“The way I like to say this, on Outlier, it’s as easy to research as it is to guess. So we’re really helping bettors make more data-driven decisions.” ~ Evan Kirkham
“But we’re definitely minting more confident bettors… I’m at the barbecue and the Cowboys game is on. And I say, I’ve got Dak Prescott, two touchdowns. In 2018, my buddy is like, yeah, let’s go… Today in 2025, my friend says, why? Why do you have Dak for two touchdowns? And I need an answer.” ~ Evan Kirkham
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In this episode of the Straight to the Point Talking Shop Podcast, I welcome back Evan Kirkham, the CEO and co-founder of Outlier, a sports betting research tool that provides bettors with data-driven insights.
We touched on numerous topics, starting with Outlier’s recent funding round led by Discerning Capital, where Evan shares a heartfelt story of rebuilding trust through in-person meetings, highlighting the firm’s focus on relationships over mere transactions.
Evan also discussed Outlier’s partnerships, including relationships with major sportsbooks like FanDuel, DraftKings, MGM, Caesars, and PrizePicks, as well as prediction markets.
We continued down the prediction market rabbit hole for a bit, with Evan contrasting prediction markets’ innovative, tech-forward approach with traditional sportsbooks’ legacy systems, predicting UI/UX improvements will drive their growth. Evan also mentioned untapped opportunities like loyalty programs for tier-two sportsbooks and integrating land-based perks.
Two other points we discussed:
The responsible gaming angle of educating bettors, to prevent impulsive betting through informed decisions and promoting bankroll management — which I compared to preventing “tilt” in poker.
Market maturation, beginning with the 2018 gold rush of first-time deposits to today’s emphasis on retention and reactivation.
My previous podcast with Evan can be found here:
Episode 33: Creating Smarter Sports Bettors with Evan Kirkham
“Research needs to be at the point of sale.” ~ Evan Kirkham
