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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.

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Latest Episodes:

Shoulda Bet More with Will Hill - Ep. 29 - Kiev O'Neil Mar 18, 2024

Show notes

The committee has made their selections and the bracket is finally out! Kiev O'Neil from The OddsBreakers returns to the pod to discuss the early look at the bracket with Will. With so many bid steals, did the committee make the correct selections? Who got snubbed? Which teams should be on upset alert? The guys also give some early looks based on the lines that came out right after the bracket released. Also some tournament futures that are worth taking. Tune in to this episode to get an edge on the books on the best tournament of the year!

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Shoulda Bet More with Will Hill - Ep. 28 - Steve Fezzik Mar 15, 2024

Show notes

We are just three days away from Selection Sunday! To get ready for the NCAA Tournament, Steve Fezzik of Pregame.com comes back onto the pod to talk college hoops with Will. The guys discuss how to win your bracket pool, who to back and who to fade in the tournament, and how to manage your bankroll to maximize your chances of winning in the tournament. As a bonus, Steve also drops some NIT betting tips so you can get a little extra cash. Tune in to hear all of that and more on today's episode!

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Shoulda Bet More with Will Hill - Ep. 27 - Tim Kurkjian Mar 13, 2024

Show notes

With Opening Day only a couple weeks away, ESPN Analyst Tim Kurkjian joins Will to discuss some MLB! The Yankees continue to be plagued with injuries. Are the Guardians underrated and will they win the divison? How has no team gone after Blake Snell in free agency? Does the MLB need a different approach to their playoff format? Tim shares who he believes will be our 2024 World Series Champions. Tune in to hear everything Tim and Will have to say as we approach the start of the season!

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Shoulda Bet More with Will Hill - Ep. 26 - Jeff Parles Mar 11, 2024

Show notes

It's time for the major conference tournaments as Jeff Parles (@jeffparles) of Sports by the Book returns to the pod to discuss college hoops and a variety of other sports with Will! Who do the guys think from the bubble teams are in and out? Who should you be betting on in the upcoming conference tournaments? Did we see a NBA Finals preview last week in Nuggets/Celtics? How does the top 10 of the NFL draft pan out? Plus, with baseball coming up soon, where will Blake Snell sign and after the Senga injury, can the Mets make the postseason? Tune in to find out their opinions and to get a betting edge!

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Shoulda Bet More with Will Hill - Ep. 25 - Reed Wallach Mar 08, 2024

Show notes

March Madness is almost upon us! Reed Wallach, Senior Editor at BedSided joins Will to discuss everyones favorite college tournament on this episode of Shoulda Bet More! The two break down some of the conference tournaments they're looking at. How they approach the last regular season weekend. Is UConn going to win it all? Will Tennessee reach the Final Four? The two also discuss some NBA. Will the Nuggets and Celtics go up against eachother in the finals? Tune in to get a betting edge!

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Shoulda Bet More with Will Hill - Ep. 24 - Adnan Virk (Oscars Special) Mar 06, 2024

Show notes

The Oscars are this Sunday! To celebrate, we have this very special midweek episode of Shoulda Bet More! From Cinephile with Adnan Virk and MLB Network, Adnan Virk joins Will on the podcast. They discuss the various Oscars categories to try to find you an angle that you should be betting on, from the more well known categories to the smaller ones as well. In addition to the Oscars, the guys also talk baseball. Where will Blake Snell end up and are there any teams that can potentially surprise this season? Plus, where will Kirk Cousins and Justin Fields end up. Tune in for Will's takes and looks for you to get your betting edge!

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Shoulda Bet More with Will Hill - Ep. 23 - "The Bear" Chris Fallica Mar 04, 2024

Show notes

It's conference tournament week! To celebrate, from Fox Sports, and the host of the Bear Bets Podcast, "The Bear" Chris Fallica joins Will on this episode of Shoulda Bet More! They discuss who they think will be getting those coveted top seeds, who's in and who's out of the bubble teams, and potential NCAA Tournament prop looks. The guys also discuss MLB season props, the NFL draft, 2024 Heisman picks, and a special Champions League winner pick! Tune in to get an edge on what is going to be a fun March.

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Shoulda Bet More with Will Hill - Ep. 22 - Jason Weingarten Mar 01, 2024

Show notes

MLB spring training has arrived! Jason Weingarten joins Will on this episode of the Shoulda Bet More podcast to discuss the upcoming MLB season. With a month to go until opening day, the two cover what lines they're looking closely at. Does Yamamoto win NL Rookie of the Year? Will a team pick up Trevor Bauer before the start of the season? Who do they like to win the World Series? What odds are even worth it with how low some of the lines are. Tune in to hear it all!

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Shoulda Bet More with Will Hill - Ep. 21 - Jonathan Von Tobel Feb 26, 2024

Show notes

The host of VSiN Primetime, Jonathan Von Trobel (@meJVT), joins Will on this episode of Shoulda Bet More! They discuss NBA Award Futures and who is worth taking at the halfway point of the season as well as potential conference champion picks. They also talk NFL Free Agency and the NFL Draft. Plus, Will has a look for an NBA team not to make the playoffs and Will's college basketball takeaways from the weekend. Tune in to get a betting edge!

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Shoulda Bet More with Will Hill - Ep. 20 - Ian Eagle Feb 23, 2024

Show notes

Legendary CBS NFL, Final Four, and Brooklyn Nets play-by-play man, Ian Eagle, joins Will on this episode of Shoulda Bet More! They discuss the direction of the Nets, the landscape of college basketball as we head into March, his feelings on doing the Final Four play-by-play for the first time, and his thoughts on Mahomes, Rodgers, the 2023 NFL Season, and what the 2024 season might look like. Plus, Will addresses his jinx of UConn on Monday's episode, a look ahead to this weekend in college basketball, his thoughts on the NBA All-Star game, and a bonus TV recommendation!

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