Gambling With an Edge - Gary Kondler

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.

podcast - https://www.spreaker.com/episode/gary-kondler-on-taxes-for-gamblers--69186322

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

Life is a Gamble - Norm Beck

Today I speak with Norm Beck, a professional bridge player, magician, and friend about a bet he won, that turned out to be a big loser.

podcast - https://www.spreaker.com/episode/life-is-a-gamble-norm-beck--69139277

Show Notes

[00:00] Introduction of Norm Beck, bridge player and magician

[00:37]  Norm’s biggest gamble

[06:40]  Clever pre-surgery research strategy

[13:07]  Hiring another doctor to translate information to family

[14:49]  Getting into the gambling business

[20:30]  Booking action on random events

[23:28]  A billion dollar bet

[31:23]  $500k bet on changing a tire 

[33:45]  “Win Your Line of Credit” blackjack tournament

[41:21]  How to contact the show

Life is a Gamble - Cowboy Buzz

Buzz Marconi moved to Las Vegas in the 1960s, and somehow transformed from an Italian kid from the south side of Chicago into Cowboy Buzz. It's a wild story.  Check it out.

podcast - https://www.spreaker.com/episode/life-is-a-gamble-cowboy-buzz--68918838

Show Notes

[00:00]  Introduction on of Cowboy Buzz

[02:07]  Moving to Las Vegas, working at The Stardust

[20:53]  Brilliant mob casino strategies

[23;10]  Tony Spilotro and Frank "Lefty" Rosenthal

[27:19]  Becoming a shift boss Foxy's Firehouse

[29:28]  Did certain dealers cheat players?

[31:06]  A wild craps swing on credit and Milton Jaffe

[35:20]  Milton Jaffe magic trick

[37:06]  Opening a restaurant in Las Vegas

[41:09]  Stories about dealers, cheating, and work ethic

[46:59]  Cowboy Buzz's juice is revealed

[48:51]  Naked women tanning at The Tropicana pool

[55:53]  Becoming "Cowboy Buzz"

[1:02:07]  Playing rugby age 73

[1:04:51]  Meeting Max Rubin

[1:09:05]  The first Blackjack Ball

[1:10:30]  Being a clown diver at Caesars Palace

Gambling With an Edge - Blackjack Ball 2025

Bob is off playing the secret game, so I get together with Max Rubin, and Colin Jones to discuss the 2025 Blackjack Ball.

podcast - https://www.spreaker.com/episode/blackjack-ball-2025--68391922

Show Notes

[00:00] Introduction of Max Rubin and Colin Jones to discuss The Blackjack Ball

[00:45] Colin’s induction into The Blackjack Hall of Fame [01:26] Changes to voting for The Hall of Fame and BJ Traveler discussion [06:55] Costume party and best costume [13:20] Ed Thorp [14:49] UCLA Gambling Studies Program [20:13] Card counting competition [24:49] Quiz and final table games (cutting and sequencing) [36:03] Evolution of The Blackjack Ball [40:23] Other highlights from this year’s Blackjack Ball Links: Interview with BJ Traveller https://youtu.be/mnQmlrxApcE UCLA Gambling Studies Program https://uclagamblingprogram.org

Life is a Gamble - Jon Rogers of Carib Sports

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.

podcast - https://www.spreaker.com/episode/jon-rogers-of-carib-sports--67798953

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

Gambling With an Edge - Anthony Curtis & NFL contests

Our guest this week is Anthony Curtis. We discuss the upcoming football contests, the big Vegas downturn, and upcoming books.

Podcast - https://www.spreaker.com/episode/anthony-curtis-nfl-contests--67534104

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

Life is a Gamble - magician Mac King

Mac King has been performing his comedy magic in Las Vegas for 25 years.  His show is hilarious, and thoroughly entertaining.

podcast - https://www.spreaker.com/episode/life-is-a-gamble-magician-mac-king--67471953

[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

Gambling With an Edge - guest Russell Fox

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?

podcast - https://www.spreaker.com/episode/russell-fox-on-taxes-for-gamblers--66989098

[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 Fox

Links:

Claytontax.com

Taxabletalk.com

Michael Kaplan - "Advantage Players"

 Bob and Richard are back to talk with Michael Kaplan about his new book, "Advantage Players."

podcast - https://www.spreaker.com/episode/kaplinbook--66463710

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

Life is a Gamble - Nigel Eccles Fan Duel Co-founder

 My guest on this episode is Nigel Eccles, co-founder of Fan Duel.

podcast - https://www.spreaker.com/episode/nigel-eccles-fan-duel-co-founder--66022137

[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 thoughts

X.com/nigeleccles
Bethog.com
Betdex.com
FanDuel.com

Buddy Frank 2025 - casinos using AI

Bob and I are back with an interview with Buddy Frank to talk about how casinos are now using AI to evaluate players.

podcast - https://www.spreaker.com/episode/buddyfrank2025--63421580

[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