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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. 176 - Jonathan Von Tobel Feb 28, 2025

Show notes

Today we bring back one of our favorite guests, Jonathan Von Tobel (@meJVT) of VSiN Primetime! We talk a little NBA to see where everything is at post All-Star Break and trade deadline. Are the Lakers a contender after a few games with Luka? Can they or anyone else in the west threaten OKC in the playoffs? Are the Knicks a legitimate contender in the East? After the news about Joel Embiid, what is the Sixers path now for this season? We also talk a little NFL as we discuss the recent news of Matt Stafford meetings and talk where QBs go in this offseason of QB musical chairs.

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Shoulda Bet More with Will Hill - Ep. 175 - Mitch Moss Feb 26, 2025

Show notes

We continue to get ready for the upcoming MLB season on today's episode by inviting back from VSiN, Mitch Moss (@MitchMossRadio)! Mitch fills us in on his favorite longshots of this upcoming season that have the potential to cash out big! He also gives us his favorite sleeper teams, his favorite win total bet, and a surprising pick to get the most home runs this season! Plus, Mitch tells us of his epic video poker win that paid out huge! Will also recaps what has been a tough spring training so far for the Mets with some pitcher injuries and how they may still be worth a division winner bet.

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Shoulda Bet More with Will Hill - Ep. 174 - Jeff Parles Feb 24, 2025

Show notes

Welcome to Shoulda Bet More, the podcast where host Will Hill and guest Jeff Parles dive deep into everything sports! From college basketball and the NBA to the upcoming MLB season and all the latest NFL rumors, they cover it all with insightful takes and plenty of banter. Tune in for your weekly fix of sports talk, analysis, and a touch of humor!

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Shoulda Bet More with Will Hill - Ep. 173 - John Jastremski Feb 21, 2025

Show notes

Today, we continue getting ready for baseball at the beginning of Spring Training and we brought back John Jastremski (@john_jastremski) of The Ringer to get his thoughts on the upcoming season! We discuss the AL and NL East as they figure to be the divisions that could go down to the wire this season and try to project who will come out on top. We also discuss win totals for some of those teams to see if they are worth betting. We take a broader look at the league as well to see who some of the sleeper teams to win divisions and the World Series are. We also touch base on some NFL offseason, as well as 2nd half NBA and a little March Madness!

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Shoulda Bet More with Will Hill - Ep. 172 - Dustin Swedelson Feb 19, 2025

Show notes

On today's episode of Shoulda Bet More, we start talking baseball with Dustin Swedelson (@dustinswedelson) from SiriusXM Mad Dog Sports Radio and VSiN! We get his takes on who the best teams are in the AL and the NL, the sleepers in the divisions, and his favorite longshots to win the World Series! We go over offseason questions for the Mets, Yankees, Red Sox, and more and see if they've improved enough to be major forces this season. We also touch on the NFL offseason to take a temperature on where certain QBs will end up and if they can improve these QB needy teams. Will also goes over what has become a broken NBA All-Star weekend and looks at the 2nd half of the NBA season!

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Shoulda Bet More with Will Hill - Ep. 171 - Todd Wishnev Feb 17, 2025

Show notes

We are just weeks away from conference tournaments and the NCAA Tournament to crown the champion of college basketball. To get us ready for the postseason, we've invited Todd Wishnev (@TWishnev) back to the pod! We recap the Auburn vs. Alabama game from the weekend and discuss whether or not anyone can stop Auburn or if they are just too dominant. We talk about some of the top teams from each of the conferences and wonder how far in the tournament they can go and what weakness could prevent them from advancing. We also talk about the sleepers from the power conferences and the mid-majors that can shake up the tournament and send a powerhouse packing. We also get you ready for some of the major games tonight so you can take advantage of the books.

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Shoulda Bet More with Will Hill - Ep. 170 - Brad Thomas Feb 14, 2025

Show notes

The Genesis Open in LA is this weekend, and to get some advice on how to bet it, we've brought Brad Thomas (@MrBradThomas) from NBC Sports and MGM Network back to the podcast! We pick his brain about who he likes to win the tournament and who he thinks is worth a flier. We also get his opinions on what has changed in the NBA after the trade deadline and if any team can stop the Thunder and Celtics from ending up in the Finals. We also talk a little NFL offseason and whether or not older QB such as Rogers, Stafford, and Cousins end up with any teams next year.

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Shoulda Bet More with Will Hill - Ep. 169 - Geoff Schwartz Feb 12, 2025

Show notes

On today's episode of Shoulda Bet More, we continue to dive into the Super Bowl postmortem. Who better to bring on to talk football than a former NFL Offensive Lineman in Geoff Schwartz (@geoffschwartz) from Fox Sports! We go in-depth on how the Eagles thoroughly dismantled the Chiefs. How much blame should Patrick Mahomes shoulder in the loss? What can we takeaway from the construction of this Eagles roster and what will other teams to do copy its success? We also begin to look forward to next season. who is most likely to go number one overall in the NFL Draft? Where will Aaron Rodgers most likely end up? Will the Chiefs still be the favorites in the AFC next season? Check out the episode to hear our thoughts!

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Shoulda Bet More with Will Hill - Ep. 168 - Gill Alexander Feb 10, 2025

Show notes

The Philadelphia Eagles are your Super Bowl LIX champions, and they won in a dominant fashion. We've invited Gill Alexander (@beatingthebook) of "A Numbers Game" and the "Beating the Book Pod" back to the pod to get his and Will's instant reaction to what we just witnessed. How did the Eagles manage to put away the Chiefs by halftime? Is this the end of the Chiefs dynasty? Do we rethink how truly good some of the other teams around the league are after this performance by the Eagles? We look towards next year where Gill gives us his early bet for the Super Bowl LX winner!

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Shoulda Bet More with Will Hill - Ep. 167 - Sammy P Feb 07, 2025

Show notes

We are just 2 days away from the Super Bowl. We continue our coverage of it today by bringing from the Chicken Dinner podcast, BetMGM, and Fox Sports, Sammy P (@spshoot)! We get Sammy's perspective on how the game will go down and the bets that he is placing because of it. In addition, Will gives the plays that he's locking in for Sunday. We also talk some college basketball to see what sleepers and longshots could go to the Final Four in March. We also discuss some baseball and have a discussion on this season's Rookie of the Year and a sneaky longshot that you can bet!

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