Shoulda Bet More

Shoulda Bet More

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GoldBoys Network Presents: Shoulda Bet More with Will Hill! A podcast that breaks down current events in sports, big sports betting news, we'll bring on a bunch of different guests, and break down the weekly betting slate to the point where you'll feel like you "shoulda bet more."

GoldBoys.com


    • Jun 27, 2025 LATEST EPISODE
    • weekdays NEW EPISODES
    • 34m AVG DURATION
    • 227 EPISODES

    Ivy Insights

    The Shoulda Bet More podcast is a must-listen for any sports betting enthusiast. Hosted by Will Hill, the podcast offers great insight and interesting opinions on a variety of sports. With entertaining and informative guests, it provides solid content that keeps listeners engaged.

    One of the best aspects of this podcast is the knowledge and expertise of Will Hill himself. As a sharp bettor, he offers valuable insights and edges on various sports. Whether you're a veteran bettor or new to sports betting, his analysis and perspectives are sure to enhance your understanding and decision-making process. Additionally, the podcast features great guests who contribute even more insights to the discussions.

    Another positive aspect of The Shoulda Bet More podcast is its focus on exploring different sports betting angles. The episodes cover a wide range of topics and provide valuable information for bettors looking to gain an edge. From discussing strategies for specific games or events to analyzing trends and statistics, the podcast offers diverse content that caters to different interests.

    While there are many positive aspects to this podcast, one potential downside could be the lack of in-depth analysis on certain topics. Given that each episode covers multiple sports, there may be limited time available for in-depth discussions on specific games or events. However, this can also be seen as a positive aspect as it allows for a broader range of topics to be covered.

    In conclusion, The Shoulda Bet More podcast with Will Hill is a fantastic listen for any sports betting enthusiast. With his knowledgeable hosting style and great guests, the podcast provides valuable insights into various sports and betting strategies. Whether you're looking for entertainment or information to improve your own betting approach, this podcast is definitely worth adding to your playlist.



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    Latest episodes from Shoulda Bet More

    Shoulda Bet More with Will Hill - Ep. 227

    Play Episode Listen Later Jun 27, 2025 24:05


    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 that could surprise at the end of the regular season?

    Shoulda Bet More with Will Hill - Ep. 226 - Drew Dinsick

    Play Episode Listen Later Jun 25, 2025 35:28


    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 like to get out of a wide open East and who do we think is worth a bet to win it all? We discuss that and all the off-season's storylines on today's episode!

    Shoulda Bet More with Will Hill - Ep. 225 - Chris Macero

    Play Episode Listen Later Jun 23, 2025 39:21


    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 talking about Kevin Durant's trade to the Rockets and which team will rise out of a wide open Eastern Conference. We also talk about futures and awards bets in baseball as we near the halfway point of the season. Finally, Chris lets us in on his preseason betting process for College Football to give you pointers on how to bet this upcoming season.

    Shoulda Bet More with Will Hill - Ep. 224 - Jonathan Von Tobel

    Play Episode Listen Later Jun 20, 2025 42:40


    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 look at the MVP market to see if any longshots are worth a bet. Also, with the draft coming up just days after game 7, we look to see the betting markets there and give you our favorite bets. We also try to predict how the offseason will go and how different the league will look next year.

    Shoulda Bet More with Will Hill - Ep. 223 - Jeff Parles

    Play Episode Listen Later Jun 18, 2025 43:48


    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 up next season, and who will be the next Head Coach for the Knicks? We discuss the baseball season up to this point as well. What are the playoff implications of the Rafael Devers trade? Are the Giants now legit title contenders? What has happened to the New York Yankees as they can't seem to buy a run. We finish off baseball talk with futures and awards markets. Finally will Aaron Rodgers help or hurt the Pittsburgh Steelers this upcoming season?

    Shoulda Bet More with Will Hill - Ep. 222

    Play Episode Listen Later Jun 16, 2025 30:38


    "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.

    Shoulda Bet More with Will Hill - Ep. 221 - Ben Wilson

    Play Episode Listen Later Jun 13, 2025 39:08


    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 is it still going to the Thunder's way? Plus, will Giannis stay with the Bucks after all the rumors surrounding him?

