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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. 196 - Sammy P Apr 16, 2025

Show notes

We've finished the first pair of NBA Play-In games, today we get you ready for the 2nd pair and the first round of the playoffs! To give his insight, we've brought back from the Chicken Dinner podcast and Fox Sports, Sammy P (@spshoot)! We go over tonight's games and give you our perspective of where we see the best value. We also look at the series prices for the first round matchups and give you our favorite plays for the series as well as the first games! Plus, with the NFL Draft coming up faster than you expect, we begin to take a deeper dive on where we think players will land!

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Shoulda Bet More with Will Hill - Ep. 195 - Jonathan Von Tobel Apr 14, 2025

Show notes

The NBA Playoffs are set and we begin them this week! To get us ready, we've invited back Jonathan Von Tobel (@meJVT) of VSiN Primetime to the pod! We go through each first round series and the play-in games to give you our takes on how we think they will play out and what bets we see that are great value! We also recap the Master's from over the weekend as JVT and Will also give a live reaction during their interview of the playoff. We also discuss the NFL Draft as we inch closer, are there any bets to be made that would give some great value!

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Shoulda Bet More with Will Hill - Ep. 194 - Aaron Schatz Apr 11, 2025

Show notes

On today's episode of Shoulda Bet More, we look towards to upcoming NFL Draft by inviting back Aaron Schatz (@ASchatzNFL) of FTN Fantasy to the pod! We discuss upcoming win total bets to see what teams will overpreform or underpreform their win totals. Can the potential top picks in the draft help turn around those team's projections? Will also goes division by division in the MLB to see the state of some teams at almost a month into the MLB season to see if there are any value bets worth taking!

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Shoulda Bet More with Will Hill - Ep. 193 - Kelley Bydlon Apr 09, 2025

Show notes

Join host Will Hill and guest Kelley Bydlon on Shoulda Bet More, where they dive into the excitement of the Masters and the NBA playoffs. With expert insights, betting tips, and plenty of banter, they’ll break down the latest action and make you feel like you should’ve bet more!

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Shoulda Bet More with Will Hill - Ep. 192 - Matt Youmans Apr 07, 2025

Show notes

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 upcoming Masters Tournament and his takeaways from the first week of the MLB season!

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Shoulda Bet More with Will Hill - Ep. 191 - Kiev O'Neil Apr 04, 2025

Show notes

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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Shoulda Bet More with Will Hill - Ep. 190 - Todd Wishnev Apr 02, 2025

Show notes

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 week. Will also gives a bit of a NFL Draft preview as well as discussing what bets could be triggered for season long win totals!

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Shoulda Bet More with Will Hill - Ep. 189 - "The Bear" Chris Fallica Mar 31, 2025

Show notes

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 teams have triggered any season long bets. We also touch on the upcoming NFL Draft and the Women's Basketball Final Four for any sneaky bets that can be placed on those events!

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Shoulda Bet More with Will Hill - Ep. 188 - Gill Alexander Mar 28, 2025

Show notes

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 games today. We also discuss the Saturday Elite Eight games and give you our predictions and analysis to find out who will go to the Final Four! We also go over the big stories from Opening Day and see if any of our opinions have changed. Plus, Will and Gil talk a little White Lotus to cap off the interview!

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Shoulda Bet More with Will Hill - Ep. 187 - NicLarson Mar 26, 2025

Show notes

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 Sixteen matchups on Thursday and gives you his best bets and his predictions on how the games will end up going.

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