Shoulda Bet More

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. With only two teams left, who will win it all? Does UConn beat Purdue to go back to back? What should the MLB do about all the pitcher injuries? Who does The Bear think will win The Masters? How many quarterbacks will be taken in th...

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 (@IainMacBets) from Betsided returns to the pod! The guys give their predictions for how they think the game will go, their leans on the Over/Unders and spreads, and their picks for Most Outstanding Player of the tournament! Plus, with the rece...

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 lean on the spread and over/under for Alabama/UConn and NC State/Purdue. What does Todd think about this historic NC State run? Can Burnes compete with Edey and give Purdue fits? Will Alabama be able to stifle this dominant UConn tea...

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 games over the weekend and to give an early preview of the Final Four next week. How truly dominant is this UConn team? How historical of a run is this for NC State? Does Zach Edey get too many foul calls in his favor? Can this Alabama t...

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? Can Marquette take down NC State? Who comes out on top between Duke and Houston? Will Tennessee advance over Creighton? Did Ohtani know anything? Tune in to this episode to hear it all! Hosted by Simplecast, an AdsWizz company. See p...

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. We talk MLB futures, awards, as well as a look ahead to Thursday's games where Will gives you his leans! Plus, a sweet sixteen betting preview where you'll get best bets with the insights to back it up. Also, we're...

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 over what was a chalky weekend and talk about what surprised them, what they learned, and if they think better or worse of some of the remaining teams in the tournament. Also, an early look at the sweet sixteen lines to see what you sh...

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 as NFL. Oakland pulls off a massive upset against Kentucky. What does this mean for Calipari's future? Will touches on Friday's games and gives a lookahead to Saturday. Ohtani's interpreter is fired and accused of theft. Was this a c...

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 host of the Bacon Bets Podcast. The two discuss everything March Madness! Did the selection committee do a bad job? Are the Mountain West teams overhyped? Will there be any crazy upsets and what will they be? Is Auburn better than U...

The committee has made their selections and the bracket is finally out! Kiev O'Neil from The OddsBreakers returns to the pod to discuss the early look at the bracket with Will. With so many bid steals, did the committee make the correct selections? Who got snubbed? Which teams should be on upset alert? The guys also give some early looks based on the lines that came out right after the bracket rel...

We are just three days away from Selection Sunday! To get ready for the NCAA Tournament, Steve Fezzik of Pregame.com comes back onto the pod to talk college hoops with Will. The guys discuss how to win your bracket pool, who to back and who to fade in the tournament, and how to manage your bankroll to maximize your chances of winning in the tournament. As a bonus, Steve also drops some NIT betting...

With Opening Day only a couple weeks away, ESPN Analyst Tim Kurkjian joins Will to discuss some MLB! The Yankees continue to be plagued with injuries. Are the Guardians underrated and will they win the divison? How has no team gone after Blake Snell in free agency? Does the MLB need a different approach to their playoff format? Tim shares who he believes will be our 2024 World Series Champions. Tu...

It's time for the major conference tournaments as Jeff Parles (@jeffparles) of Sports by the Book returns to the pod to discuss college hoops and a variety of other sports with Will! Who do the guys think from the bubble teams are in and out? Who should you be betting on in the upcoming conference tournaments? Did we see a NBA Finals preview last week in Nuggets/Celtics? How does the top 10 of the...

March Madness is almost upon us! Reed Wallach, Senior Editor at BedSided joins Will to discuss everyones favorite college tournament on this episode of Shoulda Bet More! The two break down some of the conference tournaments they're looking at. How they approach the last regular season weekend. Is UConn going to win it all? Will Tennessee reach the Final Four? The two also discuss some NBA. Will th...

The Oscars are this Sunday! To celebrate, we have this very special midweek episode of Shoulda Bet More! From Cinephile with Adnan Virk and MLB Network, Adnan Virk joins Will on the podcast. They discuss the various Oscars categories to try to find you an angle that you should be betting on, from the more well known categories to the smaller ones as well. In addition to the Oscars, the guys also t...

