It Started with a Skateboard Video
Three things I love: making videos, writing Ruby, and my family. It took me almost thirty years to get all three into the same project.
1999: the Dazzle disaster
In 1999 I was a senior in high school with a PC, a camcorder, and a crew of friends who skated everything in town. We filmed constantly. The plan was simple: capture the footage with this Dazzle hardware and software I'd bought for my PC, and edit our own skateboard videos.
The Dazzle never worked. Not once, not really. We spent months on it — installs, support calls, reinstalls, more support calls. Eventually Dazzle's own support people admitted it wasn't going to work and gave us our money back.
Then a friend said the sentence that changed my life: "Macintosh is a computer that edits video."
We dropped $2,999 on a PowerBook G3 — the Wallstreet. (I couldn't have told you at the time whether it was an "Apple" or a "Macintosh." Turns out 1999 was exactly when Apple was dropping the Macintosh name, so my confusion was period-correct.) And the thing just... worked. Within days I was editing our skate videos — on Final Cut Pro, I'm pretty sure, which had shipped that same year.
After months of fighting a PC, that mattered more than the videos did. I wasn't just making skate tapes anymore. I was hooked on computers.
Love #2
That laptop set the course: video led to graphic design, graphic design led to college, and college led to code. I did the tour — Perl, PHP, C#, ASP.NET. All of them fine. None of them felt like the PowerBook moment.
Then in July 2004, DHH released Rails. I was there the very first month. Ruby was the Wallstreet all over again: after years of fighting my tools, here was one that just worked — and was a joy on top of it. Twenty-two years later I run a Rails agency. Still writing Ruby every day. Still not tired of it.
Love #3
Every summer our whole family — the Wolfpack, fifteen of us this year — heads to Kauai. And every year I come home with hours of GoPro and iPhone footage that nobody ever watches, because editing a family movie is a weekend nobody has.
This year I finally brought all three loves together. I sat down with Claude Code and built a home-movie pipeline. In Ruby, naturally:
- A script decodes the GPS telemetry hiding inside every GoPro clip — satellite timestamps, coordinates, even how fast you were moving — and sorts nine days of footage into named sessions: Hanalei Bay, the Nā Pali coast, Tunnels Beach.
- A shot selector reads that metadata (plus historical weather and sunset times) and builds the cut — 99 shots across ten scenes, photos woven in with the video.
- ffmpeg assembles the whole thing. The kind of tool 1999-me would have sold a kidney for, sitting free on every machine.
- And the narration has no script at all. The recorder shows me a cue card for each day — where we were, what's on screen — and I just talk into the laptop mic. It even transcribes my words into subtitles automatically.
The result is a real movie. Our eleven-year vow renewal on Shipwreck Beach at golden hour. The raft up the Nā Pali coast. Tropical Storm Lala canceling our flight home and gifting us three bonus days at the Grand Hyatt. My kids doing backflips off the Hanalei pier — right around the age I was when I was pointing a camcorder at skateboards.
Full circle
In 1999, making one skate video took months of failure, a refund from Dazzle, and a $2,999 laptop. In 2026, I described the movie I wanted in plain English, kept the interesting parts in Ruby scripts I can read and change, and recorded the narration in my own voice from a terminal.
The tools changed. The reason didn't. I wanted to make videos of the people I love doing the things we love. That's what the Dazzle couldn't do, what the Mac barely could, and what Ruby — with an AI pair programmer — now does in an afternoon.
Yet another awesome trip.