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Ep. 137 | Digital Asset Reporting 101 episode artwork

May 27, 2025 27 min

Ep. 137 | Digital Asset Reporting 101

from Teaching Tax Flow: The Podcast Hosted by Chris Picciurro and John Tripolsky

Digital Asset Reporting 101: What You Need to Know | Teaching Tax Flow Ep. 137 Join tax expert Tynisa "Ty" Gaines, EA, as she breaks down the essentials of cryptocurrency and digital asset tax reporting. Learn how the IRS views digital assets, when transactions are taxable, and how to prepare for upcoming reporting requirements. KEY TAKEAWAYS: • Digital assets are treated as property by the IRS, not as currency • Every sale, trade, or purchase using cryptocurrency creates a taxable event • Cost basis tracking is critical - without it, the IRS assumes zero basis • New 1099-DA reporting forms are coming for tax year 2025 • Even "innocent" transactions like buying coffee with crypto must be reported EPISODE BREAKDOWN: How Digital Assets Are Classified for Tax Purposes Common Reporting Mistakes Taxpayers Make Cost Basis Tracking Methods and Best Practices Understanding the New 1099-DA Form Requirements Special Considerations for Business Owners Accepting Crypto SPONSORED BY: Wealth Builders Mortgage Group Visit wealthbuildersmortgagegroup.com for specialized lending strategies for investors (00:02) - Exploring IRS Treatment of Digital Assets with Expert Ty Gaines (05:25) - From Military Spouse to Digital Asset Tax Professional (08:25) - University Rivalries, Military Education, and Campus Visits (11:33) - Tax Reporting for Digital Assets and Cryptocurrency Transactions (14:09) - Tracking Crypto Cost Basis and Tax Reporting Responsibilities (18:48) - Tax Implications of Cryptocurrency Transactions and Market Volatility (22:29) - Understanding New 1099 DA Reporting Requirements for Digital Assets (25:03) - Navigating Tax Forms with Humor and Professional Guidance

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Ep. 137 | Digital Asset Reporting 101

0:00 27:19

Chapters

  1. 0:02 Exploring IRS Treatment of Digital Assets with Expert Ty Gaines
  2. 5:25 From Military Spouse to Digital Asset Tax Professional
  3. 8:25 University Rivalries, Military Education, and Campus Visits
  4. 11:33 Tax Reporting for Digital Assets and Cryptocurrency Transactions
  5. 14:09 Tracking Crypto Cost Basis and Tax Reporting Responsibilities
  6. 18:48 Tax Implications of Cryptocurrency Transactions and Market Volatility
  7. 22:29 Understanding New 1099 DA Reporting Requirements for Digital Assets
  8. 25:03 Navigating Tax Forms with Humor and Professional Guidance

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This episode is 27 minutes long.

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This episode was published on May 27, 2025.

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