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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. 355 Luke Swain Jun 23, 2026

Show notes

On this episode the Shoulda Bet More podcast Will Hill gives his finals thoughts on the NBA Draft. Then, expert draft bettor Luke Swain (Vegas Refund) joins to give out best bets for the NHL and NBA Draft, and breaks down what surprises we could get. 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. 354 Gill Alexander Jun 22, 2026

Show notes

On this episode of the Shoulda Bet More podcast, Will Hill gives his take on the NBA Draft and some ways to bet the futures market. Also on the show, VSiN's A Numbers Game co-host Gill Alexander joins the show to chat MLB futures in the American and National League, World Cup action, French Open, NBA Draft, movies to watch right now 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. 353 Dave Ross Jun 19, 2026

Show notes

On this episode of the Shoulda Bet More podcast, Will Hill gives his take on when and where Giannis will get traded. Then, Dave Ross of VSIN By The Books joins to discuss the U.S. Open, the World Cup, MLB 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. 352 Geoff Schwartz Jun 17, 2026

Show notes

On this episode of the Shoulda Bet More podcast, Will Hill looks ahead to the NBA Draft and gives a long shot NFL Award bet. Then, from Fox Sports is Geoff Schwartz, former NFL offensive lineman joins to discuss the World Cup, NFL, and College and Football bets, tv shows to catch up on during the summer, 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. 351 Chris Fallica Jun 15, 2026

Show notes

On this episode of the Shoulda Bet More podcast, Will Hill reacts to the Knicks winning the NBA Finals and whether or not the Spurs blew it on the way. Also on the show, Chris "The Bear" Fallica joins to chat the NBA Finals and next year's futures, Monday's World Cup matchups, MLB outlooks, U.S. Open, early Heisman odds 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. 350 Jensen Lewis Jun 12, 2026

Show notes

On this episode of the Shoulda Bet More podcast, Will Hill reacts to an epic Game 4 of the NBA Finals and the Knicks making a historic comeback against the Spurs, then what to bet in Game 5. Also on the show, VSiN By The Books co-host Jensen Lewis joins to chat the NBA Finals, College World Series and MLB.

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. 349 Kelley Bydlon Jun 10, 2026

Show notes

On this episode of the Shoulda Bet More podcast, Will Hill reacts to Game 3 of the NBA Finals and looks ahead to Game 4. Plus, Kelley Bydlon from a A Numbers Game joins to discuss all things NBA Finals, the Draft and offseason.

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. 348 Jeff Parles Jun 08, 2026

Show notes

On this episode of the Shoulda Bet More podcast, Will Hill recaps the Knicks taking a 2-0 series lead in the NBA Finals and if the Spurs have any chance at making a comeback, as well as a tied series in the Stanley Cup Final. Also on the show, Jeff Parles from ESPN Las Vegas drops by with his thoughts on the Finals, storylines around the Knicks and Spurs and headlines around Major League Baseball.

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. 347 Jonathan Von Tobel Jun 05, 2026

Show notes

On this episode of the Shoulda Bet More podcast, Will Hill reacts to the Knicks Game 1 victory in the NBA Finals and looks ahead to Game 2. Then, Jonathan Von Tobel of Money Moves joins to break down the NBA Finals, discuss a few sleepers for MVP of the series, and talk NBA Draft 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. 346 Chris Macero Jun 03, 2026

Show notes

On this episode of the Shoulda Bet More podcast, Will Hill gives his thoughts on the NBA Finals and the Aaron Judge injury’s impact on the AL MVP race. Then, pro sports bettor Chris Macero joins to talk Knicks / Spurs, the Stanley Cup Final, the Belmont, 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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