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

Gambling With an Edge - guest Russell Fox 12/01/2022

Our guest this week is tax expert Russell Fox on to talk about what gamblers can do before the end of the year to help with their taxes.

We welcome your questions - send them to us at gamblingwithanedge@gmail.com, or you can find me at @RWM21 on Twitter or https://www.facebook.com/GamblingWithAnEdge.

podcast - https://www.spreaker.com/user/7418966/fox12012022

Show Notes

[00:00]  Introduction of gambling tax professional, Russel Fox

[00:42]  Form 1099-K

[03:59]  Gambling winnings as a U.K. resident

[08:39]  Sports betting partnerships

[09:42]  Can gambling losses be carried over to future years?

[10:46]  Session recording for sports betting, related transactions

[15:10]  Reporting income earned by family members

[17:30]  Can an EIN be used for W2G's?

[18:28]  W2Gs for online table games play, session accounting

[20:40]  State taxes on phantom gambling income, deductions

[21:52]  Gambling logs, audits

[26:17]  Horse racing W2G's, 300x rule

[28:09]  Incorrect SSN on W2G

[29:32]  Sessions at different casinos

[30:40]  U.K. and US tax treaty for slot jackpots, lotteries

[32:50]  Nevada taxes on sports betting

[35:32]  Commercials

[38:50]  Tax on futures wagers

[39:50]  Combined gambling records when filing jointly, community property states

[41:35]  Form 5754, issuing 1099s

[44:57]  Good and bad states for gambling

[48:03]  Gambling wins and losses as part of a diversified portfolio

[48:53]  Withholding on W2G

[50:01]  Recommended:  James Fridman, ProHealth Longevity NMN Pro Complete, Blood and Iron by Katja Hoyer

Sponsored Links:

http://SouthPointCasino.com

http://BlackjackApprenticeship.com

http://VideoPoker.com/gwae

http://Unabated.com

Recommended:

http://Jamesfridman.com

http://Prohealth.com/pages/uthever-nmn

Blood and Iron by Katja Hoyer - https://amzn.to/3izxVSk

Park v Commissioner - https://www.govinfo.gov/app/details/USCOURTS-caDC-12-01058/USCOURTS-caDC-12-01058-0

Our guest this week is tax expert Russell Fox on to talk about tax stuff for gamblers.  He provided updates for the latest edition of Tax Help For Gamblers

We welcome your questions - send them to us at gamblingwithanedge@gmail.com, or you can find me at @RWM21 on Twitter or https://www.facebook.com/GamblingWithAnEdge.

.

https://www.spreaker.com/user/7418966/rfox08022022
Click to listen. Alt click to download

Show Notes

[00:00]  Introduction of Russel Fox from Clayton Tax Services

[00:37]  Tax implications of sports betting in different states

[03:14]  Splitting a large DFS jackpot

[04:17]  Reporting recreational horse player income

[07:40]  Shared sports betting at online sites

[08:47]  FBAR

[11:13]  Crypto and FBAR

[12:15]  RV expenses

[14:46]  Paypal reporting transactions, 1099-K

[17:08]  Group slot pulls

[20:03]  W-2 G from a Native American casino

[23:23]  Gambling partnerships

[25:22]  Cherokee North Carolina winnings

[27:08]  https://SouthPointCasino.com

[28:00]  https://BlackjackApprenticeship.com

[28:31]  https://VideoPoker.com/gwae

[29:21]  Withholding SSN on W-2 G

[31:40]  Tax liability for WSOP Main Event

[34:54]  Deducting gambling losses

[36:29]  Filing as a professional for part of the year

[37:15]  S-corp for professional gamblers

[42:12]  Frequently overlooked tax deductions

[43:15]  Constructive receipt

[45:00]  Taxes and beard accounts

[49:56]  Recommended:  Blood and Treasure by Bob Drury and Tom Clavin, Something Missing by Matthew Dicks, For Good and Evil by Charles Adams

Sponsored Links:

https://SouthPointCasino.com

https://BlackjackApprenticeship.com

https://VideoPoker.com/gwae

Guest Links:

Claytontax.com

Tax Help For Gamblers - https://amzn.to/3P1sSEM

Recommended:

Blood and Treasure by Bob Drury and Tom Clavin - https://amzn.to/3zWFkkA

Something Missing by Matthew Dicks - https://amzn.to/3P1cjsv

For Good and Evil by Charles Adams - https://amzn.to/3zTV5Jc

Gambling With an Edge - guest Russell Fox

Our guest this week is tax expert Russell Fox on to talk about what gamblers can do before the end of the year to help with their taxes.

