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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. 286 Chris "The Bear" Fallica Jan 07, 2026

Show notes

On this episode of the Shoulda Bet More podcast, Will Hill gives his thoughts and best bets for the two CFP semifinal games. Then “The Bear” Chris Fallica of Fox Sports joins to preview the big games, predict the title winner, give his best bets for NFL playoffs, as well his thoughts on the Jets and Yankees offseason.

Get instant access to expert picks, public betting splits data, and pro betting tools when you join VSiN pro. Grab your first month for only $9.99 or take over 15% off an annual subscription when you use promo code: POD25. 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 Jonathan Von Tobel - Ep. 285 Jan 05, 2026

Show notes

On this episode of the Shoulda Bet More podcast, Will Hill recaps Week 18 of the NFL and gives his initial thoughts on the playoff matchups. Then Jonathan Von Tobel of Money Moves joins to react to a crazy Ravens-Steelers ending, NFL awards finals thoughts, playoff picks, and more.

Get instant access to expert picks, public betting splits data, and pro betting tools when you join VSiN Pro. Grab your first month for only $9.99 or take over 15% off an annual subscription when you use promo code: POD25. 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. 284 Jan 02, 2026

Show notes

On this episode of the Shoulda Bet More podcast, Will Hill recaps the CFP Quarterfinals, and gives his early thoughts looking ahead to the semifinals. Then he breaks down Week 18 in the NFL and gives 4 best bets for the weekend.

Get instant access to expert picks, public betting splits data, and pro betting tools when you join VSiN pro. Grab your first month for only $9.99 or take over 15% off an annual subscription when you use promo code: POD25. 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. 283 Kiev O'Neil Dec 31, 2025

Show notes

On this episode of the Shoulda Bet More podcast, Will Hill gives his thoughts on NFL MVP and previews the CFP games with a best bet on each. Then, Kiev O’Neil of the oddsbreakers joins to breakdown the CFP matchups, bowl games, and his best NFL bets.

Get instant access to expert picks, public betting splits data, and pro betting tools when you join VSiN pro. Grab your first month for only $9.99 or take over 15% off an annual subscription when you use promo code: POD25. 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. 282 Jeff Parles Dec 29, 2025

Show notes

On this episode of the Shoulda Bet More podcast Will Hill recaps a wild week 17, and looks ahead to week 18. Then Jeff Parles of ESPN Las Vegas joins to discuss a classic Sunday night game, the playoff picture, best bets and more. Get instant access to expert picks, public betting splits data, and pro betting tools when you join VSiN pro. Grab your first month for only $9.99 or take over 15% off an annual subscription when you use promo code: POD25. Click Here to get started. vsin.com/subscribe?tpcc=shoulda-bet-more

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. 281 Dec 26, 2025

Show notes

On this episode of the Shoulda Bet More podcast, Will Hill reacts to Thursday's NFL games, shares his thoughts on the Netflix broadcast, and gives his best bets for College Football Bowl Games and NFL Week 17.

Get instant access to expert picks, public betting splits data, and pro betting tools when you join VSiN pro. Grab your first month for only $9.99 or take over 15% off an annual subscription when you use promo code: POD25. 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. 280 Jensen Lewis Dec 24, 2025

Show notes

On this episode of the Shoulda Bet More podcast Will Hill breaks down the NFL Xmas games, and Jensen Lewis of Vsin By The Books joins to preview the upcoming NFL weekend, give his thoughts on the CFP, and discuss the MLB offseason.

Get instant access to expert picks, public betting splits data, and pro betting tools when you join VSiN Pro. Grab your first month for only $9.99 or take over 15% off an annual subscription when you use promo code: POD25. 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. 279 Geoff Schwartz Dec 22, 2025

Show notes

In this episode of the Shoulda Bet More podcast Will Hill recaps the weekend in NFL and College Football and gives his best bet for 49ers/Colts. Then Geoff Schwartz of Fox Sports joins to discuss the NFL Playoff picture, the CFP Quarterfinal matchups, holiday cooking tips and more.

Get instant access to expert picks, public betting splits data, and pro betting tools when you join VSiN pro. Grab your first month for only $9.99 or take over 15% off an annual subscription when you use promo code: POD25. Click vsin.com/subscribe?tpcc=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. 278 Brad Powers Dec 19, 2025

Show notes

On this episode of the Shoulda Bet More podcast, Will Hill recaps an instant classic on Thursday Night Football, and gives his best bets for the weekend. Then, pro bettor Brad Powers joins to handicap all four College Football Playoff matchups, bowl games, and gives his pick for who wins it all!

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. 277 Dave Ross Dec 17, 2025

Show notes

On this episode of the Shoulda Bet More podcast, Will Hill previews a huge Rams-Seahawks game and looks at the AFC North race after the Steelers Monday night win. Then, Dave Ross of VSIN By the Books joins to discuss Thursday Night Football, the NFL Playoff Picture, College Football Playoff, as well as the Mets quiet offseason.

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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