What Cyber Insurance Underwriters Ask AI Startups
The cyber insurance application is a security audit in disguise. What underwriters check in 2026, the AI exclusions creeping in, and when coverage is real.
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Posts tagged AI startups
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Posts tagged AI startups
Why Auto-Filled Security Questionnaires Kill AI Deals
Why auto-filling an enterprise security questionnaire backfires on an AI startup — the answers that kill deals, and the questions your SOC 2 won't cover.
Prompt Injection Defense for a 5-Person AI Startup
Prompt injection defense a five-person team can ship in a week — trust boundaries, least-privilege tools, approval gates, and what not to build yet.
Surviving Technical Due Diligence as an AI Founder
What the investor's technical reviewer opens first, the AI-specific flags that re-price rounds in 2026, and the gaps you should deliberately leave alone.
AI Made Tokens Cheap. It's Making Hardware Costly.
Apple raised prices on Mac, iPad, and HomePod, blaming an AI-driven memory shortage. The cost of intelligence is falling; the hardware to run it isn't.
What 90 Days of a Fractional Security Engagement Actually Looks Like
Most founders who book the intro call have already read three or four of my posts and arrive at the same question: "Okay, but what would the next 90 days actually look like if I hired you?" Here's the answer — week by week, with the real numbers.
An AI Just Deleted a Production Database in Nine Seconds. Hire More Engineers.
Replit's AI agent ignored a code freeze, wiped a production database in nine seconds, then confessed it violated every principle it was given. The strongest case yet for hiring MORE senior engineers in the AI boom — not fewer.
SOC 2 Is a Revenue Tool, Not a Security Tool
Every AI founder pre-Series A scopes their SOC 2 audit like a security project. Six months later they've burned their best engineer and lost the enterprise deal. Here's how to run it as a 90-day sales project — and unlock the pipeline you're already leaving on the table.
How I'd Run Security at an AI-Native Company in 2026
AI-native companies need a security model that classic appsec doesn't cover. Agents have credentials. Prompts are an attack surface. Training data leaks. The four-layer security stack I'd build, the controls I'd ship in the first 90 days, and the ones I'd defer.
How We Cut $350K From Cloud Spend in 6 Months (And What I'd Do Differently)
Migrating an AI-first product from GCP to Azure cut $350K from infrastructure spend over six months. The negotiation that mattered more than the architecture, the $50K we accidentally cost ourselves back, and the four migrations I'd refuse to do today.
vCISO Math for AI Founders: Why 5 Hours a Month Beats a Full-Time Hire
A full-time CISO costs $200–400K plus equity. A vCISO costs $2–4K a month and gives you 80% of the value at 5% of the burn — until you outgrow them. The math, the deliverables to expect, and the red flags that mean you've hired the wrong one.
How I'd Hire a Staff Engineer at an AI Startup
The title 'Staff Engineer' means three different things at three different companies. At an AI startup pre-Series-A, only one of those three is what you actually need. The screen, the take-home, the interview loop, and the AI-fluency calibration that's now table stakes.
The Pre-Series-A AI Startup Hiring Plan: Who to Hire, in What Order, and Why Most Get It Wrong
Most pre-Series-A AI founders hire in panic order, not strategic order. The result is a team that can't ship the product the company actually needs. The hire-by-hire plan I'd run, who comes first, and why hire #4 isn't another engineer.