All Episodes
Displaying 91 - 120 of 149 in total
Shoulda Bet More with Will Hill - Ep. 59 - Adam Kaufman
With the Celtics sweeping the Pacers and reaching the NBA Finals, we thought to bring on Adam Kaufman (@AdamMKaufman) of WRKO 680 in Boston to give us a Boston perspec...
Shoulda Bet More with Will Hill - Ep. 58 - Dave Ross
Happy Memorial Day! Will invites a new guest, the host of Sunday Bet Prep on VSiN, Dave Ross (@drosssports)! The guys talk everything from MLB, NFL, NBA, UFC, and the ...
Shoulda Bet More with Will Hill - Ep. 57 - Mitch Moss
It's Memorial Day weekend and to get you guys some great picks heading into the long weekend, Will has invited from "Follow the Money" on VSiN, Mitch Moss (@MitchMossR...
Shoulda Bet More with Will Hill - Ep. 56 - Dustin Swedelson
Joining Will on the pod for this episode, from VSiN and the Double Play Podcast on the DraftKings Network, Dustin Swedelson! We are just about two months into the base...
Shoulda Bet More with Will Hill - Ep. 55 - Gill Alexander
What. Just. Happened? Coming directly off the heels of the Nuggets blowing a 20 point lead against the Timberwolves in game 7, Gill Alexander (@beatingthebook) of "A N...
Shoulda Bet More with Will Hill - Ep. 54 - Jonathan Von Tobel
One of our favorite guests, Jonathan Von Tobel (@meJVT) of VSiN Primetime returns to the pod to talk NBA Playoffs and NFL Futures after the release of the schedule! Af...
Shoulda Bet More with Will Hill - Ep. 53 - Brad Thomas
From NBC Sports and GoldBoys, Brad Thomas (@MrBradThomas) joins will to talk a number of sports on the pod. Will and Brad talk break down each NBA Playoffs series from...
Shoulda Bet More with Will Hill - Ep. 52 - Scott Seidenberg
From Pregame.com, Scott Seidenberg joins the podcast to talk all things NBA, NFL, NHL, and MLB with Will! How have the Nuggets got themselves back into this series wit...
Shoulda Bet More with Will Hill - Ep. 51 - Mike Sando
NFL Senior Writer for The Athletic, Mike Sando (@SandoNFL) returns to the podcast to chat NFL with Will! In it, they talk about which teams have had a good or bad offs...
Shoulda Bet More with Will Hill - Ep. 50 - NicLarson
On today's episode, NicLarson (@NicLarsonGB) from GoldBoys stops by to talk the ongoing NBA Playoffs and the MLB season so far. He talks about his day to day betting p...
Shoulda Bet More with Will Hill - Ep. 49 - Andy McCollough
On this episode of Shoulda Bet More, Andy McCollough, Senior Writer (@ByMcCullough) for The Athletic, comes onto the pod to talk about his new book, "The Last of His K...
Shoulda Bet More with Will Hill - Ep. 48 - Drew Dinsick
It's Derby time! The Kentucky Derby is tomorrow and to give his take on the race, Drew Dinsick (@whale_capper) of NBC Sports joins the pod with Will. The guys talk abo...
Shoulda Bet More with Will Hill - Ep. 47 - Brandon Anderson
In this episode of Shoulda Bet More, Brandon Anderson (@wheatonbrando) from Action Network joins the show to talk some NBA playoffs and some post-draft NFL. The Knicks...
Shoulda Bet More with Will Hill - Ep. 46 - Raheem Palmer
The NFL Draft is complete. The NBA Playoffs continue. Raheem Palmer from The Ringer (@iamrahstradamus) joins Will on this episode of the Shoulda Bet More podcast. Can ...
Shoulda Bet More with Will Hill - Ep. 45 - Matkafee
Night one of the NFL Draft is in the books and boy was it chaotic. Here to recap and react to everything we just saw is Will and Matkafee (@matkafee) from GoldBoys. Wh...
