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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. 19 - Todd Wishnev Feb 19, 2024

Show notes

Professional Bettor, Todd Wishnev, join Will on the Shoulda Bet More podcast to talk some college basketball. We discuss this weekend's results. Is UConn head and shoulders above the rest of the country? What is the best way to bet them for the NCAA Tournament. Speaking of the tournament, what other teams or longshots are worth betting? Which teams are overrated/underrated? How you should be looking to live bet college basketball games. Plus, what can be done about the NBA All Star Weekend to make it more interesting.

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Shoulda Bet More with Will Hill - Ep. 18 - Kelley Bydlon Feb 16, 2024

Show notes

On this episode of the Shoulda Bet More podcast, one final post mortem of the Super Bowl as Will reacts to the reaction of Kyle Shanahan's decision making. Kelley Bydlon (@KelleyBydlon) of VSiN join Will on the pod today to discuss the NBA. What are the bettable lines for NBA Awards including MVP? Should we be worried about the Nuggets? Which teams are contenders and which are pretenders? Plus some NBA All-Star weekend looks.

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Shoulda Bet More with Will Hill - Ep. 17 - Gill Alexander Feb 12, 2024

Show notes

In this post-Super Bowl LVIII edition of Shoulda Bet More, Gill Alexander (@beatingthebook) of "A Numbers Game" and the "Beating the Book Pod" joins the show in which he and Will give their raw reactions to what just happened. Where did Kyle Shanahan and the 49ers go wrong? Where does Patrick Mahomes rank among the greats? Where does Super Bowl LVIII itself rank? Find out the answers to these questions and many others by tuning in!

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Shoulda Bet More with Will Hill - Ep. 16 - Matt Hamilton Feb 09, 2024

Show notes

Matt Hamilton, Producer of the Up & Adams show on FanDuel TV, joins Will to discuss Super Bowl LVIII. Will finally has his pick on who he has winning. The two discuss their favorite picks ahead of the big game. Can San Francisco turn their defense around? Will the Chiefs be able to stop Christian McCaffrey? Matt expresses his love for nachos. Be sure to tune in!

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Shoulda Bet More with Will Hill - Ep. 15 - Jeff Parles Feb 05, 2024

Show notes

Jeff Parles of Sports by the Book joins the show to discuss his best bets on Super Bowl props, O/U, and his pick against the spread. How does Jeff feel about Dan Campbell's decision making in the NFC Championship Game? What is the go-to Super Bowl food choice? Will also gives his early week Super Bowl looks. Plus Jeff and Will talk baseball. How will Jeff's Mets fare this year? Can the Yankees win the pennant with the addition of Juan Soto? MVP Futures and O/U win totals on some teams. Tune in for some great betting insight!

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Shoulda Bet More with Will Hill - Ep. 14 - Kiev O'Neil Feb 02, 2024

Show notes

This episode Kiev O'Neil of The OddsBreakers, joins Will to discuss the Super Bowl as well as college basketball. Will we see the line move to three for the big game? Does Deebo Samuel have a shot at winning Super Bowl MVP? Kiev and Will share their thoughts and also dive deep into whats on the menu for their Super Bowl Party. Is North Carolina overrated? Is UConn the best team this year? Find out more by tuning in!

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Shoulda Bet More with Will Hill - Ep. 13 - Julian Edlow Jan 29, 2024

Show notes

Will sits down with Julian Edlow of the DraftKings Network to do a post-mortem on the Conference Championship games. Did Dan Campbell make the right calls to go for it? What happened to the Ravens? When should you be betting the Super Bowl spread and props and an early Super Bowl MVP look. Plus, who is going to be this year's Florida Atlantic in March Madness and is UConn the best team in the nation? Tune in to today's episode to get the betting edge.

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Shoulda Bet More with Will Hill - Ep. 12 - Drew Dinsick Jan 26, 2024

Show notes

In this episode of the Shoulda Bet More podcast, Drew Dinsick, NBC Sports analyst and co-host of the Bet The Edge podcast, joins Will to discuss the upcoming NFL Conference Championships this weekend. Patrick Mahomes extends his Conference Championship streak to six years. Will the Lions bring their amazing post-season run all the way to the Super Bowl? Does Lamar Jackson win MVP? Find out what Will and Drew are looking at by listening to this episode!

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Shoulda Bet More with Will Hill - Ep. 11 - Iain MacMillan Jan 22, 2024

Show notes

On this episode of the Shoulda Bet More Podcast, Senior Editor of Fansided and host of the Bacon Bets Podcast Iain MacMillan joins Will to discuss the Divisional Round and have an early look forward to the Conference Championship games. Plus a CBB futures bet that Iain thinks has value. Also, was this the last chance for the Bills? Are the 49ers able to preform without Deebo? Can the Lions win on the road? Do Mahomes and the Chiefs matchup well against the Ravens? Find out Will's thoughts by tuning in to today's episode!

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Shoulda Bet More with Will Hill - Ep. 10 - Stuckey Jan 19, 2024

Show notes

NFL Divisional Weekend is upon us and Will gives you his picks and his best bets for the weekend. Is bringing back Mike McCarthy a good idea for the Cowboys? From Action Network, Senior Betting Analyst, and the Prime Minister of Degenerate Nation, Stuckey comes onto the pod. Will and Stuckey go in depth game by game to give you the insights you need to bet this weekend's playoff games. Plus, who is the most underrated college basketball team this season?

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