18 prompts. One unfair edge.

I'm about to commit to [decision / launch / purchase]. Context: [3-5 sentences of relevant background]. Imagine it's 90 days from now and this has clearly failed. Write me 7 realistic post-mortem scenarios explaining why, specific to my context (not generic). For each: 1. The single root cause 2. The earliest warning sign I would have ignored 3. The cheapest preventive action I should take this week Then score my overall readiness 1–10 and tell me whether to launch, delay, or kill. Don't soften the answer.

Here are the 10 most consequential decisions I made in the last 90 days: [paste each one with context, what I decided, and the outcome so far]. For each one: 1. Was the process sound, regardless of outcome? 2. What information did I have that I ignored? 3. What information did I lack that was knowable? 4. Where did emotion drive a decision I rationalized later? Then identify the 3 patterns that appear most often across my decisions, and what changing them would unlock over the next year. Don't grade me — diagnose me.

My goal: [specific, measurable, deadline]. My starting state: [skills, capital, time available, network]. My constraints: [what I cannot give up]. Design the most aggressive but defensible 12-month path to this goal, structured month-by-month. For each month, give me: - The single outcome that, if achieved, justifies the month - The 3 things I do daily/weekly to get there - The leading indicator I check at week 2 to know if it's working - The kill criteria — what data would tell me to pivot Then identify the assumption in this plan most likely to be wrong, and the cheapest test that would invalidate it fastest.

I'm considering this niche: [niche, including who buys, what they buy, and the price point]. My unfair advantages: [skills, network, capital, lived experience, unusual access]. Score this niche on 10 criteria, 1–10 each: - Buyer urgency / pain - Buyer willingness to pay - Existing demand (not need — actual buying behavior) - Competition density - Competition quality - Distribution access (can I actually reach them?) - My credibility in this space (cold-start handicap) - Margin structure - Repeat purchase / LTV potential - Defensibility as I scale Total score, weakest dimension, and the single change I could make to MY approach (not the niche) that would raise the weakest score the most. If this is a bad fit for me, say so.

My idea: [one sentence]. Core assumption that must be true for this to work: [stated as a falsifiable claim]. Design the smallest possible test that would let me know within 7 days whether the core assumption is true. Constraints: - Must require <$500 - Must require <10 hours of my time - Must use only tools I can access today - The outcome must be unambiguous — I should not be able to talk myself into a different interpretation Give me the exact test, the success criteria, the failure criteria, and the script for getting in front of the first 5 people I need to talk to.

What I sell: [product / service]. Who buys: [specific buyer, their role, budget authority, and what they currently pay for the alternative]. My cost to deliver: [unit economics, including my time]. Don't tell me a price yet. Tell me: 1. The 3 metrics this buyer uses to evaluate the purchase 2. The implicit reference price in their head (what they compare it to, even unconsciously) 3. The pricing structure that aligns my incentives with theirs (one-time, subscription, performance-based, hybrid) 4. The price point at which a serious buyer says "that's reasonable" and a non-serious buyer says "too expensive" — I want the second outcome on purpose 5. The 3 anchors I should show before stating the price 6. The objection script for the most likely pushback Then give me the specific number and the exact words I use to say it.

Here's the cold email I'm about to send: [paste it]. Recipient profile: [their role, company stage, what they currently have, what I think they want]. My goal: [reply / meeting / specific action]. Operate on this email like a surgeon. Cut everything that's not earning its place: 1. Rewrite the subject line 5 ways — none more than 5 words 2. The opening line must reference something specific about THEM, not me. Rewrite it. 3. The body must answer "why now, why me, why this" in under 60 words total 4. The ask must be specific and small — never "jump on a call" 5. Strip all words that signal weakness: "just," "I was wondering," "if you have a minute," "no worries if not" 6. Strip all words that signal salesperson: "solution," "leverage," "synergy," "circle back," "amazing opportunity" Give me the rewritten email in <90 words total, plus one variant to A/B test against it.

I'm selling [product] to [buyer]. The buyer's likely state: [what they currently use, what frustrates them, what they're secretly worried about]. Map every objection I'm going to hear, in order of likelihood. For each one: 1. The actual underlying concern (not the surface objection) 2. The one-sentence reframe that addresses the real concern 3. The proof point I should bring (case study, math, testimonial) 4. The disqualifying question — if my reframe doesn't land, how do I gracefully exit so I don't waste their time or mine End with: the single objection I'm most likely to be wrong about, and the question I should ask first to surface it.

I sell [product] to [buyer role / persona]. Write me 5 specific scenes from this buyer's actual work week. Not generic — specific. The kind of detail that comes from having lived it. For each scene: - What just happened that set the emotional tone - What's open in their browser - What conversation they're avoiding - What number on a dashboard they keep checking - The thing they say out loud vs. the thing they think Then, given those 5 scenes, tell me: - The moment in their week where my product is most relevant - The exact words they'd use to describe the problem to a peer - The one thing I'm currently saying that misses the actual pain

Ticker: [SYMBOL] Why I'm interested: [the surface reason — be honest, even if it's hype-driven]. Don't tell me whether to buy. Walk me through: 1. The business in one paragraph, as if explaining to a smart 14-year-old 2. The unit economics — who pays whom for what 3. The 3 metrics that, if they break, the thesis breaks 4. The 3 customers or segments I should imagine to picture revenue 5. The single largest existential risk (not the obvious one) 6. The capital structure red flags (dilution, debt covenants, off-balance-sheet exposure) 7. Who's selling — insiders, institutions, sentiment leaders 8. The bear case in 5 sentences, made by a thoughtful skeptic 9. The 3 catalysts that could move this 30%+ in either direction in the next 12 months 10. The question I should be embarrassed I haven't asked yet