We welcome your questions - send them to us at gamblingwithanedge@gmail.com, or you can find me at @RWM21 on Twitter or https://www.facebook.com/GamblingWithAnEdge.

 

Show Notes

[00:00] Introduction of Russell Fox, tax expert from Clayton Tax
[01:02] What's going to be in the next tax law?
[02:09] Has the pandemic affected Russell's professional life?
[03:02] Do Canadian poker players owe income tax?
[05:14] Can YouTubers deduct gambling losses in excess of winnings?
[06:30] Have the tax implications on DFS changed?
[12:27] Taxation of credit card rewards redemption
[12:51] Process of reporting winning for a recreational advantage player
[18:06] How is travel time handled if IRS questions full-time gambler status?
[18:52] Lost or misplaced W2Gs
[20:58] Is it better to file as a professional gambler if you're a slot AP with many W2Gs?
[22:29] What are the acceptable ways for an amateur to define a sports betting session?
[24:31] Tax on futures bet, rule of constructive receipt
[25:11] Should a bettor clear balances from all sports betting apps every year
[25:34] Tax treatment of free bets
[30:52] South Point Casino October Promotions - $500k+ Monster Money casino-wide progressives, Prime Time Mondays for people 55 and older
[32:19] http://BlackjackApprenticeship.com - card counting training website and community with many betting, tracking, and analytical tools
[32:52] http://VideoPoker.com/gwae - Gold Membership offers correction on most games, free Pro Membership trial for GWAE listeners
[33:56] Is a casino win/loss statement from a casino sufficient for tax purposes?
[35:51] Beard accounts in sports betting
[39:53] Splitting a sports bet
[41:16] At what point does it make sense to file as a professional gambler?
[43:26] Audit risk for professional gamblers
[46:05] Tax professionals who specialize in gambling
[48:01] TurboTax
[48:35] Costs to file as a professional gambler
[51:44] Changes to cryptocurrency laws
[54:41] How to contact Russell Fox
[55:25] Recommended: Maid on Netflix, A Most Clever Girl by Stephanie Marie Thorton, Circus Circus steakhouse


Sponsored Links:
http://SouthPointCasino.com
http://BlackjackApprenticeship.com
http://VideoPoker.com/gwae


Guest Links:
http://Claytontax.com
http://Twitter.com/russcfox


Recommended:
Maid on Netflix  http://Netflix.com/title/81166770
A Most Clever Girl by Stephanie Marie Thorton  https://amzn.to/3CmJgtQ
http://Circuscircus.com/restaurants-1/the-steak-house/

Gambling With an Edge - guest Russell Fox

Our guest this week is tax expert Russell Fox on to talk about what gamblers can do before the end of the year to help with their taxes.

We welcome your questions - send them to us at gamblingwithanedge@gmail.com, or you can find me at @RWM21 on Twitter or https://www.facebook.com/GamblingWithAnEdge.

podcast
Click to listen - Alt click to download

Show Notes

[00:00] Introduction of tax advisor, Russell Fox
[00:41] Recent changes to tax law
[03:31] Self-employment tax for professional gamblers
[07:42] Deductions for gambler vloggers
[09:09] Underpayment penalties for recreational gamblers
[12:10] Deducting bad debts
[14:16] Foreigner gamblers and U.S. tax
[16:33] Declaring winning from a chip bank
[21:10] Taxation of points
[24:31] Common tax mistakes
[30:58] Contributions and IRA contributions
[31:44] South Point Casino November Promotions - Half-priced Amazon and Walmart gift cards
[32:45] Predictit.org/promo/edge - place small wagers on various political events, $20 deposit match for GWAE listeners
[33:29] VideoPoker.com/gwae - Gold Membership offers correction on most games
[34:48] Off-setting a hand pay with losses
[38:40] Listing W2Gs as a professional gambler
[40:48] Self-dealing and IRAs
[42:13] 529 plans
[45:29] Depositing large amounts of cash
[48:05] Setting up an off-shore corporation
[51:03] Recommended - Sal Piacente on Youtube, Nittaya's Secret Kitchen


