1985 – 1995
From Amiga to NeXT
Commodore Amiga 500 / 1200
While I was learning to code on an Amiga 500, Steve Jobs was in exile building NeXT. Two parallel paths that wouldn’t converge for another decade. The Amiga multitasked before the Mac did and rendered graphics the PC couldn’t dream of. It also died. Riding a technically superior platform into irrelevance teaches you something no computer science class covers: merit and survival are separate arguments. Meanwhile, NeXT was building the Mach kernel and BSD foundations that would become OS X — the operating system I’d eventually spend thirty years on.
1996 – 2001
The conversion
Apple PowerBook 190 · PowerBook 1400c · 33.6 modem · AOL
College bookstore. Academic discount. The Amiga was dead and I needed a platform that would outlive me. Classic Mac OS was neither the best nor the most logical choice. It was the most interesting one. That distinction has mattered for thirty years.
Three defects. Three returns. Apple sent a 1400c — newer, better, no charge. Connected via 33.6 modem to AOL: the first breath of the public internet. A company that answers failure with generosity earns loyalty that outlasts product cycles. The G3 years followed — dreaming of affording one while Apple transitioned to OS X.
2002 – 2007
G4 · Network admin · LAMP
G4 Quicksilver · G4 PowerBook → MacBook Pro · OS X 10.2 → Tiger
Bought a G4 Tower and my first G4 PowerBook — which became the MacBook Pro mid-generation. OS X reveals the Unix soul that NeXT put there. Apache, MySQL, PHP — running natively on hardware that enterprise didn’t take seriously. Network admin by day, LAMP stack developer by night. The market catches on years later. By then I’ve been shipping from this stack since the G4 tower in the spare room.
This is the pattern that repeats for thirty years: Apple’s platform advantages become obvious in hindsight. Being there first isn’t luck — it’s paying attention to what the architecture implies before the marketing explains it.
2008 – 2012
iOS engineer · PlainJoe · AOL
iPhone 1 → iPhone 4S · Objective-C · App Store 2008
The iPhone SDK changes everything. Self-taught Objective-C, then transformed from network admin into an actual iOS engineer. PlainJoe first, then AOL in Palo Alto — closing the most unlikely loop in this timeline: the same company whose dial tone got me online in 1996.
I rode my bicycle to work past a house on Waverley Street before I understood whose it was. Apple trees in the front yard. A bicycle for the mind, ridden past the house of the man who named it that.
2012 – 2017
MapQuest · The geospatial payoff
iPhone 5 → iPhone 7 · Swift from day one · MapKit
In 2007 I stood outside the Glendale Galleria Apple Store and waited in line for the first iPhone before it was cool to do that. Launched the Maps app. It inspired me to become an iOS developer so I could work in geospatial technology. That bet paid off my first day at MapQuest. Swift arrived in 2014 and I adopted it from day one.
2018 – 2025
Architect · Wayfair · APG
MacBook Pro · Swift 5 · Apple Silicon announced 2020
The transition from building features to designing systems. Software architect and team lead, first at Wayfair then at APG. Apple Silicon announced in 2020 — and the implications for edge computing are immediately apparent to anyone who’s been watching the architecture. The AI governance thesis begins to form here: what happens when the tools that builders use to think and build are themselves becoming intelligent.
2025 → now
Solo governance architect · Technical writer
Mac Mini M4 Pro · 6-node Kubernetes · Mac Studio M5 Ultra (incoming)
Six-node Kubernetes on Intel Mac Minis for the control plane. Mac Mini M4 Pro as the edge AI lab with ClawLaw’s constitutional governance layer between Claude and the filesystem. Mac Studio M5 Ultra arriving for large model inference. The full stack from philosophy to firmware, running in one room.