In partnership with
AI can play the skeptic you don't have on staff. One prompt, 8 hard questions, and you'll know exactly where your plan is fragile.
Master ChatGPT for Work Success
ChatGPT is revolutionizing how we work, but most people barely scratch the surface. Subscribe to Mindstream for free and unlock 5 essential resources including templates, workflows, and expert strategies for 2025. Whether you're writing emails, analyzing data, or streamlining tasks, this bundle shows you exactly how to save hours every week.
42% of failed startups share one thing in common: they built something nobody wanted.
Not because they were stupid. Not because they lacked talent. Because they never stress-tested their assumptions before they believed them.
CB Insights analyzed over 100 startup post-mortems. "No market need" topped the list — ahead of running out of cash, getting outcompeted, or bad timing.
Here's the uncomfortable part: most founders thought they'd validated their idea. They talked to friends. Got encouraging feedback. Maybe even ran a survey.
But friendly questions produce friendly answers. And friendly answers don't prepare you for unfriendly markets.
The Problem Isn't Bad Ideas — It's Untested Confidence
McKinsey calls it a "premortem": imagining your project has already failed, then working backward to find out why. Research shows it surfaces risks that optimism buries.
But premortems have a weakness. You're still the one asking the questions. And your brain is very good at protecting ideas it's already attached to.
What you need is an outside perspective. Someone who doesn't benefit from believing you.
Enter the Competitor Interview
Instead of asking AI to analyze your plan, ask it to interrogate you.
You answer. AI probes. One question at a time.
This works because:
Vague confidence collapses under specifics
Weak assumptions reveal themselves without drama
You hear your own answers out loud — and notice which ones feel thin
The most useful lens to start with: a smart competitor. Not hostile. Not ignorant. Just someone with zero emotional investment in your success.
Most people don't make it past 6-8 questions before they learn something uncomfortable. That discomfort is the value.
The Prompt (Copy This)
Use this once before any decision that's hard to reverse — a launch, a hire, a pricing change, a partnership.
You are a well-run competitor evaluating my next move.
Interview me with one question at a time.
Your goal is to understand:
- Where this idea is fragile
- What assumptions I'm making without evidence
- Whether this move is defensible or easy to copy
Do not give advice.
Do not summarize.
Only ask clear, skeptical questions.
Wait for my answer before asking the next one.
Want a second perspective? Run this immediately after:
Now switch roles.
You are a potential partner who could help this succeed — but doesn't need this deal.
Interview me to decide:
- Whether this creates leverage or friction
- Whether incentives are aligned
- What would make you walk away
Ask one question at a time.
Do not suggest improvements.
Only interview.
🛠️ Tool Worth Knowing: Claude Projects
If you run these interviews regularly, Claude's Projects feature lets you save the prompt as a permanent instruction — so every new conversation starts in "interviewer mode" without re-pasting.
How to Set It Up:
🌐 Web: claude.ai → Projects → New Project
📱 Mobile: Claude app → Projects tab
💻 Desktop: Claude desktop app → Projects
Add the competitor prompt to "Project Instructions" and every chat inside that project starts skeptical.
🗞️ Quick Bites
META'S SECRET AI MODELS ARRIVE
Meta's Superintelligence Labs delivered its first internal AI models
this month. No details on capabilities — just "significant promise."
Translation: they built something and aren't ready to show it yet.
────────────────────────────────────────────────────────────────
NEURIPS PAPERS CAUGHT WITH FAKE CITATIONS
AI detection company GPTZero found 100+ hallucinated citations
across 51 papers at one of AI's most prestigious conferences.
Fake author names. Non-existent DOIs. All peer-reviewed and accepted.
────────────────────────────────────────────────────────────────
2026: THE "SHOW ME THE MONEY" YEAR
Menlo Ventures partner Venky Ganesan says enterprises will demand
real ROI this year — not pilots, not demos. "Boards will stop
counting tokens and start counting dollars."
⚡ Your Action Step
Before your next big decision, run the competitor interview once — in writing.
Don't defend. Just answer. Pay attention to questions where you hesitate, answers that feel thin, or claims you can't back up without "trust us" language.
That's where the work is.
📚 Sources
STATS & RESEARCH
CB Insights: Top Reasons Startups Fail — 42% failed due to no market need
McKinsey: Biases in Decision-Making — Premortem methodology for surfacing risks
Inc: 42% of Startups Trip Over This One Point — Analysis of market need failures
NEWS BITES
HumAI Blog: AI News January 2026 — Meta Superintelligence Labs, GPTZero NeurIPS findings
Axios: AI 2026 Trends — "Show me the money" year for AI ROI
|
Pro‑Grade Material Weights in SecondsBuilt for contractors, architects, and engineers.
Trusted by Pros Nationwide. |
About This Newsletter
AI Super Simplified is where busy professionals learn to use artificial intelligence without the noise, hype, or tech-speak. Each issue unpacks one powerful idea and turns it into something you can put to work right away.
From smarter marketing to faster workflows, we show real ways to save hours, boost results, and make AI a genuine edge — not another buzzword.
Get every new issue at AISuperSimplified.com — free, fast, and focused on what actually moves the needle.
|
If you enjoyed this issue and want more like it, subscribe to the newsletter.
Brought to you by Stoneyard.com • Subscribe • Forward • Archive