Sponsored Links:
SouthPointCasino.com
Predictit.org/promo/edge
VideoPoker.com/gwae


Recommended:
Nittayassecretkitchen.com
Sal Piacente https://www.youtube.com/results?search_query=sal+piacente
.
Russel Fox's Previous Episodes:
Lasvegasadvisor.com/gambling-with-an-edge/podcast-guest-russell-fox

Lasvegasadvisor.com/gambling-with-an-edge/podcast-tax-adviser-russell-fox

Many more episodes with Russell are available on GamblingWithAnEdge.com

 

Gambling With an Edge - listener emails 9/3/20

 No guest this week as Bob and I once again dip into the mail bag.

We welcome your questions - send them to us at gamblingwithanedge@gmail.com, or you can find me at @RWM21 on Twitter or https://www.facebook.com/GamblingWithAnEdge.

podcast

Click to listen - Alt click to download

Show Notes

[00:00] Introduction
[00:56] Is online advantage play becoming more or less valuable?
[03:22] Are large jackpots paid in Bitcoin taxable?
[05:15] 9/5 Triple Bonus Poker Plus
[07:20] A listener thanks GWAE the education and entertainment
[09:21] Jackpot promotion question
[13:53] Graveyard shift etymology
[15:12] Video poker pay table calculations
[17:32] Scouting tips
[18:38] Earning tier credits at Caesar's properties
[22:34] Super Times Pay and Magic Deal frequencies
[25:01] Blackjack bet sizing, chip management, and CTRs
[27:29] Playing blackjack through heat while unrated
[29:56] Royal flush frequency
[31:24] $1 DDB calculations
[33:25] South Point Casino September Promotions - $500,000 Guaranteed Money Madness
[35:37] Predictit.org/promo/edge - place small bets on political events, $20 deposit match for GWAE listeners

[36:15] BlackjackApprenticeship.com - blackjack training site and card counting community
[36:45] VideoPoker.com/gwae - Gold Membership offers correction on most games

[37:52] Surveillance is monitoring masks
[39:37] Ways to get a new player's card
[43:34] Trips gone wrong
[49:58] Recommended - 99 Second Storytelling competition, Risk of Ruin podcast


Books Referenced:

Comp City by Max Rubin https://amzn.to/34YObTS

Sponsored Links:
SouthPointCasino.com
Predictit.org/promo/edge
VideoPoker.com/gwae
BlackjackApprenticeship.com 

Recommended:
Storytelling Competition https://www.facebook.com/events/325624952211013
Risk of Ruin Podcasts.apple.com/us/podcast/risk-of-ruin/id1527018692

Gambling With an Edge - guest Russell Fox

Our guest this week is tax expert Russell Fox. Interesting tax items discussed include taxes on crypto-currency, reviewing the criteria for whether or not you are a professional gambler, the implications of not having a tax home, and how the WSOP Main Event final table winners actually did after taxes.

We welcome your questions - send them to us at gamblingwithanedge@gmail.com, or you can find me at @RWM21 on Twitter.

podcast
Click to listen - Alt click to download

Show Notes

[00:00] Introduction of tax advisor, Russell Fox of TaxableTalk.com and ClaytonTax.com

[00:30] Recent changes in tax laws, foreign crypto currency exchanges

[06:03] Coinbase summons letters

[11:20] Schedule C filing as a part time professional gambler

[13:47] Does having many W2G's increase audit risk?

