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. 296 Kiev O'Neil Jan 30, 2026

Show notes

On this episode of the Shoulda Bet More podcast, Will Hill previews Michigan / Michigan State and gives his thoughts on the Giannis trade market. Then, Kiev O’Neil of The Oddsbreakers joins to discuss his favorite SB props, the weekend in college hoops, 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 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. 295 Jensen Lewis Jan 28, 2026

Show notes

On this episode of the Shoulda Bet More podcast, Will Hill gives a best bet for SB MVP, reacts to the fallout of the AFC Title Game, and gives his thoughts on the recent coaching carousel in the NFL. Then former major leaguer Jensen Lewis joins to preview the MLB season with a best for each division and gives his thoughts on the Super Bowl.

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. 294 Jonathan Von Tobel Jan 26, 2026

Show notes

On this episode of the Shoulda Bet More podcast, Will Hill reacts to the conference title games and gives his early thoughts on the Super Bowl. Then, Jonathan Von Tobel of Money Moves joins to discuss the day in the NFL. Did Sean McVay and Sean Payton screw up? Also Seahawks / Pats Part 2.

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. 293 John Jastremski Jan 23, 2026

Show notes

On this episode of the Shoulda Bet More Podcast, Will Hill gives his final thoughts and best bets on the NFL Conference Championship Games. Plus, Will reacts to the latest MLB moves with the Mets and Yankees. Then, John Jastremski of SNY and the Ringer joins the show to break down the NFL Conference Championship Games and MLB hot stove.

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. 292 Julian Edlow Jan 21, 2026

Show notes

On this episode of the Shoulda Bet More podcast, Will Hill recaps Indiana winning the national title, and gives his thoughts on the conference championship games. Then, Julian Edlow of DK Network joins to break down Patriots/Broncos, Seahawks/Rams, and some thoughts on college basketball and the NBA.

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. 291 Jan 19, 2026

Show notes

On this episode of the Shoulda Bet More podcast Will Hill recaps an epic Divisional Weekend, and gives his pick for the CFP Title Game. Then Jeff Parles of ESPN Las Vegas joins to react to Rams/ Bears, and all the action this weekend. 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. 290 Mitch Moss Jan 16, 2026

Show notes

On this episode of the Shoulda Bet More podcast, Will Hill goes through every NFL Playoff game with best bets. Then, Mitch Moss of Follow The Money joins to discuss the weekend of NFL action, the CFP National Title Game, gameday snacks, 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 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. 289 Dave Ross Jan 14, 2026

Show notes

On this episode of the Shoulda Bet More podcast, Will Hill reacts to Mike Tomlin stepping down after an ugly loss to the Texans, and gives a few best bets for the Divisional Round of the NFL Playoffs. Then, Dave Ross of VSIN By The Books joins the pod to discuss all 4 NFL Playoff games coming up, Miami vs Indiana, 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 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. 288 Gill Alexander Jan 12, 2026

Show notes

On this episode of the Shoulda Bet More podcast, Will Hill recaps an epic weekend of football, and Gill Alexander of A Numbers Game joins to react to all the weekend action, look ahead to Texans / Steelers, as well as early thoughts for next week’s games.

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. 287 Sam Panayotovich Jan 09, 2026

Show notes

On this episode of the Shoulda Bet More podcast, Will Hill reacts to Miami defeating Ole Miss, and gives a best bet for all 6 playoff games. Then, Sammy P of Fox Sports joins to discuss Wild Card Weekend, Indiana vs Oregon, Futures, 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 over 15% off an annual subscription when you use promo code: POD25. 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