Shoulda Bet More

Shoulda Bet More

Hosted by Will Hill · VSiN

4.9from 84 ratings

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399
Episodes
96
Transcribed
84
Ratings
Daily
Cadence
2023
First episode

About 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.

Publisher
VSiN
Category
news · sports · sports
Language
en
Explicit
No
First episode
22 Dec 2023
Latest episode
7 Oct 2026
Apple PodcastsWebsiteRSS feed

Latest episodes

96 of 399 episodes have a transcript.

  1. 7 Oct 2026TRANSCRIPT

    Shoulda Bet More with Will Hill - Ep. 398 Mitch Moss

  2. 5 Oct 2026TRANSCRIPT

    Shoulda Bet More with Will Hill - Ep. 397 John Jastremski

  3. 2 Oct 2026TRANSCRIPT

    Shoulda Bet More with Will Hill - Ep. 396 Jeff Parles

Inside a recent episode

Shoulda Bet More with Will Hill - Ep. 398 Mitch Moss

Published 7 Oct 2026 · Transcript excerpt

[…] Although I'm going to have FOMO because I was all over him last year and he never really had a chance, which I couldn't believe. Also, I make an annual bet on Kyle Shanahan because I love the guy. With all these injuries, going back to what we said, if they win that division and somehow are the one seed, 14-1 on Shanahan. And look, I mean... These voters are not afraid to give it to the same person multiple times. Stefanski's won it twice already in Cleveland. What if they win 10 games in Atlanta? Is there an angle here where, and here's another thing too. Award voters are not afraid to give the same team multiple awards. […]

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Who has been a guest on Shoulda Bet More

Names identified in recent episode analyses. Showing up to five guests.

  • Mitch Moss
  • John Jastremski
  • Jeff Parles
  • Jensen Lewis
  • Kiev O’Neil

Reach and audience

Public platform figures. Ratings count people who left a rating, not total listeners.

Apple Podcasts (US)
4.9 / 5
84 ratings

Contact Shoulda Bet More

Guest appearances
Books guests

Based on episode analysis; this does not confirm that the show is currently accepting guests.

Questions about Shoulda Bet More

Who hosts Shoulda Bet More?

Will Hill host the show. Published by VSiN.

How often do new episodes come out?

The show publishes daily, based on its RSS feed.

Does Shoulda Bet More take guests?

Yes. Guests have been identified in episode analyses.

Where can I read transcripts?

96 of 399 episodes have a transcript on Pod Engine. Full transcripts are available with a Pod Engine plan.

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