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Rating

★★★★★

4.9

from

85 reviews

Description

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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Check latest episodes from Shoulda Bet More podcast

Shoulda Bet More with Will Hill - Ep. 406 Chris Fallica

2026/10/28

On this episode of the Shoulda Bet More podcast Will Hill recaps a wild Rays comeback and Chris Fallica of Fox Sports joins to discuss the CFB slate, the playoff picture , NFL bets and more. 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. 405 Jeff Parles

2026/10/26

On this episode of the Shoulda Bet More podcast Will Hill recaps the day in the NFL and looks ahead to Mondays games. Then Jeff Parles of ESPN Las Vegas joins to react to the day in football , discuss the World Series, college football and more. 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. 404 Jensen Lewis

2026/10/23

On this episode of the Shoulda Bet More podcast Will Hill previews the World Series and give his football picks for the weekend . Then Jensen Lewis of vsin by the books joins to break down the fall classic, sleeper mvp bets and more. 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. 403 Kiev O'Neil

2026/10/19

On this episode of the Shoulda Bet More podcast Will Hill recaps a wild weekend of football and looks ahead to MNF. Then, Kiev O’Niel of the Oddsbreakers joins to discuss all the action, analyze the futures and awards markets and try to make sense of all the upsets in College Football. 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. 402 Ben Wilson

2026/10/16

On this episode of the shoulda bet more podcast Will Hill reacts to the Brewers sweeping the Dodgers and another OT NFL primetime game. Then Ben Wilson of Fox sports joins to react to the Brewers NL title , look ahead of the World Series and give his favorite plays of the weekend. 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. 401 Dave Ross

2026/10/14

On this episode of the Shoulda Bet More podcast Will Hill recaps a wild Bills victory over the Rams and previews Seahawks/Broncos. Then, Dave Ross of VSIN By the Books joins to give his thoughts on the NFL through 5 weeks, look at his best bets for Week 6, and discuss the NLCS. 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. 400 Gill Alexander

2026/10/12

On this episode of the shoulda bet more podcast, Will Hill recaps another wild day in the NFL, and looks ahead to Monday night football and the ALCS. Then Gill Alexander of a numbers game joins to review the day that was in NFL and give his thoughts on the MLB playoffs 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. 399 Matt Youmans

2026/10/09

On this episode of the shoulda bet more podcast Will Hill reacts to the Yankees getting swept by the Rays and gives his thoughts on the NFL + CFB games this weekend. Then Matt Youmans of vsin primetime joins to recap the Yankees exit , preview dodgers brewers and give his best bets for the weekend 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. 398 Mitch Moss

2026/10/07

On this episode of the Shoulda Bet More podcast Will Hill previews the day in MLb playoffs and gives a couple of NFL best bets. Then Mitch Moss of follow the money joins to discuss the NFL futures and awards market and give his thoughts on week 5 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. 397 John Jastremski

2026/10/05

On this episode of the Shoulda Bet More podcast Will Hill recaps a wild Week 4 in the NFL and looks ahead to the Monday action. Then, John Jastremski of SNY joins to discuss the Yanks Rays series and react to the day that was in the NFL. 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. 396 Jeff Parles

2026/10/02

On this episode of the Shoulda Bet More podcast Will Hill reacts to the Browns win on Thursday night and previews the divisional round in the mlb playoffs. Then Jeff parles of espn Las Vegas joins to preview the weekend in football and give his picks for the AL and NL division rounds 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. 395 Jensen Lewis

2026/09/30

On this episode of the Shoulda Bet More podcast Will Hill recaps day 1 of the MLB playoff and looks ahead to Wednesdays action. Then, Jensen Lewis of VSIN By the Books joins to give his thoughts on all of the Game shares his World Series bet 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. 394 Kiev O'Niel

2026/09/28

In this episode of the Shoulda Bet More podcast, Will Hill is joined by Kiev O’Neil of the Oddsbreakers as they recap all the action we saw in Week 3 of the NFL season and look ahead to the Monday Night Football game between the Bears and Eagles. 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. 393 Jonathan Von Tobel

2026/09/25

On this episode of the shoulda bet more podcast Will gives his picks in NFL and college, then Jonathan Von Tobel choice to discuss his best bets in the NFL and a loaded college slate. 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. 392 Chris Fallica

2026/09/23

On this episode of the Shoulda Bet More podcast Will Hill reacts to the Jackson Dart injury and evaluates the Giants options, and gives a preview and best bet for TNF. Then Chris Fallica, the Bear, of Fox sports joins to break down a great weekend of college football, as well as bets in MLB and NFL that he’s eying. Hosted by Simplecast, an AdsWizz company. See pcm.adswizz.com for information about our collection and use of personal data for advertising.

Podcast reviews

Read Shoulda Bet More podcast reviews

4.9 out of 5

85 reviews

★★★★★

JDL from Jacksonville 2026/08/16

Best pod for MLB bets

Can’t wait for MLB playoffs discussion. Whatever he picks for series winners, bet it! @GusZernialSox

★★★★★

Rjr58 2026/08/03

Great Podcast

By far one of the best sports Podcasts out there. Will is one of the few people I can listen to when talking sports without a guest. That’s a rare tra...

★★★★★

partypete3 2026/07/31

Great Podcast

Always listen, great guests, props to Will

★★★★★

JR34240 2026/07/24

Favorite pod

Always a must listen. Good rotation of guests, covers wide range of topics

★★★★★

Lindy Moderate 2026/07/10

5 star pod

One of the best sports gambling pods out there. Great variety of guests. Perfect length - 25-45 minutes per episode - never overdone.

★★★★★

Mikerouse91 2026/05/13

Will Hill

Will is great and has superb guests.

★★★★★

keven70 2026/04/20

One of my favorites

Great content. Great guests. Love this podcast.

★★★★★

tstelly18 2026/03/09

Great show

Great show. Great content. The only feedback I’d give is the volume levels are a little low. I need to turn my car volume up to usually 35 to hear eve...

★★★★★

Zsport23 2026/02/13

Excellent Pod

Informative show with a great format! Will’s multi-sport knowledge and diverse lineup of guests make this podcast a must listen. I never miss an episo...

★★★★★

Colby Marchio 2026/02/06

Will Rocks

Highly recommend giving a listen to the Colby Marchio episode.

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