Sparrow named Gaston

wCTO Month 2: 500 Deployments, 3 Business Processes, 1 Sparrow

After 500 deployments and 137k lines of code, the biggest lesson is business beats code every time.

Published on July 7, 2025 · Last updated on July 7, 2025 · 9 min · 1834 words · Jon Shaffer
One Does Not Simply Upload Photos

wCTO Weeks 5 & 6: One Does Not Simply Upload Photos

Two weeks of architectural refactoring, expensive naps, and the deceptively complex journey of building a simple upload button.

Published on June 22, 2025 · Last updated on June 25, 2025 · 4 min · 721 words · Jon Shaffer
WIF Infrastructure vs Legacy Secrets scoreboard

wCTO Week 4: When AI Agents Meet Reality (and Your Basement Floods)

AI agents, missed deadlines, and over 60 gallons of basement water. Trust level: 35%.

Published on June 8, 2025 · Last updated on June 9, 2025 · 6 min · 1170 words · Jon Shaffer

wCTO Week 3: The Infrastructure Grind and My 8-Year Apple Developer Identity Crisis

Shipped to TestFlight, automated releases, and learned that ‘infrastructure week’ doesn’t impress spouses.

Published on June 1, 2025 · Last updated on June 9, 2025 · 6 min · 1278 words · Jon Shaffer
Marketing website animated screenshot

wCTO Week 2: 2 weeks ago I started as a wCTO (wife's CTO).

Built features that save 73% of photo processing time. Wife’s response: ‘What about the other 27%?’

Published on May 25, 2025 · Last updated on June 9, 2025 · 3 min · 512 words · Jon Shaffer
Script-generated code planning diagram

wCTO Week 1: I just added my first open source swift package

My wife sells vintage clothes. I’m building her an app. What could go wrong?

Published on May 18, 2025 · Last updated on June 9, 2025 · 2 min · 385 words · Jon Shaffer
Script-generated code planning diagram

wCTO Day 1: What took me weeks took Gemini Pro 2.5 12 hours and $80

Built a Swift app in 12 hours with zero Swift experience. Gemini Pro 2.5 + $80 = mind blown.

Published on May 7, 2025 · Last updated on June 9, 2025 · 2 min · 262 words · Jon Shaffer