Shoulda Bet More

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. 

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.

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. 

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 Warriors against the Timberwolves? JVT and Will discuss their favorite bets heading into tonight's games, and a potential Conference Finals. Plus, is the NBA Draft Lottery rigged or is it rightly stopping tanking?

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 series after a dramatic last second goal brought them back in the series? We also discuss a little MLB to look at the big picture this far into the season. The Rockies fired their manager Bud Black, is it really his fault though? Do they reach 40 wins this season? Who is the most disappointing team thus far and which team could make a surprise push? Finally, we also talk a little UFC and PGA to round out all of Dave's knowledge!

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 the pressure? We also talk about the other shocking 2-0 series as the Pacers are up going back home over the Cavs. Do we think the Pacers can pull off the series upset? Plus, is it inevitable that we are headed for 7 games in Denver/OKC? 

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? Which team in the National League will be left out of the postseason come October? Finally, we discuss which team is right now the best in the MLB.

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 like to see Cooper Flagg end up in the NBA?

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 in the NBA playoffs and we take a look at where we are in the NHL Playoffs as well!

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 pitchers in the league. We also touch on whether or not the Rockies can make even 40 wins this season and what is the franchise's plan? We also discuss some of our takeaways of the NFL Draft. Plus, Will updates us on where we are at in the NBA playoffs and weighs in on the NBA vs. NHL Playoffs debate.

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!

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.

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 than expected on Thursday. Plus we recap each of the series so far in the NBA Playoff and give you our favorite picks for today's games and discuss whether some series underdogs are worth taking at this point!

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 or will the Grizzlies be able to put up any fight? Plus, we discuss what the 76ers do moving forward into the offseason, will Embiid ever be able to play going forward? 

On today's episode, we touch on a little of everything with Jeff Parles (@jeffparles) of "Sports By The Book!" Jeff and Will discuss the first round of the NBA Playoffs to get their opinions on the best series prices and where we can find value from this weekend's games to the Finals. We also talk some baseball as we get Jeff's reactions to the first month of the season. Are the Giants for real and could they murky the waters of the National League playoff picture? Do any teams from the American League pose a threat? Plus, we also touch on next week's NFL Draft and NFL season win totals that may be worth getting in before the draft changes some prices!

We've finished the first pair of NBA Play-In games, today we get you ready for the 2nd pair and the first round of the playoffs! To give his insight, we've brought back from the Chicken Dinner podcast and Fox Sports, Sammy P (@spshoot)! We go over tonight's games and give you our perspective of where we see the best value. We also look at the series prices for the first round matchups and give you our favorite plays for the series as well as the first games! Plus, with the NFL Draft coming up faster than you expect, we begin to take a deeper dive on where we think players will land!

The NBA Playoffs are set and we begin them this week! To get us ready, we've invited back Jonathan Von Tobel (@meJVT) of VSiN Primetime to the pod! We go through each first round series and the play-in games to give you our takes on how we think they will play out and what bets we see that are great value! We also recap the Master's from over the weekend as JVT and Will also give a live reaction during their interview of the playoff. We also discuss the NFL Draft as we inch closer, are there any bets to be made that would give some great value!

Join host Will Hill and guest Kelly Bydlon on Shoulda Bet More, where they dive into the excitement of the Masters and the NBA playoffs. With expert insights, betting tips, and plenty of banter, they'll break down the latest action and make you feel like you should've bet more! 

We started with 68 and now we are down to 2, Florida vs. Houston. To get you ready for the National Championship game, we've brought back Matt Youmans (@mattyoumans247) of VSiN! We go over how we got here, including Duke's epic collapse against Houston. We preview the game by giving your our analysis of each teams strengths and where they can shine. We also give you our favorite bets in this game and who we think will become champion! We also get Matt's longshots and winners for the upcoming Masters Tournament and his takeaways from the first week of the MLB season!

