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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. 335 Mitch Moss May 08, 2026

Show notes

On this episode of the Shoulda Bet More podcast, Will Hill previews the Friday night NBA games and recaps the Pistons victory over the Cavs. Then, Mitch Moss of Follow The Money joins to discuss the MLB awards markets, NBA + NHL Playoffs, Vrabel's job status, 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. 334 Sammy P May 06, 2026

Show notes

On this episode of the Shoulda Bet More podcast, Will Hill previews Game 2 of Sixers/Knicks and Wolves/Spurs, the AL Cy Young, and the passing of John Sterling. Then, Sammy P of Fox Sports joins to discuss the NBA + NHL Playoffs, MLB long shot bets, 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. 333 Jonathan Von Tobel May 04, 2026

Show notes

On this episode of the Shoulda Bet More podcast, Will Hill reacts to the weekend of action in the NBA, then Jonathan Von Tobel of Money Moves joins to look ahead to Round 2 of the Playoffs, what went wrong for the Celtics, and who may be on upset alert.

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. 332 Chris Macero May 01, 2026

Show notes

In this episode of the Shoulda Bet More podcast, Will Hill previews Friday's NBA games. Plus, Chris Macero, Professional Sports Bettor joins to break down the Kentucky Derby, NBA playoffs, NHL playoffs and the struggles of the Red Sox.

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. 331 Chris Fallica Apr 29, 2026

Show notes

On this episode of the Shoulda Bet More podcast, Will Hill recaps the night in the NBA and looks ahead to Wednesday and Thursday action. Then “the Bear” Chris Fallica of Fox Sports joins to discuss what to look for in the Kentucky Derby Saturday, as well as futures and takeways so far in MLB and the NHL 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 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. 330 Doug Kezirian Apr 27, 2026

Show notes

On this episode of the Shoulda Bet More podcast, Will Hill recaps this weekend's NBA Playoff games and looks ahead to Monday's games. Plus, Will shares his takeaways from the NFL Draft. Also, Doug Kezirian from BetRivers joins to discuss the playoffs, the NFL Draft 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. 329 Apr 24, 2026

Show notes

On this episode of the Shoulda Bet More podcast, Will Hill recaps a wild first round of the NFL draft and analyzes some of the surprising picks, and recaps the night in the NBA playoffs and looks ahead to the games this weekend. 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. 328 Jeff Parles Apr 22, 2026

Show notes

On this episode of the Shoulda Bet More podcast, Will Hill previews the Wednesday NBA Playoff action and the NFL Draft. Then, Jeff Parles of ESPN Las Vegas joins to discuss the draft, the NBA Playoffs, and the struggling Mets.

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. 327 Geoff Schwartz Apr 20, 2026

Show notes

On this episode of the Shoulda Bet More podcast, Will Hill reacts to the opening weekend of the NBA Playoffs and gives his thoughts on the Giants / Bengals trade. Plus, Geoff Schwartz of Fox Sports joins to discuss Monday's NBA Playoff games, the NFL Draft 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. 326 Jonathan Von Tobel Apr 17, 2026

Show notes

On this episode of the Shoulda Bet More podcast, Will Hill previews the two remaining NBA Play-In games and discussed all six playoff series that are set. Then, Jonathan Von Tobel of Money Moves joins to breakdown Hornets/Magic, Warriors/Suns, and go through the weekend of playoff action.

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.

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