Shoulda Bet More - TopPodcast.com

View Top 200 Chart

Back to Rankings Page

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.

Copyright: © 2024 GoldBoys.com

Latest Episodes:

Shoulda Bet More with Will Hill - Ep. 316 Gill Alexander Mar 23, 2026

Show notes

On this episode of the Shoulda Bet More podcast, Will Hill is joined by Gill Alexander of A Numbers Game to recap the weekend in college hoops, look ahead to the sweet 16, and talk about his favorite MLB bets

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. 315 John Laghezza Mar 20, 2026

Show notes

On this episode of the Shoulda Bet More podcast Will Hill recaps the opening day of the NCAA Tournament, and previews the Friday games including some best bets . Then 2025 Fantasy Baseball Writer of the Year John Laghezza joins to preview the upcoming MLB season. Get instant access to expert picks, public betting splits data, and pro betting tools when you join VSiN pro. Grab the Hoops Special for only $29.99 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. 314 Kiev O’Neil Mar 16, 2026

Show notes

On this episode of the Shoulda Bet More podcast Will Hill reacts to the bracket reveal, and gives his best bets for Round 1. Then, Kiev O’Neil of the Oddsbreakers joins to discuss his takeaways from the bracket, who he’s bet + much more. Get instant access to expert picks, public betting splits data, and pro betting tools when you join VSiN pro. Grab the Hoops Special for only $29.99 or take 17% off an annual subscription when you use promo code: POD26. Click https://www.vsin.com/subscribe?tpcc=shoulda-bet-more&utm_source=podcast&utm_medium=simplecast&utm_campaign=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. 313 Tim Murray Mar 13, 2026

Show notes

On this episode of the Shoulda Bet More podcast, Will Hill reacts to the day in CBB on Thursday and talks WBC. Then Tim Murray of VSIN Primetime joins to break down Miami Ohio's chances to make the tourney, Friday's Best Bets, and more.

Get instant access to expert picks, public betting splits data, and pro betting tools when you join VSiN Pro. Grab the Hoops Special for only $29.99 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. 312 Chris Fallica Mar 11, 2026

Show notes

On this episode of the Shoulda Bet More podcast, Will Hill gives his thoughts on conference tournament week, including some best bets. Then “The Bear” Chris Fallica of FOX Sports joins to discuss the ACC tournament, long shot tourney bets, WBC, and more.

Get instant access to expert picks, public betting splits data, and pro betting tools when you join VSiN pro. Grab the Hoops Special for only $29.99 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. 311 Jeff Parles Mar 09, 2026

Show notes

On this episode of the Shoulda Bet More Podcast, Will Hill reacts to this weekend's college basketball games and World Baseball Classic action. Plus, Jeff Parles of ESPN Las Vegas joins to discuss conference tournament futures, his long-shots, and favorite MLB 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 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. 310 Jonathan Von Tobel Mar 06, 2026

Show notes

On this episode of the Shoulda Bet More Podcast, Will Hill previews tonight's college basketball games. Plus, Jonathan Von Tobel joins to discuss college basketball conference tournaments, the surging Charlotte Hornets, his MLB 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. 309 Mar 04, 2026

Show notes

On this episode of the Shoulda Bet More podcast Will Hill gives his breakdown of the WBC, with best bets, a couple of long shots for MVP, and a pick to win it all. Then Will discusses NFL draft + free agency with a bet for who will go 2nd overall. 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 https://www.vsin.com/subscribe?tpcc=shoulda-bet-more&utm_source=podcast&utm_medium=simplecast&utm_campaign=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. 308 Kiev O’Neil Mar 02, 2026

Show notes

On this episode of the Shoulda Bet More podcast, Will Hill reacts to the weekend in college hoops and gives a best for conference tournament week. Then Kiev O’Neil of The Oddsbreakers joins to break down conference tournament odds, the bubble , Miami Ohio 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 https://www.vsin.com/subscribe?tpcc=shoulda-bet-more&utm_source=podcast&utm_medium=simplecast&utm_campaign=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. 307 Jensen Lewis Feb 27, 2026

Show notes

On this episode of the Shoulda Bet More podcast Will Hill reacts to UConn embarrassing St John’s Wednesday night, and discusses their shot at a #1 seed. Then, Jensen Lewis of VSIN By the Books joins to break down the WBC, his favorite MLB bets, facing A-Rod, Manny, and Jeter, 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.

Related Podcasts