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Shoulda Bet More

VSiN
NFL
College Football
Major League Baseball
NBA Playoffs
Oklahoma City Thunder
Indiana Pacers
NBA Finals
NBA
Yankees
College Basketball
Miami
Kansas City Chiefs
World Series
Toronto Blue Jays
MLB
Seattle Seahawks
Red Sox
College Football Playoff
College Baseball
Uconn

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 wh... more

PublishesDailyEpisodes344Founded9 months ago
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Artwork for Shoulda Bet More

Latest Episodes

On this episode the Shoulda Bet More podcast, Will Hill reacts to the Knicks making the NBA Finals and discusses their chance in the NBA Finals. Then, Jensen Lewis of ESPN and VSIN By the Books joins to talk MLB awards, futures, the College Baseball ... more

On this episode of the Shoulda Bet More podcast, Will Hill previews the NBA Conference Finals and if the Knicks have a shot at winning it all. Also on the show, sports betting analyst Doug Kezirian joins the show to discuss the playoffs, NBA free age... more

On this episode of the Shoulda Bet More podcast, Will Hill previews Game 3 of Spurs / Thunder and shares his thoughts on some MLB storylines entering the weekend. Then, Brad Thomas of CBS Sports joins to break down the NBA and NHL Playoffs, the World... more

On this episode of the Shoulda Bet More podcast, Will Hill previews Game 2 of Spurs / Thunder and relives a classic Game 1. Then, Jonathan Von Tobel of Money Moves joins to discuss the Conference Finals, the NBA offseason, NFL early thoughts, and mor... more

Key Facts

Accepts Guests
Accepts Sponsors
Contact Information
Podcast Host
Number of Listeners
Find out how many people listen to this podcast per episode and each month.

Recent Guests

Chris Macero
Professional sports bettor
Real Gauge
Episode: Shoulda Bet More with Will Hill - Ep. 332 Chris Macero
Doug Kezirian
Doug Kezirian, sportsbook executive and media personality
BetRivers / The Athletic / New York Post (mentioned)
Episode: Shoulda Bet More with Will Hill - Ep. 330 Doug Kezirian
Jeff Parles
ESPN Las Vegas analyst and frequent betting commentator
ESPN Las Vegas
Episode: Shoulda Bet More with Will Hill - Ep. 328 Jeff Parles
Geoff Schwartz
Fox Sports contributor, former NFL offensive lineman
Fox Sports
Episode: Shoulda Bet More with Will Hill - Ep. 327 Geoff Schwartz
Kelley Bydlon
Hardwood Handicapper, A Numbers Game
A Numbers Game / Hardwood Handicappers
Episode: Shoulda Bet More with Will Hill - Ep. 325 Kelley Bydlon
Steve Fezzik
Professional sports bettor, two-time Super Contest winner
Fezzik Sports
Episode: Shoulda Bet More with Will Hill - Ep. 320 Steve Fezzik
Ian Eagle
Play-by-play announcer for CBS/TNT/Yes Network, voice of the Final Four
CBS, TNT, Yes Network
Episode: Shoulda Bet More with Will Hill - Ep. 319 Ian Eagle
John Laghezza
Baseball analyst, Corked Stats Podcast; Substack baseball writer of the year, fantasy
Corked Stats / Substack / The Athletic (fantasy)
Episode: Shoulda Bet More with Will Hill - Ep. 315 John Laghezza
Adam Burke
Managing editor at VSIN
VSIN
Episode: Shoulda Bet More with Will Hill - Ep. 305 Adam Burke

Host

Will Hill
Host of the Shoulda Bet More podcast, focusing on betting angles, line moves, and strategy across sports.

Reviews

4.9 out of 5 stars from 81 ratings
  • One of my favorites

    Great content. Great guests. Love this podcast.

    Apple Podcasts
    5
    keven70
    United Statesa month ago
  • The best pod for baseball and NBA playoffs!

    My go to all spring and summer. By far the best!

    Apple Podcasts
    5
    JDL from Jacksonville
    United States2 months ago
  • Great show

    Great show. Great content. The only feedback I’d give is the volume levels are a little low. I need to turn my car volume up to usually 35 to hear everything. Then I get blasted when the podcast is over and my car goes to radio.

    Apple Podcasts
    5
    tstelly18
    United States3 months ago
  • Excellent Pod

    Informative show with a great format! Will’s multi-sport knowledge and diverse lineup of guests make this podcast a must listen. I never miss an episode and have learned a lot from the varied content.