[18:43] Using player's club data during an audit

[20:50] Taxation of private football pool entry, winnings, losses

[25:35] California proposal to end deduction of gambling losses

[26:52] California law requiring primary candidates to release tax returns

[28:38] South Point Casino August promotions - South Point logo merchandise, free play, free video poker classes

[30:13] VideoPoker.com - Gold membership offers correction on most games

[31:44] Filing lost W2Gs, reconciling inaccurate W2Gs

[42:24] Can traveling expenses be deducted if you live on the road?

[44:46] WSOP final table tax liabilities

[49:23] How to properly stake a poker player, Form 5754, 1099-MISC

[52:25] Tax Help for Gamblers by Jean Scott and Marissa Chien

[53:30] Sending a tax return by regular mail

[56:25] Contact Russell at rcfox@claytontax.com

SouthPointCasino.com
VideoPoker.com
TaxableTalk.com
ClaytonTax.com
BobDancer.com/seminars


Tax Help for Gamblers by Jean Scott and Marissa Chien https://amzn.to/344mvtS

Gambling With an Edge - Russell Fox

Our guest this week is tax advisor Russell Fox.  We discuss various tax situations that affect gamblers and other citizens.

podcast
click to listen - alt click to download

Show Notes

[00:00] Intro of Russel Fox of Clayton Financial and TaxableTalk.com, rcfox@ClaytonTax.com
[00:35] Draft Kings daily fantasy sports special at the Las Vegas Advisor.
[01:43] Do new tax laws affect end of year planning?
[03:39] Are there any recent legal decisions that affect gamblers and taxes?
[05:14] Could the next Congress pass any important tax bills?
[06:53] Could you postpone claiming a jackpot for tax purposes?
[10:49] Are lottery tickets deductible from gambling winnings?
[15:11] Does the IRS accept win/loss statements?
[17:16] How will the larger standard deduction negatively affect amateur gamblers with only a few W2Gs?
[19:52] Would claiming $100,000 in wins and $100,000 in losses trigger an audit?
[25:21] Would gambling winnings in the U.K be transmitted to the IRS?
[27:07] Discussion "gambling sessions."
[32:10] SouthPoint Casino - Walmart gift card promotion, Thanksgiving Hot Seat promotion, Senior Day Mondays
[33:17] AutoSlash.com - six things that listeners should know about saving money on rental cars.
[35:03] Videopoker.com - free membership offer for GWAE listeners, "Stack the Deck" is the game of the week.
[36:58] Do poker winnings in Texas have to be reported?
[38:02] Discussion of the tax implications for a team consisting of an amateur gambler and a professional gambler.
[43:52] Does being barred from a casino affect a player's ability to get win/loss records?
[47:16] Can a professional gambler take the foreign earned income exclusion?
[51:30] Should enrolled agents violate federal law or state law when there is a conflict?

ClaytonTax.com
TaxableTalk.com
LasVegasAdvisor.com
DraftKings.com

AutoSlash - http://autoslash.com
SouthPoint Casino - https://southpointcasino.com/
https://www.videopoker.com/gwae

Gambling With an Edge - Tax Adviser Russell Fox

Our guest this week is tax adviser Russell Fox.  Russell is a tax adviser with many professional gamblers as clients.  We talk about the new tax laws, and how they effect both professional gamblers, as well as the recreational player.

podcast
Click to listen - Alt-click to download

Show Notes

Gambling With an Edge - guest tax man Russell Fox

Our guest this week is Russell Fox. Russell is a certified tax professional who handles many professional gamblers. We talk about strategies that effect people with gambling income.

podcast 

click to listen - alt click to download 

Show Notes

[00:49] Tax evasion v.s. tax avoidance

[01:43] The federal tax bill and its relevance to gamblers and non-gamblers

[08:29] What is the best way to list W2G’s for a professional gambler using schedule C?

[15:23] Online casinos in New Jersey require W2G’s for slot machine winnings of $1200 or more. In general, is free play taxable? Is the free room from the casino taxable?  

