Shoulda Bet More

On this Black Friday edition of Shoulda Bet More, we invite a new guest! From Follow the Money on VSiN, Paul Howard (@paulyhoward)! We recap the Thanksgiving games and discuss the puzzling end to the Bears/Lions game where the Bears go home with a timeout in their pocket. We discuss our favorite bets for the rest of week 13 including today's game between the Raiders and the Chiefs. We also talk th...

Tomorrow is Thanksgiving and we've got the analysis you need so that while you are stuffing your face with turkey, you are also stuffing your wallet with cash from your bets. To go over every game on Thursday, we've brought back from WKRO 680 and iHeartRadio Boston, Adam Kaufman (@AdamMKaufman)! We give our betting angles for Bears vs. Lions, Giants vs. Cowboys, and Dolphins vs. Packers. Adam also...

Coming off what was a wild NFL Sunday with many games turned on their head, we invite Jeff Parles (@jeffparles) from "Sports By The Book" back to the pod! We recap and react to all the games, many of which had late lead switches and improbable plays. We give you our takeaways for what this week means moving forward in the season. We preview the Har-bowl in tonight's Monday Night Football game betw...

On this episode of Shoulda Bet More, we get you ready for Week 12 in the NFL with John Jastremski (@john_jastremski) of The Ringer returning to the pod! We go over our favorite bets for the weekend so you can get the edge on the books. We do a mid-season check on our futures and awards to see how confident we are that they hit. Also, who do we think ends up getting those last playoff spots when th...

Iain MacMillan (@IainMacBets) of Sports Illustrated returns to the pod on this episode of Shoulda Bet More to talk all things NFL. We discuss where we find value on betting division winners this far into the season. Could the Chargers or the Steelers be surprise Super Bowl contenders? What should the Ravens do about a suddenly human Justin Tucker? Why are there so many bad teams in the NFL? Is the...

After a weekend with some big NFL matchups, we've brought back Doug Kezirian (@DougKezirian) from OnlyPlayers.com to the pod! We give our reactions to Week 11 in the NFL. What does it mean for the Bills to beat the Chiefs? Can anyone stop the Lions? Are the 49ers in danger of missing the playoffs? We talk about the Coach of the Year and MVP races to see where we can get value in betting. We also t...

Join Will Hill and returning guest @ Matkafee as they dive into the world of sports betting, covering the NFL, NBA, and their opinions on some futures awards picks. Get expert analysis, sharp insights, and winning strategies for your next bet, whether you're looking at season-long bets or breaking down upcoming matchups. Tune in for your edge in the game! Hosted by Simplecast, an AdsWizz company....

We only have a few weeks left of College Football, so we've brought back Brad Thomas (@MrBradThomas) from NBC Sports and GoldBoys to discuss where we are as we get closer to the selection of the College Football Playoff! We go over the various scenarios that can get the bubble teams in and the various conference championship games that could affect it. We also go over this week in betting College...

On this episode of Shoulda Bet More, we have Gill Alexander (@beatingthebook) of "A Numbers Game" and the "Beating the Book Pod" back on the podcast to recap what we saw this weekend in NFL and College Football! We recap Week 10 in the NFL and give our reactions to everything we witnessed. Are the Cardinals a contender? How do the Chiefs continue to squeak out wins? Who is the worst of the bottom...

We witnessed what might have been the game of the year in the NFL. Will recaps and reacts to last night's Ravens win over the Bengals and what it means going forward. We've also brought Jonathan Von Tobel (@meJVT) of VSiN Primetime back to the pod! We talk to him about takeaways from the NBA only two weeks into the season. Which teams are proving to be legit? Which players should we be looking to...

On today's episode, we've brought back "The Bear" Chris Fallica (@chrisfallica) from Fox Sports to the pod so we can take a view at the state of the NFL at the trade deadline. We take a look at the playoff picture of the AFC and the NFC as we try to determine which teams will stay in, fall out, and grab those elusive wild card spots. We discuss which team we favor in a hypothetical Super Bowl of t...

On today's episode, we've brought back Kiev O'Neil (@OBKiev) of The Odds Breakers not only to talk about this weekend in football, but to preview the upcoming College Basketball season! With the season beginning today, we discuss the way to find the edge in betting for tonight and beyond for the rest of the season. We also go over the teams we think will be competing to win the National Championsh...

The World Series is now in the books with the Los Angeles Dodgers beating the New York Yankees in 5 games. Will recaps the wild 5th inning in game 5 and gives the Dodgers their props and the Yankees their postmortem. We also bring on from the Chicken Dinner podcast, Bet QL, and Fox Sports, Sammy P (@spshoot) to talk about this weekend in football. Sammy P gives us his best bets for this weekend in...

