Win Cash During Season-Long Fantasy Leagues with SidePrize

The Fantasy Sports platform lets you raise the stakes on a week-to-week or day-to-day basis. 

Say what you will to Adam Wexler. Just don’t call his fantasy game start-up, SidePrize, a gambling operation.  “I don’t the say the word gambling,” he points out, even though SidePrize traffics in a world that seems to be all about taking monetary risk. “What we’re involved with here is a game of skill and a competition.”

His reticence is understandable when you consider that SidePrize is a gambling add-on—sorry Adam, it is—to season-long fantasy football that makes it play more like daily or weekly iterations. But with everybody from Joe Namath to Bill Simmons taking pot-shots at embattled fantasy sports giants DraftKings and FanDuel, he may have good reason to be touchy.

Especially since his product will soon stand to function as a work-around for daily fantasy sports participants who happen to live in states where the activity has been deemed unlawful. And for savvy players in legal jurisdictions, it might eventually be a way to earn easy money.

SidePrize allows participants in friendly season-long leagues to go up against one another for as much as $100 (a sum that is due to increase) on any given week.

“It’s peer to peer,” says Wexler, craftily leaving out the word gambling. “We get money from both sides, via PayPal, and streamline the process of putting your money where your mouth is. Usually, when people do this among themselves, the pain in the ass part is collecting money from the loser. It’s such a pain that the money usually rolls over into the next week. Then, if one guy’s team is good enough to keep winning, the sum gets so large that it will never be paid off.”

Because you’re competing with the football team you chose in September, and it will be patently better or worse than that of the guy you’re betting against, SidePrize has a function that allows you to give or receive points on the wager. With that recently added component, it’s a pretty cool way of juicing up your ongoing fantasy action—and compensating for having a lousy team.

But there is one serious drawback: you can only make SidePrize wagers with people who are already in your league. For some people, that’s a good thing. For others—people who prefer betting against strangers because they plan on crushing them—not so much.

By next year, anticipates Wexler, the outer-league restriction will be lifted. Essentially, you’ll be able to post your team and open up shop for people to bet against you with their teams. That you’ll be negotiating a unique pointspread with each opponent will be labor intensive, but it will also provide unique edges for those who are most knowledgeable—i.e. winning daily fantasy sports players—and know how to value both sides of the wager. If you end up taking 10 points from me, when you really should be getting 15 points, my advantage will be huge.

Once Wexler raises the betting limits, opens things up, and builds a decent amount of liquidity, he is likely to have something really special – for him (he collects five percent vig on each total amount wagered) and for astute daily fantasy players. It’s something that he seems to know all too well.

“When we open up to allow participation from outside of your fantasy league, we’ll be opening ourselves up to a world of hurt,” he says, presumably recognizing that SidePrize will operate as a sort of reverse engineered version of DFS, with players outsmarting one another on setting pointspreads rather than on constructing teams.

“There are so many intricacies and so many ways of gaming the system and we’ll be dealing with a different clientele. DFS tends to be poker guys and Wall Street guys. Season-long fantasy is for obsessive sports fans who like sports more than they like gambling.”

By being a step removed from people actually picking players and theoretically promoting season-long fantasy, he may have figured out a legal way for DFS enthusiasts to satisfy their gambling needs. Wexler does not disagree, but he does emphasize, “Just to clarify: the verbiage we use is challenge. You challenge your friends to win prizes.”

 We’re not betting on his verbiage catching on.

Photos by WB Digital / Stone / Gettty