Paul Barron and David Kemmerer unpack the seismic shift coming to cryptocurrency taxation with the introduction of the 1099 DA form for the 2025 tax year. As brokers begin reporting crypto transactions on a per-wallet basis, investors face both new compliance challenges and strategic opportunities—from leveraging tax-loss harvesting to offset gains (with no wash-sale rule restrictions, unlike traditional securities) to understanding how DeFi yields are treated as ordinary income while crypto-backed loans remain non-taxable events. The discussion cuts through the confusion surrounding capital gains reporting, warns against the pitfalls of overreporting due to misunderstood 1099 forms, and offers practical guidance on everything from disposing of worthless tokens to utilizing carry-forward losses indefinitely, making it a must-listen for anyone navigating the increasingly complex regulatory landscape of digital asset investing.

~ Looking for the best tax havens for Crypto? Free Month with iTrust Capital ➜ Use PROMO CODE - PAUL BARRON https://rebrand.ly/PAULBARRON

00:00 - Introduction to Tax Strategies for Crypto
02:03 - Understanding the 1099 DA and Wallet Reporting
04:00 - Crypto Catalyst for 2026
11:01 - Navigating Capital Gains and Losses
19:52 - Crypto Catalyst + DeFi and Tax Implications
27:58 - Tax Planning for 2026 and Beyond
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