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The Tax Tip Vault

Uncommon tax tips for W-2 earners, freelancers, founders, and equity comp earners.

How Peter Thiel Turned $1,700 Into $5 Billion Tax-Free

In 1999, Peter Thiel put $1,700 of PayPal founder stock into a Roth IRA. By 2019 it was worth $5 billion. Federal tax owed: zero. Here's the structure he used.

tax strategyRoth IRAfounder equitypre-IPOtech workers

Should I File an Extension? A Decision Tool for CPAs

Answer 5 questions about your client's situation and get an instant file-or-extend recommendation with a downloadable PDF summary.

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How AI Tax Prep Automation Works: A Guide for CPA Firms

Learn how AI automation is helping CPA firms prepare 5x more returns with zero manual data entry. A practical guide to automated tax preparation with Drake and UltraTax.

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1040 Safe Harbor Checker

Free tool for tax pros: instantly check if your client hit safe harbor for 2025. Enter 3 numbers from the prior-year return for an instant IRS ยง6654 verdict.

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