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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.

Copyright: © 2024 GoldBoys.com

Latest Episodes:

Shoulda Bet More with Will Hill - Ep. 116 - Dave Ross Oct 09, 2024

Show notes

We have been treated to four tight and extremely competitive Division Series matchups and to go over them, we've invited back Dave Ross (@drosssports) from Sunday Bet Prep on VSiN! We discuss how his Mets have come from rock bottom all the way to within one game of the NLCS. Are the Padres going to be able to finish the job against the Dodgers? Should the Yankees be worried with how their series is going with Aaron Judge seemingly missing? With Detroit's 9th inning blast to give them the win Monday, do they actually have a chance at upsetting Cleveland? Plus we go over the huge news of the Jets firing Robert Saleh. What does this mean for the Jets moving forward, will they be able to salvage their season? Finally, we get an early look at some Week 6 bets!

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Shoulda Bet More with Will Hill - Ep. 115 - Gill Alexander Oct 07, 2024

Show notes

What a wild sports weekend. So many College Football upsets, some wild NFL games, and some intense baseball series. To break it all down with an eye on what to take advantage of betting wise, we've invited back Gill Alexander (@beatingthebook) of "A Numbers Game" and the "Beating the Book Pod!" We recap week 5 in the NFL and provide our takeaways. Are the Vikings a championship contender? Will Cleveland be picking first overall? We talk about some of the wild MLB postseason games that have been happening in the AL/NLDS and discuss if some of the best series lines to take at this point. Plus, we touch on what College Football will look like after this upset-filled weekend!

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Shoulda Bet More with Will Hill - Ep. 114 - Mitch Moss Oct 04, 2024

Show notes

The Division Series round is all set as we head into the weekend and to preview that round, we've invited from "Follow the Money" on VSiN, Mitch Moss (@MitchMossRadio) back to the pod! We break down the series' and the betting angles we like from them. Should the Orioles postseason performances of the past 2 years get Brandon Hyde fired? Does the Wild Card round change our opinion of any of these teams? We also go over this weekend of College and NFL football and give you our best bets from each so you can ahead on the books!

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Shoulda Bet More with Will Hill - Ep. 113 - Jeff Parles Oct 02, 2024

Show notes

Join host Will Hill in this episode of "Shoulda Bet More" as he sits down with passionate Mets fan Jeff Parles (@jeffparles) to dive into the excitement of the first day of the 2024 MLB playoffs. They’ll break down the day's thrilling matchups, share their predictions for what’s next, and explore what the future holds for their favorite teams. Whether you’re a die-hard baseball fan or just looking to get in on the playoff action, tune in for insights, hot takes, and a bit of banter that only true fans can appreciate. Don’t miss out on the fun—let’s talk playoffs!

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Shoulda Bet More with Will Hill - Ep. 112 - MLB Postseason Preview with NicLarson Oct 01, 2024

Show notes

After an exciting final day of baseball, it's finally here, the MLB Postseason! We've brought NicLarson (@NicLarsonGB) from the Goldboys discord onto the show to give you all the edge you need on betting this postseason. We recap the wild doubleheader that was Mets vs. Braves and discuss if the quick turnaround for each team will affect them in the Wild Card round. We go over each series and give you our best betting angles and predictions for how each series will go. We also go over full postseason bets, our World Series bets, and some lesser known bets that you can find the edge on by tuning in!

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Shoulda Bet More with Will Hill - Ep. 111 - Kiev O'Neil Sep 30, 2024

Show notes

It was a busy week 4 in the NFL on Sunday and we have the recaps and reactions from Will and Kiev O'Neil (@OBKiev) of The Odds Breakers! Are the Jets truly a contender after their upset loss to the Broncos at home? The Vikings continue to impress as they come away with a win at Green Bay, are they truly a title contender? Who is going to be the Rookie of the Year, Jayden Daniels or Malik Nabers? We look ahead to week 5 based on the early lines and give out our early leans. We also discuss some college ball reactions from this weekend and give you our early bets for week 6 on Saturday. Plus, the double header to decide the final NL Wild Card spots happens today, Will gives the scenarios and what he think will happen. Look for a preview show on Tuesday for the MLB Postseason as we give you our best bets on how we think these series will go.

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Shoulda Bet More with Will Hill - Ep. 110 - Chris Macero Sep 27, 2024

Show notes

We have a big weekend coming up, it's the final weekend of the MLB Regular Season. We are at the end of these division and wild card races and we've brought professional sports bettor and VSiN contributor, Chris Macero (@RealGadge), onto the pod to give us his analysis and betting perspective of the Postseason. We preview the final weekend of the season and give our final predictions on which teams will nab those final wild card spots. Chris gives insight on how he handicaps the Postseason and what he looks for in a World Series competing team. We give analysis on some of the biggest competitors and whether or not they can win the World Series, and Chris gives out some of his World Series exacta bets! Plus, Chris gives us his best bets for this weekend in College Football and the NFL and details why the Washington Commanders could be a very sneaky team the rest of the way this season. Plus, Will gives us his best bets for week 4 in the NFL and also gives us a rant on how the WNBA has fumbled with Caitlyn Clark.

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Shoulda Bet More with Will Hill - Ep. 109 - Stuckey Sep 25, 2024

Show notes

On this midweek episode of Shoulda Bet More, Stucky (@Stuckey2) from Action Network returns to the podcast to talk some football! We recap both games from Monday night. After 0-3 starts, is the season over for the Bengals and the Jaguars? Which of them, if either, still stand a chance at making the playoffs? How have the Minnesota Vikings started out the season on fire with Sam Darnold? We talk about Thursday night's matchup between the Cowboys and the Giants and give you our favorite leans and bets. Plus, a preview at Saturday's huge Georgia vs. Alabama game!

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Shoulda Bet More with Will Hill - Ep. 108 - Scott Seidenberg Sep 23, 2024

Show notes

Join us as we get the instant reaction to Sunday's week 3 slate with Scott Seidenberg (@ScottsOnAir) from Pregame.com! After a narrow victory against the Saints, does the seat get a little cooler for Eagles HC, Nick Siriani? The Seahawks, Steelers, and Vikings are all 3-0; are they actually for real? Is the Bryce Young era truly over after the Panthers get a big win with Andy Dalton? We also go over Kyle Shanahan's major call to attempt to kick a field goal that ended up costing them the game against the Rams. We look forward to two Monday Night Football games and give you our best bets on them. Plus, we look to baseball in the final week to try to determine who will be in and out in the wild card race!

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Shoulda Bet More with Will Hill - Ep. 107 - Femi Abebefe Sep 20, 2024

Show notes

We have a jampacked football weekend coming up and to get you ready, we've brought back from BetQL, Femi Abebefe (@FemiAbebefe)! Femi gives us the NFL teams he thinks are contenders and pretenders, which of the 0-2 teams will be able to recover, and his betting preview for week 3! We also get a look at potential NFL awards as well as where we are at for MLB awards with just over one week to go! Femi also gives us his favorite College Football bets this weekend. Plus, Will gives his week 3 plays and a quick postseason race recap as the MLB season winds down.

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