Yes. The bot recognises that RSU vests are typically withheld at the 22% federal supplemental rate up to $1M of compensation and at 37% above that, while the prospect's actual marginal rate is usually 32% to 37% federal plus state. The withholding shortfall plus the resulting quarterly estimated-tax true-up is one of the first practical issues the bot raises with any RSU-heavy prospect, because it's the thing that surprised them in April.

Yes, at the framing level. The bot explains the bargain element, the AMT preference item, the 90-day post-termination exercise window, and the disqualifying-disposition tradeoff that turns long-term capital gains back into ordinary income. It will not recommend an exercise strategy because that depends on the prospect's full picture - tax bracket, AMT carryforwards, employer health, and cash position. The recommendation conversation is with the CFP.

Yes. QSBS Section 1202 has specific requirements - C-corp issuer, $50M gross assets at issuance, five-year hold - and the bot walks the eligibility checklist. For secondary tender offers at late-stage private companies (the Stripe, SpaceX, OpenAI pattern), the bot covers the tax treatment of secondary sales versus a 409A-priced exercise and routes the conversation to your pre-IPO specialist.

Yes. The bot recognises insider-level executives and covers the 10b5-1 framework - the mandatory cooling-off period (currently 90-120 days under the 2023 SEC amendments), the certification requirements, and the operational reality of running a plan through the company counsel. Routing to the 10b5-1 specialist at your firm happens automatically once the conversation surfaces an executive title.

Yes. Double-trigger RSUs at private companies vest in two stages - time-based plus a liquidity event - and the tax recognition is at the second trigger, not the first. The bot covers the planning framework for double-trigger RSUs (post-IPO 180-day lockup, tax recognition on settlement, the option to sell into the IPO window) at a high level and defers the actual strategy to the CFP after the lockup terms are reviewed.

California has its own AMT, no QSBS conformity (a major issue for the pre-IPO pattern), and a 13.3% top marginal that compounds the federal supplemental withholding gap badly. The bot recognises California addresses or California-specific questions and applies the state-specific framing. The bot also flags the planning conversation around residency changes - the trailing nexus and exit-tax-equivalent issues - and routes that to the CFP.

Yes. The bot covers the two-year-from-grant and one-year-from-purchase holding requirements for qualifying disposition, the ordinary-income-on-discount treatment for disqualifying disposition, and the same-day-sale operational pattern. It will not tell the prospect which to do, because the answer depends on the prospect's full tax picture and the company stock concentration math. The CFP runs that on the planning call.

Yes. The bot captures the unvested value, the title or role, and the company stage early in the conversation. Senior IC at FAANG goes to the equity-comp generalist; VP+ at a public company goes to the executive-comp specialist who handles 10b5-1 plans; pre-IPO employees go to the pre-IPO specialist. Multibot can also run separate bots for the public tech and pre-IPO content sections of your site.