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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. 136 - Jeff Parles Nov 25, 2024

Show notes

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 between the Ravens and the Chargers. We also discuss the College Football Playoff as the field gets clearer as we head towards the final week of conference play. Who do we think the committee will leave in and out? Plus, we discuss Juan Soto's free agency and how is MLB allowing 2 teams to be playing in Minor League ballparks this upcoming season?

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Shoulda Bet More with Will Hill - Ep. 135 - John Jastremski Nov 22, 2024

Show notes

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 the regular season is all said and done? Also, we talk MLB free agency to figure out where the big name free agents like Juan Soto and Roki Saski sign.

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Shoulda Bet More with Will Hill - Ep. 134 - Iain MacMillan Nov 20, 2024

Show notes

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 there a new contender for Offensive Rookie of the Year? We also preview Thursday Night Football to give you our favorite bets and leans as well as our favorite on the Sunday slate of games! Plus, Will recaps and reactions to the award winners for MLB!

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Shoulda Bet More with Will Hill - Ep. 133 - Doug Kazirian Nov 18, 2024

Show notes

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 talk Monday Night Football between the Texans and Cowboys and give our betting preview of it. Plus, we talk the Jake Paul/Mike Tyson fight and the struggling production issues from Netflix.

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Shoulda Bet More with Will Hill - Ep. 132 - Matkafee Nov 15, 2024

Show notes

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!

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Shoulda Bet More with Will Hill - Ep. 131 - Brad Thomas Nov 13, 2024

Show notes

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 Football for games tonight through the weekend. Also, after the Miami Dolphins win on Monday, are they back in the playoff race? We also have a TNF betting preview between the Commanders and the Eagles. Who will win the Juan Soto sweepstakes? We discuss these all and more!

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Shoulda Bet More with Will Hill - Ep. 130 - Gill Alexander Nov 11, 2024

Show notes

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 feeders and will get the first pick of the draft? We also discuss what will be the biggest conundrum the CFP committee will have when picking the 12 best teams for the College Football Playoff. We also talk a little Heisman to see where we are at after some big upsets occurred this weekend.

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Shoulda Bet More with Will Hill - Ep. 129- Jonathan Von Tobel Nov 08, 2024

Show notes

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 to bet on season awards? We also go into this weekend in NFL as we go over our favorite bets of the weekend that you should take. We also talk some College Football as we are getting closer to the end of the season. Will the CFP committee have to make any tough decisions down the stretch? We also give out our favorite college football plays for the weekend as well.

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Shoulda Bet More with Will Hill - Ep. 128 - "The Bear" Chris Fallica Nov 06, 2024

Show notes

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 the current 1 seeds, the Lions and the Chiefs. We give our thoughts on the MVP, Coach of the Year, and Offensive Player of the Year races. We also take a look into this weekend in College Football. As we get closer to the College Football Playoff, do we think there could be any surprises that squeeze into the field? We'll also give you our early leans for this weekend in College Football and The Bear has a special soccer pick he likes this week to give out!

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Shoulda Bet More with Will Hill - Ep. 127 - Kiev O'Neil Nov 04, 2024

Show notes

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 Championship in April. We also give our reactions to this weekend in NFL and give our Monday Night Football betting preview for the Buccaneers and Chiefs. We also begin to look forward to this weekend in College Football and give some early plays that we like for Saturday.

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