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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. 66 - Matt Grissom Jun 14, 2024

Show notes

We are down to 8 teams and the College World Series officially starts today! We've brought back from CollegeBaseballInsiders.com and VSiN, Matt Grissom (@GrissomOnX) to get an update on what we've seen so far in the tournament, and to get his thoughts and predictions on the 8 teams remaining! We get Matt's best bets on each matchup in the first round, plus who he thinks will come out of each bracket to meet in the finals. Also, with Boston up 3-0 in the NBA Finals, is there any chance that Dallas can avoid being swept? Get ready for a big weekend of betting by tuning in!

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Shoulda Bet More with Will Hill - Ep. 65 - Ben Wilson Jun 12, 2024

Show notes

As the NBA and Stanley Cup Finals keep going on, Ben Wilson (@Ben_Wilson_1) from ESPN+, FOX, and VSiN joins the podcast to give his perspective on how each series is going! Ben and Will discuss which team has a better chance of climbing out of their 0-2 deficit, the Mavericks or the Oilers. Ben and Will give their bets and predictions for how each series will end. They also talk about the upcoming NBA draft! Will the draft class being weak provide the ability to get good lines on where players end up going? Which teams look the best going into this weekend's College World Series? Find out all of that and more on today's episode!

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Shoulda Bet More with Will Hill - Ep. 64 - Jonathan Von Tobel Jun 10, 2024

Show notes

The Celtics have taken a commanding 2-0 lead in the NBA Finals. To discuss how the Celtics are doing it, we've brought Jonathan Von Tobel (@meJVT) of VSiN Primetime back to the pod! Will and JVT go over what the Celtics have done right, what the Mavericks have done wrong, and what the Mavericks can do to get back into this series. Jayson Tatum is currently the favorite to win Finals MVP, but is that truly the smart bet? Plus, some early NBA Futures for next season! Tune in to get the betting edge!

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Shoulda Bet More with Will Hill - Ep. 36 - Todd Wishnev Apr 03, 2024

Show notes

We are drawing closer to Final Four weekend and to prepare, professional bettor, Todd Wishnev (@TWishnev), joins Will again on the pod! In it, they discuss where they lean on the spread and over/under for Alabama/UConn and NC State/Purdue. What does Todd think about this historic NC State run? Can Burnes compete with Edey and give Purdue fits? Will Alabama be able to stifle this dominant UConn team? Plus Todd give his personal betting tips for how to bet baseball, especially after this first weekend of games as well as some of his sneaky looks. Also, Will has a baseball futures longshot worth taking. Tune in to learn from one of the best and get ahead of the books!

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Shoulda Bet More with Will Hill - Ep. 35 - Jeff Parles Apr 01, 2024

Show notes

And then there were four, UConn, Alabama, Perdue and NC State! Jeff Parles of Sports by the Book returns to the pod to talk about what we witnessed the tournament games over the weekend and to give an early preview of the Final Four next week. How truly dominant is this UConn team? How historical of a run is this for NC State? Does Zach Edey get too many foul calls in his favor? Can this Alabama team prove to be a threat to UConn? Plus, what are the early thoughts after the first weekend and series of the MLB season? Can the Yankees keep the momentum until Cole is able to return? It's a packed episode, so tune in to hear all the advice the guys have to offer!

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Shoulda Bet More with Will Hill - Ep. 34 - Stuckey Mar 29, 2024

Show notes

On this episode of the Shoulda Bet More podcast, Stuckey, from Action Network, joins Will in breaking down the Sweet Sixteen! Will UConn be putting up another banner? Can Marquette take down NC State? Who comes out on top between Duke and Houston? Will Tennessee advance over Creighton? Did Ohtani know anything? Tune in to this episode to hear it all!

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Shoulda Bet More with Will Hill - Ep. 33 - Mitch Moss Mar 27, 2024

Show notes

We are just a day away from MLB Opening Day! We're excited and are ready to talk some baseball. Mitch Moss of "Follow the Money" on VSiN joins Will on this edition of Shoulda Bet More. We talk MLB futures, awards, as well as a look ahead to Thursday's games where Will gives you his leans! Plus, a sweet sixteen betting preview where you'll get best bets with the insights to back it up. Also, we're one month out from the NFL Draft, so what do we think the top 5 picks will look like?

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Shoulda Bet More with Will Hill - Ep. 32 - Jonathan Von Tobel Mar 25, 2024

Show notes

We are two rounds into March Madness and to go over the weekend's events with Will, Jonathan Von Tobel (@meJVT) of VSiN Primetime comes back to the pod! The guys go over what was a chalky weekend and talk about what surprised them, what they learned, and if they think better or worse of some of the remaining teams in the tournament. Also, an early look at the sweet sixteen lines to see what you should consider betting on. Plus the guys go over some updated NBA futures you might want to keep your eye on! Tune in to hear the takes that will best help you beat the books!

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Shoulda Bet More with Will Hill - Ep. 31 Mar 22, 2024

Show notes

The first day of March Madness comes to a close. On this episode of the Shoulda Bet More Podcast, Will recaps day 1 of the NCAA tournament and covers some MLB as well as NFL. Oakland pulls off a massive upset against Kentucky. What does this mean for Calipari's future? Will touches on Friday's games and gives a lookahead to Saturday. Ohtani's interpreter is fired and accused of theft. Was this a coverup and secretly Ohtani betting? Some NFL free agency moves. Tune in to hear what all Will has to say!

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Shoulda Bet More with Will Hill - Ep. 30 - Iain MacMillan Mar 20, 2024

Show notes

The best time of the year for sports bettors has arrived! On this episode of the Shoulda Bet More Podcast, Will brings on Iain MacMillan, Senior Editor of Fansided and host of the Bacon Bets Podcast. The two discuss everything March Madness! Did the selection committee do a bad job? Are the Mountain West teams overhyped? Will there be any crazy upsets and what will they be? Is Auburn better than UConn? Tune in to hear what Will and Iani have to share!

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