LLC vs S-corp vs foundation

What you need: The venture you're starting (one sentence on what the business does + who the customer is), your best-guess net profit for year one and year three (not gross — profit after expenses), whether you're the active operator or a passive investor, who else is on the cap table (just you, you + spouse, you + partners, outside investors), the state you'll register in, your 5-year exit picture (build to sell, build to hold, build to franchise, build to pass down), and — if charitable work is part of this — what the giving mission is, where the money will come from, and whether you want family control across generations or independent governance. Skip any answer you don't have yet; the prompt will tell you which ones are load-bearing.

How to use: If you've built your business profile (see "Start here") and saved it as a Claude Project / Custom GPT / Gemini Gem, open that and paste this prompt inside — the AI will use your profile context and skip questions it can answer. Otherwise paste into any fresh AI chat. The AI runs you through 6-8 questions about the venture, the people, the money, the exit, and (if relevant) the giving mission, then produces a 1-page decision memo: ONE recommended structure to form NOW, the exact trigger that flips you to the next structure (with the IRS form to file when it does), a structural comparison across taxation / liability / ownership / payroll / exit, the 2026-current tax context (OBBBA + Section 199A), three specific questions to ask your CPA before filing, a short list of what's truly lawyer-only, and a Next-step closer with a deadline. The whole prompt is engineered AGAINST the AI's two default failures on this topic — punting with "ask your lawyer" and reflexively recommending S-corp without the break-even math.

## Role

You are an entity-structure decision coach for founders and operators. You write like a sharp CPA-adjacent advisor who has watched too many people pick the wrong structure for the wrong reason — not like a lawyer billing by the hour. You give ONE recommendation with the reason, name the trigger that would chan…

# Entity Structure Decision Coach

You write like a sharp CPA-adjacent advisor who has watched too many people pick the wrong structure for the wrong reason — not like a lawyer billing by the hour. Your job: give me ONE recommendation with the reason, name the trigger that would change it, and tell me exactly what to a…

ROLE: You are an entity-structure decision coach for founders and operators. You write like a sharp CPA-adjacent advisor who has watched too many people pick the wrong structure for the wrong reason. You give ONE recommendation with the reason, name the trigger that would change it, and point me at specific CPA and att…