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PODCAST

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

sports football

All Episodes

29:31

Shoulda Bet More with Will Hill - Ep. 192 - Matt Youmans

Shoulda Bet More ·

2025/04/07

We started with 68 and now we are down to 2, Florida vs. Houston. To get you ready for the National Championship game, we've brought back Matt Youmans (@mattyoumans247) of VSiN! We go over how we got here, including Duke's epic collapse against Houston. We preview the game by giving your our analysis of each teams strengths and where they can shine. We also give you our favorite bets in this game and who we think will become champion! We also get Matt's longshots and winners for the

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39:38

Shoulda Bet More with Will Hill - Ep. 191 - Kiev O'Neil

Shoulda Bet More ·

2025/04/04

Join Will Hill and special guest Kiev O'Neil for a thrilling episode as they dive into the excitement of Final Four weekend in college basketball! They'll break down the high-stakes action, along with some early MLB talk and a sneak peek at the upcoming NFL season. Tune in for expert analysis, hot takes, and all things sports!

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38:18

Shoulda Bet More with Will Hill - Ep. 190 - Todd Wishnev

Shoulda Bet More ·

2025/04/02

We are drawing closer to the Final Four this weekend. To get you ready for the weekend's games, we've brought back Todd Wishnev (@TWishnev)! We discuss Houston vs. Duke and Florida vs. Auburn and give you our favorite bets for the games and Todd gives out his championship pick from the four remaining teams. We talk Women's Final Four as well to give you our favorite picks from that field. We also discuss a little baseball as Todd gives us his favorite betting looks so far after the first

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43:46

Shoulda Bet More with Will Hill - Ep. 189 - "The...

Shoulda Bet More ·

2025/03/31

We have our Final Four! For the first time since 2008, the four remaining teams are all 1 seeds. We are gonna get some competitive matchups and we are here to help you get an edge to bet them! We've brought back "The Bear" Chris Fallica from Fox Sports to go over the matchups! We recap what we just saw this weekend and talk about what gives each of the remaining teams the best chance to win it all. We also discuss the opening weekend in MLB and see if some unexpected starts from certain

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40:41

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

Shoulda Bet More ·

2025/03/28

On today's episode of Shoulda Bet More, we bright back Gil 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 games today. We also discuss the Saturday Elite Eight games and give you our predictions and

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40:26

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

Shoulda Bet More ·

2025/03/26

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 matchups to give your our favorite bets for the day! Will also looks forward to the Sweet

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43:40

Shoulda Bet More with Will Hill - Ep. 186 - Jonathan...

Shoulda Bet More ·

2025/03/24

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!

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43:31

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

Shoulda Bet More ·

2025/03/21

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.”

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36:28

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

Shoulda Bet More ·

2025/03/19

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

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38:04

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

Shoulda Bet More ·

2025/03/17

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

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39:40

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

Shoulda Bet More ·

2025/03/14

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

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38:07

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

Shoulda Bet More ·

2025/03/12

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

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36:13

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

Shoulda Bet More ·

2025/03/10

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

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33:56

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

Shoulda Bet More ·

2025/03/07

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

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34:03

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

Shoulda Bet More ·

2025/03/05

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!

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31:06

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

Shoulda Bet More ·

2025/03/03

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

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39:00

Shoulda Bet More with Will Hill - Ep. 176 - Jonathan...

Shoulda Bet More ·

2025/02/28

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 the Sixers path now for this season? We also talk a little NFL as we discuss the recent news

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31:07

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

Shoulda Bet More ·

2025/02/26

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 epic video poker win that paid out huge! Will also recaps what has been a tough spring

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39:27

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

Shoulda Bet More ·

2025/02/24

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!

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30:14

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

Shoulda Bet More ·

2025/02/21

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 to see if they are worth betting. We take a broader look at the league as well to see who some

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