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Shoulda Bet More — Sports
Shoulda Bet More

Ever have that gut feeling and wish you’d bet more? This is the podcast for you. Join VSiN and Fox Sports contributor Will Hill as he breaks down the biggest betting news and reveals the sharpest plays across the sports world. Each episode is a deep dive into betting strategies, odds analysis, and the data you need to find an edge.

Whether it’s NFL, NBA, MLB, or college football, we’ll tell you which side to be on and why. From dissecting the latest line moves to uncovering valuable props and futures, Will and his guests—the best minds in sports betting—ensure you’re always one step ahead.

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Latest Episodes:

Shoulda Bet More with Will Hill - Ep. 126 - Sammy P Nov 01, 2024

Show notes

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 Week 9 NFL and we go over the huge matchup between Ohio St. and Penn St. that will have playoff implications. We also look at the state of the NFL MVP race halfway through the season to see which player's price is worth betting on.

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Shoulda Bet More with Will Hill - Ep. 125 - Jeff Parles Oct 30, 2024

Show notes

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 matchups, player performances, and strategies. Whether you’re a seasoned bettor or just looking to get in on the action, this podcast is your go-to source for analysis, tips, and a bit of fun. Don’t miss out—after all, you shoulda bet more!

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Shoulda Bet More with Will Hill - Ep. 124 - Scott Seidenberg Oct 28, 2024

Show notes

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 game between the Giants and the Steelers. We also do a deep dive into the World Series, recap and reactions from both Will and Scott on how it's gone so horribly wrong for the Yankees. What do the Yankees need to do to get the series at the very least, back to Los Angeles. We also talk about what you should be betting on for game 3 tonight.

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Shoulda Bet More with Will Hill - Ep. 123 - Tommy Lorenzo Oct 25, 2024

Show notes

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 each other, their favorite bets for the game tonight, their looks for World Series MVP, and their prediction on who wins the World Series and in how many games. Plus, we also get betting looks for this weekend in College Football and the NFL. Finally, we recap yesterday's Thursday Night Football game and how the referees could have missed an obvious facemask.

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Shoulda Bet More with Will Hill - Ep. 122 - Chris Macero Oct 23, 2024

Show notes

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 bet in the NBA that he loves and a team he thinks can surprise this season. We also give a preview at what we may see in the World Series and give you our predictions on if the Dodgers or Yankees will take home the Commissioner's Trophy.

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Shoulda Bet More with Will Hill - Ep. 121 - Dave Ross Oct 21, 2024

Show notes

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 sports fan or just love a good debate, tune in for expert analysis and engaging banter.

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Shoulda Bet More with Will Hill - Ep. 120 - Matt Youmans Oct 18, 2024

Show notes

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 has been the ref show in the NFL. Will also recaps a wild game 3 in the ALCS, the Dodgers taking a commanding 3-1 lead in the NLCS, and what he thinks the best bets are this weekend and whether or not we even see the Championship Series continuing through next week.

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Shoulda Bet More with Will Hill - Ep. 119 - Reed Wallach Oct 16, 2024

Show notes

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 Heisman conversation as we approach the midpoint of the season. Are there any sneaky bets that can be made? Finally, we recap the NL/ALCS so far and talk about if the Guardians can get back into their series and can the Mets take control of the NLCS? Plus, reactions to some blockbuster trades in the NFL and the benching of Justin Fields in PIttsburgh!

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Shoulda Bet More with Will Hill - Ep. 118 - Jeff Parles Oct 14, 2024

Show notes

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 with analysis, hot takes, and the excitement of the game. Don’t miss out—let’s make those bets count!

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Shoulda Bet More with Will Hill - Ep. 117 - Brad Powers Oct 11, 2024

Show notes

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 games that are flying under the radar, but are great spots to make some bets. Will also goes over his NFL bets for the weekend and where we are at in the MLB Postseason and where we might end up at in the World Series.

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