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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. 375 Jeff Parles Aug 12, 2026

Show notes

On this episode of the shoulda bet more podcast, Will Hill breaks down week 1 of the NFL preseason, then Jeff Parles of ESPN Las Vegas joins to discuss the NFL season, sleeper teams, the MLB races, and much more.

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Shoulda Bet More with Will Hill - Ep. 374 John Jastremski Aug 10, 2026

Show notes

On this episode of the Shoulda Bet More podcast. Will Hill breaks down the MLB races, including some best bets. Then John Jastremski of SNY joins to discuss MLB futures, division races, and NFL bets he likes.

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Shoulda Bet More with Will Hill - Ep. 373 Brad Powers Aug 05, 2026

Show notes

On this episode of the shoulda bet more podcast, Will Hill and Brad Powers preview the college football season, with a look at futures, win totals, early-season games, 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. 372 Mitch Moss Aug 03, 2026

Show notes

On this episode of The Shoulda Bet More podcast, Will Hill breaks down the latest in Major League Baseball, including the huge trade of Tarik Skubal to the Dodgers, and some of his early NFL plays. Also on the show, VSiN's Follow the Money and Pod To The Futures podcast co-host, Mitch Moss, drops by to chat some MLB storylines and futures, as well as what he's looking at in the National Football League.

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. 371 Kiev O'Neil Jul 31, 2026

Show notes

On this episode of The Shoulda Bet More podcast Will Hill gives his thoughts on the MLB trade deadline and pennant races with a best bet. Then Kiev O'Niel of the Oddsbreakers joins to discuss all things college football betting 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. 370 Steve Fezzik Jul 29, 2026

Show notes

On this episode of the Shoulda Bet More podcast, Will Hill gives out a long shot MLB award bet. Plus, Steve Fezzik joins to discuss prediction markets, the NFL preseason and win totals.

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. 369 Jonathan Von Tobel Jul 27, 2026

Show notes

On this episode of the Shoulda Bet More podcast, Will Hill breaks down LeBron James taking his talents to the Philadelphia 76ers, how he'll impact the team and how the move impacts the NBA overall. Also on the show, VSiN's Money Moves and Pod To The Futures podcast co-host Jonathan Von Tobel drops by with his thoughts on the deal, including the favorite to win the Eastern Conference and increased excitement for the season. JVT also gives out some of his favorite NBA and NFL futures, including some sleeper teams, and some of his early bets in college football.

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. 368 Dustin Swedelson Jul 24, 2026

Show notes

On this episode of the Shoulda Bet More podcast, Will Hill welcomes VSiN's Dustin Swedelson to discuss his favorite NFL bets, the MLB Trade Deadline, and go head-to-head in Immaculate Grid.

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. 367 Jensen Lewis Jul 22, 2026

Show notes

On this episode of the Shoulda Bet More Podcast, Will Hill gives out some AL longshot futures and shares his thoughts on NL MVP. Plus, Jensen Lewis, VSiN By The Books Host and Former MLB Pitcher joins to discuss the MLB trade deadline, his best MLB bets and the recent surge in home runs.

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. 366 Tim Murray Jul 20, 2026

Show notes

On this episode of the Shoulda Bet More podcast, Will Hill takes a look at some early odds and storylines around college football before chatting some storylines happening in the MLB. Also on the show, VSiN PrimeTime and cohost and VSiN's The College Football Betting Podcast host, Tim Murray, joins with some of his best bets for college football, including conference winners, Heisman hopefuls, over/unders, College Football Playoff thoughts 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.

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