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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
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

GCP Professional Cloud Architect (2025) Visual Reference

References - Section 1 - Section 2 - Section 3 - Section 4 - Section 5 - Section 6 - Combined I created some diagrams & tables for last minute certification prep and wanted to share them. This guide covers detail from each subsection with explanatory diagrams and decisions trees to help you master key trade-offs and references for the exam. Enjoy! Section 1 – Designing Cloud Solution Architectures Exam Weight: 28% Post Word Count: 1733 Design scalable, reliable, and secure architectures. Learn how to map business and technical requirements to GCP services. ...

Published on March 31, 2025 · Last updated on June 9, 2025 · 4 min · 829 words · Jon Shaffer

LinkedIn Learning Access From Your Library

tl;dr for Pittsburghers: Sign up for Carnegie Library and login with your Library Card. More info at carnegielibrary.org. While studying for the CISSP, I discovered that you can access LinkedIn Learning for free through partnerships with local libraries! This is a fantastic opportunity to access a wealth of professional courses without the usual subscription fees. What Is It? LinkedIn Learning, formerly known as Lynda.com, offers thousands of courses on topics ranging from technology and business to creative skills. Many libraries have partnered with LinkedIn Learning to provide their patrons with free access to this extensive library of courses. ...

Published on September 15, 2024 · Last updated on June 9, 2025 · 2 min · 415 words · Jon Shaffer

Tips and Resources for Passing the 2024 CISSP

On July 25th, I was thrilled to learn that I had passed the CISSP exam 🥳. In this blog post, I’d like to share my experience, the resources that helped me, and some tips for those preparing for the CISSP exam. Passing the exam allowed me to fully enjoy a much-needed vacation with my wife, celebrating both the Olympics and this personal achievement without worrying about domain knowledge for two whole weeks. ...

Published on September 15, 2024 · Last updated on June 9, 2025 · 9 min · 1705 words · Jon Shaffer