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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. 266 Kelley Bydlon Nov 21, 2025

Show notes

On this episode of the Shoulda Bet More Podcast, Will Hill gives his college and NFL picks for the weekend. Then, Kelley Bydlon of A Numbers Game joins to give his best bets in the NFL, discuss the awards markets, and share his thoughts on the NBA so far.

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Shoulda Bet More with Will Hill - Ep. 265 Jeff Parles Nov 19, 2025

Show notes

On this episode of the Shoulda Bet More Podcast, Will Hill gives a few best bets for College Football this weekend, as well as a long shot NBA Future. Then, Jeff Parles of ESPN Las Vegas joins to discuss the College Football Playoff picture, best bets, the NFL playoffs, and if OKC can break the Warriors regular season wins record.

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Shoulda Bet More with Will Hill - Ep. 264 Geoff Schwartz Nov 17, 2025

Show notes

On this episode of the Shoulda Bet More Podcast, Will reacts to the day in the NFL, and gives a couple of Best Bets. Then former NFL offensive lineman Geoff Schwartz joins to discuss if the Chiefs will actually miss the playoffs, who is the team to beat in the AFC, the college football playoff picture and more.

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Shoulda Bet More with Will Hill - Ep. 263 Jonathan Von Tobel Nov 14, 2025

Show notes

On this episode of the Shoulda Bet More Podcast, Will Hill gives his NFL and College Picks for the weekend. Then, Jonathan Von Tobel of VSIN joins to break down the weekend in the NFL, give his bets, discuss the MVP race, and can OKC actually break the record?

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Shoulda Bet More with Will Hill - Ep. 262 Chris "The Bear" Fallica Nov 12, 2025

Show notes

On this episode of the Shoulda Bet More Podcast, Will Hill gives a best bet for Jets/Patriots and shares a couple of College Football plays. Then, Chris Fallica of Fox Sports joins to discuss the College Football Playoffs Picture, best bets for the week, and more.

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Shoulda Bet More with Will Hill - Ep. 261 Gill Alexander Nov 10, 2025

Show notes

On this episode of the Shoulda Bet More podcast , Will Hill reacts to the day in the NFL, and previews next week. Then Gill Alexander of A Numbers Game joins to discuss the games of the day, takeaways, and preview Packers Eagles.

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Shoulda Bet More with Will Hill - Ep. 260 Mitch Moss Nov 07, 2025

Show notes

On this episode of the Shoulda Bet More podcast, Will Hill gives his NFL and college best bets for the weekend, as well as a college basketball future. Then, Mitch Moss of Follow The Money joins to discuss all things awards and futures across NFL and CFB.

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Shoulda Bet More with Will Hill - Ep. 259 Tim Murray Nov 05, 2025

Show notes

On this episode of the Shoulda Bet More podcast, Will Hill gives a few best bets for CFB and Raiders / Broncos, and reacts the Jets trades. Then, Tim Murray of VSIN joins to give his thoughts on the College Football Playoffs outlook, best bets for the weekend, and Heisman race.

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Shoulda Bet More with Will Hill - Ep. 258 Dave Ross Nov 03, 2025

Show notes

On this episode of the Shoulda Bet More podcast, Will Hill reacts to an exciting day in the NFL and gives his takeaways from Sunday. Then, Dave Ross, VSIN Host joins the show to discuss a heartbreaking loss on his Blue Jays World Series bet. Plus, the guys recap Game 7 of the World Series and give out their bets bets for Monday Night Football.

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Shoulda Bet More with Will Hill - Ep. 257 Jensen Lewis Oct 31, 2025

Show notes

On this episode of the Shoulda Bet More Podcast, Will Hill previews Game 6 of the World Series, and gives his bets in football for the weekend. Then, former Major League pitcher Jensen Lewis joins to break down the World Series and more.

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