Join Will Hill and special guest Kiev O'Neil for a thrilling episode as they dive into the excitement of Final Four weekend in college basketball! They'll break down the high-stakes action, along with some early MLB talk and a sneak peek at the upcoming NFL season. Tune in for expert analysis, hot takes, and all things sports!

We are drawing closer to the Final Four this weekend. To get you ready for the weekend's games, we've brought back Todd Wishnev (@TWishnev)! We discuss Houston vs. Duke and Florida vs. Auburn and give you our favorite bets for the games and Todd gives out his championship pick from the four remaining teams. We talk Women's Final Four as well to give you our favorite picks from that field. We also discuss a little baseball as Todd gives us his favorite betting looks so far after the first week. Will also gives a bit of a NFL Draft preview as well as discussing what bets could be triggered for season long win totals!

We have our Final Four! For the first time since 2008, the four remaining teams are all 1 seeds. We are gonna get some competitive matchups and we are here to help you get an edge to bet them! We've brought back "The Bear" Chris Fallica from Fox Sports to go over the matchups! We recap what we just saw this weekend and talk about what gives each of the remaining teams the best chance to win it all. We also discuss the opening weekend in MLB and see if some unexpected starts from certain teams have triggered any season long bets. We also touch on the upcoming NFL Draft and the Women's Basketball Final Four for any sneaky bets that can be placed on those events!

On today's episode of Shoulda Bet More, we bright back Gil Alexander (@beatingthebook) of "A Numbers Game" and the "Beating the Book Pod" to go over everything that happened in basketball and baseball yesterday, and what to look forward to this weekend! We discuss yesterday's Sweet Sixteen games including the wild Arkansas/Texas Tech game and give you our favorite bets on the second half of the games today. We also discuss the Saturday Elite Eight games and give you our predictions and analysis to find out who will go to the Final Four! We also go over the big stories from Opening Day and see if any of our opinions have changed. Plus, Will and Gil talk a little White Lotus to cap off the interview!

Tomorrow is Opening Day of the MLB Regular Season! To get you ready, we've brought NicLarson (@NicLarsonGB) from GoldBoys onto the show! We discuss every betting angle you'll want for this upcoming season from World Series futures to end of season awards! Which teams do we think will blow past their projected win totals? Which teams will end up struggling? We also go over some of the Opening Day matchups to give your our favorite bets for the day! Will also looks forward to the Sweet Sixteen matchups on Thursday and gives you his best bets and his predictions on how the games will end up going.

With the first weekend of the NCAA Tournament behind us, we've invited back Jonathan Von Tobel (@meJVT) of VSiN Primetime to get his and Will's reactions to what we all have seen. We recap each region of the bracket and go over what amazed us, what we expected to happen, and what has surprised us about the first two rounds of the tournament. We also take an early look at next weekend for the Sweet Sixteen and the Elite Eight so you can get a head start against the books!

Join host Will Hill and Guest Stuckey as they break down Day 1 of the NCAA Tournament and look ahead to the entire weekend. From key matchups to upsets and predictions, They will give their take on the latest action and what bettors should be watching. If you missed out on the big plays, you'll definitely be saying, “Shoulda bet more.” 

It is finally time. The tournament is set, the matchups made, and we are ready to begin March Madness! To celebrate and get you ready for the first round, we've brought back  Iain MacMillan (@IainMacBets) of Sports Illustrated to the pod! Will and Iain go through their favorite matchups that they can get an edge on against the books. Are there any high seeded teams that should be on upset alert this first round? Is there any chance of the number one overall seed, Auburn, losing in the first two rounds? Will and Iain also give their Final Four picks and talk about if there is any chance we see a Cinderella this year!

Welcome to Shoulda Bet More. Hosted by Will Hill, we dive into the chaos and excitement of Selection Sunday and the madness that follows. From the best bets to the hottest futures, Will breaks down everything you need to know to stay ahead of the game. Whether you're looking to get the inside scoop on this year's tournament or make smarter bets on March Madness, this podcast is your go-to guide. Tune in for expert analysis, strategic picks, and plenty of advice on how not to miss out on the action—because you shoulda bet more. 

