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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. 306 Chris Fallica Feb 23, 2026

Show notes

On this episode of the Shoulda Bet More podcast, Will Hill reacts to the U.S. winning gold in hockey, as well as the weekend in college hoops. Then, “the Bear” Chris Fallica from Fox Sports joins to give his thoughts on the Gold medal game, CBB Futures, MLB early 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 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. 305 Adam Burke Feb 20, 2026

Show notes

On this episode of the Shoulda Bet More podcast, Will Hill reacts to UConn’s recent struggles, gives his thoughts on Duke/Michigan, and an MLB long shot future. Then, Adam Burke, managing editor of VSIN, joins to break down MLB division by division, awards and future bets, lockout thoughts, 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 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. 304 Brad Thomas Feb 18, 2026

Show notes

On this episode of the Shoulda Bet More podcast, Will Hill gives his thoughts on NBA Futures coming out of the All Star Break, and Brad Thomas of PGA Tour joins to discuss his favorite golf outrights, NBA futures, awards, 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 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. 303 Todd Wishnev Feb 16, 2026

Show notes

On this episode of the Shoulda Bet More podcast, Will Hill recaps the weekend in college hoops, and pro bettor Todd Wishnev joins to discuss college basketball futures, how many teams can win it all, playing tennis vs Steve Fezzik, 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 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. 302 Ryan Glasspiegel Feb 13, 2026

Show notes

In this episode of the Shoulda Bet More Will Hill gives his thoughts on the NBA All-Star break. Plus, Will gives his MLB futures best bet. Then Ryan Glasspiegel of Front Office Sports joins to give his thoughts on NBA tanking, Kalshi controversies and visiting Las Vegas.

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 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. 301 Dave Ross Feb 11, 2026

Show notes

On this episode of the Shoulda Bet More podcast, Will Hill looks at the NFL odds for next year, and gives his thoughts on the tanking issue in the NBA. Then, Dave Ross of VSIN By the Books joins to discuss SB odds for next year, MLB bets he’s made, golf, UFC, 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 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. 300 Gill Alexander Feb 09, 2026

Show notes

On this episode of the Shoulda Bet More podcast, Will Hill reacts to the Seahawks dominant win over the Patriots. Then, Gill Alexander of A Numbers Game joins to discuss his takeaways from the game, what we can learn from this Seahawks surprise run, and what bets he likes in CBB and MLB now that football is over.

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 $60 off an annual subscription when you use promo code: SUPER. 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. 299 Jeff Parles Feb 06, 2026

Show notes

In this episode of Shoulda Bet More, Will Hill gives his final take on Super Bowl LX and adds his best bets. Plus, Jeff Parles of ESPN Las Vegas joins the show to break down the big game and give his best prop bets, MVP long shot, and discuss the college basketball landscape.

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 $60 off an annual subscription when you use promo code: SUPER. 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. 298 Kelley Bydlon Feb 04, 2026

Show notes

On this episode of the Shoulda Bet More podcast, Will Hill gives his thoughts on the NBA trade deadline, and recaps his bets for Pats/Seahawks. Then, Kelley Bydlon of A Numbers Game and Long Shots joins to discuss NBA moves, the Super Bowl, and his golf picks for the week.

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 $60 off an annual subscription when you use promo code: SUPER. 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. 297 Colby Marchio Feb 02, 2026

Show notes

On this episode of the Shoulda Bet More podcast Will Hill reacts to the weekend in college hoop and discusses a couple of SB prop bets. Then, Colby Marchio of yourbettingnews joins to discuss Patriots/Seahawks, Mondays CBB card, a long shot MLB bet + 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 $60 off an annual subscription when you use promo code: SUPER. Click https://www.vsin.com/subscribe?tpcc=shoulda-bet-more&utm_source=podcast&utm_medium=simplecast&utm_campaign=shoulda_bet_more to get started.

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