Simon Smith on AI (Archive)

These are my archived Substack posts from 2025 and 2026. I stopped maintaining Substack because it did not feel like the right medium for me given the pace of AI progress. I mostly post on X now, with occasional posts on LinkedIn. My simple personal card page is at simonsmith.ca.

  1. How to Prepare Your Business for the Coming Wave of AI Agents
    March 11, 2026 — Digital employees are near, and they'll need skills, tools, context, and new workflows and organizational structures to be successful
  2. The Case for the AI Context Librarian
    November 17, 2025 — Decentralization worked in the copilot era, but autonomous agents need a single source of truth
  3. You're Not Extrapolating Enough
    September 18, 2025 — Most people still plan for AI as if today’s limits will last. They won’t.
  4. Proprietary Data Won’t Save You From AI Disruption
    September 14, 2025 — Speed to scale matters more, and if your data is truly valuable it will be valuable enough to get in other ways
  5. Five Keys to Successful AI Transformation
    August 27, 2025 — What I've seen work—and not—across hundreds of companies, case studies, and reports
  6. A Million Tokens Won’t Pay Your Rent
    July 31, 2025 — Universal Basic Compute is an interesting idea, but like income and services it falls short on its own
  7. The AI Browser Wars Have Begun
    July 11, 2025 — A smarter front end for the web is coming—and with it, a very different internet economy
  8. The Disappearing Interface
    June 26, 2025 — From screens to protocols: AI is disrupting decades of reliance on apps and websites
  9. Welcome to the Latent Reputation Economy
    June 9, 2025 — In a world where AI never forgets, your actions today define how it treats you, your brand, and your business—forever
  10. Stop Building Internal Chatbots
    May 31, 2025 — With AI products improving rapidly and employees using them in secret, companies that build instead of buy risk slowing teams and increasing risks
  11. ChatGPT 2026
    May 14, 2025 — Sam Altman's vision is clear: A personalized, pervasive, proactive superintelligence that acts as your life's operating system
  12. From General Intelligence to Personal Intelligence
    May 9, 2025 — Memory turns good AI into great AI but also raises the stakes, so learn how to use it before it uses you
  13. Better Ways to Benchmark AI Today
    May 2, 2025 — A practical guide for when leaderboards don’t tell the full story
  14. Be Careful What You Wish For
    April 28, 2025 — How optimizing AI models for human preference backfired
  15. The End of the Centaur Era
    April 26, 2025 — How The Intelligence Curse changed my mind about the future of work—someone using AI may take your job, but AI may take theirs, and undemocratic institutions may take the future
  16. Why Gen Z’s ChatGPT Boycott Backfires
    April 24, 2025 — Virtue signaling over AI is sabotaging students academically and professionally
  17. I Work in AI. Here’s How I’m Preparing My Kids for the Future.
    April 22, 2025 — Instead of banning them in schools, let's use ChatGPT and similar transformative tools to empower children