On today's episode, we recap the NBA Draft. What surprised Will and what he thought of the picks. Also ESPN's coverage of the draft was not good, is there anything that can be done about it? Will also discusses the state of the MLB as we near the midway point of the season. The Yankees have been ceding ground in the AL East. Could they end up losing the division? Do we have a competition for the AL MVP between Cal Raleigh and Aaron Judge? Are there any teams out of the playoff picture right now ...
Jun 27, 2025•24 min•Ep. 227
Now that the NBA season is over, we turn our attention to the NBA Draft which already happens tonight! To give a betting preview, we've invited Drew Dinsick (@whale_capper) of NBC Sports back to the pod! We preview the draft beyond just the first couple of picks to get an idea of where draftees will end up so you can know whether to be their over/unders. We also catch up on the trades over the first 2 days of the offseason as we look beyond the draft and towards next season's futures. Who do we ...
Jun 25, 2025•35 min•Ep. 226
The Oklahoma City Thunder are the NBA Champions after winning in what was an anti-climatic game. To talk about it and more we've brought back professional sports bettor and VSiN contributor, Chris Macero (@RealGadge)! We go over game 7 and talk about Haliburton's injury early in the game and how it shaped the rest of the game. We discuss if the NBA season being too long is what leads to injuries like Haliburton's and if the regular season needs to be shortened. We look towards next season by tal...
Jun 23, 2025•39 min•Ep. 225
It all comes down to one game, Sunday night we will have game 7 between the Pacers and the Thunder. We invite back Jonathan Von Tobel (@meJVT) of VSiN Primetime to discuss how we've ended up here and what we believe will happen in game 7. We recap what we just saw in what was a fairly easy win by the Pacers and what effect does it have on how game 7 will play out. We look at the betting lines for game 7 and discuss if we may see a very tight defensive game that will affect the game total. We loo...
Jun 20, 2025•43 min•Ep. 224
Today, we bring back our favorite guest, Jeff Parles (@jeffparles) of "Sports By The Book!" We recap the Stanley Cup Finals as the Florida Panthers become back to back champions. We also recap Game 5 of the NBA Finals. As the Thunder look to win one more to capture the championship, can the Pacers overcome a potential injury to Haliburton? If the Thunder win it all, where do they rank on some of the all-time teams? We talk a little offseason as we try to figure out where Durant and Giannis end u...
Jun 18, 2025•44 min•Ep. 223
"Shoulda Bet More" is your go-to sports betting podcast hosted by Will Hill. From NBA buzzer-beaters to MLB home runs and everything in between, Will breaks down the latest action, hottest takes, and sharpest plays across the sports world. Tune in, get the edge, and maybe next time… you shoulda bet more .
Jun 16, 2025•31 min•Ep. 222
The College World Series begins today, and we have invited Ben Wilson (@Ben_Wilson_1) from ESPN+, FOX, and VSiN back to the podcast to give us the rundown. We discuss which of the 8 teams has the best path to the National Championship, which team can surprise, and which team we think will win it all. We also go over each of the first round games beginning today for our favorite bets! We also recap and react to Indiana's win in game 3 of the NBA Playoffs. Have they taken control of the series or ...
Jun 13, 2025•39 min•Ep. 221
With the College World Series upon us on Friday, we bring on Sammy P (@spshoot) of the Chicken Dinner podcast and Fox Sports to give us a preview of the final 8 teams! We go through each of the teams and we give our favorite plays to win it all and discuss the underdogs that are worth a shot. We discuss Fanduel's new 50 cent tax on Illinois better and whether or not it will discourage users from using Fanduel. Will other books begin charging the tax? We also touch on the state of the NBA Finals ...
Jun 11, 2025•34 min•Ep. 220
On today's episode we bring in NBA Twitter legend, Ricky G (@jrichardgoodman), to talk the NBA Finals after the Thunder have evened up the series against the Pacers. Is this dominant win the beginning of the end of the series? Will the Pacers be able to conjure up more comeback magic? We preview game 3 and discuss if the Thunder can finally cover on the road in the playoffs. We talk a little offseason to see where we think superstars like Kevin Durant and Giannis Antetokounmpo end up. Also, was ...
Jun 09, 2025•30 min•Ep. 219
The Indiana Pacers pull off another playoff comeback! With Tyrese Haliburton hitting a last second shot to put the Pacers up by a point, the Pacers have taken a 1-0 series lead over the Thunder. We have an instant reaction feature Jonathan Von Tobel (@meJVT) of VSiN Primetime as he returns to the podcast! We recap game 1 and detail how the Pacers were able to comeback in the 4th quarter and how they have been doing it all throughout the playoffs. How will this game affect the series going forwar...