    Apple Podcasts
    5
    Zsport23
    United States4 months ago
  • Will Rocks

    Highly recommend giving a listen to the Colby Marchio episode.

    Apple Podcasts
    5
    Colby Marchio
    United States4 months ago

Listeners Say

Key themes from listener reviews, highlighting what works and what could be improved about the show.

Listeners appreciate the sharp, data-driven betting angles and diverse guest lineup.
Many praise actionable insights and calm, knowledgeable hosting.
Some note volume issues but rate content as highly valuable.

Chart Rankings

How this podcast ranks in the Apple Podcasts, Spotify and YouTube charts.

Apple Podcasts
#230
Australia/Sports/Football
Apple Podcasts
#172
Ireland/Sports/Football

Talking Points

Recent interactions between the hosts and their guests.

Shoulda Bet More with Will Hill - Ep. 336 Gill Alexander
Q: Is the lottery rigged?
The guest and host discuss the lottery as a complex, opaque process with skeptics and believers, leaning toward it not being rigged but acknowledging the intrigue and drama and the reality that teams strategize around outcomes regardless of the exact process.
Shoulda Bet More with Will Hill - Ep. 335 Mitch Moss
Q: Mitch, what's up, man? Thanks for coming on.
Mitch agrees to discuss futures across MLB, NBA, and NHL, highlighting bets on AL Cy Young and playoff series dynamics, plus season-long NFL perspectives.
Shoulda Bet More with Will Hill - Ep. 318 Jonathan Von Tobel
Q: JVT, this was fun, man. Appreciate it. Where can we find you?
JVT provides his social and podcast platform handles and promotes upcoming appearances on Money Moves, Harvard Handicaps, and Pod to the Futures.
Shoulda Bet More with Will Hill - Ep. 318 Jonathan Von Tobel
Q: What do you got in UConn, Illinois?
JVT discusses Illinois' path, UConn's form, and the market dynamics, noting edge for UConn or look-ahead biases and how line movement may reflect public perception.
Shoulda Bet More with Will Hill - Ep. 318 Jonathan Von Tobel
Q: We'll get his thoughts on the game, the final four, maybe get into some NBA that is next to this.
JVT shares candid reactions to the dramatic finish, endorsing the narrative around UConn's toughness and Hurley's coaching while also weighing the implications for the Final Four matchups and potential NBA talk.

Audience Metrics

Listeners, social reach, demographics and more for this podcast.

Listeners per Episode
Gender Skew
Location
Interests
Professions
Age Range
Household Income
Social Media Reach

Frequently Asked Questions About Shoulda Bet More

What is Shoulda Bet More about and what kind of topics does it cover?

Sharp, data-driven betting analysis drives each episode, with Will Hill breaking down line moves, futures, and value plays across NFL, NBA, MLB, and college football. Guests are seasoned bettors and analytics-focused experts who share market insights, predictive models, and practical strategies to find edges in real-time wagering. The show pairs accessible handicapping with long-form conversations about how markets react to news, injuries, and scheduling, making it valuable for both serious bettors and marketing/promo teams seeking smart betting-focused sponsorships. A notable strength is the consistent emphasis on actionable angles, live bet opportunities, and a wide mix of sports, from baseball to basketball to football, often featuring c... more

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How many listeners does Shoulda Bet More get?

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To see how many followers or subscribers Shoulda Bet More has on Spotify and other platforms such as Castbox and Podcast Addict, simply upgrade your account. You'll also find viewership figures for their YouTube channel if they have one.

Which podcasts are similar to Shoulda Bet More?

These podcasts share a similar audience with Shoulda Bet More:

1. Beating The Book with Gill Alexander
2. A Numbers Game
3. Bear Bets: A FOX Sports Gambling Show
4. Long Shots: VSiN's Golf Betting Podcast
5. VSiN Best Bets

How many episodes of Shoulda Bet More are there?

Shoulda Bet More launched 9 months ago and published 344 episodes to date. You can find more information about this podcast including rankings, audience demographics and engagement in our podcast database.

How do I contact Shoulda Bet More?

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What guests have appeared on Shoulda Bet More?

Recent guests on Shoulda Bet More include:

1. Chris Macero
2. Doug Kezirian
3. Jeff Parles
4. Geoff Schwartz
5. Kelley Bydlon
6. Steve Fezzik
7. Ian Eagle
8. John Laghezza

To view more recent guests and their details, simply upgrade your Rephonic account. You'll also get access to a typical guest profile to help you decide if the show is worth pitching.

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