From Stamps to Servers: How I Stumbled Into a Career in Tech
There's no straight line from packing boxes at a shipping store in Marin County to managing a team of security engineers at one of the world's largest network companies. But looking back, I can trace every step — and most of them were happy accidents. What looks like a winding career path was actually something simpler: a decades-long project of turning a personal obsession into a profession.
It Started Before the Career Did
Long before I had a job title, I had a hobby that most people around me didn't fully understand.
In middle school, while other kids were doing other things, I was dialing into bulletin board systems — BBSs. This was the pre-internet internet: text-based, slow, deeply nerdy, and absolutely captivating. You'd connect to a local BBS, leave messages, download files, and if you were lucky, find your way into networks like FidoNet, which stitched together BBSs across the country into something that felt, in retrospect, like a crude but genuine precursor to the web.
From there it was Usenet, early online communities, and eventually AOL — which for a lot of people was their first taste of being online, but for those of us who'd already been lurking in the BBS world, felt almost too polished.
Alongside the networking obsession came PC gaming — not just playing games, but the tinkering that came with it. Getting games to run meant learning DOS, understanding memory management, editing config files, and developing an intuition for how software and hardware talked to each other. Frustration was the curriculum.
And then there were the operating systems. Where most people were content to use whatever came preloaded, I wanted to understand the alternatives. Linux and FreeBSD were a revelation — open, configurable, demanding. Alongside macOS and Windows, working across multiple OSes built a kind of platform-agnostic thinking that would prove useful for the rest of my career.
None of this was a career plan. It was just what I did for fun.
The Beginning: Mail Boxes Etc., Mill Valley, CA
My first real job was at a Mail Boxes Etc. in Mill Valley, California. If you grew up in the Bay Area, you know Mill Valley — tucked into the hills of Marin County, boutique and a little sleepy. My job was decidedly unglamorous: packing boxes, processing shipments, helping people navigate fax machines. Not exactly a launchpad for a tech career.
A year in, I moved to a second MBE location over in Corte Madera. Same work, slightly different zip code. It taught me something I still use every day: how to talk to people who are frustrated, in a hurry, or just want the thing to work without explanation. Customer patience isn't born — it's forged behind a counter.
The Pivot: Stream International, 1997
In 1997, life took a turn. I relocated and landed at Stream International, a major outsourced tech support operation. This was the era of dial-up internet, modems, and the explosion of consumer tech — and Stream was right in the middle of it.
This is where the hobby and the job finally started to converge. The kid who had spent years on BBSs and wrestling with Linux configs was now getting paid to understand why networks broke and how to explain it to people who just wanted to get online. My teams gave me exposure to the industry at scale:
- Sprint — Telecommunications, early internet service, learning how networks actually move data
- EarthLink — One of the early ISPs that brought millions of people online; I lived in the trenches of "why can't I connect" calls
- 3Com — Networking hardware, modems, and the gear that wired homes and offices together
The vocabulary I'd built tinkering at home suddenly had professional context. It wasn't a career change — it was a career beginning.
The Enterprise Detour: adidas via EDS
From consumer support, I stepped into the enterprise world as a contractor through EDS (Electronic Data Systems), placed at adidas. This was a different universe — structured IT environments, global infrastructure, the discipline that comes with serving a major international brand.
EDS placements had a way of exposing you to how large organizations actually ran their IT. Less "why won't my modem connect" and more "how do we keep global systems running." The contrast was sharp, and the experience invaluable.
Bay Dynamics: Where Security Got Serious
Next stop: Bay Dynamics. This is where the cybersecurity thread of my career began to pull tighter. Bay Dynamics was doing security analytics — user behavior, risk scoring, the kind of work that would become table stakes in enterprise security a decade later. Being there during that phase gave me early exposure to concepts that are now core to zero trust architectures and modern security operations.
The through-line back to those early BBS days was becoming clearer. Understanding networks at a deep level — how they were built, how they broke, how people moved through them — was exactly the foundation security work required.
The Launch: A Nudge from Chris Gray
Every career has a turning point, and mine had a name: Chris Gray.
Chris — now at OPSWAT — saw something in me before I fully saw it in myself. He nudged me into the Solutions Engineering track and then backed it up with action, bringing me over to Symantec where the real work began.
Symantec: Finding My Territory
At Symantec I was paired with Rich Young, and together we covered the Pacific Northwest territory. It was a formative stretch — enterprise security sales cycles, deep technical evaluations, and learning what it actually means to be a trusted advisor to organizations trying to protect their infrastructure.
The Pacific Northwest has its own character: a mix of established enterprises, aggressive tech companies, and a regional culture that values substance over flash. Rich and I built something real there, and those years sharpened every skill I had developed to that point.
That chapter ran until 2019, when Broadcom acquired Symantec's enterprise security business. Acquisitions are a fact of life in enterprise tech, but they're rarely clean. This one prompted a decision point — and a move.
Relocation: Portland to Dallas
With the Broadcom transition came a second major relocation in my career. I packed up Portland, Oregon and moved to Dallas, Texas — a different pace, a different market, and a new chapter.
BeyondTrust: A Stepping Stone
Dallas opened the door to BeyondTrust, a privileged access management company with a serious enterprise security pedigree. They gave me the opportunity to make the move work, and I'm grateful for that. But over the course of a year it became clear the cultural fit wasn't there for the long term. Knowing when a role isn't right for you is just as important as recognizing when one is — and I moved on.
Area 1 Security: The Right Room at the Right Time
The next stop turned out to be one of the most consequential: Area 1 Security, a cloud-native email security company built around stopping phishing attacks before they land. The product was sharp, the team was sharp, and the culture fit in a way that BeyondTrust hadn't.
Then came the news: Cloudflare acquired Area 1 Security. What had been a great role at a focused startup became a seat inside one of the most ambitious companies in enterprise networking and security. The acquisition wasn't an ending — it was an on-ramp.
Where It Led
Today I'm a Solutions Engineering Manager at Cloudflare, focused on Zero Trust and cybersecurity. I lead a team of specialists helping organizations rethink how they secure their networks and users.
When I think about the kid who was dialing into BBSs in Marin County, reading FidoNet message threads, and staying up too late trying to get Linux to boot — this is where that curiosity led. Not in a straight line. Not on a plan. But the obsession was always there, quietly driving everything else.
The through-line isn't obvious until you look backwards. Mail Boxes Etc. taught me to serve people under pressure. Stream taught me that networks break and customers need someone who speaks human. EDS and adidas taught me enterprise scale. Bay Dynamics taught me that security is a discipline, not a feature. Chris Gray and Symantec turned that raw material into a career. BeyondTrust taught me to trust my instincts about fit. Area 1 Security — and the acquisition that followed — landed me exactly where I was supposed to be.
Not every path into tech looks like a CS degree and a bootcamp. Sometimes it looks like a kid with a 2400 baud modem and too many questions.