Shoulda Bet More

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 forward in the ser...

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 deserve a lifetime...

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 well as the MVP a...

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 Finals are set and...

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 Patriots out-pace th...

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! Hosted by Simplecast, an AdsWizz com...

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 longshots to win the...

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 baseball season, so how do the guys think the rest of the season is going to shake out? We get their takes on some of the competing teams. Dustin also has some end of season awards bets and a World Series future he really likes. A previe...

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 Numbers Game" and the "Beating the Book Pod" returns to the podcast with Will to give their raw reactions to what we all just witnessed. They also talk about how the Pacers took care of the Kicks in MSG in that game 7. An early look a...

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! After the Timberwolves blew out the Nuggets in game 6, we get the best words in sports: game 7. Will and JVT talk about how we ended up here and who they feel will come out on top and why after what has been a crazy back and forth seri...

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 an analytical and betting perspective, giving you some picks they like for individual games and each series as a whole. They also go over the upcoming PGA Championship, where Brad gives some of his favorite looks and why it might no...

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 with Minnesota and will they end up winning the series? Will Tom Thibodeau playing his players too long be the reason the Knicks potentially lose the series to the Pacers? Can the Cavaliers put up any fight against the Celtics? Who ends...

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 offseason after we've had some time to process the draft. They also talk about the QB tier list and which QBs they expect to rise and fall in the upcoming season, and will the Chargers be immediately competitive with the hiring of Jim Ha...

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 process and how he looks for the lines that he likes, looks for each league's Cy Young award at this point, and some stories about working in a AA clubhouse back in the day with some soon to be major leaguers. Also, can Denver fight t...

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 Kind," a biography of Clayton Kershaw. We get a little preview about some of the topics in the book such as talks about his regular season success vs. his postseason struggles and him and the Dodgers finally winning the World Series i...

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 about how to bet the Derby, whether it's worth it to take the favorite, and the horses that may surprise. They also go over their plays for the NBA Playoff games today and a preview of the 2nd round along with some of their plays for th...

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 were unable to close out their series last night, should they be worried going into game 6? The guys go through each of the still ongoing series and give their best bets on the each series and some props to play on the upcoming game...

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 the Sixers rally back against the Knicks? Can the Mavericks take down the Clippers? Is Lebron able to carry the Lakers to be the first team in the NBA to come back from being down three? Will the Cavs turn it around after losing two...

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. What did the guys think of the Michael Penix Jr. pick by the Falcons? What other surprises were there on night one? Who are the booms and busts from the first round? Plus, very early Offensive/Defensive Rookie of the Year betting looks...

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) comes on to talk about his new book, "Freezing Cold Takes: NFL: Football Media’s Most Inaccurate Predictions—and the Fascinating Stories Behind Them." They talk about the origin of the famous account, some of the NFL Draft's most fr...

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 Kelley talk about each series and what they've learned from the first batch of games. What would winning and losing mean to the teams in the playoffs? Which team has the best chance to upset the possible Nuggets/Celtics final? Plus, the g...

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 goes over what teams he thinks have had good and bad offseason so far, where the rookie QBs may land, and what his models think various teams' win totals will be! Will also gives out some NFL draft looks for various teams that you m...

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 the last day of the season. The guys give their opinion on the state of the NBA while looking forward to the playoffs and discussing who they think will win it all. Also, after the Women's College Basketball final scored record viewe...

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? Are the early season pitching injuries changing the way to bet Cy Young? What is going on with the Marlins? The guys also go through some of the teams playing well in the early season and say if they can keep it up for the rest of the...

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 our way over to Augusta for The Masters. Can Tiger hold up physically? Who does Matt have winning it all this year? The NFL Draft is quickly approaching. What quarterbacks are going where? Tune in to hear what all Will and Matt have...