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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.

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Latest Episodes:

Shoulda Bet More with Will Hill - Ep. 236 - Jonathan Von Tobel Sep 12, 2025

Show notes

On this episode of Shoulda Bet More, Will gives out his college and NFL picks for the weekend. Then, Jonathan Von Tobel of VSiN joins to discuss his favorite NFL bets, teams he’s changed his mind on after a week, and some best bets in college football. JVT also shares his thoughts on the MLB playoff picture.

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Shoulda Bet More with Will Hill - Ep. 235 - Chris “The Bear” Fallica Sep 10, 2025

Show notes

On this episode of the Shoulda Bet More Podcast, Will reacts to a wild Monday Night Football game, previews TNF, and gives his best bets as well as an awards bet in the NFL. Then, Chris “ The Bear” Fallica from Fox Sports joins to discuss his bets for college football this weekend, a team he still thinks has value in the futures market, the MLB playoff picture, and college towns with the best restaurants.

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Shoulda Bet More with Will Hill - Ep. 234 - Geoff Schwartz Sep 08, 2025

Show notes

On this episode, Will Hill reacts to week 1, and then former NFL offensive lineman Geoff Schwartz of Fox Sports joins the pod to discuss his takeaways from the weekend. The guys preview Monday Night Football, discuss who is the best team in college football, what Geoff eats when he watches football, and more.

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Shoulda Bet More with Will Hill - Ep. 233 - Mitch Moss Sep 05, 2025

Show notes

On this episode, Will Hill gives his college + NFL Picks for the weekend, including a long shot NFL bet. Then, Mitch Moss from Follow the Money joins and goes over all of his futures /awards bets in the NFL, his NFL+ College Picks, his thoughts on Belichick and UNC, and more

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Shoulda Bet More with Will Hill - Ep. 232 - John Jastremski Sep 03, 2025

Show notes

On this episode, Will Hill gives his thoughts on UNC losing to TCU and gives out his pick for the Cowboys /Eagles. Then, John Jastremski of The Ringer joins and discusses Thursday Night football, his best bets for NFL Week 1, survivor, and the MLB Playoff Picture.

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Shoulda Bet More with Will Hill - Ep. 231 - Gill Alexander Sep 01, 2025

Show notes

Will Hill reacts to Week 1 of the College Football season, gives his thoughts and a pick for TCU /UNC, breaks down the MLB Pennant Races, then Gill Alexander of A Numbers Game joins to discuss the game Monday night, the US Open, NFL, and More

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Shoulda Bet More with Will Hill - Ep. 230 - Kiev O'Neil Aug 29, 2025

Show notes

Will Hill gives his thoughts on Week 1 of the college football season and has a few plays on the biggest games. Also, Kiev O’Neil from the oddsbreakers joins to break down the college slate, share his thoughts on futures, and discuss what foods go best with football.

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Shoulda Bet More with Will Hill - Ep. 229 - "The Bear" Chris Fallica Jul 02, 2025

Show notes

As we begin July, we've brought back from Fox Sports, "The Bear" Chris Fallica (@chrisfallica) to discuss what's going to be worth betting in the days to come. We talk some MLB to get an idea of where teams and divisions are at the halfway point of the season. Which teams are worth taking at over/under their projected win totals? Will we see any surprise teams in the 2nd half of the season? Which teams are worth taking the market for July wins? We discuss Chris's approach to College Football betting. How he analyzes teams, how he determines which teams he wants to bet on, and which players he's looking at for the Heisman before the season begins. Plus, Chris gives us his favorite bets for the upcoming Women's Euro so you can get ahead of the books and win some money.

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Shoulda Bet More with Will Hill - Ep. 228 - Gill Alexander Jun 30, 2025

Show notes

To start your week right, we bring back Gill Alexander (@beatingthebook) of "A Numbers Game" and the "Beating the Book Pod!" We recap this past weekend in baseball to catch you up on what you may have missed. We discuss how the Rafael Devers trade has worked out so far for Gill's Giants. We talk big picture as we approach the halfway point of the season, which team is the best in baseball? Which teams can make a run? Is there any chance that Cal Raleigh takes the AL MVP award from Aaron Judge? Gill also gives us tips on his day to day process for betting in baseball so you can get a leg up on the books. We also discuss Wimbeldon which begins this week. We go through the Men's and Women's bracket and give you our picks and insight for the tournament!

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Shoulda Bet More with Will Hill - Ep. 227 Jun 27, 2025

Show notes

On today's episode, we recap the NBA Draft. What surprised Will and what he thought of the picks. Also ESPN's coverage of the draft was not good, is there anything that can be done about it? Will also discusses the state of the MLB as we near the midway point of the season. The Yankees have been ceding ground in the AL East. Could they end up losing the division? Do we have a competition for the AL MVP between Cal Raleigh and Aaron Judge? Are there any teams out of the playoff picture right now that could surprise at the end of the regular season?

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