It's conference tournament week! To celebrate, from Fox Sports, and the host of the Bear Bets Podcast, "The Bear" Chris Fallica joins Will on this episode of Shoulda Bet More! They discuss who they think will be getting those coveted top seeds, who's in and who's out of the bubble teams, and potential NCAA Tournament prop looks. The guys also discuss MLB season props, the NFL draft, 2024 Heisman p...

MLB spring training has arrived! Jason Weingarten joins Will on this episode of the Shoulda Bet More podcast to discuss the upcoming MLB season. With a month to go until opening day, the two cover what lines they're looking closely at. Does Yamamoto win NL Rookie of the Year? Will a team pick up Trevor Bauer before the start of the season? Who do they like to win the World Series? What odds are ev...

The host of VSiN Primetime, Jonathan Von Trobel (@meJVT), joins Will on this episode of Shoulda Bet More! They discuss NBA Award Futures and who is worth taking at the halfway point of the season as well as potential conference champion picks. They also talk NFL Free Agency and the NFL Draft. Plus, Will has a look for an NBA team not to make the playoffs and Will's college basketball takeaways fro...

Legendary CBS NFL, Final Four, and Brooklyn Nets play-by-play man, Ian Eagle, joins Will on this episode of Shoulda Bet More! They discuss the direction of the Nets, the landscape of college basketball as we head into March, his feelings on doing the Final Four play-by-play for the first time, and his thoughts on Mahomes, Rodgers, the 2023 NFL Season, and what the 2024 season might look like. Plus...

Professional Bettor, Todd Wishnev, join Will on the Shoulda Bet More podcast to talk some college basketball. We discuss this weekend's results. Is UConn head and shoulders above the rest of the country? What is the best way to bet them for the NCAA Tournament. Speaking of the tournament, what other teams or longshots are worth betting? Which teams are overrated/underrated? How you should be looki...

On this episode of the Shoulda Bet More podcast, one final post mortem of the Super Bowl as Will reacts to the reaction of Kyle Shanahan's decision making. Kelley Bydlon (@KelleyBydlon) of VSiN join Will on the pod today to discuss the NBA. What are the bettable lines for NBA Awards including MVP? Should we be worried about the Nuggets? Which teams are contenders and which are pretenders? Plus som...

In this post-Super Bowl LVIII edition of Shoulda Bet More, Gill Alexander (@beatingthebook) of "A Numbers Game" and the "Beating the Book Pod" joins the show in which he and Will give their raw reactions to what just happened. Where did Kyle Shanahan and the 49ers go wrong? Where does Patrick Mahomes rank among the greats? Where does Super Bowl LVIII itself rank? Find out the answers to these ques...

Matt Hamilton, Producer of the Up & Adams show on FanDuel TV, joins Will to discuss Super Bowl LVIII. Will finally has his pick on who he has winning. The two discuss their favorite picks ahead of the big game. Can San Francisco turn their defense around? Will the Chiefs be able to stop Christian McCaffrey? Matt expresses his love for nachos. Be sure to tune in! Hosted by Simplecast, an AdsWizz co...

Jeff Parles of Sports by the Book joins the show to discuss his best bets on Super Bowl props, O/U, and his pick against the spread. How does Jeff feel about Dan Campbell's decision making in the NFC Championship Game? What is the go-to Super Bowl food choice? Will also gives his early week Super Bowl looks. Plus Jeff and Will talk baseball. How will Jeff's Mets fare this year? Can the Yankees win...

This episode Kiev O'Neil of The OddsBreakers, joins Will to discuss the Super Bowl as well as college basketball. Will we see the line move to three for the big game? Does Deebo Samuel have a shot at winning Super Bowl MVP? Kiev and Will share their thoughts and also dive deep into whats on the menu for their Super Bowl Party. Is North Carolina overrated? Is UConn the best team this year? Find out...