Shoulda Bet More - TopPodcast.com

View Top 200 Chart

Back to Rankings Page

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. 206 - Adam Kaufman May 09, 2025

Show notes

What is going on right now in Boston is stunning. The Knicks have taken a 2-0 series lead over the Celtics and to talk about it and the rest of the NBA Playoffs, we've invited back from WKRO 680 and iHeartRadio Boston, Adam Kaufman (@AdamMKaufman)! We talk about what has happened to Boston, how have they melted down in consecutive games that they have had 20 point leads in? Will this be sustainable for the Knicks? Will Porzingis be able to play at 100%? Are the Celtics finally starting to feel the pressure? We also talk about the other shocking 2-0 series as the Pacers are up going back home over the Cavs. Do we think the Pacers can pull off the series upset? Plus, is it inevitable that we are headed for 7 games in Denver/OKC?

Hosted by Simplecast, an AdsWizz company. See pcm.adswizz.com for information about our collection and use of personal data for advertising.

Shoulda Bet More with Will Hill - Ep. 205 - John Jastremski May 07, 2025

Show notes

On today's episode, we talk the NBA Playoffs with our good friend John Jastremski (@john_jastremski) of The Ringer! We go over what was a surprising game 1's for the underdog Nuggets and Knicks! Do either of those teams have any chance of upsetting the favorites? What lessons can we takeaway from the first round? We also give you our favorite plays for each of the game 2's on Wednesday! We also talk MLB to see a state of the league through a month. Who are the best teams in the American League? Which team in the National League will be left out of the postseason come October? Finally, we discuss which team is right now the best in the MLB.

Hosted by Simplecast, an AdsWizz company. See pcm.adswizz.com for information about our collection and use of personal data for advertising.

Shoulda Bet More with Will Hill - Ep. 204 - Kelley Bydlon May 05, 2025

Show notes

The first round of the NBA playoff is all wrapped up and we look towards round two with Kelley Bydlon (@KelleyBydlon) of VSiN's "A Numbers Game!" Will and Kelly react to game 7 between the Warriors and the Rockets to see how Golden State ended up advancing. We then preview each series in the second round to try to bet on which team wins the series and in how many games. We try to predict the rest of the playoffs from the teams remaining. Plus, with the NBA Draft Lottery coming up, where would we like to see Cooper Flagg end up in the NBA?

Hosted by Simplecast, an AdsWizz company. See pcm.adswizz.com for information about our collection and use of personal data for advertising.

Shoulda Bet More with Will Hill - Ep. 203 - Mike Somich May 02, 2025

Show notes

The race for the Triple Crown begins tomorrow with the Kentucky Derby! To get you ready to bet this event, we've brought on the host of 'Ready, Set, Bet' on VSiN, Mike Somich (@Somobomb18)! We discuss what to expect from the race, whether or not the favorite is worth betting on, horses to stay away from, and the longshot that might pay out huge! We also discuss some of the races taking place today at Churchill Downs to get an edge on some of the less bet races. Plus Will recaps where we are at in the NBA playoffs and we take a look at where we are in the NHL Playoffs as well!

Hosted by Simplecast, an AdsWizz company. See pcm.adswizz.com for information about our collection and use of personal data for advertising.

Shoulda Bet More with Will Hill - Ep. 202 - NicLarson Apr 30, 2025

Show notes

We are a month into baseball season, so we though it would be a great time to bring back NicLarson (@NicLarsonGB) from GoldBoys! We talk about which teams have surprised and disappointed us so far this season. How do you handicap a weak American League this year? What longshot teams are worth betting to make the playoffs? Where are we in the race for the Cy Young? We get Nic's go-to markets this season for making money and how he has been making money off of some of the overrated/underrated pitchers in the league. We also touch on whether or not the Rockies can make even 40 wins this season and what is the franchise's plan? We also discuss some of our takeaways of the NFL Draft. Plus, Will updates us on where we are at in the NBA playoffs and weighs in on the NBA vs. NHL Playoffs debate.

Hosted by Simplecast, an AdsWizz company. See pcm.adswizz.com for information about our collection and use of personal data for advertising.

Shoulda Bet More with Will Hill - Ep. 201 - Geoff Schwartz Apr 28, 2025

Show notes

Host Will Hill is joined by former NFL lineman Geoff Schwartz to break down the latest in the NBA and NHL playoffs, share insights on the NFL Draft, and talk all things sports betting. Sharp takes, big opinions, and a little bit of hindsight – don't miss it!

Hosted by Simplecast, an AdsWizz company. See pcm.adswizz.com for information about our collection and use of personal data for advertising.

Shoulda Bet More with Will Hill - Ep. 200 - Gill Alexander Apr 25, 2025

Show notes

Shoulda Bet More is your go-to pod for smart sports talk with just the right amount of hindsight. Hosted by Will Hill, this episode breaks down the biggest surprises and steals of the NFL Draft first round, then shifts focus to what's heating up in the NBA Playoffs. Whether you’re kicking yourself for not betting more or planning your next move, we’ve got you covered.

Hosted by Simplecast, an AdsWizz company. See pcm.adswizz.com for information about our collection and use of personal data for advertising.

Shoulda Bet More with Will Hill - Ep. 199 - Drew Dinsick Apr 23, 2025

Show notes

It's finally time for the NFL Draft! This episode, we get you completely ready for the first round on Thursday night by bringing back Drew Dinsick (@whale_capper) of NBC Sports to the pod! What are the chances that we see any major surprises in the top 4 picks of the draft? We dive into the murkier 5-10 picks of the first round to see what longshot picks that we think some teams could make. We also talk about what positions we expect to slide in the draft and which positions will see more picks than expected on Thursday. Plus we recap each of the series so far in the NBA Playoff and give you our favorite picks for today's games and discuss whether some series underdogs are worth taking at this point!

Hosted by Simplecast, an AdsWizz company. See pcm.adswizz.com for information about our collection and use of personal data for advertising.

Shoulda Bet More with Will Hill - Ep. 198 - Raheem Palmer Apr 21, 2025

Show notes

The NBA Playoffs have officially begun this past weekend and we brought Raheem Palmer from The Ringer (@iamrahstradamus) back to the pod to discuss what we've saw! We recap this past weekend's game 1's and talk about what surprised us and what, if any, thoughts we had coming into the series have changed. We also give you our favorite bets for the upcoming game 2's. Also, if the Bucks lose in the first round, what will they end up doing with Giannis? Will the Thunder go on to sweep the Grizzlies or will the Grizzlies be able to put up any fight? Plus, we discuss what the 76ers do moving forward into the offseason, will Embiid ever be able to play going forward?

Hosted by Simplecast, an AdsWizz company. See pcm.adswizz.com for information about our collection and use of personal data for advertising.

Shoulda Bet More with Will Hill - Ep. 197 - Jeff Parles Apr 18, 2025

Show notes

On today's episode, we touch on a little of everything with Jeff Parles (@jeffparles) of "Sports By The Book!" Jeff and Will discuss the first round of the NBA Playoffs to get their opinions on the best series prices and where we can find value from this weekend's games to the Finals. We also talk some baseball as we get Jeff's reactions to the first month of the season. Are the Giants for real and could they murky the waters of the National League playoff picture? Do any teams from the American League pose a threat? Plus, we also touch on next week's NFL Draft and NFL season win totals that may be worth getting in before the draft changes some prices!

Hosted by Simplecast, an AdsWizz company. See pcm.adswizz.com for information about our collection and use of personal data for advertising.

Related Podcasts