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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. 96 - Ian Eagle Aug 23, 2024

Show notes

As we head into the final weekend of the NFL preseason, we wanted to get a perspective of the game from someone who calls it, so we've invited back Ian Eagle! The NFL on CBS play-by-play man gives us insight into how he prepares to call a game, and how it allows him to analyze the league differently than most other tv analysts. As a New York guy, we get his insight into how the Jets and Giants offseason have gone and where they can go this upcoming season. Since announcing is the family business, we talk about his son Noah Eagle working play-by-play for Olympic Basketball. It's also never too early to start talking NBA basketball and as Ian also does work with TNT and the YES Network for the Nets, we discuss what the Nets have done this offseason and how it might affect their future!

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Shoulda Bet More with Will Hill - Ep. 95 - John Laghezza Aug 21, 2024

Show notes

We are getting so close to the final month of the MLB season! We thought do to a check in on where we are at as we prepare for the postseason, so we've brought from The Athletic, John Laghezza (@JohnLaghezza)! We talk about which teams are making the postseason and who will claim the last wild card spots as the race is coming down to the wire. John gives us his state of the game opinions such as pace of play changes, umpiring calls, and more! John also gives us his takes on the overrated and underrated teams heading into the upcoming NFL season. Plus, Will previews week 0 of College Football on Saturday. Tune in to get the best bets for this upcoming weekend and beyond!

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Shoulda Bet More with Will Hill - Ep. 94 - "The Bear" Chris Fallica Aug 19, 2024

Show notes

Welcome to Shoulda Bet More, the podcast where sports betting meets sharp analysis and lively conversation. Hosted by Will Hill, a seasoned expert in the world of wagers, this show dives deep into the latest action across the NFL, MLB, College Football, and occasionally, even tennis.

In this episode, Will is joined by Chris Fallica, renowned sports analyst from Fox Sports. He's back!! Together, they break down the latest games, uncover betting trends, and offer their predictions for the weeks ahead. Whether you're a seasoned bettor or just curious about the odds, Shoulda bet more delivers the information and entertainment you need to up your game.

Tune in for a mix of expert advice, engaging banter, and all the insights you need to make informed bets. Don’t miss out—listen now and find out why you shoulda bet more!

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Shoulda Bet More with Will Hill - Ep. 93 - Scott Seidenberg Aug 16, 2024

Show notes

Join Will Hill and Scott Seidenberg (@ScottsOnAir) as they dive into the high-stakes drama of MLB pennant races and break down the latest buzz from NFL training camps. Get the inside scoop on what’s really happening in the sports world and discover where you shoulda bet more! 🎙️🏆🏈

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Shoulda Bet More with Will Hill - Ep. 92 - Gill Alexander Aug 14, 2024

Show notes

On today's pod, we've asked Gill Alexander (@beatingthebook) of "A Numbers Game" and the "Beating the Book Pod" to return to give his looks for the upcoming NFL season. He supplies us with his hot takes and previews some of his favorite teams as well as teams he thinks could have wildly differing outcomes for this upcoming season. We also talk baseball as we head into the final month and a half of the season. How are the awards looking and which of the teams that are competing for a playoff spot the biggest threats to win the World Series? We also get a quick US Open tennis preview!

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Shoulda Bet More with Will Hill - Ep. 91 - Mitch Moss Aug 12, 2024

Show notes

Week 1 of the NFL Preseason is in the books and we've brought back from "Follow the Money" on VSiN, Mitch Moss (@MitchMossRadio) to talk about some of his season long NFL bets! We also discuss MLB division races, Cy Young awards, Rookie of the Year Awards, and MVP awards for the AL and the NL. Also talked about is the way to bet baseball with a different postseason in the past, are longshots more viable than ever? Plus, Will recaps a crazy ending to the gold medal game in Olympic basketball and gives some bets for upcoming MLB games.

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Shoulda Bet More with Will Hill - Ep. 90 - Matt Youmans Aug 09, 2024

Show notes

On today's episode, we invite Matt Youmans (@mattyoumans247) from VSiN onto the pod to talk some MLB Postseason races and some football! We get Matt's take on which teams will win each division and the ones who will take up the wild card spots. Could the Braves possibly miss the postseason altogether? Matt gives us some Over/Under wins plays that are worth a look for NFL and College Football! We also get a preview at Matt's famed top 50 fast food power rankings. Plus, Will has a play worth taking for the Olympic basketball final between the US and France!

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Shoulda Bet More with Will Hill - Ep. 89 - Steve Fezzik Aug 07, 2024

Show notes

The first week of the NFL Preseason begins tomorrow, and to get the edge on preseason betting, we've invited Steve Fezzik (@FezzikSports) from Pregame.com back to the pod! Steve gives us his approach to preseason betting and how he reads shifting lines and bets to his advantage. We also get his opinion on how the new kickoff will affect over/under betting. We discuss if it's right that the NFL is ending games in the preseason early when games are being bet on through their gaming partners. We also talk the new surcharge that DraftKings is implementing in some states and how it reminds Steve of another product that had to be walked back on. Tune in for the most informative content you'll get for the NFL Preseason!

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Shoulda Bet More with Will Hill - Ep. 88 - Jeff Parles Aug 05, 2024

Show notes

He's back! To discuss what has suddenly become some very competitive MLB division races, Jeff Parles (@jeffparles) returns to the pod! We talk about how the Phillies and Dodgers have let the teams below them slowly creep up to first place, so which team is more likely to blow the division? We get Jeff's opinion on the AL East race between the Yankees and the Orioles with the trade deadline wrapped up. We also discuss which teams are going to get those last wild card spots in the AL and NL. Plus, Jeff gives us some of his new NFL takes and an excellent analysis on the knockout round in Olympic Basketball.

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Shoulda Bet More with Will Hill - Ep. 87 - John Jastremski Aug 02, 2024

Show notes

Now that we've had time to digest what's happened at the trade deadline, we've brought on from SNY and the "New York, New York" podcast on the Ringer, John Jastremski (@john_jastremski)! We go over what the Yankees and Mets did at the deadline and was it enough for either team? We look at the rest of the league and try to predict the division races from here on out as well as which teams will take the wild card spots? Plus, John also gives us some of his NFL opinions on which teams are overvalued/undervalued?

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