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PODCAST

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

sports football

All Episodes

00:29:50

Shoulda Bet More with Will Hill - Ep. 269 Brad Powers

Shoulda Bet More ·

2025/11/28

On this episode of the Shoulda Bet More Podcast, Will Hill reacts to a great day of Thanksgiving NFL action and gives his best bets for the weekend. Then, professional bettor Brad Powers joins the show to discuss his Week 14 college football picks and the playoff picture. Hosted by Simplecast, an AdsWizz company. See pcm.adswizz.com for information about our collection and use of personal data for advertising.

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00:36:14

Shoulda Bet More with Will Hill - Ep. 266 Kelley Bydlon

Shoulda Bet More ·

2025/11/21

On this episode of the Shoulda Bet More Podcast, Will Hill gives his college and NFL picks for the weekend. Then, Kelley Bydlon of A Numbers Game joins to give his best bets in the NFL, discuss the awards markets, and share his thoughts on the NBA so far. Hosted by Simplecast, an AdsWizz company. See pcm.adswizz.com for information about our collection and use of personal data for advertising.

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00:42:48

Shoulda Bet More with Will Hill - Ep. 265 Jeff Parles

Shoulda Bet More ·

2025/11/19

On this episode of the Shoulda Bet More Podcast, Will Hill gives a few best bets for College Football this weekend, as well as a long shot NBA Future. Then, Jeff Parles of ESPN Las Vegas joins to discuss the College Football Playoff picture, best bets, the NFL playoffs, and if OKC can break the Warriors regular season wins record. Hosted by Simplecast, an AdsWizz company. See pcm.adswizz.com for information about our collection and use of personal data for advertising.

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00:40:09

Shoulda Bet More with Will Hill - Ep. 264 Geoff Schwartz

Shoulda Bet More ·

2025/11/17

On this episode of the Shoulda Bet More Podcast, Will reacts to the day in the NFL, and gives a couple of Best Bets. Then former NFL offensive lineman Geoff Schwartz joins to discuss if the Chiefs will actually miss the playoffs, who is the team to beat in the AFC, the college football playoff picture and more. Hosted by Simplecast, an AdsWizz company. See pcm.adswizz.com for information about our collection and use of personal data for advertising.

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00:46:29

Shoulda Bet More with Will Hill - Ep. 262 Chris "The...

Shoulda Bet More ·

2025/11/12

On this episode of the Shoulda Bet More Podcast, Will Hill gives a best bet for Jets/Patriots and shares a couple of College Football plays. Then, Chris Fallica of Fox Sports joins to discuss the College Football Playoffs Picture, best bets for the week, and more. Hosted by Simplecast, an AdsWizz company. See pcm.adswizz.com for information about our collection and use of personal data for advertising.

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00:45:45

Shoulda Bet More with Will Hill - Ep. 261 Gill Alexander

Shoulda Bet More ·

2025/11/10

On this episode of the Shoulda Bet More podcast , Will Hill reacts to the day in the NFL, and previews next week. Then Gill Alexander of A Numbers Game joins to discuss the games of the day, takeaways, and preview Packers Eagles. Hosted by Simplecast, an AdsWizz company. See pcm.adswizz.com for information about our collection and use of personal data for advertising.

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00:43:48

Shoulda Bet More with Will Hill - Ep. 259 Tim Murray

Shoulda Bet More ·

2025/11/05

On this episode of the Shoulda Bet More podcast, Will Hill gives a few best bets for CFB and Raiders / Broncos, and reacts the Jets trades. Then, Tim Murray of VSIN joins to give his thoughts on the College Football Playoffs outlook, best bets for the weekend, and Heisman race. Hosted by Simplecast, an AdsWizz company. See pcm.adswizz.com for information about our collection and use of personal data for advertising.

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00:42:52

Shoulda Bet More with Will Hill - Ep. 258 Dave Ross

Shoulda Bet More ·

2025/11/03

On this episode of the Shoulda Bet More podcast, Will Hill reacts to an exciting day in the NFL and gives his takeaways from Sunday. Then, Dave Ross, VSIN Host joins the show to discuss a heartbreaking loss on his Blue Jays World Series bet. Plus, the guys recap Game 7 of the World Series and give out their bets bets for Monday Night Football. Hosted by Simplecast, an AdsWizz company. See pcm.adswizz.com for information about our collection and use of personal data for advertising.

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00:30:35

Shoulda Bet More with Will Hill - Ep. 257 Jensen Lewis

Shoulda Bet More ·

2025/10/31

On this episode of the Shoulda Bet More Podcast, Will Hill previews Game 6 of the World Series, and gives his bets in football for the weekend. Then, former Major League pitcher Jensen Lewis joins to break down the World Series and more. Hosted by Simplecast, an AdsWizz company. See pcm.adswizz.com for information about our collection and use of personal data for advertising.

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00:39:32

Shoulda Bet More with Will Hill - Ep. 256 Jeff Parles

Shoulda Bet More ·

2025/10/29

On this episode of the Shoulda Bet More podcast, Will Hill reacts to the Blue Jays tying the World Series once again, and gives his best bets for Game 5 and TNF. Then, Jeff Parles of ESPN Las Vegas joins the pod to discuss the World Series - can someone on LA, other than Ohtani, win the MVP? Also, they talk about the NFL and College Football weekend ahead. Hosted by Simplecast, an AdsWizz company. See pcm.adswizz.com for information about our collection and use of personal data for advertising.

