Eras
1985 My NeXT Amiga 1996 I’m a Mac 2002 Terminal EDGE 2008 Mobile Developer 2012 Geolocated 2018 Boston Flight 2025 Singularity ●
1985 – 1995
My NeXT Amiga
Commodore Amiga 1000 / 500 / 1200
In 1985, Commodore launched the Amiga 1000 and Steve Jobs left Apple to found 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. When Commodore collapsed in 1994, Jobs was preparing his return to Apple — bringing NeXT’s Mach kernel and BSD foundations that would become OS X, the operating system I’d eventually spend forty years on.
1996 – 2001
I’m a Mac
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 forty 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. Searched my surname “Sweeney” and discovered my MacSweeney lineage.
2002 – 2007
Terminal EDGE
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 forty 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
Mobile Developer
iPhone 1 → iPhone 4S · Objective-C · App Store 2008
The iPhone SDK changes everything. Self-taught Objective-C using Aaron Hillegass’ book, transforming a network admin into an actual iOS engineer. Just a PlainJoe making his way to AOL in Palo Alto — I was now a super commuter, a literal mobile developer.
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
Geolocated
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
Boston Flight
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
Singularity
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.