuperBook has joined the majority at -3 (meaning the Chiefs are favored by 3 points) and feels comfortable the line should hold until at least Saturday. Thus far, there seems to be a lack of a consensus among sharp bettors. But they’re also more apt to wait and see how the line is nudged in the days leading up to the Super Bowl and then react accordingly.

2. What About Props?

The most-discussed Super Bowl action comes in the form of propositional wagers (or props), where the bets are taken on the performance of an individual player or whether a specific event will occur. Want to bet the opening coin toss will turn up heads? That prop is available everywhere, but shop around for the most favorable odds. Think Kansas City’s Patrick Mahomes will throw for more than 329.5 passing yards? The SuperBook offers it as an over/under, meaning you can wager on whether he throws for more or less than that amount, with both sides at -110 (meaning you bet $110 to win $100). Also a fan of the NBA? Consider betting that Los Angeles Clippers forward Kawhi Leonard will score more against the Sacramento Kings that day than the Chiefs do against the Bucs, with Kansas City favored by 4.5.

3. Crossbar Action?

On Monday’s Bill Simmons Podcast, self-proclaimed degenerate gambler “Cousin Sal” Iacono offered his best prop bet ahead of Super Bowl LV. His favorite offer by FanDuel, a sponsor, is “Will an extra point or field goal attempt hit an upright? (Excludes crossbar).” He referred to the bet as “frisky” and mentioned how the kickers for both teams have missed extra points in recent weeks. “You could watch this with your eyes closed — just listen for the doink!” Iacono exclaimed. Could the bet hold an additional advantage, one where everyone wins? Even with 36 pages of props, the SuperBook doesn’t offer such a bet in case the ball indistinctly grazes the upright, or vertical part of the goal post. “That turns into a nightmare because you've just got to pay both sides,” Beyers says, as gamblers will parse video replays on a play that’s not always easy to judge. It’s unclear if FanDuel would address such an issue the same way, but it’s easy to see the mess that would ensue.

4. Propositional Advice

In his nine previous Super Bowl appearances (each with the New England Patriots), Tom Brady–led offenses have never scored more than 3 points in the first quarter. Given the knowledge of Brady’s early-game struggles, does that dictate laying -180 against the Tampa Bay Buccaneers signal-caller throwing a touchdown pass in the first quarter? First of all, it’s just a nine-game sample. Plus, it’s not as if this information slipped by Beyers and his colleagues at the SuperBook (hint: it’s less consequential than you may think). Simply put, a lot more goes into making educated picks. Rather than assume you’ve outsmarted the oddsmakers, try examining the behavior of the majority.

5. There’s Value as the Contrarian

The sports betting market is often biased based on the habits of recreational gamblers. “They don’t like to bet against things happening because it’s less fun,” says Rufus Peabody, a professional sports gambler renowned for his prowess as a prop bettor. Thus, betting the under on most player props may be advantageous. Also, the public’s propensity for betting overs tends to cause prop totals to increase over the course of the two weeks between the conference championship weekend and the Super Bowl. So keep that in mind. “I’m not going to bet the under on Tyreek Hill receiving yards now,” Peabody says. “I’m going to bet it as close to kickoff as I can.”

Carlos laughs harder than he has in 20 years. Don’t miss this hilarious episode with stand-up comedian Jo Koy. He talks about his breakthrough on The Tonight Show With Jay Leno, how his mom’s struggles as an immigrant helped make him funny, and the impressive class of comedians he came up with. Fall in love with Jo Koy just like Carlos does.

1. Super Bowl Betting Isn’t Mandatory

More than any other age demographic, adults in their 20s seem to approach gambling with reckless disregard. According to the National Council on Problem Gambling, just 58 percent of 18-to-24-year-old participants strongly agreed with the statement: “It’s my responsibility to spend only money that I can afford to lose.” For those between 25 and 34, the number is 65 percent. It’s a majority, but you’d still hope to see more concurring unequivocally. Additionally, marketing gimmicks and the growing popularity of sports-gambling-related content may instill the belief that it’s a social mandate to bet every angle and act on every hot tip you read about. The truth is, there’s no shame in sitting out an event such as the Super Bowl. Think you might have a problem? Call or text the National Council on Problem Gambling hotline at 800-522-4700.

2. Know Your Limits

Still intend to bet on the big game? In the majority of instances, state regulations require mobile sportsbooks to offer responsible gaming tools. Such functions allow customers to set personal limits for specified periods of time. For instance, you may cap yourself at $100 per day in total wagers and $10 per bet. Try to exceed either of those figures and the app will prevent you from doing so. At the very least, going through the thought process of what you’re comfortable losing can be beneficial.

