Where strategy meets execution — exploring how AI is transforming businesses, markets, and value.
| Platform |  | Pricing | Freemium | Publishes | Twice weekly |
|---|---|---|---|---|---|
| Issues | 103 | Founded | a year ago | Last Issue | 10 days ago |
| Active | |||||
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cashandcache.substack.comLatest Issues
Your Claude Skills Are Passing Every Check and Still Wrong.
Four times in one afternoon, a Claude Skill or the system running it quietly did something other than what it looked like. Here's what I found, and what catches it automatically now.
A blank permissions field almost gave a scheduled AI tas...
Your AI Sounds Confident About Your Portfolio. Make It Prove It.
Four years on a desk taught me there's no correct portfolio. Only weights, and what each one quietly costs you.
🧠TL;DR: Asking AI “what is a bond” gets you a fluent, generic, useless answer. Instead: ground it in the real document (Gemi...
The 3-Layer AI Accuracy Framework (Most People Only Use 1)
Why polished AI output gets checked less, and how Second Memory automates the fix.
The output didn’t get more accurate. Instead, it got more convincing.
Your Org Remembers Everything. It Understands Less.
🧠TL;DR: AI is solving institutional memory. Meetings recorded, decisions documented, context retrievable in seconds. The paradox: organizations may remember more while understanding less. Neha Kabra, McKinsey partner and returning Cash &...
The Advantage Is Not Using More AI. It's Choosing Better.
🧠 TL;DR: A year of running this newsletter on the same AI stack we write about taught us three things. Our readers don't share one job, so they shouldn't share one stack — and the right entry point depends entirely on where you're starti...
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Authors
The writers behind this newsletter.
I make sense of AI and tech for the people doing the work — PMs, investors, operators, and builders. Ex-quant trader. I care about what works in production, not what sounds good in a pitch deck.
I write LinkedIn content for High Ticket Online Coaches which makes your dream clients DM you. Insights to attract and close more (high quality) leads by creating less but right content.
Security Engineer | M.S. Cybersecurity, CISSP | AWS, NSA, USMC.
Senior Technology Consultant | Co-founder @ Cash&Cache | Venture Capital Fellow & Scout | M.Sc Financial Engineering
Builds With AI | I write about execution friction, for ND workers (Between Thinking and Doing) and teams rolling out AI (The Data Letter)
Enter an unusually curious room for thinking, noticing, and making with AI. You’ll dissect ideas, explore systems with taste, go down cultural rabbit holes, and (always) be joined by classy robots who finally escaped the circus.
Visual brand strategist for solopreneurs building with AI. The most fun you'll have learning AI branding and you'll come out looking like a real brand. Join 1,500+ flamingos building full brand systems that drive consistent subscriber growth. \ud83e\ude77\ud83e\udda9
McKinsey Partner. Business is changing faster than organisations can adapt. I write about the decisions that shape complex choices across AI, technology, leadership and execution - helping leaders think more clearly about what comes next.
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