Gambling With an Edge

Our guest today is Antonino De Rosa, also known as "Ant."  Ant went from professional Magic the Gathering player to working for Pinnacle sports book and from there became a professional sports bettor.

Show Notes

[00:00]  Introduction of sports bettor, Antonio De Rosa
[00:42]  Playing Magic The Gathering professionally
[04:56]  Comparing Magic variance and skills to gambling?
[08:29]  Getting a job at Pinnacle
[12:07]  NBA totals at Pinnacle
[14:05]  Dealing with losses, risk management
[17:57]  Bad beats
[20:39]  Leaving Pinnacle for Plannatech
[23:29]  Becoming a bettor
[27:04]  Market efficiency, manipulation, limiting players, etc
[32:34]  New female accounts
[33:49]  Identifying sharp play
[36:44]  BetBash story
[39:37]  Life lessons from gambling
[42:15]  Favorite non-casino restaurant in Vegas

Books Referenced:
Fooled by Randomness by Nassim Nicholas Taleb

We have 3 guests today. Blair Rodman, Anthony Curtis, and Frank B. They are coauthors of the new book All About Sports Betting.

Show Notes

[00:00]  Introduction of Blair Rodman, Anthony Curtis, and Frank B., authors of All About Sports Betting:  The Definitive Guide
[00:42]  What makes this book so unique?
[01:55]  The genesis of All About Sports Betting
[05:59]  Prop bets, parlays, same game parlays, and teasers
[10:27]  QR codes within the book that link to additional information
[13:17]  Violence in Puerto Vallarta
[15:37}  Touts
[18:33]  Bottom up, top down, and modeling
[24:05]  Evolution of sports betting markets, future editions of the book
[25:24]  Prediction markets
[29:39]  Betting splits and other useless statistics
[31:49]  Understanding variance and related behavioral biases
[38:42]  Offshore sportsbooks, betting on credit, posting up, and settling up
[43:33]  Optimal use of bonus bets at Caesars

Links:
All About Sports Betting - https://amzn.to/4kP8FU1
X.com/capjack2000
Unabated.com

Charlie is a sports bettor, slot player, and influencer. Charlie got scammed while making bets at a DraftKings kiosk at the Golden Nugget in Biloxi. It's a crazy story, not just the scam, but the way the casino, and Gaming Enforcement reacted.

Show Notes

[00:00]  Introduction of advantage player Chuck’s Lucks
[00:40]  How did Chuck become an AP?
[04:14]  Chuck’s second trip to Vegas and a $2500/spin slot
[07:16]  Accounting for the W2Gs
[08:45]  Getting scammed while betting sports in Mississippi
[22:55]  YouTube influencers, deals, permission to record
[28:59]  Plaza’s social media room and livestream
[31:32]  Leverage as an influencer for deals, rebates, offsets, etc
[32:48]  Filming AP slots, disguising entry points
[35:00]  Editing videos and efficient use of content 
[37:05]  Selling influencer merchandise
[37:30]  ChucksLuck and LeapingLizards channels
[37:59]  Large jackpot payments and security concerns
[40:27]  Favorite restaurant in Las Vegas that is not in a casino?

Related Links:
Lasvegasadvisor.com/gambling-with-an-edge/
Youtube.com/@LeapingLizardSlots
Youtube.com/@ChucksLuck777
Tacoselgordobc.com

This week we talked with long-time Vegas bookmaker Art Manteris.  We discussed his new book, "The Bookie."

Show Notes

[00:00]  Introduction of Art Manteris, author of The Bookie
[00:47]  Bookmakers from Western Pennsylvania
[01:47]  Legendary bookmaker Uncle Jack Franzi
[05:21]  Working at the mob-controlled Stardust
[08:27]  Why did Art move to Las Vegas?
[09:46]  Billy Walters stories
[11:57]  PASPA, using computers across sportsbooks and racetracks
[15:18]  Art's concerns about the expansion of gambling
[17:00]  Frank Rosenthal at the Stardust
[18:18]  Tony Spilatro
[20:26]  Meeting Ron Sacco and sportsbooks in the Caribbean 
[23:56]  Pinnacle
[25:58]  Sports betting in Nevada, climate and regulations
[29:53]  Will "Refrigerator" Perry touchdown prop
[31:40]  Negotiating huge prize fights in Vegas with Don King and Bob Arum
[34:13]  Building the sportsbook at the Hilton
[35:27]  Did Art sweat big positions and games?
[37:04]  Setting open lines
[39:13]  Being the first to post Super Bowl props
[40:44]  Prop betting on college sports
[43:17]  Circa sports book
[44:26]  Parlays
[46:58]  Using analytics to analyze payouts on parlays, teaser, and contests
[48:36]  Did any bosses or owners want to take positions on games?
[52:23]  Favorite restaurant in Las Vegas that is not in a casino?
[53:56]  Can listeners contact Art on social media?

Get Art's book, "The Bookie" https://amzn.to/45nzCYp

Bob and Richard sit down with Gary Kondler to talk about taxes for gamblers after the big beautiful bill.  It may not be as bad for some of us as we all thought. Spoiler alert - but some gamblers are just screwed.

Show Notes

[00:00]  Introduction of gambling tax expert Gary Kondler from Kondler & Associates
[01:36]  W2Gs under the new tax law
[05:24]  Reconciling W2s with session win/loss
[09:43]  An example of casino gambling profit and discussion of similar case law
[18:04]  Sports betting example
[20:46]  Could a day of betting across different sportsbooks be considered a single session?
[24:28]  Arbitrage bettors versus poker players 
[27:06]  What type of gambler would benefit from creating an S corp
[30:00]  Casino generated win/loss statements
[31:54]  Should clients file on time or file an extension?
[37:49]  IRS layoffs 
[40:57]  How can listeners contact Gary?
[42:45]  Brian Camp’s legal opinion
[44:55]  Kalshi and other predictive markets
[47:48]  Professional versus non-professional gambler
[51:34]  Does filing with losses affect the professional gambler classification?

Links:
Kondlercpa.com

https://www.taxnotes.com/special-reports/gains-and-losses/taxation-gambling-after-obbba/2025/08/14/7sxhn