Reticent would be one way to describe the tone Adam Wexler takes in describing himself as a “serial entrepreneur.” Although his aversion towards the description is palpable in our conversation, he can’t help but to use the phrase twice because it couldn’t be more apt. Just 30 years old, Wexler has been involved in creating five startups including the social relationship intelligence platform InsightPool. Last summer Wexler, along with his co-founder, was examining the role of fantasy sport commissioner and how it was “the most thankless job in the world.” Born from this realization was SidePrize, where he now sits as CEO.
A “time/money equation imbalance” for participants of fantasy sports is what Wexler referred to as the beginnings of SidePrize. Known for finding market inefficiencies and capitalizing on them, Wexler saw the countless hours invested by fantasy commissioners and the little to no incentive they received for doing so. With companies like LeagueSafe already in the space of helping commissioners collect league dues, Wexler quickly pivoted SidePrize to capture the market in between daily and season-long fantasy leagues. In standard NFL fantasy leagues a dozen teams can slog through three and a half months of trades, setting lineups and scouring the free agent pool, with just one emerging as champion. This title is compensated by either bragging rights or a large portion of the pool of dues collected by each commissioner at the beginning of the season. But within each week exists so much of the trash-talk that makes fantasy so much fun, and Wexler has successfully turned “this behavior that was taking place offline into on-line.”
As NFL season begins this week, fantasy players using ESPN, Yahoo, NFL.com, MyFantasyLeague, Head2Head, and Rotowire can integrate SidePrize to challenge their league-mates to one-week challenges with money prizes. To entice leagues to sign-up, SidePrize offers credits for the site and gift cards to Domino’s and WalMart as well as a grand $500 prize to sponsor a draft party.
About 70% of the $15 billion fantasy market accounts for just football, so this is the peak time of year for SidePrize, but they also have recent accomplishments that will help keep them even busier. In late August, SidePrize was picked as one of the ten startups to participate in the Los Angeles Dodgers Accelerator Program. Wexler and his team were one of the over 600 applicants that were finally selected, and the three-month accelerator program in partnership with R/GA will assist them with branding, advertising, mentoring and other “additive” endeavors. This opportunity means more time in LA for the Atlanta based company, but Wexler will in addition be focusing his efforts to close SidePrize’s most recent round of funding.
With some prior experience pitching to investors, Wexler says this time with SidePrize has been different because of the demographics of fantasy players. He says when meeting with potential investors aged into their mid-40’s the conversation has been less about value of the market because so many have grown up playing fantasy. For those above 50 however, he enjoys “breaking down the history of season long, the advent of daily fantasy, and where SidePrize fits in” to them. In their seed funding round Wexler has drawn from his experiences in consumer and B2B based prior ventures because SidePrize combines both platforms.
With all of this going on, SidePrize’s dozen or so employees consisting of both engineers and forward-facing personnel are bustling to keep up with demand. University students interested in the sports/technology market can look forward to an opportunity to help SidePrize grow through a “college ambassador” program Wexler says should launch this football season. The season-long format of fantasy leagues has been slow to innovate, while daily fantasy leagues are creating unicorns, and Wexler and SidePrize are finding their sweet spot in-between the two.