Shoulda Bet More with Will Hill - Ep. 44 - Fred Segal (Freezing Cold Takes)
The NFL Draft is tomorrow and we are excited and ready to see who goes where! In this episode of Shoulda Bet More, Fred Segal of Freezing Cold Takes (@OldTakesExposed)...
Shoulda Bet More with Will Hill - Ep. 43 - Kelley Bydlon
The NBA Playoffs have started and to talk what happened over the weekend, Kelley Bydlon (@KelleyBydlon) from VSiN's "A Numbers Game" returns to the pod! Will and Kelle...
Shoulda Bet More with Will Hill - Ep. 42 - Aaron Schatz
In the final episode before a mini break for the show, Will brings on Aaron Schatz of FTN Fantasy to talk the NFL offseason and the upcoming draft! The creator of DVOA...
Shoulda Bet More with Will Hill - Ep. 41 - Ryan Glasspiegel
The NBA season is about to draw to a close as Will welcomes Ryan Glasspiegel (@sportsrapport) from the New York Post onto the pod! We discuss the scenarios going into ...
Shoulda Bet More with Will Hill - Ep. 40 - Jason Weingarten
On this episode of Shoulda Bet More, Jason Weingarten (@Spreadapedia) from VSiN returns to the pod to talk some baseball. What's the latest on the Ohtani situation? Ar...
Shoulda Bet More with Will Hill - Ep. 39 - Matt Youmans
Will is joined Matt Youmans of VSiN on this epsiode of the Shoulda Bet More podcast. UConn wins it all once again. With the college basketball season over, we now make...
Shoulda Bet More with Will Hill - Ep. 38 - "The Bear" Chris Fallica
The Bear, Chris Fallica, makes a return to the Shoulda Bet More podcast. We're down to the final game of the NCAA tournament! UConn beat Alabama. Purdue beat NC State....
Shoulda Bet More with Will Hill - Ep. 37 - Iain MacMillan
It's finally here, Final Four weekend. We have 3 games left in the tournament and to break down the semifinals games this weekend with Will, Iain MacMillan (@IainMacBe...
Shoulda Bet More with Will Hill - Ep. 36 - Todd Wishnev
We are drawing closer to Final Four weekend and to prepare, professional bettor, Todd Wishnev (@TWishnev), joins Will again on the pod! In it, they discuss where they ...
Shoulda Bet More with Will Hill - Ep. 35 - Jeff Parles
And then there were four, UConn, Alabama, Perdue and NC State! Jeff Parles of Sports by the Book returns to the pod to talk about what we witnessed the tournament game...
Shoulda Bet More with Will Hill - Ep. 34 - Stuckey
On this episode of the Shoulda Bet More podcast, Stuckey, from Action Network, joins Will in breaking down the Sweet Sixteen! Will UConn be putting up another banner? ...
Shoulda Bet More with Will Hill - Ep. 33 - Mitch Moss
We are just a day away from MLB Opening Day! We're excited and are ready to talk some baseball. Mitch Moss of "Follow the Money" on VSiN joins Will on this edition of ...
Shoulda Bet More with Will Hill - Ep. 32 - Jonathan Von Tobel
We are two rounds into March Madness and to go over the weekend's events with Will, Jonathan Von Tobel (@meJVT) of VSiN Primetime comes back to the pod! The guys go ov...
Shoulda Bet More with Will Hill - Ep. 31
The first day of March Madness comes to a close. On this episode of the Shoulda Bet More Podcast, Will recaps day 1 of the NCAA tournament and covers some MLB as well ...
Shoulda Bet More with Will Hill - Ep. 30 - Iain MacMillan
The best time of the year for sports bettors has arrived! On this episode of the Shoulda Bet More Podcast, Will brings on Iain MacMillan, Senior Editor of Fansided and...