Jun 06, 2025•24 min•Ep. 218
Today, we touch on a little of everything with Mitch Moss (@MitchMossRadio) from VSiN! We talk some baseball and get a snapshot of where we are this season. Is it a viable betting strategy to bet on the Rockies losing? Which division races are the most intriguing this season? Are we going to see Ohtani pitch this season? Which teams do we think will end up making the playoffs in each League? We also touch on where we are at for end of season awards. We recap the wild first weekend in the NCAA Ba...
Jun 04, 2025•32 min•Ep. 217
You read the title right, today is just Will! Will recaps a Game 6 of the ECF that saw the Pacers put away the Knicks and advance to face the Thunder in the NBA Finals. He go over what the Knicks will need to do in the upcoming offseason to try to get over the hump. Will also previews the NBA Finals and is there any chance that the Pacers pull off what may be the upset of a lifetime? Will also talks baseball. He goes over where we are at the start of June in the MLB. He goes over bets that are w...
Jun 02, 2025•29 min•Ep. 216
The NCAA Baseball Tournament begins this weekend as start the road to Omaha and the College World Series. To get us ready for the entire tournament, we've brought back Matt Grissom (@GrissomOnX) of CollegeBaseballInsiders.com and VSiN! We go over the College Baseball season to see how we got here and who the favorites are heading into the tournament. We go through the regionals to see who we like to advance to the Super Regionals and if we think any underdogs can advance. We go through some of o...
May 30, 2025•32 min•Ep. 215
Both NBA Conference Finals series may nearly be over. With both series being 3-1 in favor of the Thunder and Pacers, we bring Kelley Bydlon (@KelleyBydlon) of VSiN's "A Numbers Game!" to get his opinion on each series. Is there any chance we see each series extended? Are either the Knicks or the Timberwolves worth a bet to come back from these longshot odds? Will the Thunder even lose a game for the rest of this postseason? Tune in to see what we think and to get an edge on the books.
May 28, 2025•30 min•Ep. 214
On today's episode, we get a snapshot of where we are at in the Conference Finals with Gill Alexander (@beatingthebook) of "A Numbers Game" and the "Beating the Book Pod!" We go over the Knicks stunning rally against the Pacers as we finally have a series. Do we think the Knicks can take advantage or is this just a speed bump for the Pacers? We also touch on whether or not the Thunder can take a stranglehold on their series against the Timberwolves. We talk a little Tennis with the upcoming Fren...
May 26, 2025•35 min•Ep. 213
Wednesday night had one of the craziest NBA games we've ever seen in Game 1 of the Eastern Conference Final between the Pacers and the Knicks and we have to react to what we saw. To get his opinion on the game and the series moving forward, we invite Brad Thomas (@MrBradThomas) from NBC Sports back to the pod! How were the Pacers able to come back in that game, what did the Knicks do wrong that made them choke their lead? Will the Knicks be able to recover from this game or is it the Pacers' ser...
May 23, 2025•33 min•Ep. 212
Shoulda Bet More is your go-to sports betting hangout. This episode we dive into the latest Knicks vs. Pacers action, MLB highlights, and fresh takes on the future NFL schedule. Plus, get early insights and hot takes on future NBA Finals bets. If you’ve ever said, “Man, I shoulda bet more,” this pod’s for you.
May 21, 2025•35 min•Ep. 211
Shoulda Bet More dives into the hottest topics in sports and sports betting. This episode breaks down the NBA Finals, the Mets vs. Yankees Subway Series, and some heated NHL playoff action. Whether you're a die-hard fan or just here for the odds, we've got picks, predictions, and plenty of takes you shoulda bet more on.
May 19, 2025•34 min•Ep. 210
Shoulda Bet More dives into the upcoming NFL schedule and the latest action from the NBA Semifinals. If you're into bold predictions, near-miss bets, and smart takes on what's next in sports, this is your weekly fix.
May 16, 2025•23 min•Ep. 209
On today's episode we continue our talk on the NBA Playoffs with one of our favorite guests, Jonathan Von Tobel (@meJVT) of VSiN Primetime! After a huge win by the Warriors, do we think they can close out their series against the Nuggets on the road? After Indiana stunned the top seeded Cavaliers in the East, what do we think of their chances going forward in the playoffs? Do the Celtics have any chance of prolonging their series against the Knicks tonight? Is there any hope for the Curry-less W...
