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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.

Copyright: © 2024 GoldBoys.com

Latest Episodes:

Shoulda Bet More with Will Hill - Ep. 106 - Iain MacMillan Sep 18, 2024

Show notes

On this episode of Shoulda Bet More, we invite from Sports Illustrated and noted Falcons fan, Iain MacMillan (@IainMacBets) back to the podcast! We recap and reacted to the wild ending between the Falcons and the Eagles from Monday night. We do a lookahead to Thursday Night Football and the rest of Week 3 as we give you our best bets. Bryce Young has been benched by the Panthers, what do they do with him next and is their season outlook any better than it was before? Iain tells us who he believes are the contenders and pretenders of the NFL after week 2. Plus, since when has the "E" in ESPN stood for Eagles? Was bringing Jason Kelce on a good idea?

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Shoulda Bet More with Will Hill - Ep. 105 - Doug Kazirian Sep 16, 2024

Show notes

Week 2 is in the books and we've brought Doug Kezirian (@DougKezirian) onto the pod where him and Will give you their reactions to everything we saw this weekend. After 2 weeks, which teams are better or worse than we originally thought? After the number of upsets this weekend, can we still take advantage of the books as they lag behind? Who is it worth betting on for the first coach to be fired? Plus, a week 3 lookahead and Will gives his Monday Night Football best bet between the Falcons and the Eagles.

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Shoulda Bet More with Will Hill - Ep. 104 - Jeff Parles Sep 13, 2024

Show notes

On today's episode, we get you ready for Week 3 in College Football and Week 2 in the NFL. We've brought back one of our favorites, from Sports by the Book, Jeff Parles (@jeffparles)! Jeff gives his overreactions from Week 1 in the NFL. The guys discuss if the Cincinnati Bengals should be concerned going forward. They also give their best bets for this weekend in the NFL and College Football. Plus, Jeff and Will talk about who they think will be in and out of the postseason at the end of the MLB season in just a few weeks!

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Shoulda Bet More with Will Hill - Ep. 103 - Jason Weingarten Sep 11, 2024

Show notes

Now that week 1 is officially in the books, we can turn our attention a bit back to baseball. Jason Weingarten (@Spreadapedia) from VSiN returns to the pod to talk about the close division races and wild card races. With 3 weeks to go, which teams do Jason think end up making the postseason? Do the Yankees or Orioles take the AL East? Will the Braves be on the outside looking in? We also talk awards with Jason. We look at the odds compared to what they were at the start of the year, and are there still bets worth making for a possible upset? Jason also gives us his week 1 takeaways and early looks at week 2 plays. We also talk about Colorado and whether the Deion experiment will last.

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Shoulda Bet More with Will Hill - Ep. 102 - Matkafee Sep 09, 2024

Show notes

Welcome to Shoulda Bet More, the podcast where host Will Hill and special guest @matkafee dive deep into the upcoming NFL action. In this episode, Will and Matkafee break down the first weekend of the season, sharing insider insights, game predictions, and betting tips to help you make the most informed picks. Whether you're a seasoned bettor or just a football fan eager for a sneak peek, tune in to get the edge you need before kickoff!

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Shoulda Bet More with Will Hill - Ep. 101 - Adam Kaufman Sep 06, 2024

Show notes

What a way to open the NFL Regular Season, but we aren't done because we have a special Friday night game in Brazil! The Packers play the Eagles in São Paulo and to get the best bets for it, we've brought Adam Kaufman (@AdamMKaufman) from WKRO 680 and iHeartRadio Boston back to the pod! We do a quick preview of the game and give our best bets for it. We also preview the rest of Sunday's slate of games for week 1. Adam was high on the Patriots the last time we spoke, does he still feel optimistic about the direction of the team? We also get Adam's Super Bowl matchup and winners. Plus, Will recaps and reacts to the wild Ravens vs. Chiefs game and what it means for both teams moving forward. Also, Will previews week 2 of college football and gives his favorite bets of the weekend.

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Shoulda Bet More with Will Hill - Ep. 100 - Sammy P Sep 04, 2024

Show notes

We've made it to 100! Thanks to everyone that has tuned into the pod, we are glad you are enjoying it. More importantly, the NFL Regular Season begins tomorrow! To dive into the upcoming season and more specifically, Thursday's game between the Ravens and Chiefs, we've brought from the Chicken Dinner podcast, Bet QL, and Fox Sports, Sammy P (@spshoot)! We get his hottest take for the season, his favorite longshot awards plays, his and Will's best bets for Thursday's game as well as Sunday's games! Plus, we get the biggest takeaways from week 1 in College Football and some bets to look forward to on Saturday for week 2! You'll get your football fix on this episode, we promise.

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Shoulda Bet More with Will Hill - Ep. 99 - FranchiseKF Aug 30, 2024

Show notes

Tomorrow, we finally get the first full slate of College Football. It's week 1 time! We've invited College Football handicapper FranchiseKF (@FranchiseKF) to give us all the info we need as we truly kick off the season. We talk about what we witnessed in week 0 and discuss some takeaways. We also go over some of the biggest games and give you the best bets for this weekend so you can start adding to your bankroll. FranchiseKF also has sleeper picks to make the Playoff as well as to win the Heisman to get in now before the odds begin to lower! Plus, Will talks the MLB postseason races as we enter the final month of the season!

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Shoulda Bet More with Will Hill - Ep. 98 - Mike Sando Aug 28, 2024

Show notes

We are just one week away from the start of the NFL Regular Season! That also means that Mike Sando (@SandoNFL) of The Athletic has released his yearly QB Tiers list! We've invited Mike back onto the pod to talk the list as voted on by NFL coaches and executives so we can discuss how everything shook out. We discuss who rose and fell in the rankings and which players' rankings surprised us. Also, what do some QBs need to do heading into the year to improve their perception around the league. Plus, Mike also gives us the teams he thinks will be big sleepers this year!

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Shoulda Bet More with Will Hill - Ep. 97 - Joey Isaks Aug 26, 2024

Show notes

The US Open tennis tournament begins this week, so to help you get ready to hit some tennis bets for the next two weeks we've invited professional bettor, Joey Isaks (@joeyisaks) onto the pod! We discuss the favorites, the longshots, the first round matchups, and Joey gives us his favorite bets to win it all in the men's bracket as well as the women's bracket! Joey also gives us his tips when trying to do courtside betting at the matches. Tune in to get a jump start to your bankroll for one of the biggest tennis tournaments of the year!

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