Are Prediction Market Profits Gambling Income?
Quick answer (read this first): The short answer: It depends and the IRS has not told you which answer applies. What the question actually means: Whether prediction market profits are […]
Crypto Cost Basis: What to Do When Exchange History Is Gone
Quick answer (read this first): The problem: Exchange records are unavailable due to platform shutdown, lost credentials, incomplete exports, or years of unreconciled self-custody. Crypto cost basis is undocumented and […]
The Complete Guide to Crypto Cost Basis Reconstruction & Historical Accounting
Quick answer (read this first): What it is: Crypto cost basis reconstruction is the process of rebuilding your digital asset transaction history at the tax-lot level by establishing what you […]
Section 1256 and Prediction Markets: Do Kalshi and Event Contracts Qualify?
Prediction markets now operate within formal regulatory infrastructure and, in certain instances, under direct CFTC supervision. Platforms such as Kalshi function as Designated Contract Markets and list standardized event-based contracts […]
Crypto Tax Reporting: CARF & DAC8 Readiness for Investors, Founders, and Platforms
This article is written for three overlapping audiences who are now being pulled into the same global crypto tax reporting system. Investors holding, trading, staking, or deploying crypto across borders […]
Kalshi Tax Reporting: What Your 1099 Leaves Out
Kalshi is no longer an experimental corner of the internet. It is the first CFTC-regulated event-contract exchange operating in the United States, and it now sits at the intersection of […]
Prediction Market Taxes Explained: Why U.S. Tax Characterization Remains Unsettled
Prediction markets are no longer a niche experiment. They now sit at the intersection of trading, information aggregation, and real capital deployment. What has not evolved at the same pace […]
The Architecture of Digital Asset Compliance
Digital asset markets have transitioned from a period of limited reporting visibility to one characterized by structured information reporting, automated data reconciliation, and systematized compliance evaluation. This transition has altered […]
I Already Filed My Crypto Taxes: Why 1099-DA Still Puts You at Risk
For many digital-asset investors, the prevailing assumption is simple: “I filed every year. I’m done and compliant.” The risk introduced by Form 1099-DA is a structural change in how crypto […]
Form 1099-DA and the Risk of Undocumented Early-Year Crypto Activity
Form 1099-DA introduces standardized, third-party reporting for digital-asset dispositions at scale. That reporting gives the IRS a reliable anchor point for automated matching and discrepancy analysis across tax years, accounts […]
