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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
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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
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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
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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