A premortem is a gut check you run before you build something, not after it breaks. Instead of waiting for a launch to fail and doing an autopsy, you sit down beforehand and ask what would have caused this to fail, then fix those things before they happen.
I run a premortem on every AI product or automation I build, and I've started using Claude to do it systematically. Before anything ships, I ask Claude to stress test the idea across three lenses.
Tech stack: will this break something else, does it introduce a dependency that's fragile, a rate limit I'll hit, an integration that's one API update away from failing.
Customer experience: does this improve the experience, degrade it, or is it neutral, since AI features are easy to ship and easy to get wrong.
Business perspective: does this increase costs, increase revenue, or create new problems, since new tools have a way of solving one thing and quietly creating three others around billing, support load, or compliance.
HERE IS THE PROMPT:
Run a premortem on this idea before I build it: [describe your idea]. Assume it failed. Tell me why, looking at three angles: 1) Tech — what could break or become a fragile dependency, 2) Customer experience — does this improve, degrade, or not change the experience, 3) Business — does this raise costs, raise revenue, or create new problems. Be specific and blunt.
Running this before you build, instead of discovering it in production, is the whole point. It's cheaper to catch a bad assumption in a conversation with Claude than in a client escalation.
E-commerce watch. The "golden age" pitch actually has teeth this time. Shopify president Harley Finkelstein has been making the rounds saying AI is ushering in a golden age of entrepreneurship, and normally I'd roll my eyes at that kind of headline. But the specific features he's pointing to are real and live right now: Sidekick (Shopify's built-in AI assistant), automated product descriptions, AI-handled customer support. If you run an e-commerce store and haven't touched any of these, that's a short to-do list worth ticking through.
Tools Worth a Look
· AdAnt AI: AI agents that handle your paid social ad strategy, creation, and iteration across TikTok and Instagram. For small business owners running paid social without an agency.
· Prelint: Reviews AI-written code against your past architecture decisions before it ships. For technical founders or small dev teams using Cursor, Copilot, or Claude Code.
· Aegisora: Open-source proxy that intercepts risky AI agent actions, masks customer data on the fly, and logs everything for compliance. Free. For small businesses running AI agents that touch customer data or external APIs.
Also Worth Knowing
· AI in a broken process just automates the chaos: A founder post-mortem on exactly this problem. If your workflow is a mess before you automate it, it'll be a faster mess afterward. Read this before your next automation project and run premortem on everything.
· AI vendors are starting to charge only when they deliver results: Instead of flat SaaS fees, some vendors are moving to outcome-based pricing, meaning you pay when the AI actually does something measurable. Early signal, but worth knowing before you sign your next contract.
· AI is now influencing small business loan approvals: If you're thinking about a line of credit or a growth loan, the model reviewing your application may not be human. Worth understanding how that changes your preparation.
-Scott
SmartOwner is published (almost) daily by the team at DigitalTreehouse. Want AI consulting or automations for your business? Reply to this email.