Fusing the excitement of gambling with the precision of tax planning, hosts Chris Piccuirro and John Tripolsky navigate the complexities of one's obligations to the IRS following those auspicious wins or painfully remembered losses. Both Piccuirro and Tripolsky pepper their discussion with humor and relatable anecdotes that easily resonate with their audience. This episode especially appeals to listeners eyeing the upcoming Super Bowl, the biggest betting event of the year, and those curious about the tax impact of their potential gambling earnings.
Driven by the rapid increase in online and app-based wagering, the duo sheds light on the critical aspects of gambling wins and losses and the importance of honest reporting.
They unpack the intricacies of federal and state tax regulations, emphasizing the significance of obtaining W-2G forms when required and understanding how winnings - both cash and non-cash - are taxed differently. Additionally, they emphasize the crucial nature of record-keeping to ensure compliance and protect against potential audits.
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