Insights

Expert perspectives on crypto taxation, tax planning, and wealth preservation from a former Big Four CPA.

Crypto options taxes 2026 hero image showing an option payoff curve and three instrument types
Crypto Tax

Crypto Options Taxes (2026): A CPA's Guide to Premiums, Exercise, Assignment, and the 60/40 Question

Deribit options, IBIT covered calls, and CME futures options are taxed three different ways. A CPA prices premium, exercise, expiry, and assignment, and settles the 60/40 question per instrument.

Garrett Taylor·Jul 9, 2026·21 min read
Crypto perpetual futures taxes 2026 hero image showing three platform tiers and a perps chart
Crypto Tax

Crypto Perpetual Futures Taxes (2026): A CPA's Guide to Perps on Every Platform, Funding, and Liquidations

Perps now trade on three regulatory tiers with three tax stories. A CPA maps Section 1256 per tier, funding both directions, liquidations, collateral traps, and a full worked year.

Garrett Taylor·Jul 9, 2026·22 min read
Hero image for TokenTax review 2026 showing TokenTax as both software and an accounting firm
Crypto Tax

TokenTax Review 2026: A Crypto Tax CPA's Honest Walkthrough

A crypto tax CPA reviews TokenTax for 2026: real pricing from $49 to $3,499, the software vs full-service question, and where you still need your own CPA.

Garrett Taylor·Jul 9, 2026·17 min read
Hero image showing a 1099-DA, personal records, and tax software output displaying three different gain numbers
Crypto Tax

Your 1099-DA Doesn't Match Your Records: The Three-Record Problem, Fixed (2026)

Your 1099-DA, your wallet history, and your tax software all disagree. A CPA explains the five common mismatches and the exact reconciliation workflow.

Garrett Taylor·Jul 9, 2026·19 min read
Hyperliquid taxes 2026 hero image showing a perps chart, hourly funding clock, and the tax form Hyperliquid never issues
Crypto Tax

Hyperliquid Taxes (2026): A CPA's Guide to Perps, Funding Payments, and the Airdrop the IRS Never Saw

Hyperliquid issues no tax forms and the IRS has no perp guidance. A CPA covers perps, hourly funding, the HYPE airdrop, and a full worked year with real numbers.

Garrett Taylor·Jul 9, 2026·21 min read
Hero image for I Got a 1099-DA Now What showing a 1099-DA form with proceeds filled in and an empty cost basis box
Crypto Tax

I Got a 1099-DA, Now What? A CPA Walks Through Every Box (2026)

Form 1099-DA reports your crypto proceeds to the IRS, usually with no cost basis. A CPA explains every box, what to do before filing, and when to amend.

Garrett Taylor·Jul 9, 2026·20 min read
Gambling loss deduction 2026 hero image showing a loss bar with the top 10 percent sliced off and marked no longer deductible
Crypto Tax

The New Gambling Loss Deduction Rules (2026): The 90% Cap, the Itemizing Trap, and What It Means for Event Contract Traders

From 2026, gambling losses deduct at only 90%, itemizers only. A CPA runs the phantom income math, the standard deduction trap, the session question, and what event contract and crypto traders should do about it.

Garrett Taylor·Jul 9, 2026·19 min read
Robinhood prediction market taxes 2026 hero image showing the consolidated 1099 for stocks next to the missing 1099 for event contracts
Crypto Tax

Robinhood Prediction Market Taxes (2026): The Statement You Get, the 1099 You Don't, and What You Owe

Robinhood issues no 1099 for event contracts, just an Annual Statement the IRS never sees. A CPA explains the form gap, four tax treatments, and a full worked year.

Garrett Taylor·Jul 9, 2026·21 min read
Section 1256 event contracts hero image showing a 60/40 split donut chart with a question mark over prediction market icons
Crypto Tax

Section 1256 and Event Contracts (2026): Do Kalshi and Prediction Markets Get 60/40 Treatment?

Section 1256's 60/40 rate could cut a prediction market trader's federal bill by a quarter, but no platform reports event contracts that way. A CPA walks the statutory test, the math, and the Form 6781 and Form 8275 mechanics.

Garrett Taylor·Jul 9, 2026·20 min read
State taxes on prediction market winnings 2026 hero image showing a US map with a prediction contract ticket and dollar icon
Crypto Tax

State Taxes on Prediction Market Winnings (2026): The Second Bill Kalshi, Polymarket, and Robinhood Traders Forget

Your state taxes prediction market profits too, and in some states a gambling characterization means tax on gross winnings with no loss deduction. A CPA maps all 50 states, prices one trader in five of them, and covers the 2026 changes.

Garrett Taylor·Jul 9, 2026·19 min read
Prediction market taxes 2026 hero showing platforms split into fiat-settled and crypto-settled rails
Crypto Tax

Prediction Market Taxes (2026): How Kalshi, Polymarket, Robinhood and Every Major Platform Gets Taxed

How prediction market taxes work on Kalshi, Polymarket, Robinhood and more. A CPA splits platforms by settlement type and shows exactly what to report.

Garrett Taylor·Jul 2, 2026·18 min read
Kalshi taxes 2026 hero image showing the four narrow 1099 forms Kalshi issues and the missing form for event contract trading
Crypto Tax

Kalshi Taxes (2026): A CPA's Guide to the Forms You'll Get, the One You Won't, and What You Owe

Kalshi sends 1099s for interest, rewards, and crypto conversions, but nothing for your trading profit. A CPA walks through every form, four tax treatments, and one full worked year.

Garrett Taylor·Jul 2, 2026·23 min read