Join host Will Hill and Returning Guest Jeff Parles as they dive deep into the exciting world of sports betting on this week’s episode of "Shoulda Bet More." Tune in as they break down Game Five of the World Series, sharing insights and predictions that will keep you on the edge of your seat. But that’s not all—Will and Jeff will also tackle Thursday Night Football, offering their takes on matchup...

We had a wild sports-filled weekend, and to give a recap and reaction, we've brought Scott Seidenberg (@ScottsOnAir) from VSiN and Pregame.com back to the podcast! Will and Scott give their takeaways from NFL week 8. Can Jameis Winston turn the Browns around? After an atrocious loss against the lowly Patriots, what can the Jets do to salvage their season? We also get a preview of tonight's MNF gam...

The World Series begins tonight and we have the bets and analysis you need for tonight's game 1 between the New York Yankees and the Los Angeles Dodgers and for the series as a whole. To counter Will's Yankees fandom, we've brought on LA native, from the Cover the Weekend Podcast, Tommy Lorenzo (@sportsbooktom)! Will and Tommy discuss each teams strengths and weakness, how they matchup against eac...

On this midweek episode of Shoulda Bet More, we invite back professional sports bettor and VSiN contributor, Chris Macero (@RealGadge) to the podcast! We get you ready for the TNF Vikings vs. Rams game, the start of the NBA regular season, and the World Series. Chris and Will give you some of their best bets for week 8 in the NFL and week 9 in College Football. Chris also gives us a season long be...

Join host Will Hill in a lively discussion with sports enthusiast Dave Ross on Shoulda Bet More. In this episode, they dive into the thrilling Mets vs. Dodgers Game 6 showdown, dissecting key moments. They also gaze into the future of MLB, speculating on the upcoming World Series and its potential. Plus, don't miss their insights on the latest NFL updates and predictions. Whether you're a die-hard...

We've got your football bets for the weekend as we've invited back Matt Youmans (@mattyoumans247) of VSiN to talk all things football. We've got Matt's best bets for Week 8 in College and Week 7 in the NFL. We go over the major games such as Georgia vs. Texas, Vikings vs. Lions, Chiefs vs. 49ers, and more! We talk which teams are the best in the NFL and College Football, and Matt talk about what h...

On this midweek episode of Shoulda Bet More, we invite Reed Wallach (@ReedWallach) of The Early Reed Podcast and Sports Illustrated back to the podcast to talk some College Football and his New York Mets! Reed gives us some of his best bets for Week 8 of CFB. From Georgia/Texas and Alabama/Tennessee, to matchups not in the power conferences, we've got the bets you need. We also dive into the Heism...

Join us in this episode of Shoulda Bet More as we dive into the latest MLB standings and break down the thrilling world of Monday Night Football predictions with our special guest, Jeff Parles. Tune in as we explore team performances, key matchups, and betting insights that could give you the edge in your next wager. Whether you're a seasoned bettor or just a sports fan, this episode is packed wit...

This is gonna be a big weekend. Baseball's Championship Series begins, we get a great NFL slate, and we get a powerhouse College Football Saturday with marquee matchups. To give his analysis and bets on those games, we've brought Brad Powers (@BradPowers7) of the Bet The Board Podcast back to the podcast! We get his opinion on Texas/Oklahoma, Penn St./USC, and Ohio St./Oregon as well as some other...

We have been treated to four tight and extremely competitive Division Series matchups and to go over them, we've invited back Dave Ross (@drosssports) from Sunday Bet Prep on VSiN! We discuss how his Mets have come from rock bottom all the way to within one game of the NLCS. Are the Padres going to be able to finish the job against the Dodgers? Should the Yankees be worried with how their series i...

What a wild sports weekend. So many College Football upsets, some wild NFL games, and some intense baseball series. To break it all down with an eye on what to take advantage of betting wise, we've invited back Gill Alexander (@beatingthebook) of "A Numbers Game" and the "Beating the Book Pod!" We recap week 5 in the NFL and provide our takeaways. Are the Vikings a championship contender? Will Cle...

The Division Series round is all set as we head into the weekend and to preview that round, we've invited from "Follow the Money" on VSiN, Mitch Moss (@MitchMossRadio) back to the pod! We break down the series' and the betting angles we like from them. Should the Orioles postseason performances of the past 2 years get Brandon Hyde fired? Does the Wild Card round change our opinion of any of these...