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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. 325 Kelley Bydlon Apr 14, 2026

Show notes

On this episode of the Shoulda Bet More podcast Will Hill gives his best bets on the Play-In games, then Kelley Bydlon of A Numbers Game joins to break down the NBA playoffs/play-in and shares his best bets for every series. Get instant access to expert picks, public betting splits data, and pro betting tools when you join VSiN pro. You can take 17% off an annual subscription when you use promo code: POD26. Click https://www.vsin.com/subscribe?tpcc=shoulda-bet-more&utm_source=podcast&utm_medium=simplecast&utm_campaign=shoulda_bet_more to get started.

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Shoulda Bet More with Will Hill - Ep. 324 Gill Alexander Apr 13, 2026

Show notes

On this episode of the Shoulda Bet More podcast, Will Hill recaps a wild Masters tournament and gives his thoughts on the NBA Play-In Games and the weekend in MLB. Then Gill Alexander of A Numbers Game joins to recap Rory’s win and talk MLB and NBA Playoffs. Get instant access to expert picks, public betting splits data, and pro betting tools when you join VSiN pro. You can take 17% off an annual subscription when you use promo code: POD26. Click https://www.vsin.com/subscribe?tpcc=shoulda-bet-more&utm_source=podcast&utm_medium=simplecast&utm_campaign=shoulda_bet_more to get started.

Hosted by Simplecast, an AdsWizz company. See pcm.adswizz.com for information about our collection and use of personal data for advertising.

Shoulda Bet More with Will Hill - Ep. 323 Dave Ross Apr 10, 2026

Show notes

On this episode of the Shoulda Bet More podcast, Will Hill recaps the first round of The Masters and reacts to Joel Embiid news ahead of the last weekend of the NBA regular season, including a bet in the NBA awards market. Then, Dave Ross of VSiN By The Books to discuss The Masters, MLB, and more.

Get instant access to expert picks, public betting splits data, and pro betting tools when you join VSiN pro. You can take 17% off an annual subscription when you use promo code: POD26. Click Here to get started.

Hosted by Simplecast, an AdsWizz company. See pcm.adswizz.com for information about our collection and use of personal data for advertising.

Shoulda Bet More with Will Hill - Ep. 322 Chris Fallica Apr 08, 2026

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On this episode of the Shoulda Bet More podcast, Will Hill reacts to Michigan defeating UConn and looks at next year's odds. Then, “The Bear” Chris Fallica from FoxSports joins to recap the National Title Game, and look ahead to some bets in the Masters, MLB, and the NFL Draft.

Get instant access to expert picks, public betting splits data, and pro betting tools when you join VSiN pro. Grab the Hoops Special for only $29.99 or take 17% off an annual subscription when you use promo code: POD26. Click Here to get started.

Hosted by Simplecast, an AdsWizz company. See pcm.adswizz.com for information about our collection and use of personal data for advertising.

Shoulda Bet More with Will Hill - Ep. 321 Matt Youmans Apr 06, 2026

Show notes

On this episode of Shoulda Bet More, Will Hill previews UConn-Michigan and gives a long shot bet for AL MVP. Plus, Matt Youmans from VSIN joins the show to discuss the National Championship Game, the Masters and his thoughts on the MLB season so far.

Get instant access to expert picks, public betting splits data, and pro betting tools when you join VSiN pro. Grab the Hoops Special for only $29.99 or take 17% off an annual subscription when you use promo code: POD26. Click Here to get started.

Hosted by Simplecast, an AdsWizz company. See pcm.adswizz.com for information about our collection and use of personal data for advertising.

Shoulda Bet More with Will Hill - Ep. 320 Steve Fezzik Apr 03, 2026

Show notes

On this episode of the Shoulda Bet More podcast, Will Hill previews the two Final Four matchups and gives his best bets. Then, pro bettor Steve Fezzik joins to discuss his thoughts on the National semifinals, betting angles, the rise of exchanges, tennis vs Todd Wishnev, and so much more.

Get instant access to expert picks, public betting splits data, and pro betting tools when you join VSiN pro. Grab the Hoops Special for only $29.99 or take 17% off an annual subscription when you use promo code: POD26. Click Here to get started.

Hosted by Simplecast, an AdsWizz company. See pcm.adswizz.com for information about our collection and use of personal data for advertising.

Shoulda Bet More with Will Hill - Ep. 319 Ian Eagle Apr 01, 2026

Show notes

On this episode of the Shoulda Bet More podcast, Will Hill takes a look at Most Outstanding Player odds for March Madness and discusses the Final 4 matchups. Then, Ian Eagle of CBS Sports joins to relive calling the final moments of Duke/UConn, what he expects this weekend, and much more.

Get instant access to expert picks, public betting splits data, and pro betting tools when you join VSiN pro. Grab the Hoops Special for only $29.99 or take 17% off an annual subscription when you use promo code: POD26. Click Here to get started.

Hosted by Simplecast, an AdsWizz company. See pcm.adswizz.com for information about our collection and use of personal data for advertising.

Shoulda Bet More with Will Hill - Ep. 318 Jonathan Von Tobel Mar 30, 2026

Show notes

On this episode of the Shoulda Bet More Podcast, Will Hill reacts to a classic UConn - Duke game in the Elite Eight. Plus, Jonathan Von Tobel from Money Moves joins the show to recap UConn-Duke, preview the Final Four and NBA Playoffs.

Get instant access to expert picks, public betting splits data, and pro betting tools when you join VSiN pro. Grab the Hoops Special for only $29.99 or take 17% off an annual subscription when you use promo code: POD26. Click Here to get started.

Hosted by Simplecast, an AdsWizz company. See pcm.adswizz.com for information about our collection and use of personal data for advertising.

Shoulda Bet More with Will Hill - Ep. 317 Jeff Parles Mar 26, 2026

Show notes

On this episode of the Shoulda Bet More podcast, Will Hill previews the Sweet 16 games for Friday. Then Jeff Parles of ESPN Las Vegas joins to break down Friday's college basketball games and give his predictions for the MLB season.

Get instant access to expert picks, public betting splits data, and pro betting tools when you join VSiN Pro. Grab the Hoops Special for only $29.99 or take 17% off an annual subscription when you use promo code: POD26. Click here to get started.

Hosted by Simplecast, an AdsWizz company. See pcm.adswizz.com for information about our collection and use of personal data for advertising.

Shoulda Bet More with Will Hill - Ep. 317 Mitch Moss Mar 25, 2026

Show notes

On this episode of the Shoulda Bet More podcast, Will Hill gives his best bets for the Sweet Sixteen, and previews MLB Opening Day. Then, Mitch Moss of Follow the Money joins to share his thoughts on the NCAA Tournament, MLB Bets, and more.

Get instant access to expert picks, public betting splits data, and pro betting tools when you join VSiN pro. Grab the Hoops Special for only $29.99 or take 17% off an annual subscription when you use promo code: POD26. Click Here to get started.

Hosted by Simplecast, an AdsWizz company. See pcm.adswizz.com for information about our collection and use of personal data for advertising.

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