VSiN

Shoulda Bet More

Sports EN ↓ 363 episodes

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.

Author

VSiN

Category

Sports

Podcast website

vsin.com

Latest episode

Jul 10, 2026

Where to listen?

Podcasts in the app Replaio Radio Coming soon

Podcasts are coming to the app soon. Install now and be the first to see a whole new take on podcasts

Get it on Google Play Install for free Android 5M+ downloads · 4.8 rating iOS soon

Episodes

Shoulda Bet More with Will Hill - Ep. 188 - Gill Alexander 28.03.2025

On today's episode of Shoulda Bet More, we bright back Gill Alexander (@beatingthebook) of "A Numbers Game" and the "Beating the Book Pod" to go over everything that happened in basketball and baseball yesterday, and what to look forward to this weekend! We discuss yesterday's Sweet Sixteen games including the wild Arkansas/Texas Tech game and give you our favorite bets on the second half of the g...

Shoulda Bet More with Will Hill - Ep. 187 - NicLarson 26.03.2025

Tomorrow is Opening Day of the MLB Regular Season! To get you ready, we've brought NicLarson (@NicLarsonGB) from GoldBoys onto the show! We discuss every betting angle you'll want for this upcoming season from World Series futures to end of season awards! Which teams do we think will blow past their projected win totals? Which teams will end up struggling? We also go over some of the Opening Day m...

Shoulda Bet More with Will Hill - Ep. 186 - Jonathan Von Tobel 24.03.2025

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...

Shoulda Bet More with Will Hill - Ep. 185 - Stuckey 21.03.2025

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...

Shoulda Bet More with Will Hill - Ep. 184 - Iain MacMillan 19.03.2025

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 th...

Shoulda Bet More with Will Hill - Ep. 183 - Jeff Parles 17.03.2025

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. T...

Shoulda Bet More with Will Hill - Ep. 182 - Ian Eagle 14.03.2025

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...

Shoulda Bet More with Will Hill - Ep. 181 - Reed Wallach 12.03.2025

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...

Shoulda Bet More with Will Hill - Ep. 180 - Dave Ross 10.03.2025

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...

Shoulda Bet More with Will Hill - Ep. 179 - John Laghezza 07.03.2025

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 seas...

Shoulda Bet More with Will Hill - Ep. 178 - Reed Wallach 05.03.2025

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 clos...

Shoulda Bet More with Will Hill - Ep. 177 - Kiev O'Neil 03.03.2025

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 bra...

Shoulda Bet More with Will Hill - Ep. 176 - Jonathan Von Tobel 28.02.2025

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...

Shoulda Bet More with Will Hill - Ep. 175 - Mitch Moss 26.02.2025

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...

Shoulda Bet More with Will Hill - Ep. 174 - Jeff Parles 24.02.2025

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!  Hosted by Simplecast, an AdsWizz company. See pc...

Shoulda Bet More with Will Hill - Ep. 173 - John Jastremski 21.02.2025

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 t...

Shoulda Bet More with Will Hill - Ep. 172 - Dustin Swedelson 19.02.2025

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...

Shoulda Bet More with Will Hill - Ep. 171 - Todd Wishnev 17.02.2025

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 t...

Shoulda Bet More with Will Hill - Ep. 170 - Brad Thomas 14.02.2025

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...

Shoulda Bet More with Will Hill - Ep. 169 - Geoff Schwartz 12.02.2025

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 Ea...

Shoulda Bet More with Will Hill - Ep. 168 - Gill Alexander 10.02.2025

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...

Shoulda Bet More with Will Hill - Ep. 167 - Sammy P 07.02.2025

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 a...

Shoulda Bet More with Will Hill - Ep. 166 - Kiev O'Neil 05.02.2025

Today, we are kicking our Super Bowl coverage into high gear by bringing back Kiev O'Neil (@OBKiev) of The Odds Breakers to the pod! We take a deep dive into Sunday's game by looking at each of the main markets in-depth and the best player props that stick out to us. Kiev gives us his methods of attacking Super Bowl betting so he can end the biggest game of the year on top. We also talk about the...

Shoulda Bet More with Will Hill - Ep. 165 - Jeff Parles 03.02.2025

Welcome to Shoulda Bet More , your go-to podcast for all things sports! In this episode, we dive into the upcoming Super Bowl, breaking down the key matchups and what to expect. Plus, we’re talking about the jaw-dropping NBA trade that’s shaking up the league: Anthony Davis for Luka Dončić. You won’t want to miss this one. Tune in! Hosted by Simplecast, an AdsWizz company. See pcm.adswizz.com for...

Shoulda Bet More with Will Hill - Ep. 164 - Jason Weingarten 31.01.2025

We are nearing the date of pitchers and catchers arriving for Spring Training. To get ready for that date, we've brought back Jason Weingarten (@Spreadapedia) of VSiN to give us his outlook on the upcoming season of baseball. We get his reaction to the offseason moves and how he feels about the Dodgers spending money on their free agents. We get Jason's favorite future bets for this season with th...

Listen to the Shoulda Bet More podcast in Replaio

Radio and podcasts in one app - free, with no sign-up. Install today and do not miss the launch

Get it on Google Play

Replaio is not a podcast publisher; show names, artwork and audio belong to their authors and are distributed through public RSS feeds.