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Chasing That Paper!

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Chasing That Paper! is hosted by Joe Osborne, and airs weekdays at 11AM ET on the VegasInsider YouTube Channel. Joe is joined by a rotating cast of cohosts from around the industry, including Iain MacMillan from BetSided and Devin Walker from MTV's The Challenge. This show is filled with fast-paced, actionable betting content, but never takes itself too seriously. Both the hosts and audience are in this thing together, trying to do their best to pick winners across the sports world on a daily basis. Audience interaction is a daily part of the program, and our hosts are held accountable for bad betting advice! Chasing That Paper! is must-see-internet-TV for the football season, and beyond!

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Meet Our Team

Joe Osborne

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Joe Osborne is a sports betting analyst and host of our daily show Chasing That Paper! Joe has been working in the sports betting industry in a variety of roles for close to ten years. Prior to breaking into the industry, he received a diploma in broadcast journalism and an advanced diploma in public relations. He has a passion for numbers and likes to cater to the casual sports bettor with his stat-driven analysis. His main areas of focus are the NFL, MLB, NBA, NHL and UFC. His favorite sports memory is watching Joe Carter hit the walk-off home run for his beloved Toronto Blue Jays in the 1993 World Series. When he’s not locked-in on sports, he enjoys spending time with his family, eating steak and lifting extremely heavy weights.

Iain MacMillan

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Iain MacMillan is a Senior Editor for BetSided. He's been in sports media in some fashion since his days writing for the school newspaper at the University of New Brunswick in Canada, but has been covering sports betting since 2018. He loves the process of deciding who to bet on just as much as he loves winning the bet itself. The NFL is his biggest strength, but he also focuses his betting on golf, college basketball, NHL, MLB, and UFC. He is a diehard fan of the Atlanta Falcons and the Toronto Maple Leafs, who have both been breaking his heart his entire life.

Devin Walker

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Devin Walker is an equal opportunity sports bettor and host of the weekly show Bet On Devin on the VegasInsider Podcast. As the youngest of four brothers, Devin's been handicapping family events to give himself a chance since he was 9 years old. A reality TV personality by trade, Devin is best known for his multiple appearances on America's fifth major sport, MTV's The Challenge. Self-proclaimed as a man who never met a beer or a parlay he didn't like, you'll be sure not to confuse Devin with an analytical bettor. But if it's long odds and hot takes you're looking for, he's your guy! Although he specializes in NFL, college football, college basketball, and UFC, don't be surprised to find Devin with an open ticket on WNBA or even table tennis. When he's not frequenting the cash counter, Devin enjoys golfing (21 handicap), BBQ-ing, and having beers with the boys. Catch him on Wednesdays on Chasing That Paper!

Tito Benach

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Tito Benach is a media producer at VegasInsider, and is the daily producer of Chasing That Paper! He’s been working in sports media since early in his college days, from covering high school and college football, all the way to working in digital media with CBS Sports and ESPN. Tito was born and raised in Miami, FL, and is a Miami sports fan through and through. His favorite sports memory is being at game 6 of the 2013 NBA Finals for the legendary Ray Allen game-tying 3-pointer that helped the Miami Heat win the game and series. He considers himself a “foodie,” and has an array of opinions on food that are sure to raise some eyebrows.

Five Questions with Joe Osborne!