    Shoulda Bet More with Will Hill - Ep. 220 - Sammy P

    Play Episode Listen Later Jun 11, 2025 34:04


    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 and the Stanley Cup Finals and talk about our favorite bets that can be placed at this point in the series. We also have US Open preview in golf that you can get some bets in with!

    Shoulda Bet More with Will Hill - Ep. 219 - Ricky G

    Play Episode Listen Later Jun 9, 2025 30:16


    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 Tom Thibodeau's firing by the Knicks deserved? Who is going to replace him? We also talk about the amazing French Open final yesterday and the Red Sox taking 2 of 3 from the Yankees over the weekend.

    Shoulda Bet More with Will Hill - Ep. 218 - Jonathan Von Tobel

    Play Episode Listen Later Jun 6, 2025 23:52


    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 forward? Should the Thunder still be a heavy favorite, or will the books begin to respect the Pacers? Tune in to see how we think the rest of this series goes and how you should bet it!

    Shoulda Bet More with Will Hill - Ep. 217 - Mitch Moss

    Play Episode Listen Later Jun 4, 2025 32:03


    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 Baseball Tournament as well as betting previews for the NBA Finals and the Stanley Cup Finals!

    Shoulda Bet More with Will Hill - Ep. 216 - Will Hill!

    Play Episode Listen Later Jun 2, 2025 28:59


    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 worth taking for division winners, teams to make the playoffs, season awards, the Rockies futility, and more!

    Shoulda Bet More with Will Hill - Ep. 215 - Matt Grissom

    Play Episode Listen Later May 30, 2025 32:12


    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 our favorite bets to reach the College World Series and we also discuss how the NCAA can better promote the game so as to get more attention during the regular season. Will also recaps Game 5 of the Eastern Conference Final in the NBA and previews this weekend's Yankees/Dodgers World Series rematch series!

    Shoulda Bet More with Will Hill - Ep. 214 - Kelley Bydlon

    Play Episode Listen Later May 28, 2025 29:54


    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.

    Shoulda Bet More with Will Hill - Ep. 213 - Gill Alexander

    Play Episode Listen Later May 26, 2025 35:20


    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 French Open. Gill gives us some of his favorite futures from the event and some of the other plays he's looking at. Plus, we talk about the dreadful Rockies. How much farther can they fall and at what line would we take their over win total on the season?

    Shoulda Bet More with Will Hill - Ep. 212 - Brad Thomas

    Play Episode Listen Later May 23, 2025 33:29


    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' series moving forward? In the West, is there anything that will stop the Thunder, or will the Timberwolves be able to show some fight? We also talk some offseason College Football with Brad as it comes faster than you expect. We get his offseason betting approach and some win totals that he is looking to bet for the upcoming season!

    Shoulda Bet More with Will Hill - Ep. 211 - Dustin Swedelson

    Play Episode Listen Later May 21, 2025 34:36


    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 with Will Hill - Ep. 210 - Jeff Parles

    Play Episode Listen Later May 19, 2025 33:45


    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 with Will Hill - Ep. 209

    Play Episode Listen Later May 16, 2025 22:49


    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. 

    Shoulda Bet More with Will Hill - Ep. 208 - Jonathan Von Tobel

    Play Episode Listen Later May 14, 2025 40:16


    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?

    Shoulda Bet More with Will Hill - Ep. 207 - Dave Ross

    Play Episode Listen Later May 12, 2025 41:44


    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!

    Shoulda Bet More with Will Hill - Ep. 206 - Adam Kaufman

    Play Episode Listen Later May 9, 2025 33:34


    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? 

    Shoulda Bet More with Will Hill - Ep. 205 - John Jastremski

    Play Episode Listen Later May 7, 2025 28:12


    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.

    Shoulda Bet More with Will Hill - Ep. 204 - Kelley Bydlon

    Play Episode Listen Later May 5, 2025 28:34


    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?

    Shoulda Bet More with Will Hill - Ep. 203 - Mike Somich

    Play Episode Listen Later May 2, 2025 22:26


    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!