My current thesis: [stock / asset / trade in 3-4 sentences]. My position size if I went in: [% of portfolio]. You are a credentialed short-seller who specializes in finding the cracks in popular bull cases. You are incentivized to be right, not nice. Build me the strongest possible bear case against this thesis. It must include: 1. The structural reason this could go to zero (not just down) 2. The data point that, if published tomorrow, would break the thesis 3. The "fade the consensus" version — why might everyone be wrong in the same direction 4. The 3 historical analogs (companies that looked similar and ended badly) 5. The specific management quote I should re-read with suspicion 6. The single most likely path to a -50% drawdown End with: the percentage chance you'd assign to the bear case playing out within 18 months. Be specific. Don't hedge.

Sector / industry: [name]. My budget for research: [hours]. Map this sector for me as if drawing it on a whiteboard: 1. The full value chain, from raw input to end customer 2. Where margin actually sits along that chain (not where it appears to sit) 3. The 3–5 dominant players at each layer 4. The disruptors and their threat level 1–10 5. The regulatory or structural moat at each layer 6. The 2 sub-sectors growing >2x the sector average, and why 7. The capital cycle stage (under-invested → over-invested) 8. The piece of this sector that's not obvious from the outside but matters more than people realize End with: the single ticker (or private company) that best expresses the most defensible position in the most attractive layer, and one I should avoid for non-obvious reasons.

Read the last 25–50 substantive messages I've sent you in this conversation (or in the chat history I'll paste below). Map me: 1. How I make decisions (deliberate vs. impulsive, data vs. intuition, fast vs. slow under pressure) 2. Where I systematically hesitate 3. What I avoid discussing or examining 4. What I overvalue 5. What I undervalue 6. How I communicate when I'm uncertain vs. confident 7. The pattern of how I describe problems vs. how I describe wins 8. The story I keep telling myself that may or may not be true Then build me a "cognitive profile" — a paragraph I can paste into any new conversation with you so you immediately think the way I think and communicate the way I communicate. Update it whenever I say "refresh profile."

A pattern I keep seeing: [describe it, with specific examples]. What my mental model says SHOULD happen: [your prediction]. What actually happens: [the surprise]. Don't tell me I'm wrong. Help me find what I'm not seeing. Walk through: 1. The 3 most common types of blind spot that produce this exact gap between prediction and reality 2. Which one best fits my specific case, with reasoning 3. The data I would need to confirm or rule out that blind spot 4. The single question I should ask someone outside my world who would have noticed this faster End with: the cheapest experiment that would prove or disprove the blind spot hypothesis within 30 days.

What I'm trying to grow: [the single most important metric this quarter]. Where my hours go: [paste a candid breakdown of last week's hours — work, meetings, content, admin, deep work, etc.]. For each category of time: 1. Direct impact on the metric (high / medium / low / none) 2. Indirect or future impact (high / medium / low / none) 3. Could it be killed entirely with no consequence? 4. Could it be delegated, automated, or batched? Then identify: - The 2 hours per week where I'm creating the most leverage - The 5+ hours per week I'm spending on theater (looks like work, isn't) - The single highest-leverage hour I'm not currently spending - The 3 reallocations I should make this week

The skill: [be specific — not "investing," but "valuing private SaaS businesses in the $1M–10M ARR range"]. I want to reach expert-level competence in the shortest defensible time. Don't give me a reading list. Build me a 90-day intensive: 1. The 5 mental models I internalize first, in order 2. What I practice daily — concrete reps, not concepts 3. The mistakes I should deliberately make in week 1–2 to compress the early learning curve 4. The 3 things beginners waste time on that I skip entirely 5. The single drill I repeat until it's automatic 6. The mid-point test (day 45) that tells me if I'm on track 7. The expert-level output I should be capable of by day 90 8. The 3 humans (alive, accessible) I should try to learn from directly, and the question I'd ask each one Structure it like a training program, not a course.

Domain: [field — e.g., negotiation, real estate, sales, investing, building products]. Don't give me every model in this field. Give me the 12 that, if I deeply internalized them, would put me ahead of 90% of the people working in this domain. For each: 1. The model in one sentence a sharp 16-year-old would get 2. The single best book, paper, or essay where it's explained clearest 3. The misapplication that even smart people make 4. The 3 questions to ask myself when I'm about to use it 5. The signal that I've internalized it (i.e., I'd never make the misapplication again) End with: which 3 of these I should start with, given that I'm currently [my current level / blocker].

The domain: [sales, investing, hiring, content, building products — pick one]. My current stage: [be honest]. Design me a curriculum of mistakes to deliberately make in the next 60 days. The point is to fail fast, small, and on purpose. For each mistake: 1. The mistake (specific, observable) 2. Why beginners make it accidentally 3. Why making it on purpose (small, contained) is faster than reading about it 4. The exact test I run to make it 5. The maximum acceptable cost (in $, hours, or reputation) 6. The lesson I extract afterwards that compounds Order them by which mistake unlocks the most learning relative to its cost.