Shoulda Bet More

We are down to 8 teams and the College World Series officially starts today! We've brought back from CollegeBaseballInsiders.com and VSiN, Matt Grissom (@GrissomOnX) to get an update on what we've seen so far in the tournament, and to get his thoughts and predictions on the 8 teams remaining! We get Matt's best bets on each matchup in the first round, plus who he thinks will come o

As the NBA and Stanley Cup Finals keep going on, Ben Wilson (@Ben_Wilson_1) from ESPN+, FOX, and VSiN joins the podcast to give his perspective on how each series is going! Ben and Will discuss which team has a better chance of climbing out of their 0-2 deficit, the Mavericks or the Oilers. Ben and Will give their bets and predictions for how each series will end. They also talk ab

The Celtics have taken a commanding 2-0 lead in the NBA Finals. To discuss how the Celtics are doing it, we've brought Jonathan Von Tobel (@meJVT) of VSiN Primetime back to the pod! Will and JVT go over what the Celtics have done right, what the Mavericks have done wrong, and what the Mavericks can do to get back into this series. Jayson Tatum is currently the favorite to win Final

Game 1 of the NBA Finals is in the books, and what a dominant win by the Boston Celtics. Kelley Bydlon (@KelleyBydlon) from VSiN's "A Numbers Game" joins Will as he returns to the pod to get an instant reaction to what we saw and what it means for the rest of the series. What does Dallas need to do to win in game 2. How does the outcome of game 1 change betting strategies moving fo

Joining Will on this episode of Shoulda Bet More is Jason McIntyre (@jasonrmcintyre) from The Straight Fire podcast and The Herd! The two share what they're looking at as the NBA Finals approach. Should the Mavericks be the favorites to win it all? Should Angel Reese receive credit for the popularity of the WNBA or should all the credit go to Caitlin Clark? Does Tucupita Marcano de

Joining Will on the pod today is one of our favorite guests, from Sports by the Book, Jeff Parles (@jeffparles)! They talk about the takeaways from each division in baseball two months into the season. Who they think are making the postseason and who will be on the outside looking in. They also discuss who will win and who is worth betting on the Cy Young award for each league as w

The NCAA Baseball Tournament begins this weekend! Three weekends of baseball culminating in the College World Series. To get you ready, we've invited, from CollegeBaseballInsiders.com and VSiN, Matt Grissom (@GrissomOnX)! Matt goes over everything you need to know to bet the tournament, his favorites from each regionals, and his favorite bet to win the tournament! Plus, the NBA Fin

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 perspective on sports and betting! Should Boston be concerned about having such an easy path to the Finals? How do they matchup against either the Mavericks or the Timberwolves? What is Adam's Finals prediction? Can the Patr

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 PGA Tour! They discuss some of their favorite picks in each sport and how they feel about the various teams and players. Plus, Will goes though some of the baseball games to watch on Memorial Day!

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 (@MitchMossRadio)! The guys talk a ton of baseball including which longshots can possibly sneak their way the Cy Young award in each league, the threat level of the division leaders and some of those in wild card slots, and longs