From Roadie to Developer: Loading Gear for Ringo
The unlikely path from Silicon Valley celebrity roadie to AI entrepreneur.
TL;DR: Before I wrote code for a living, I loaded trucks for rock bands in Silicon Valley. The job taught me more about logistics, pressure, and execution than any computer science class. Lessons I still use when shipping software today.
A Night at the Mountain Winery
It’s the summer of 2000, the peak of the dotcom boom, and I’m twenty years old, standing in the back of a 53-foot truck at The Mountain Winery in Saratoga, California. I’m stacking road cases for Ringo Starr’s All-Starr Band. The load-in started at midnight. The show is in fourteen hours. Between now and then, every cable, every monitor, every piece of staging has to move from this truck to that stage in a specific order, because if the drum riser goes in last, everything else has to come out again.
I was a web design student at the time, picking up roadie gigs through a buddy who worked for a Bay Area production company. The pay was decent. The hours were brutal. The education was priceless.
What Roadie Work Really Is
People hear “roadie” and think groupies and guitar picks. The reality is logistics under pressure.
Load-in is a timed operation. You have a call time, a stage time, and a truck full of gear that has to be in the right place in the right order. Miss a dependency and you’re re-stacking at 6 AM while the lighting director watches.
The show is hours of invisible work. You’re backstage making real-time fixes. A monitor blows, a cable shorts, a set piece won’t lock into place. You fix it without the audience knowing anything happened.
Load-out is the reverse, faster, and usually at 1 AM after you’ve been on your feet for twenty hours. Teardown, pack, truck, drive. Do it again in another city.
I did this for acts like Ringo Starr, Cheap Trick, and Natalie Merchant. The names were fun. The work was the same every time: execute a complex plan under pressure, handle surprises without drama, and leave the venue cleaner than you found it.
What It Taught Me About Shipping Software
I didn’t realize it at the time, but roadie work was the best training I could have gotten for a career in software.
Critical paths are real. In a truck pack, if the bass rig is buried behind the lighting truss, you’re not getting to it without unpacking half the truck. In a software deployment, if your migration has to run before your schema changes, you better know that before you ship. Dependencies don’t care about your feelings.
You plan for failure before the lights go on. Every show carried backup cables, backup mics, backup power strips. Not because something always broke, but because when it did, there was no time to improvise. I build software the same way now: fallback paths, retry logic, and sane defaults for when the primary plan doesn’t survive contact with reality.
Execution is calm, fast iteration with clear ownership. Nobody screams during load-in. You just fix the problem in front of you, communicate what changed, and keep moving. The best engineering teams I’ve worked on operate exactly the same way.
The Jump to Tech
I was already designing websites in college when I was loading trucks on the side. The web work was where my head was. The roadie work was where I learned how to execute.
When I moved into software full-time, I expected the transition to feel bigger than it did. But the core skill set transferred almost perfectly: plan the work, sequence the dependencies, build in redundancy, stay calm when things go sideways, and never leave a mess for the next crew.
The biggest surprise was how much of the software industry lacks that operational discipline. Smart people building brilliant systems with no fallback plan, no staging environment, no checklist. It was like watching a crew try to load a truck without a pack list. It works until it doesn’t, and when it doesn’t, it fails in the most expensive way possible.
Key Takeaways
- The best training for software engineering might not look like software engineering. Logistics, operations, and high-pressure physical work build instincts that no tutorial can teach.
- Dependencies are real in every domain. If you can’t sequence a truck pack, you can’t sequence a deployment.
- Redundancy isn’t paranoia. It’s professionalism. Have a backup for the thing that can’t fail.
- Calm execution beats brilliance under pressure. The person who stays steady and communicates clearly will outperform the genius who panics every time.
- Leave the venue cleaner than you found it. Leave the codebase cleaner than you found it.