3. Predatory Practices?

It was only May 2018 when the U.S. Supreme Court paved the way for legalized sports gambling, meaning the American sports betting industry is still in its relative infancy, especially online. The same goes for many responsible gaming regulations. Be aware of seemingly innocent practices that could actually be considered predatory. On Jan. 15, the New Jersey Division of Gaming Enforcement informed a mobile sportsbook operating in the state that if it continued the practice of encouraging customers to cancel withdrawals, stiff consequences would follow. The practice of allowing withdrawal reversals — an option for customers to reverse their request in the days it takes for a sportsbook to “verify” their information — is growing less and less common, but many still offer this function.

1. Gadoon Kyrollos

He grew up gambling on chess matches with relatives; he was selling multi-wager “parlay cards” in grade school; he started taking bets on illicit dice games by 15. Gadoon “Spanky” Kyrollos was born to gamble. But besides his early start, what makes the New Jersey native, now in his 40s, a revered sharp — or high-dollar sports bettor — is his uncanny ability to read the line. Whether it be injury updates or observing how international markets move, Spanky has learned to lean on his own research — as well as automated systems. But because he can beat the house’s edge at any given moment, bookmakers have either given him limits or banned him altogether. Kyrollos refuses to share his picks for fear his methods will be reverse-engineered, despite receiving dozens of requests for tips. That said, he opens up about his life as a professional gambler and the field in general on his podcast, Be Better Bettors.

2. Jeff Ma

He forced the gambling world to know his name after tapping Vegas’ pockets for roughly $2 million between 1993 and 2001. A broke MIT student at the time, Ma was convinced to join a blackjack team where his natural talents made him a master card counter. Once, he was even kicked out of a riverboat casino after winning $80,000. The streak inspired the book Bringing Down the House and the movie 21 and cemented his legend in the pantheon of extraordinary risk-takers before the age of 30. Ma’s success goes beyond the gambling table to founding, then selling, developer platform tenXer to Twitter for close to $50 million in 2015, and working analytics for the San Francisco 49ers, Portland Trail Blazers and other major sports brands. Now he sits aside Rufus Peabody as co-host of Bet the Process, a podcast on sports gambling and analytics.

Winning thousands off Pope Francis kept Stewart from going into sports betting full time (don’t worry, she paid her tithes, although she no longer practices). While she put up the $300 with her bookie, who had then-Cardinal Jorge Bergoglio of Argentina at 14:1 long shot odds of becoming pope, the Kansas State grad owed an old college pal with insider information on the Catholic Church for knowing where to place the bet. The gesture opened Stewart’s eyes to the significance of intel and is the reason she’s a handicapper today. The Las Vegas resident is now the director of media relations for WagerTalk, a gambling expert at Bleacher Report and host of Bet On It, where you can catch her sharing tips on how to bet ahead.

What does a sports gambler do when there’s no sports? When leagues went dark, many of them embraced the rise of commission-free, no-account-minimum mobile investing and flocked to the stock market. But unlike serious investors who study an asset’s portfolio, mitigate accordingly and wait for a return, opportunists play the stock exchange, frequently exiting stock positions to profit from their short-term movements. Day trading, which now has user-friendly apps with jargon to suit all walks of life, provides gamblers and thrill-seekers alike the perfect model to step into: They buy and sell in short time frames, never holding on to a stock for too long. But between commission fees and low return, there’s not much money to be made that way.

2. Strategies

Day trading and gambling both have methods that can either give an edge or save money. Kyrollos places NBA bets earlier in the day because he knows the Asian market will take his money and he can get in before lines move in the North American market. His attention to sportsbooks in other parts of the world gives him a slight edge over other bettors, and the same kind of insight can be applied to trading. Even if you’re opening and closing stocks for quick gains, picking up details and context clues before pulling the trigger will heighten your success. And if you were a gambler who thinks like a suit, you’d never stick to one game. Diversifying your risk is a good strategy, regardless of the game.

3. Pitfalls

The problem with the proliferation of amateur investors, especially those taking heed from Reddit, is that it creates a volatile market, argue online brokers like Robinhood and Webull. But when the same brokerage apps blocked trading on GameStop, AMC and others amid a record boom in January, only hedge funds profited and their users took up pitchforks. While the dangers and the crash they speak of have yet to be seen, there’s no hotline to call for problem stock-market gamblers.