We are heading into the weekend of selection Sunday and we are going to get you prepped for the end of conference tournaments and the start of March Madness! To discuss the NCAA tournament we've brought on the voice of it, from CBS Sports, Ian Eagle! We recap the big stories from the major conference tournaments so far. We discuss the teams that have the best shot of winning the tournament and why they do. We also discuss the sleepers of the tournament and who teams should not take lightly. We also talk about what is defined as a successful season for some coaches/schools and which teams in the tournament are playing with house money. We also touch on the NBA to get Ian's takes on who we may see in the NBA Final this year, plus his reaction on "The Trade" and how he thinks it will go down in NBA history. As an extra bonus, Ian gives his takes on NFL Free Agency so far! 

It's week two of Conference Tournament week in college basketball and we've bought back Reed Wallach (@ReedWallach) of The Early Reed Podcast and Sports Illustrated for the second week in a row to go over all the power conferences and mid-majors that start their tournaments this week. We go over every conference to look at the high value teams that have a great price on them to go all the way and punch their ticket to the NCAA Tournament. We also look at the teams on the bubble to see what they have to do to be on the right side of the bubble on Selection Sunday. Also, Will recaps the first two days of NFL Free Agency to see if any players are going to change their new team's fortunes this upcoming season!

To start your betting week right, we've invited back Dave Ross (@drosssports) of VSiN to go over everything going on in the sports betting world! We talk with Dave about baseball and the Gerrit Cole news that has rocked the Yankees. With Cole possibly needing Tommy John Surgery, how does this affect their AL East division prices and is it worth it to bet any of the other teams in the division? We also touch on some of Dave's favorite futures around the league. We also talk some NFL offseason as well as looking at Dave's favorite in the NCAA Tournament. Will also recaps the tournaments that wrapped up over the weekend and who already has their tickets punched to March Madness.

On today's episode, we do a deep dive into the upcoming baseball season with John Laghezza (@JohnLaghezza) of The Athletic! We pick John's brain about his process for making preseason baseball bets and how he uses fantasy baseball as a tool. We get his favorite futures as well as win totals that he sees as mispriced. We go through what look to be the most competitive divisions in the MLB this season as John gives us his takes on the teams involved. Are the Yankees no longer the kings of the AL East? Will the Braves rotation carry them through the NL East? Plus, Will gives us an updated look on conference tournaments before the big conferences start next week!

On today's episode, we continue our mid-major conference tournament coverage by bringing back Reed Wallach (@ReedWallach) of The Early Reed Podcast and Sports Illustrated! We go through what has transpired so far and what we think is to come of the smaller conferences from the Atlantic Sun to the West Coast Conference. We also get Reed's take on NCAA Tournament Sleepers, NBA awards as we inch closer to the playoffs, and his take on the Mets win total this season!

It is finally March and conference tournaments begin this week. To celebrate, we get you ready for conference tournament betting with Kiev O'Neil (@OBKiev) of The Odds Breakers! We recap this weekend in college basketball by discussing what happened to Alabama as they got upset with a last second shot by Tennessee. We look towards some of the mid-major tournaments and discuss some of the wacky brackets and what longshots could win those tournaments and steal a bid to the NCAA tournament. Plus we go over our sleepers and longshots to go far in the NCAA Tournament. Tournament time is a fantastic time to bet, and we are here to help you win big so tune in!

Today we bring back one of our favorite guests, Jonathan Von Tobel (@meJVT) of VSiN Primetime! We talk a little NBA to see where everything is at post All-Star Break and trade deadline. Are the Lakers a contender after a few games with Luka? Can they or anyone else in the west threaten OKC in the playoffs? Are the Knicks a legitimate contender in the East? After the news about Joel Embiid, what is the Sixers path now for this season? We also talk a little NFL as we discuss the recent news of Matt Stafford meetings and talk where QBs go in this offseason of QB musical chairs.