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00:38:33

Shoulda Bet More with Will Hill - Ep. 254 Tommy Lorenzo

Shoulda Bet More ·

2025/10/24

On this episode of the Shoulda Bet More podcast, Will Hill gives his best bets for the weekend, previews the World Series, and reacts to the Terry Rozier and Chauncey Billups arrests and what it means for the betting world going forward. Then, Tommy Lorenzo of the Cover the Weekend Podcast joins to break down Dodgers / Jays, give an MVP Sleeper for the series, talk college football, and more. Hosted by Simplecast, an AdsWizz company. See pcm.adswizz.com for information about our collection and use

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00:38:49

Shoulda Bet More with Will Hill - Ep. 253 Chris "The...

Shoulda Bet More ·

2025/10/22

On this episode of the Shoulda Bet More podcast, Will Hill recaps a dramatic Game 7 of the ALCS, looks ahead to the World Series, and gives a few NBA Best Bets. Then, Chris “The Bear” Fallica of Fox Sports joins the podcast to discuss Dodgers / Blue Jays, College Football Playoff overview, how he would fix the Jets, and more. Hosted by Simplecast, an AdsWizz company. See pcm.adswizz.com for information about our collection and use of personal data for advertising.

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00:38:15

Shoulda Bet More with Will Hill - Ep. 252 Kiev O'neil

Shoulda Bet More ·

2025/10/20

On this episode of the Shoulda Bet More podcast, Will Hill talks about NFL week seven and is joined by Kiev O'neil to further the chaotic day 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.

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00:34:14

Shoulda Bet More with Will Hill - Ep. 250 Iain MacMillan

Shoulda Bet More ·

2025/10/15

On this episode of the Shoulda Bet More podcast, Will previews Thursday Night Football, and gives his reaction to Monday Night Football - Are the Bills in Trouble? Are the Falcons for real? Then Iain MacMillan of Sports Illustrated joins to discuss his bets for the weekend, the ALCS, and more. Hosted by Simplecast, an AdsWizz company. See pcm.adswizz.com for information about our collection and use of personal data for advertising.

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00:40:39

Shoulda Bet More with Will Hill - Ep. 249 Geoff Schwartz

Shoulda Bet More ·

2025/10/13

On this episode of the shoulda bet more podcast , Will Hill reacts to the chiefs beating the lions and all the Sunday action in the NFL, and looks ahead to the 2 Monday night football games and shares his bets for the MLB playoffs . Then , Geoff Schwartz of Fox sports joins to discuss Bills /Falcons and Bears/Commanders , give his take on James Franklin being fired and More Hosted by Simplecast, an AdsWizz company. See pcm.adswizz.com for information about our collection and use of personal data for

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00:29:59

Shoulda Bet More with Will Hill - Ep. 247

Shoulda Bet More ·

2025/10/08

On this episode of the Shoulda Bet More podcast, Will Hill recaps a wild comeback by the Yankees, previews the four MLB games on Wednesday, then dives into College Football and the games he likes for this weekend and gives some big picture thoughts on the playoff picture. Hosted by Simplecast, an AdsWizz company. See pcm.adswizz.com for information about our collection and use of personal data for advertising.

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00:40:08

Shoulda Bet More with Will Hill - Ep. 245 Ben Wilson

Shoulda Bet More ·

2025/10/03

On this episode of the Shoulda Bet More podcast, Will reacts to the Yankees beating the Red Sox, looks ahead to the ALDS and NLDS, and Ben Wilson joins to discuss the MLB playoffs, 49ers/Rams, and his NFL picks 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.

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00:39:47

Shoulda Bet More with Will Hill - Ep. 244 Jeff Parles

Shoulda Bet More ·

2025/10/01

On this episode of the shoulda bet more podcast will hill recaps a brutal Yankees loss to the Red Sox, previews game 2 , and gives his best bets for Tuesday . Then, Jeff Parles from sports by the book joins to discuss the day in MLB, Wednesdays games, NFL takeaways 4 weeks in and more Hosted by Simplecast, an AdsWizz company. See pcm.adswizz.com for information about our collection and use of personal data for advertising.

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00:41:06

Shoulda Bet More with Will Hill - Ep. 243 Nic Larson

Shoulda Bet More ·

2025/09/29

On this episode of the Shoulda Bet more Podcast, Will Hill reacts to Sunday's NFL action and discusses the Chiefs win over the Ravens. Plus, MLB handicapper Nic Larson joins the show to discuss the MLB playoffs and give his best bets. Hosted by Simplecast, an AdsWizz company. See pcm.adswizz.com for information about our collection and use of personal data for advertising.

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00:22:19

Shoulda Bet More with Will Hill - Ep. 242 Brad Powers

Shoulda Bet More ·

2025/09/26

On this episode of the Shoulda Bet More Podcast, Will Hill gives his college football and NFL picks for the weekend. Then Pro Bettor Brad Powers joins to discuss all the big college games this weekend, his best bets, and his thoughts on the Heisman and National title picture. Hosted by Simplecast, an AdsWizz company. See pcm.adswizz.com for information about our collection and use of personal data for advertising.

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251 results

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