Bonus: Crypto Tax Rules Every Investor Should Understand episode artwork

EPISODE · Jun 3, 2026 · 30 MIN

Bonus: Crypto Tax Rules Every Investor Should Understand

from Sterling Insights

Crypto taxes are getting more complicated fast — especially for investors, accountants, and financial advisors trying to keep up with new IRS reporting rules.Perry Woodin is the CEO and co-founder of Node40, a digital asset accounting and analytics platform focused on crypto tax reporting, compliance, and financial reconciliation. In this episode, Perry breaks down the growing challenges around crypto taxes, 1099-DA reporting, digital asset compliance, and how financial advisors can better manage crypto within client portfolios.He also explains how crypto investors create taxable events without realizing it, why many broker-issued crypto tax forms may be inaccurate, and how advisors and accountants can stay ahead as digital assets become more mainstream.Key Takeaways:● Crypto tax reporting is evolving quickly: New 1099-DA rules are creating confusion for investors, accountants, and advisors navigating digital asset compliance.● Many crypto tax forms may be incomplete: Investors using multiple wallets or exchanges often receive inaccurate cost-basis reporting.● Financial advisors need crypto visibility: Advisors increasingly need insight into digital asset holdings to manage full portfolio strategy and tax planning.● Blockchain creates massive data complexity: Crypto transactions, staking rewards, liquidity pools, and yield strategies generate difficult-to-track tax events.● Education remains the biggest hurdle: Many investors and professionals still underestimate the importance of understanding crypto tax obligations.

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Bonus: Crypto Tax Rules Every Investor Should Understand

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