We continue to get ready for the upcoming MLB season on today's episode by inviting back from VSiN, Mitch Moss (@MitchMossRadio)! Mitch fills us in on his favorite longshots of this upcoming season that have the potential to cash out big! He also gives us his favorite sleeper teams, his favorite win total bet, and a surprising pick to get the most home runs this season! Plus, Mitch tells us of his epic video poker win that paid out huge! Will also recaps what has been a tough spring training so far for the Mets with some pitcher injuries and how they may still be worth a division winner bet.

Welcome to Shoulda Bet More, the podcast where host Will Hill and guest Jeff Parles dive deep into everything sports! From college basketball and the NBA to the upcoming MLB season and all the latest NFL rumors, they cover it all with insightful takes and plenty of banter. Tune in for your weekly fix of sports talk, analysis, and a touch of humor! 

Today, we continue getting ready for baseball at the beginning of Spring Training and we brought back John Jastremski (@john_jastremski) of The Ringer to get his thoughts on the upcoming season! We discuss the AL and NL East as they figure to be the divisions that could go down to the wire this season and try to project who will come out on top. We also discuss win totals for some of those teams to see if they are worth betting. We take a broader look at the league as well to see who some of the sleeper teams to win divisions and the World Series are. We also touch base on some NFL offseason, as well as 2nd half NBA and a little March Madness!

On today's episode of Shoulda Bet More, we start talking baseball with Dustin Swedelson (@dustinswedelson) from SiriusXM Mad Dog Sports Radio and VSiN! We get his takes on who the best teams are in the AL and the NL, the sleepers in the divisions, and his favorite longshots to win the World Series! We go over offseason questions for the Mets, Yankees, Red Sox, and more and see if they've improved enough to be major forces this season. We also touch on the NFL offseason to take a temperature on where certain QBs will end up and if they can improve these QB needy teams. Will also goes over what has become a broken NBA All-Star weekend and looks at the 2nd half of the NBA season!

We are just weeks away from conference tournaments and the NCAA Tournament to crown the champion of college basketball. To get us ready for the postseason, we've invited Todd Wishnev (@TWishnev) back to the pod! We recap the Auburn vs. Alabama game from the weekend and discuss whether or not anyone can stop Auburn or if they are just too dominant. We talk about some of the top teams from each of the conferences and wonder how far in the tournament they can go and what weakness could prevent them from advancing. We also talk about the sleepers from the power conferences and the mid-majors that can shake up the tournament and send a powerhouse packing. We also get you ready for some of the major games tonight so you can take advantage of the books.

The Genesis Open in LA is this weekend, and to get some advice on how to bet it, we've brought Brad Thomas (@MrBradThomas) from NBC Sports and MGM Network back to the podcast! We pick his brain about who he likes to win the tournament and who he thinks is worth a flier. We also get his opinions on what has changed in the NBA after the trade deadline and if any team can stop the Thunder and Celtics from ending up in the Finals. We also talk a little NFL offseason and whether or not older QB such as Rogers, Stafford, and Cousins end up with any teams next year.

On today's episode of Shoulda Bet More, we continue to dive into the Super Bowl postmortem. Who better to bring on to talk football than a former NFL Offensive Lineman in Geoff Schwartz (@geoffschwartz) from Fox Sports! We go in-depth on how the Eagles thoroughly dismantled the Chiefs. How much blame should Patrick Mahomes shoulder in the loss? What can we takeaway from the construction of this Eagles roster and what will other teams to do copy its success? We also begin to look forward to next season. who is most likely to go number one overall in the NFL Draft? Where will Aaron Rodgers most likely end up? Will the Chiefs still be the favorites in the AFC next season? Check out the episode to hear our thoughts!