May 14, 2025•40 min•Ep. 208
On today's episode, we catch up with all things sports with Dave Ross (@drosssports) of VSiN! We recap the second round of the NBA Playoffs so far and look to see if we can find value in any underdogs in each series. Do the Knicks stand a chance or are the Celtics back? Is there a path for the Warriors without Steph Curry? Is Nuggets/Thunder going to go the distance? We also get Dave's insight on the NHL playoffs. Is the best team in the East not the top seed? Is Vegas worth a bet to win the ser...
May 12, 2025•42 min•Ep. 207
What is going on right now in Boston is stunning. The Knicks have taken a 2-0 series lead over the Celtics and to talk about it and the rest of the NBA Playoffs, we've invited back from WKRO 680 and iHeartRadio Boston, Adam Kaufman (@AdamMKaufman)! We talk about what has happened to Boston, how have they melted down in consecutive games that they have had 20 point leads in? Will this be sustainable for the Knicks? Will Porzingis be able to play at 100%? Are the Celtics finally starting to feel t...
May 09, 2025•34 min•Ep. 206
On today's episode, we talk the NBA Playoffs with our good friend John Jastremski (@john_jastremski) of The Ringer! We go over what was a surprising game 1's for the underdog Nuggets and Knicks! Do either of those teams have any chance of upsetting the favorites? What lessons can we takeaway from the first round? We also give you our favorite plays for each of the game 2's on Wednesday! We also talk MLB to see a state of the league through a month. Who are the best teams in the American League? ...
May 07, 2025•28 min•Ep. 205
The first round of the NBA playoff is all wrapped up and we look towards round two with Kelley Bydlon (@KelleyBydlon) of VSiN's "A Numbers Game!" Will and Kelly react to game 7 between the Warriors and the Rockets to see how Golden State ended up advancing. We then preview each series in the second round to try to bet on which team wins the series and in how many games. We try to predict the rest of the playoffs from the teams remaining. Plus, with the NBA Draft Lottery coming up, where would we...
May 05, 2025•29 min•Ep. 204
The race for the Triple Crown begins tomorrow with the Kentucky Derby! To get you ready to bet this event, we've brought on the host of 'Ready, Set, Bet' on VSiN, Mike Somich (@Somobomb18)! We discuss what to expect from the race, whether or not the favorite is worth betting on, horses to stay away from, and the longshot that might pay out huge! We also discuss some of the races taking place today at Churchill Downs to get an edge on some of the less bet races. Plus Will recaps where we are at i...
May 02, 2025•22 min•Ep. 203
We are a month into baseball season, so we though it would be a great time to bring back NicLarson (@NicLarsonGB) from GoldBoys! We talk about which teams have surprised and disappointed us so far this season. How do you handicap a weak American League this year? What longshot teams are worth betting to make the playoffs? Where are we in the race for the Cy Young? We get Nic's go-to markets this season for making money and how he has been making money off of some of the overrated/underrated pitc...
Apr 30, 2025•27 min•Ep. 202
Host Will Hill is joined by former NFL lineman Geoff Schwartz to break down the latest in the NBA and NHL playoffs, share insights on the NFL Draft, and talk all things sports betting. Sharp takes, big opinions, and a little bit of hindsight – don't miss it!
Apr 28, 2025•37 min•Ep. 201
Shoulda Bet More is your go-to pod for smart sports talk with just the right amount of hindsight. Hosted by Will Hill, this episode breaks down the biggest surprises and steals of the NFL Draft first round, then shifts focus to what's heating up in the NBA Playoffs. Whether you’re kicking yourself for not betting more or planning your next move, we’ve got you covered.
Apr 25, 2025•41 min•Ep. 200
It's finally time for the NFL Draft! This episode, we get you completely ready for the first round on Thursday night by bringing back Drew Dinsick (@whale_capper) of NBC Sports to the pod! What are the chances that we see any major surprises in the top 4 picks of the draft? We dive into the murkier 5-10 picks of the first round to see what longshot picks that we think some teams could make. We also talk about what positions we expect to slide in the draft and which positions will see more picks ...
Apr 23, 2025•32 min•Ep. 199
The NBA Playoffs have officially begun this past weekend and we brought Raheem Palmer from The Ringer (@iamrahstradamus) back to the pod to discuss what we've saw! We recap this past weekend's game 1's and talk about what surprised us and what, if any, thoughts we had coming into the series have changed. We also give you our favorite bets for the upcoming game 2's. Also, if the Bucks lose in the first round, what will they end up doing with Giannis? Will the Thunder go on to sweep the Grizzlies ...
Apr 21, 2025•38 min•Ep. 198
