• Shoulda Bet More with Will Hill - Ep. 338 Steve Fezzik
    May 15 2026

    On this episode of the Shoulda Bet More podcast, Will Hill previews both Game 6s in the NBA, then pro sports bettor Steve Fezzik joins to discuss the NFL schedule release, NBA Playoffs, maximizing comps in Vegas, and much more

    Get instant access to expert picks, public betting splits data, and pro betting tools when you join VSiN Pro. You can take 17% off an annual subscription when you use the promo code: POD26. Click Here to get started.


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    40 mins
  • Shoulda Bet More with Will Hill - Ep. 337 Dave Ross
    May 13 2026

    On this episode of the Shoulda Bet More podcast, Will Hill looks at the Cavs - Pistons series and gives a best bet for Game 5, and discusses the NBA offseason. Then, Dave Ross of VSiN By The Books joins to discuss the flailing Mets, the MLB landscape, the PGA championship, and more.

    Get instant access to expert picks, public betting splits data, and pro betting tools when you join VSiN pro. You can take 17% off an annual subscription when you use promo code: POD26. Click Here to get started.


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    42 mins
  • Shoulda Bet More with Will Hill - Ep. 336 Gill Alexander
    May 11 2026

    Will Hill is joined by Gill Alexander to break down several major betting storylines across the sports world.

    The guys preview key NBA Playoff matchups including Thunder at Lakers and Pistons at Cavaliers, discussing betting angles, matchups, adjustments, and market movement.

    They also react to the NBA Draft Lottery and handicap the updated odds and futures markets surrounding the top picks and teams positioned to reshape the league.

    Plus, Will and Gill dive into the 2026 MLB World Series odds, discussing value teams, market perception, and early-season futures opportunities. Plus, betting previews of Monday's MLB slate!

    Get instant access to expert picks, public betting splits data, and pro betting tools when you join VSiN Pro. You can take 17% off an annual subscription when you use promo code: POD26. Click to get started: https://vsin.com/subscribe/


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    45 mins
  • Shoulda Bet More with Will Hill - Ep. 335 Mitch Moss
    May 8 2026

    On this episode of the Shoulda Bet More podcast, Will Hill previews the Friday night NBA games and recaps the Pistons victory over the Cavs. Then, Mitch Moss of Follow The Money joins to discuss the MLB awards markets, NBA + NHL Playoffs, Vrabel's job status, and more.

    Get instant access to expert picks, public betting splits data, and pro betting tools when you join VSiN pro. You can take 17% off an annual subscription when you use promo code: POD26. Click Here to get started.


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    32 mins
  • Shoulda Bet More with Will Hill - Ep. 334 Sammy P
    May 6 2026

    On this episode of the Shoulda Bet More podcast, Will Hill previews Game 2 of Sixers/Knicks and Wolves/Spurs, the AL Cy Young, and the passing of John Sterling. Then, Sammy P of Fox Sports joins to discuss the NBA + NHL Playoffs, MLB long shot bets, and more.

    Get instant access to expert picks, public betting splits data, and pro betting tools when you join VSiN pro. You can take 17% off an annual subscription when you use promo code: POD26. Click Here to get started.


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    35 mins
  • Shoulda Bet More with Will Hill - Ep. 333 Jonathan Von Tobel
    May 4 2026

    On this episode of the Shoulda Bet More podcast, Will Hill reacts to the weekend of action in the NBA, then Jonathan Von Tobel of Money Moves joins to look ahead to Round 2 of the Playoffs, what went wrong for the Celtics, and who may be on upset alert.


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    35 mins
  • Shoulda Bet More with Will Hill - Ep. 332 Chris Macero
    May 1 2026

    In this episode of the Shoulda Bet More podcast, Will Hill previews Friday's NBA games. Plus, Chris Macero, Professional Sports Bettor joins to break down the Kentucky Derby, NBA playoffs, NHL playoffs and the struggles of the Red Sox.

    Get instant access to expert picks, public betting splits data, and pro betting tools when you join VSiN pro. You can take 17% off an annual subscription when you use promo code: POD26. Click Here to get started.


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    30 mins
  • Shoulda Bet More with Will Hill - Ep. 331 Chris Fallica
    Apr 29 2026

    On this episode of the Shoulda Bet More podcast, Will Hill recaps the night in the NBA and looks ahead to Wednesday and Thursday action. Then “the Bear” Chris Fallica of Fox Sports joins to discuss what to look for in the Kentucky Derby Saturday, as well as futures and takeways so far in MLB and the NHL playoffs.

    Get instant access to expert picks, public betting splits data, and pro betting tools when you join VSiN pro. You can take 17% off an annual subscription when you use promo code: POD26. Click Here to get started.


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    28 mins