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    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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    Copyright: © 2024 GoldBoys.com

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    Latest Episodes:
    Shoulda Bet More with Will Hill - Ep. 345 Kiev O'Neil Jun 01, 2026
    Show notes

    On this episode of the Shoulda Bet More podcast, Will Hill previews the NBA Finals between the Spurs and Knicks and some trends and numbers around the series. Also on the show, Kiev O'Neil from The Odds Breakers hops on to break down all things NFL, including division previews, team and player props, and a little college football for good measure.


    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. 344 Gill Alexander May 29, 2026
    Show notes

    On this episode of the Shoulda Bet More podcast, Will Hill reacts to another blowout in the Western Conference Finals, and then Gill Alexander of A Numbers Game joins to preview Game 7, discuss the French Open, MLB bets + 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. 343 Jensen Lewis May 27, 2026
    Show notes

    On this episode the Shoulda Bet More podcast, Will Hill reacts to the Knicks making the NBA Finals and discusses their chance in the NBA Finals. Then, Jensen Lewis of ESPN and VSIN By the Books joins to talk MLB awards, futures, the College Baseball NCAA Tournament, 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.


    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. 342 Doug Kezirian May 25, 2026
    Show notes

    On this episode of the Shoulda Bet More podcast, Will Hill previews the NBA Conference Finals and if the Knicks have a shot at winning it all. Also on the show, sports betting analyst Doug Kezirian joins the show to discuss the playoffs, NBA free agency potential moves, NFL ramping up and the WNBA.

    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.


    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. 341 May 22, 2026
    Show notes

    On this episode of the Shoulda Bet More podcast, Will Hill previews Game 3 of Spurs / Thunder and shares his thoughts on some MLB storylines entering the weekend. Then, Brad Thomas of CBS Sports joins to break down the NBA and NHL Playoffs, the World Cup, 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.


    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. 340 Jonathan Von Tobel May 20, 2026
    Show notes

    On this episode of the Shoulda Bet More podcast, Will Hill previews Game 2 of Spurs / Thunder and relives a classic Game 1. Then, Jonathan Von Tobel of Money Moves joins to discuss the Conference Finals, the NBA offseason, NFL early thoughts, 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.


    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. 339 Chris Fallica May 18, 2026
    Show notes

    On this episode of the Shoulda Bet More podcast, Will Hill previews the Conference Finals for the NBA playoffs, including the Spurs chances against the Thunder and if the Knicks are a lock to make it to the Finals, as well as some MLB talk. Also on the show, Chris "The Bear" Fallica from FOX Sports joins the show to chat the NBA, NFL storylines and futures, his favorite college football over/unders and how to bet the World Cup.

    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.


    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. 338 Steve Fezzik May 15, 2026
    Show notes

    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.


    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. 337 Dave Ross May 13, 2026
    Show notes

    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.


    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. 336 Gill Alexander May 11, 2026
    Show notes

    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/


    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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