Dennis Rappaport

Jon Rogers was an old-school bookie.  He started booking baseball with his classmates in 6th grade, graduated to parlay cards in high school, and went pro after high school.  He lived, and booked through a seismic change in the bookmaking industry.  He went from the old days of taking bets over the phone, writing on slips of paper, to moving offshore, and the rise of internet betting.Show Notes[00:00]  Introduction of bookmaker Jon Rogers of Carib Sports[00:59]  Jon’s childhood and early gambling experiences[03:52]  Booking parlays in high school and lottery numbers[08:46]  State lotteries broadcast drawings[11:11]  Kickbacks and paying for protection[13:06]  Super Bowl 1990 FBI raid[16:52]  Charges, recordings, taxes, and going to Vegas[21:37]  Antigua tax laws, bookmaking on paper, then with software[29:28]  1990 case ends[32:32]  Continuing operations in Antigua, accepting credit cards, betting volume, and margins.[35:02]  2003 raid, The Patriot Act[46:42]  The SAFE Port Act and closing down[48:44]  Life after bookmaking, settling the case, and living happily ever after

Our guest this week is Anthony Curtis. We discuss the upcoming football contests, the big Vegas downturn, and upcoming books.Show Notes[00:00]  Introduction of Anthony Curtis, owner of The Las Vegas Advisor and Huntington Press[01:12]  NCAAF and NFL football contests[04:04]  Grandissimo[06:03]  Did tax law changes affect participations in football contests?[08:15]  Contest pricing and strategies for additional entries[10:51]  The value of football knowledge versus contest theory[13:27]  Huntington Press’ upcoming books on sports betting, slots, roulette, blackjack, baccarat, and another book by James Grosjean[19:57]  Las Vegas tourism, waived resort fees, and other deals.[27:33]  Struggles Foubtainebleau, Resorts World, and The Downtown Grand

Mac King has been performing his comedy magic in Las Vegas for 25 years.  His show is hilarious, and thoroughly entertaining.[00:00]  Introduction of magician Mac King[00:50]  What’s the first magic trick that Mac remembers?[04:39]  When did Mac start doing magic?[06:06]  Mac’s paid performance[08:19]  Mac’s career plans after high school[12:36]  Working with Lance Burton[14:47]  “It’s Magic” in Los Angeles[16:38]  Life after college, comedy clubs[18:51]  Intersection of gambling, magic, and card cheating[21:06]  Mac King’s Excalibur show[22:58]  Performing with a bloody thumb[34:06]  Houdini's naked rope escape[37:47]  Future plans and why Mac still loves performing[39:58]  Life outside of magic

Our guest this week is tax expert Russell Fox.  We talk about the terrible new taxes on gamblers in the big beautiful bill.  What's a gambler to do?  Is Richard going to retire.... again?[00:00]  Introduction of gambling tax expert Russell Fox [00:48]  How does the tax bill affect gamblers?[02:25]  Session method logging[03:56]  Sports betting logs and session definition[09:14]  Advantage slot play and session definition[13:08]  Will this law be overturned?[17:08]  1099 changes, W2G backup withholding[20:16]  CTRs[20:51]  90% maximum deduction of losses and business expenses[23:06]  Long term impact on high limit rooms, DraftKings, FanDuel, and offshore books[28:02]  U.S. citizens, permanent residents, non-resident aliens, withholding[30:46]  Worldwide income, renouncing U.S. citizenship, and exit tax[34:17]  Favorable comfortable structures, tax advantages of C-corp[34:55]  IRS job cuts and audit probability[38:29]  Recreational gamblers and W2Gs[40:33]  Will this tax law increase tax fraud?[41:18]  Contacting Russell FoxLinks:Claytontax.comTaxabletalk.com

 Bob and Richard are back to talk with Michael Kaplan about his new book, "Advantage Players."Show Notes[00:00]  Introduction of Michael Kaplan, author of Advantage Players[00:43]  Michael’s background in gambling and writing[04:18]  Finding people to write about[06:46]  Definition of “advantage player”[07:21]  David Philips, the pudding guy[09:57]  Cheating, breaking the law, and advantage play[12:23]  Identifying interesting APs and stories[14:02]  Bill Benter and Alan Woods[20:59]  Phil Ivey and the benefits of humble beginnings[25:09]  Getting backed off, betting big, staying disciplined [28:57]  Don Johnson’s Atlantic City play[33:45]  Playing with James Grosjean[36:20]  Interviewing AP royaly[36:09]  Advantage play in adult films[40:40]  AP skills, qualities, mindset[43:20]  Eddie Teams[46:40]  How to order Michael’s book, Advantage Players Links:https://www.advantageplayersbook.com/Get book - https://amzn.to/4dTqk9r

My guest on this episode is Nigel Eccles, co-founder of Fan Duel.[00:00]  Introduction of Nigel Eccles, co-founder of FanDuel[00:48]  Nigel’s background and first company [02:04]  Nigel’s educational background and interest in gambling, selling variance[06:59]  Joining Flutter and prediction markets, exchange models[10:04]  Founding FanDuel, fantasy sports, sports betting[14:31]  Sports betting in Nevada, over-regulation and limited innovation[18:47]  Leaving FanDuel[20:08]  Vertical businesses, pandemic spike and whipsaw[20:59]  Bettor are getting dumber, banning winners, and the popularity of parlays[24:20]  Sharps, betting patterns, cat and mouse games, and taking sharp action[27:24]  BetHog online crypto casino, innovation, and payment processing fees[31:42]  Managing crypto volatility[33:17]  The future of online gaming and crypto [36:10]  Final thoughtsX.com/nigelecclesBethog.comBetdex.comFanDuel.com

Bob and I are back with an interview with Buddy Frank to talk about how casinos are now using AI to evaluate players.[00:00] Introduction of Buddy Frank[01:10] The evolutions of AI in casinos, falling costs, data analysis[03:52] Using data to assess how player ADT changes with hotel stay [08:58] Analyzing player performance[11:55] ChatGPT, large language models being used to finetune offers [15:51] Video poker products that calculate player specific player ADT[21:38] Cameras in machines, facial recognition, privacy concerns[23:43] MGM banning slot hustlers, persistence machines, must-hit-by [32:46] Some operators are 86'ing slot players [37:07] Misjudging players, challenges assessing table games players[42:48] Reno rewards program story, loopholes [44:29] Churn, tailoring offers mid-session [47:24] Sports betting data analysis [48:25] Adoption of AI over the next five years[53:53] Recommended: Blood Game by Jeffe Boats

Bob and I sit down at the end of 2024, and talk about what we have been doing gambling wise for the last year.  Both of us seem to be working harder than ever.[00:00]  Introduction[00:42]  Is Richard still retired?[05:19]  The U.S. sports betting market[07:52]  Betting partnership dynamics[10:39]  Successful bettors making fundamental gambling mistakes[12:33]  Bob’s sports betting[17:58]  Bob’s slot experience[26:58]  Slot hustling, getting information, solving games[34:52]  How many hours a day is Bob working?[38:08]  Beatable slots, obsolete information, and new skins[39:12]  Recommended:  Erle Stanley Gardner’s Spill The Jackpot,                                         David Baldacci books,                                         Daniel Silva books

My guest this week is Elihu Feustel.  He is on this week to talk about his new book, Beyond The Odds, which you can pick up here https://amzn.to/3Behcxf

Bob and I are back after a long hiatus to talk about this years blackjack ball. We are joined by John Chang, former head of the MIT team, Max Rubin, the host and creator of the blackjack ball, and Rick "Night Train" Blaine who was this year's inductee into the blackjack hall of fame.