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. 186 - Jonathan Von Tobel Mar 24, 2025

Show notes

With the first weekend of the NCAA Tournament behind us, we've invited back Jonathan Von Tobel (@meJVT) of VSiN Primetime to get his and Will's reactions to what we all have seen. We recap each region of the bracket and go over what amazed us, what we expected to happen, and what has surprised us about the first two rounds of the tournament. We also take an early look at next weekend for the Sweet Sixteen and the Elite Eight so you can get a head start against the books!

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. 185 - Stuckey Mar 21, 2025

Show notes

Join host Will Hill and Guest Stuckey as they break down Day 1 of the NCAA Tournament and look ahead to the entire weekend. From key matchups to upsets and predictions, They will give their take on the latest action and what bettors should be watching. If you missed out on the big plays, you’ll definitely be saying, “Shoulda bet more.”

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. 184 - Iain MacMillan Mar 19, 2025

Show notes

It is finally time. The tournament is set, the matchups made, and we are ready to begin March Madness! To celebrate and get you ready for the first round, we've brought back Iain MacMillan (@IainMacBets) of Sports Illustrated to the pod! Will and Iain go through their favorite matchups that they can get an edge on against the books. Are there any high seeded teams that should be on upset alert this first round? Is there any chance of the number one overall seed, Auburn, losing in the first two rounds? Will and Iain also give their Final Four picks and talk about if there is any chance we see a Cinderella this year!

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. 183 - Jeff Parles Mar 17, 2025

Show notes

Welcome to Shoulda Bet More. Hosted by Will Hill, we dive into the chaos and excitement of Selection Sunday and the madness that follows. From the best bets to the hottest futures, Will breaks down everything you need to know to stay ahead of the game. Whether you're looking to get the inside scoop on this year's tournament or make smarter bets on March Madness, this podcast is your go-to guide. Tune in for expert analysis, strategic picks, and plenty of advice on how not to miss out on the action—because you shoulda bet more.

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. 182 - Ian Eagle Mar 14, 2025

Show notes

We are heading into the weekend of selection Sunday and we are going to get you prepped for the end of conference tournaments and the start of March Madness! To discuss the NCAA tournament we've brought on the voice of it, from CBS Sports, Ian Eagle! We recap the big stories from the major conference tournaments so far. We discuss the teams that have the best shot of winning the tournament and why they do. We also discuss the sleepers of the tournament and who teams should not take lightly. We also talk about what is defined as a successful season for some coaches/schools and which teams in the tournament are playing with house money. We also touch on the NBA to get Ian's takes on who we may see in the NBA Final this year, plus his reaction on "The Trade" and how he thinks it will go down in NBA history. As an extra bonus, Ian gives his takes on NFL Free Agency so far!

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. 181 - Reed Wallach Mar 12, 2025

Show notes

It's week two of Conference Tournament week in college basketball and we've bought back Reed Wallach (@ReedWallach) of The Early Reed Podcast and Sports Illustrated for the second week in a row to go over all the power conferences and mid-majors that start their tournaments this week. We go over every conference to look at the high value teams that have a great price on them to go all the way and punch their ticket to the NCAA Tournament. We also look at the teams on the bubble to see what they have to do to be on the right side of the bubble on Selection Sunday. Also, Will recaps the first two days of NFL Free Agency to see if any players are going to change their new team's fortunes this upcoming season!

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. 180 - Dave Ross Mar 10, 2025

Show notes

To start your betting week right, we've invited back Dave Ross (@drosssports) of VSiN to go over everything going on in the sports betting world! We talk with Dave about baseball and the Gerrit Cole news that has rocked the Yankees. With Cole possibly needing Tommy John Surgery, how does this affect their AL East division prices and is it worth it to bet any of the other teams in the division? We also touch on some of Dave's favorite futures around the league. We also talk some NFL offseason as well as looking at Dave's favorite in the NCAA Tournament. Will also recaps the tournaments that wrapped up over the weekend and who already has their tickets punched to March Madness.

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. 179 - John Laghezza Mar 07, 2025

Show notes

On today's episode, we do a deep dive into the upcoming baseball season with John Laghezza (@JohnLaghezza) of The Athletic! We pick John's brain about his process for making preseason baseball bets and how he uses fantasy baseball as a tool. We get his favorite futures as well as win totals that he sees as mispriced. We go through what look to be the most competitive divisions in the MLB this season as John gives us his takes on the teams involved. Are the Yankees no longer the kings of the AL East? Will the Braves rotation carry them through the NL East? Plus, Will gives us an updated look on conference tournaments before the big conferences start next week!

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. 178 - Reed Wallach Mar 05, 2025

Show notes

On today's episode, we continue our mid-major conference tournament coverage by bringing back Reed Wallach (@ReedWallach) of The Early Reed Podcast and Sports Illustrated! We go through what has transpired so far and what we think is to come of the smaller conferences from the Atlantic Sun to the West Coast Conference. We also get Reed's take on NCAA Tournament Sleepers, NBA awards as we inch closer to the playoffs, and his take on the Mets win total this season!

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. 177 - Kiev O'Neil Mar 03, 2025

Show notes

It is finally March and conference tournaments begin this week. To celebrate, we get you ready for conference tournament betting with Kiev O'Neil (@OBKiev) of The Odds Breakers! We recap this weekend in college basketball by discussing what happened to Alabama as they got upset with a last second shot by Tennessee. We look towards some of the mid-major tournaments and discuss some of the wacky brackets and what longshots could win those tournaments and steal a bid to the NCAA tournament. Plus we go over our sleepers and longshots to go far in the NCAA Tournament. Tournament time is a fantastic time to bet, and we are here to help you win big so tune in!

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

Related Podcasts