Step 06 · Ask HELM (the AI specialist)
Tier-1 specialist. Never a "ChatGPT in finance skin."
Claude Sonnet 4.5, trained on tax code (IRS §1091, §1202, §1031, §170, SECURE 2.0). Persistent threads, 60-day context against your portfolio data. Every output ends with a "confirm with your CPA" line — educational, never advisory.
Persistent threads 60-day context Compliance floor
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Sample chat live
You: What if I exercise 1,000 ISOs at $4 strike with $42 FMV?
HELM: Cash needed: $4,000 (1,000 × strike). Bargain element added to AMT income: $38,000 (1,000 × ($42 − $4)). Estimated AMT impact ~$10,640 if you'd otherwise hit the AMT exemption phase-out at your projected $450K MAGI. Total cash out-of-pocket if you exercise this year: ~$14,640. Hold >1 year + sell >2 years from grant date for LTCG treatment on the spread.
Educational only · confirm AMT modeling with your CPA before executing.