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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. 76 - "The Bear" Chris Fallica Jul 08, 2024

Show notes

The Bronx is burning! The Yankees have been struggling for the past month and to talk about their struggles, we've brought back "The Bear" Chris Fallica (@chrisfallica) from Fox Sports! Will and Chris discuss how the Yankees have got to this point, whether or not they can hold on to a playoff spot, and what needs to be done for them to right the ship. They also talk about the upcoming college football season. Which teams Chris thinks are overrated and underrated, and who he thinks has sneaky potential to win the Heisman Award. Plus, Chris gives his takes and bets on the Euros and Copa America tournaments. Tune in to get the edge on the books!

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Shoulda Bet More with Will Hill - Ep. 75 - Jeff Parles Jul 05, 2024

Show notes

One of our favorite guests, from Sports by the Book, Jeff Parles (@jeffparles) is back! Will and Jeff talk about how Jeff's Mets is having a post Grimace-First-Pitch resurgence. Is it worth a bet on them to make the postseason with the run they've been making? On the other side of the city, the Yankees have struggled. What do they need to do to keep pace with the Orioles to try to win the AL East? What futures bets does Jeff like at this stage of the season? We also get Jeff's reaction to the NBA offseason and where he sees the upcoming NBA season going. We also talk the most intriguing NFL team this season and Jeff gives us his favorites to make the College Football Playoff in the first season of a 12 team playoff!

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Shoulda Bet More with Will Hill - Ep. 74 - Reed Wallach Jul 03, 2024

Show notes

On this episode of Shoulda Bet More, Reed Wallach (@ReedWallach) of The Early Reed Podcast and Sports Illustrated swings by to give his thoughts on NBA Free Agency and College Football! We discuss the Free Agency moves that have been made and which teams are best situated coming into the season to win the NBA Finals. With College Football coming up in a little over a month, we go over how teams will fare in their new conferences, overrated and underrated teams, and who the Playoff and National Championship threats are. Plus, Reed gives us a Heisman bet he likes coming into the season!

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Shoulda Bet More with Will Hill - Ep. 73 - Gill Alexander Jul 01, 2024

Show notes

July has begun which means it's time for Wimbledon. To talk some lawn tennis, we've brought back Gill Alexander (@beatingthebook) of "A Numbers Game" and the "Beating the Book Pod." Gill gives us some of his analysis of the men's and women's tournament that lead to the bets he likes for the first round of the tournament all the way to the finals. Gill also gives us his football hot takes for the upcoming NFL season and how it may lead to a possible longshot playoff contender. Plus Will gives us a look at how NBA Free Agency is going.

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Shoulda Bet More with Will Hill - Ep. 72 - Brad Powers Jun 28, 2024

Show notes

As summer starts, football draws ever closer. On this episode of Shoulda Bet More, we've invited Brad Powers (@BradPowers7) of the Bet The Board Podcast onto the pod to give us his analysis on this upcoming season of College Football. In it we discuss the overrated and underrated teams of the upcoming season, over/under on win totals, Heisman Trophy bets, National Championship bets, week 0 and 1 bets, and College Football Playoff bets now that it has expanded to 12 teams. How will teams like Oregon and Texas do in the Big Ten and SEC respectively? Will Alabama be able to preform at the same level as in the Saban era with him now retired? Plus, Will recaps/analyzes the NBA Draft and the huge trade that went down between the Kicks and the Nets.

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Shoulda Bet More with Will Hill - Ep. 71 - Drew Dinsick Jun 26, 2024

Show notes

Now that we are officially in the NBA offseason, it's time for the NBA Draft. To give his analysis and predictions, we've invited Drew Dinsick (@whale_capper) of NBC Sports back onto the podcast. We get his thoughts on who the first 6 picks will be, what the Hawks should do with the number 1 pick, where Zach Edey will end up in the draft, and what he thinks will happen this offseason when it comes to big name free agents and trades. Plus, with the Olympics coming up, Drew gives his thoughts on how many golds USA Swimming can get in Paris, and how he goes about handicapping swimming. Also, we get his NFL hot takes on the upcoming season and how it's affecting one of the bets he's looking at for the Super Bowl. Tune in to the pod get the edge on the big name sports plus more!

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Shoulda Bet More with Will Hill - Ep. 70 - Alex B. Smith Jun 24, 2024

Show notes

The best two words in sports...Game Seven. Tonight, the Stanley Cup Winner is decided between the Edmonton Oilers and the Florida Panthers. To give the best insight on the game tonight, we've invited Alex B Smith (@axmithsports) of The Ice Guys to the pod to give his best bets and leans. We talk about how the series has gotten to this point as it looked like the Panthers were going to coast to a championship up three games to none. Even if the Oilers lose, is there anyway Connor McDavid doesn't win the Conn Smythe Award? Plus, O/U leans and finally, Will's and Alex's pick for who wins it all tonight. Get ready for an epic game seven by getting the biggest betting edge and tuning in!

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Shoulda Bet More with Will Hill - Ep. 69 - Adam Chernoff Jun 21, 2024

Show notes

Will is joined by Adam Chernoff (@adamchernoff) on this episode of the Shoulda Bet More podcast. The two touch briefly on the NHL Stanley Cup Finals before diving deep into the upcoming NFL season. Can the Oilers force a game seven against the Panthers. Adam shares some of his controversial takes for the upcoming season. Will the Carolina Panthers be a wildcard contender? Will Breece Hall win Offensive Player of the Year? Will the Broncos be the worst team in the league? Can the Chargers make the playoffs? Tune in to hear everything these two have to share!

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Shoulda Bet More with Will Hill - Ep. 68 - Jason Weingarten Jun 19, 2024

Show notes

We are nearing the end of June, so we've brought Jason Weingarten (@Spreadapedia) from VSiN back to the pod to talk some baseball. We get his takeaways on the division races and end of season awards such as league MVPs, Cy Youngs, and Rookies of the Year. Where those bets stand, who he likes, and who he's keeping an eye on who may not be a favorite right now! Plus, the Celtics have won the NBA Finals! Will gives a post-mortem on them and the NBA Playoffs as a whole. Also, Jason goes over some of his bad golf beats and how he's planning on righting the ship!

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Shoulda Bet More with Will Hill - Ep. 67 - Scott Seidenberg Jun 17, 2024

Show notes

Scott Seidenberg (@ScottsOnAir) from Pregame.com returns to the pod as we get his takes on the NBA Finals, Stanley Cup Finals, and on the MLB season! With both the NBA and the NHL's Finals mirroring each other, do we see both series get extended to a game 6? Will Jaylen Brown or Jason Tatum win Finals MVP if the Celtics close it out? Is there any chance Connor McDavid can win the Conn Smythe Award even if the Oilers lose? Who is the favorite to win the NL MVP now that Mookie Bets is out with a broken hand? Plus, trade talk for the teams who plan to be seriously competing for the World Series this year.

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