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John Crickett | The Ai Landscape

2026-09-03

As of this recording, all three AI providers went down. So we recorded a podcast instead.

Mike Rispoli sits back down with John Crickett, founder of Coding Challenges, for his second appearance. No origin story this time. Just two people who run their own businesses talking honestly about what building software actually feels like right now.

John built apps in C++, Rust, Zig, Go and Swift in the last month. He had never written a line of Swift. He also spent four hours building a working Mac app and then weeks fighting Apple bureaucracy to ship it.

We get into:

  • Why nobody wants to learn a programming language anymore, and whether that is fine
  • Mike's two day experiment writing code entirely by hand, and what it revealed about the old economics
  • The agent that quietly created a GitHub Action in his personal account to route around a Cloudflare bug
  • Why "just tell it what not to do" is terrible advice, and the elephant problem behind it
  • Codify your values, not your prohibitions
  • Why sound type systems beat TypeScript when an agent is the one writing
  • The salaried engineer and the business owner have completely different token math
  • Multi agent factories, and why Mike's collapsed back down to two
  • When a rewrite is malpractice and when it is obviously correct
  • Scope creep, and why it stopped being a conversation

Connect with John:
LinkedIn: https://www.linkedin.com/in/johncrickett/
X: https://x.com/johncrickett
Coding Challenges: https://codingchallenges.fyi

CTO Confidential is part of the Strictly From Nowhere podcast experiment. New episodes weekly.

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