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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. 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.

Shoulda Bet More with Will Hill - Ep. 391 Gill Alexander

2026/09/21

On this episode of the Shoulda Bet More podcast Will Hill reacts to a wild week 2 in the NFL, and Gill Alexander joins to recap the games , preview MNF and look ahead to next week. 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. 390 Jeff Parles

2026/09/18

On this episode of the shoulda bet more podcast Will Hill gives his NFL week 2 picks , then Jeff parles of espn Las Vegas joins to recap lions Bills and look ahead to week 2 and preview the final week of the mlb season 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. 389 Dave Ross

2026/09/16

On this episode of the shoulda been more podcast Will Hill previews Thursday night football between the Lions and Bills with a best bet , and Dave Ross, of VSiN By the Books joins to look ahead to week two 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. 388 Geoff Schwartz

2026/09/14

On this episode of the Shoulda Bet More podcast Will Hill reacts to Week 1 of the NFL and looks ahead to to MNF. Then, Geoff Schwartz of Fox Sports joins to recap the week, look ahead to Week 2 , and react to Oregon’s loss 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. 387 Dustin Swedelson

2026/09/11

On this episode of the shoulda bet more podcast Will Hill breaks down week 1 of the nfl and reacts to the first 2 games. Then Dustin Swedelson of Cashing out joins to discuss the nfl, his best bets in college and the mlb races. 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. 386 Jensen Lewis

2026/09/09

On this episode of the Shoulda Bet More podcast Will Hill gives his NFL Division and SB Picks + best bet for Pats/ Seahawks . Then Jensen Lewis joins to give week 1 nfl picks , week 2 college picks , discuss mlb playoff races + 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. 385 Jeff Parles

2026/09/07

On this episode of the Shoulda Bet More podcast Will Hill reacts to the controversial ending in the Michigan win, and recaps the rest of Week 1 while looking ahead to Week 2. Then, Jeff Parles of ESPN Las Vegas joins to discuss his bets in College football , the NFL and the MLB races. 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. 384 Jonathan Von Tobel

2026/09/04

On this episode of the Shoulda Bet More podcast, Will Hill gives his take on Kawhi Leonard and the Clippers sanctions, and Jonathan Von Tobel joins to break down week 1 of college football, the Kawhi news, survivor strategy, and more. 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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