[18:10] Keeping a diary of gambling wins and losses

[21:33] Can a player form a C-corp so that he can present his tax ID rather than his SSN when he hits jackpot

[24:11] Playing under an assumed name and producing an identification for the real name and the form W-9

[28:33] Is the U.S. the only country that taxes gambling winnings?

[29:10] If you hit a $20,000 royal flush and take it in cash, is CTR filled out on top of W2G?

[33:20] What should a U.K. citizen be worried about if he visits Las Vegas for a vacation and wins a significant amount of money?

[37:31] The tax implications for both the investor and the players of a blackjack team

[40:59] Should you pay taxes on gambling overseas?

[41:51] Are capital gains on cryptocurrency taxable events?

[48:29] Do you report gambling wins/losses for games that occurred on international waters?

[48:47] If you have a SEP IRA and a solo 401k, is there any downside for using solo 401k just for the $18,000 elected deferral and use SEP IRA for roughly 18.5% of the net contributions?

[50:15] 5 silly things that Russel heard from his clients

Russel Fox:

RCFox@Claytontax.com 

http://www.taxabletalk.com/

http://claytontax.com/nevada/

Gambling With an Edge - guest tax man Russell Fox

Our guest this week is Russell Fox.  Russell is a certified tax professional who handles many professional gamblers. We talk about strategies that effect people with gambling income.

podcast

click to listen - alt click to download

Show Notes

[1:00] Can professional gamblers use IRA accounts to even out year-to-year fluctuations?

[5:20] 4 ways for non-US players to retrieve the 30% of money that is withheld due to W2G’s

[8:26] Is it a taxable event if you pick up as cash $100 worth of cash-back or free-play?

[11:19] In case of winning a drawing for $10,000, is there any tax difference between receiving cash with a 1099 form and free play without a 1099 form?

[14:43] For professional gamblers using schedule C on US tax return, what qualifies as legitimate schedule C business expenses?

[17:08] You play enough to get a "free” cruise which costs $600 in taxes, port fees, and gratuities. Assume the cruise has a retail value of $2,500 plus the $600 in fees. Is there any part of this cruise that is taxable?

[21:01] Assume you’re a video poker professional and you decided go on a cruise ship and lose $4,000. The casino gives you another cruise. Is any part of that $4,000 deductible? Is it actual losses rather than the daily amount?

[22:31] Claiming more losses than what shows on W2G’s and the importance of keeping records.

[24:36] Implications on W2G’s when giving the casinos an address other than the actual home address such a P.O. box. Is there a problem?

[29:00] How would Trump’s new tax plan affect gamblers?

[31:43] Will the W2G’s $12,000 threshold increase in the foreseeable future in order to keep up with the inflation?

[32:20] The difference in the W2G threshold amount for jackpot at the tracks and the casinos

[37:41] Can you correct W2G errors after the fact? Can casinos refuse to provide the W2G’s after the fact?

[40:50] What are the W2G rules on electronic table games?

[47:42] Russel's 5 “Bozo Tips,” why keeping cash in a deposit box could cause trouble, and when CTR’s are your friends.

You can contact Russell Fox at rcfox@claytontax.com 

You can visit his website at Claytontax.com or http://www.taxabletalk.com/

Gambling With an Edge - guest tax man Russell Fox

Our guest this week is Russell Fox.  Russell is a certified tax professional who handles many professional gamblers. We talk about end of the year strategies for saving on your taxes, and analyze the winners of the final table of the WSOP to see how they did after taxes.

podcast

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Gambling With an Edge - guest Russell Fox #2

This week we talk with tax professional Russell Fox. Russell is based in Las Vegas and handles many professional gamblers. We discuss things like - how teams handle W2Gs, 1099s, and K1s. We talk about how to be smart about having residences in 2 states, and some tips on an HSA.

podcast

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Gambling With an Edge - guest Russell Fox

This week we talk with tax professional Russell Fox. Russell is based in Las Vegas and handles many professional gamblers. We get some year end tax advice, and ask him questions like: Can I form an LLC? Can a professional gambler carry losses forward? Can I choose not to file as a professional, and is there a benefit to that?

podcast

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