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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. 166 - Kiev O'Neil Feb 05, 2025

Show notes

Today, we are kicking our Super Bowl coverage into high gear by bringing back Kiev O'Neil (@OBKiev) of The Odds Breakers to the pod! We take a deep dive into Sunday's game by looking at each of the main markets in-depth and the best player props that stick out to us. Kiev gives us his methods of attacking Super Bowl betting so he can end the biggest game of the year on top. We also talk about the best foods to have while watching the Super Bowl! We also get into late season College Basketball! As we get closer to the tournament time, who are the most underrated/overrated teams that you should bet on or stay away from? Also, Will gives his final thoughts about the Luka trade and the Fox to the Spurs trade!

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Shoulda Bet More with Will Hill - Ep. 165 - Jeff Parles Feb 03, 2025

Show notes

Welcome to Shoulda Bet More, your go-to podcast for all things sports! In this episode, we dive into the upcoming Super Bowl, breaking down the key matchups and what to expect. Plus, we’re talking about the jaw-dropping NBA trade that’s shaking up the league: Anthony Davis for Luka Dončić. You won’t want to miss this one. Tune in!

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Shoulda Bet More with Will Hill - Ep. 164 - Jason Weingarten Jan 31, 2025

Show notes

We are nearing the date of pitchers and catchers arriving for Spring Training. To get ready for that date, we've brought back Jason Weingarten (@Spreadapedia) of VSiN to give us his outlook on the upcoming season of baseball. We get his reaction to the offseason moves and how he feels about the Dodgers spending money on their free agents. We get Jason's favorite future bets for this season with the offseason coming to a close. We take a quick discussion of awards futures to see if there are any longshots that have a great chance of winning. We also take a look at betting the Caribbean Series that begins today to crown the best club in the Caribbean (and Japan)!

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Shoulda Bet More with Will Hill - Ep. 163 - Kelley Bydlon Jan 29, 2025

Show notes

With the NFL in a hibernation period until the Super Bowl, we turn our eyes to NBA basketball! To get a temperature of where we are at in the middle of the season, we've invited Kelley Bydlon (@KelleyBydlon) from VSiN's "A Numbers Game!" Is a Celtics vs. Thunder Final inevitable? Which teams have the best chance of stopping it come playoffs? What trades could we possibly see as we approach the midseason mark? Plus, who are the front runners for awards and what longshots could surprise? We also touch on Kelley's Super Bowl bets to see what he likes!

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Shoulda Bet More with Will Hill - Ep. 162 - Jonathan Von Tobel (JVT) Jan 27, 2025

Show notes

Shoulda Bet More is the ultimate podcast for NFL fans who love the thrill of the game and the excitement of placing a bet. Join Will Hill and returning guest JVT as they break down the Conference Championship games, analyzing key plays, standout performances, and those crucial moments that made or broke the odds. Get expert takes on the big game, plus insider tips and predictions for the upcoming Super Bowl showdown. Whether you’re a casual fan or a die-hard gambler, Shoulda Bet More is the perfect place to fuel your football fix and prepare for the biggest game of the year!

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Shoulda Bet More with Will Hill - Ep. 161 - Dave Ross Jan 24, 2025

Show notes

It's Conference Championship weekend, and we are continuing to go to VSiN collaborators to get the best in-depth look look at the games by inviting back Dave Ross (@drosssports)! We take a deep dive into the Commanders vs. Eagles and the Bills vs. Chiefs and give you our favorite props and leans. We try to get Dave's picks for the weekend and for who he thinks will win the Super Bowl in two weeks! Lastly, we get Dave's reaction to how the Mets have done this offseason beyond the Juan Soto signing and if he thinks they can win the NL East and beyond.

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Shoulda Bet More with Will Hill - Ep. 160 - Matt Youmans Jan 22, 2025

Show notes

With the National Championship Game in the rear-view, we only have 3 football games remaining. To discuss what we've seen and what we will see, we've brought back from VSiN, Matt Youmans (@mattyoumans247)! We go over Ohio State's victory against Notre Dame to put a bow on a great College Football season. We preview Conference Championship weekend in the NFL by discussing our favorite bets so far with these early lines. Can the Bills finally overcome Patrick Mahomes and Chiefs in the playoffs? Will Jayden Daniels and the Commanders stun the Eagles and go to the Super Bowl? We also go over where we are at in the College Basketball season and if there are any sleepers that could make it to the Final Four. Finally, we discuss what the Dodgers have done and Matt's opinion of what they and the rest of the MLB has done in free agency.

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Shoulda Bet More with Will Hill - Ep. 159 - Jeff Parles Jan 20, 2025

Show notes

What a great weekend of football we had, but we aren't done yet! Today is the National Championship game between Ohio State and Notre Dame. To give us his betting looks for the game, we've invited back Jeff Parles (@jeffparles) from "Sports By The Book!" We do a deep dive into the game and give you our favorite to win and our betting leans that show where we think this game is headed. We also recap an awesome divisional round and get into the upsets and controversies from the weekend. Is the Lions window closed after this weekend's brutal loss? Just how much of a problem were the refs in Kansas City? We also take an instant reaction to next week's betting lines and give you our thoughts and feelings on them. Finally, after the Roki Sasaki and Tanner Scott signings by the Dodgers, we take a deep look into how MLB Free Agency has gone and what it means for the future of the sport of baseball.

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Shoulda Bet More with Will Hill - Ep. 158 - John Jastremski Jan 17, 2025

Show notes

It's Divisional Round weekend! To expand on what we were talking about with early previews on Wednesday's episode, we've brought back John Jastremski (@john_jastremski) of The Ringer to give us more betting viewpoints of this weekend's games! We do an in-depth dive on Texans/Chiefs, Commanders/Lions, Rams/Eagles, and Ravens/Bills, giving your our favorite betting looks in each game and who we ultimately think we will be seeing in the Conference Championships! We discuss some of the coaching carousel going around the league's non-playoff teams and say who we think is going to fill vacant head coaching positions. Plus, we get John's take on MLB free agency this far into the offseason and see if he thinks any free agents may give a team an edge this upcoming season!

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Shoulda Bet More with Will Hill - Ep. 134 - Iain MacMillan Jan 15, 2025

Show notes

With the first round of the NFL Playoffs officially in the books, we look forward to the Divisional round. To give us an early look, we've brought back Iain MacMillan (@IainMacBets) of Sports Illustrated to the pod! We react to the Monday night beatdown by the Rams and what that means for the Vikings going forward. Do they keep Sam Darnold, or is the future JJ McCarthy? With the Chiefs' starters not playing in Week 18, have they rested too long? We look at the matchups for this round and discuss how each team matches up to their opponent. Iain also gives us his Super Bowl winner out of the remaining teams!

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