The Philadelphia Eagles are your Super Bowl LIX champions, and they won in a dominant fashion. We've invited Gill Alexander (@beatingthebook) of "A Numbers Game" and the "Beating the Book Pod" back to the pod to get his and Will's instant reaction to what we just witnessed. How did the Eagles manage to put away the Chiefs by halftime? Is this the end of the Chiefs dynasty? Do we rethink how truly good some of the other teams around the league are after this performance by the Eagles? We look towards next year where Gill gives us his early bet for the Super Bowl LX winner!

We are just 2 days away from the Super Bowl. We continue our coverage of it today by bringing from the Chicken Dinner podcast, BetMGM, and Fox Sports, Sammy P (@spshoot)! We get Sammy's perspective on how the game will go down and the bets that he is placing because of it. In addition, Will gives the plays that he's locking in for Sunday. We also talk some college basketball to see what sleepers and longshots could go to the Final Four in March. We also discuss some baseball and have a discussion on this season's Rookie of the Year and a sneaky longshot that you can bet!

Today, we are kicking our Super Bowl coverage into high gear by bringing back Kiev O'Neil (@OBKiev) of The Odds Breakers to the pod! We take a deep dive into Sunday's game by looking at each of the main markets in-depth and the best player props that stick out to us. Kiev gives us his methods of attacking Super Bowl betting so he can end the biggest game of the year on top. We also talk about the best foods to have while watching the Super Bowl! We also get into late season College Basketball! As we get closer to the tournament time, who are the most underrated/overrated teams that you should bet on or stay away from? Also, Will gives his final thoughts about the Luka trade and the Fox to the Spurs trade!

Welcome to Shoulda Bet More, your go-to podcast for all things sports! In this episode, we dive into the upcoming Super Bowl, breaking down the key matchups and what to expect. Plus, we're talking about the jaw-dropping NBA trade that's shaking up the league: Anthony Davis for Luka Dončić. You won't want to miss this one. Tune in!

We are nearing the date of pitchers and catchers arriving for Spring Training. To get ready for that date, we've brought back Jason Weingarten (@Spreadapedia) of VSiN to give us his outlook on the upcoming season of baseball. We get his reaction to the offseason moves and how he feels about the Dodgers spending money on their free agents. We get Jason's favorite future bets for this season with the offseason coming to a close. We take a quick discussion of awards futures to see if there are any longshots that have a great chance of winning. We also take a look at betting the Caribbean Series that begins today to crown the best club in the Caribbean (and Japan)!

With the NFL in a hibernation period until the Super Bowl, we turn our eyes to NBA basketball! To get a temperature of where we are at in the middle of the season, we've invited Kelley Bydlon (@KelleyBydlon) from VSiN's "A Numbers Game!" Is a Celtics vs. Thunder Final inevitable? Which teams have the best chance of stopping it come playoffs? What trades could we possibly see as we approach the midseason mark? Plus, who are the front runners for awards and what longshots could surprise? We also touch on Kelley's Super Bowl bets to see what he likes!

Shoulda Bet More is the ultimate podcast for NFL fans who love the thrill of the game and the excitement of placing a bet. Join Will Hill and returning guest JVT as they break down the Conference Championship games, analyzing key plays, standout performances, and those crucial moments that made or broke the odds. Get expert takes on the big game, plus insider tips and predictions for the upcoming Super Bowl showdown. Whether you're a casual fan or a die-hard gambler, Shoulda Bet More is the perfect place to fuel your football fix and prepare for the biggest game of the year!

It's Conference Championship weekend, and we are continuing to go to VSiN collaborators to get the best in-depth look look at the games by inviting back Dave Ross (@drosssports)! We take a deep dive into the Commanders vs. Eagles and the Bills vs. Chiefs and give you our favorite props and leans. We try to get Dave's picks for the weekend and for who he thinks will win the Super Bowl in two weeks! Lastly, we get Dave's reaction to how the Mets have done this offseason beyond the Juan Soto signing and if he thinks they can win the NL East and beyond.