Complete Webcast: Tax and Retirement Planning for Gamblers.

by | Jun 13, 2023 | SEP IRA | 10 comments




An overview of tax and retirement strategies that every serious gambler should consider. This webcast is slanted towards gamblers who file as professionals, but there is content applicable to all gamblers.

Book Recommendation:
Tax Help for Gamblers (4th Edition) :

Timeline:
Disclaimer! – 0:00
Overview of Gambling and Taxes – 1:30
Recreational Gambling and Taxes – 4:30
Why Recreational Gamblers Need to Avoid W2G Forms – 7:10
Professional Gambling and Taxes – 9:10
Schedule C v. S-Corp – 10:20
Audit Risk – 13:40
Using Expense Deductions to Lower Taxable Income – 16:10
The Deductions They Don’t Talk About – 18:08
The QBI Deduction – 22:00
Using Marriage To Lower Taxable Income – 23:24
Professional Gambling and Retirement Contributions – 25:35
Traditional IRA v. Roth IRA – 26:30
SEP-IRA v. Solo 401k – 27:30
The IRA Type They Don’t Talk About – 28:42
The Roth IRA Rollover Backdoor – 30:28
Things to Do in a Good Year v. Bad Year – 31:25
Scenarios to Explain Everything – 33:20
Q&A – 39:55…(read more)


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As a gambler, it is essential to think about your tax and retirement strategies to ensure your financial well-being. In a recent webcast, experts discussed several tips and tricks to help you make the most of your gambling income.

Firstly, it’s important to understand that all gambling winnings are taxable and must be reported to the IRS. This includes winnings from casinos, lotteries, horse racing, and sports betting. To avoid any penalties or fines, keep accurate records of all your gambling activities, including wins and losses. You will need to report these on your tax return, and failure to do so may result in an audit.

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One tax strategy for gamblers is to deduct your gambling losses from your winnings. You can only do this if you itemize your deductions, but it can be a significant tax benefit. Gambling losses are deductible up to the amount of your winnings, but you must have documentation to support your losses, such as receipts, tickets, and statements.

Another tax strategy is to establish a professional gambling status. This means you treat gambling as your primary source of income, and you can deduct business expenses related to your gambling activities, such as travel, lodging, meals, and equipment. You must meet specific criteria to establish a professional gambling status, such as keeping records, showing a profit motive, and devoting substantial time and effort to gambling.

When it comes to retirement strategies, gamblers can benefit from various investment vehicles. One option is to contribute to a traditional or Roth IRA, depending on your income and tax bracket. Traditional IRAs allow you to deduct your contributions from your income, while Roth IRAs offer tax-free growth and withdrawals.

Another option is to invest in a 401(k) or a solo 401(k) if you are self-employed. These retirement accounts allow for tax-deferred growth and contributions, reducing your overall tax burden while saving for your future.

In conclusion, as a gambler, it is essential to have a solid tax and retirement strategy in place to ensure financial stability. Deducting losses, establishing a professional gambling status, and investing in retirement accounts are all viable options to consider. Remember to keep accurate records and consult with a financial professional to make the most of your gambling income.

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10 Comments

  1. Status Quo

    Hey Captain Jack,
    great video they really need to change the gambling tax laws because it screws over the recreational gamblers too assuming they file correctly. I'm in PA and I plan to just combine each book's (Draftkings, FanDuel, FoxBet, Barstool) win/loss and come to a final number and just report that . These books don't even send us any tax forms ( I have not got a single one for 2020) so how does the IRS expect us to report it correctly. Is this a bad idea?

  2. Jorge Posada

    Wow, this was great, as with most your videos I learned a lot, thank you! Filing as a single professional can you max out more than one retirement option in the same year? For ex, can you do the max on a solo 401k, traditional IRA, Roth IRA, and sep IRA, or some combination there of?

  3. robert nunn

    Another note about HSA. It can also be used for retirement and non medical after the age of 65. You just have to pay regular taxes on it then.

  4. DaviD Zhao

    the site every all REAL gamblers should follow! quality content champ!

  5. Andrew Pessotti

    Hey Cap Jack, quick question but first thank you very much for all these! It’s awesome content. Regarding taxes, if someone has a full time job outside of sports betting working for a corporation where the profits from betting are just side income how would you suggest they file taxes? Also, would someone file differently if it were profit from US books, overseas books like Bookmaker or locals?

  6. Darren Wilson

    Allow me to add a small correction. CFA refers to a Chartered Financial Analyst. CFP is a Certified Financial Planner. Financial Advisor is a very suspect term, that frequently involves little accredation and many financial advisors are not fiduciaries.

  7. Yoda_Trader1

    Thanks for all the great videos Captain Jack. Great job.

  8. Jason Sylva

    Elite work Jack. Thank you for sharing.

  9. darin

    Thank you for all these videos, love that youre not trying to sell plays, instead trying to provide information to help people become successful on their own.

  10. MOLON LABE

    You pay income taxes? King-sized idiot!

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