    Shoulda Bet More with Will Hill - Ep. 202 - NicLarson

    Play Episode Listen Later Apr 30, 2025 26:32


    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.

    Shoulda Bet More with Will Hill - Ep. 201 - Geoff Schwartz

    Play Episode Listen Later Apr 28, 2025 37:26


    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 with Will Hill - Ep. 200 - Gill Alexander

    Play Episode Listen Later Apr 25, 2025 41:27


    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.

    Shoulda Bet More with Will Hill - Ep. 199 - Drew Dinsick

    Play Episode Listen Later Apr 23, 2025 32:24


    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!

    Shoulda Bet More with Will Hill - Ep. 198 - Raheem Palmer

    Play Episode Listen Later Apr 21, 2025 38:03


    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? 

    Shoulda Bet More with Will Hill - Ep. 197 - Jeff Parles

    Play Episode Listen Later Apr 18, 2025 34:08


    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!

    Shoulda Bet More with Will Hill - Ep. 196 - Sammy P

    Play Episode Listen Later Apr 16, 2025 33:45


    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!

    Shoulda Bet More with Will Hill - Ep. 195 - Jonathan Von Tobel

    Play Episode Listen Later Apr 14, 2025 33:48


    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!

    Shoulda Bet More with Will Hill - Ep. 194 - Aaron Schatz

    Play Episode Listen Later Apr 11, 2025 30:28


    Shoulda Bet More with Will Hill - Ep. 193 - Kelly Bydlon

    Play Episode Listen Later Apr 9, 2025 41:14


    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! 

    Shoulda Bet More with Will Hill - Ep. 192 - Matt Youmans

    Play Episode Listen Later Apr 7, 2025 29:31


    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!

    Shoulda Bet More with Will Hill - Ep. 191 - Kiev O'Neil

    Play Episode Listen Later Apr 4, 2025 39:38


    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!

    Shoulda Bet More with Will Hill - Ep. 190 - Todd Wishnev

    Play Episode Listen Later Apr 2, 2025 38:18


    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!

    Shoulda Bet More with Will Hill - Ep. 189 - "The Bear" Chris Fallica

    Play Episode Listen Later Mar 31, 2025 43:46


    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!

    Shoulda Bet More with Will Hill - Ep. 188 - Gill Alexander

    Play Episode Listen Later Mar 28, 2025 40:41


    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!

    Shoulda Bet More with Will Hill - Ep. 187 - NicLarson

    Play Episode Listen Later Mar 26, 2025 40:26


    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.

    Shoulda Bet More with Will Hill - Ep. 186 - Jonathan Von Tobel

    Play Episode Listen Later Mar 24, 2025 43:40


    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!

    Shoulda Bet More with Will Hill - Ep. 185 - Stuckey

    Play Episode Listen Later Mar 21, 2025 43:31


    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.” 

    Shoulda Bet More with Will Hill - Ep. 184 - Iain MacMillan

    Play Episode Listen Later Mar 19, 2025 36:28


    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!

    Shoulda Bet More with Will Hill - Ep. 183 - Jeff Parles

    Play Episode Listen Later Mar 17, 2025 38:04


    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. 

    Shoulda Bet More with Will Hill - Ep. 182 - Ian Eagle

    Play Episode Listen Later Mar 14, 2025 39:40


    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! 

    Shoulda Bet More with Will Hill - Ep. 181 - Reed Wallach

    Play Episode Listen Later Mar 12, 2025 38:07


    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!

    Shoulda Bet More with Will Hill - Ep. 180 - Dave Ross

    Play Episode Listen Later Mar 10, 2025 36:13


    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.

    Shoulda Bet More with Will Hill - Ep. 179 - John Laghezza

    Play Episode Listen Later Mar 7, 2025 33:56


    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!

    Shoulda Bet More with Will Hill - Ep. 178 - Reed Wallach

    Play Episode Listen Later Mar 5, 2025 34:03


    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!

    Shoulda Bet More with Will Hill - Ep. 177 - Kiev O'Neil

    Play Episode Listen Later Mar 3, 2025 31:06


    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!

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