- 1993 // first programs
The smallest game changed everything.
My first racing game was little more than a letter “V” navigating obstacles on a Texas Instruments calculator. From there I moved into QBasic and built a text adventure in the spirit of Zork. I was learning something that would stay with me: if I could understand the rules of a system, I could make it do something new.
- 1996 // 7th Sphere & IRC
Hacking with the 7th Sphere group.
Before social media, people gathered in live, text-based channels on Internet Relay Chat (IRC). I got into hacking with the 7th Sphere group, using mIRC and writing channel-takeover bots. Channel operators held the permissions that determined who controlled a channel, while automated scripts and bots could defend that control or challenge it. This was my early education in network protocols, permissions, automation, and adversarial programming... learning how systems worked by discovering where they could be pushed, manipulated, or broken.
- 1997 // zeppo.com
The school library became my first publishing platform.
The name Zeppo came with me from IRC, and in 1997 I built zeppo.com using Perl and CGI. Other students could log in, manage their profiles, and contribute categorized updates... books read, jokes, and athletic personal bests. I kept it running from the school library. We weren’t calling it “user-generated content” back then. I just wanted students to be able to publish for themselves. Lycos named zeppo.com Teen Built Site of the Month, and Yahoo! featured it as Site of the Day.
- Oct 1998 – Mar 2003 // U.S. Air Force
From the 606th to Wing Command and the Pentagon.
I joined the military just out of high school. Serving with the 606th Air Control Squadron, I supported Operation ALLIED FORCE during the 1999 Kosovo campaign. I later deployed to Kuwait in support of Operation SOUTHERN WATCH, where I developed the base's first intranet. After returning, I was promoted into a Wing Command assignment and joined the SCIP team for USAFE-wide server consolidation and implementation. That work opened the door to contributing to a classified battlefield-management tasking system for the Joint Chiefs of Staff at the Pentagon.
My service brought USAFE Communication & Information Professional of the Year recognition in both 2000 and 2001, an Air Force Commendation Medal, three Air Force Achievement Medals, the Armed Forces Expeditionary Medal and National Defense Service Medal, and a commendation from the Pentagon’s J-3 Directorate.
- Dec 2003 – Jun 2005 // Aston / ResortQuest Hawaii
From military systems to the business of travel.
As a civilian, my first move was to join Aston Hotels & Resorts in Hawaii in 2003 as Director of Web Innovation. Travelers were increasingly finding and booking rooms online, while most established hospitality operations were still figuring out how to make the web part of the business. I led corporate and property-level web services, bringing together online commerce, guest-facing experiences, and intranet and extranet systems. It was less about launching another website than helping a hotel chain operate in a new digital economy.
- 2004–2008 // WebOS & Empowered Internet Solutions
Invented WebOS. Built and sold the platform.
I kept encountering the same inefficiency: each new website required too much repetitive development. By 2004, I was developing WebOS[1], a content-management platform that standardized publishing, and later filed a patent application for its foundational web-platform architecture. I took the product to market, founded Empowered Internet Solutions, grew it to 700 clients, and eventually sold the platform. What began as a way to build sites more efficiently became a software product and an operating business at scale.
- From 2009 // Agency & consulting work
Not just the platform. The people and business behind it.
Across the software and marketing agencies I founded and led, I served over 1,000 clients. The work ranged from establishing teams and repeatable delivery systems to technical architecture, search, analytics, and brand strategy for Fortune 100 and Fortune 500 companies and national brands... including Domino’s Pizza, Hilton, LegalZoom, AutoZone, and Time Warner Cable. Building a company meant being responsible for the idea, the customer, and the work that happened after the sale.
- 2010–2018 // University of Hawaii & early social web
@Rob on Twitter. Teaching what came next.
As an early Twitter adopter, I used @Rob and sent what was reported as Hawaii’s first tweet. I joined Klout’s advisory group, developed Klokal to map local influencers, and taught emerging marketing technologies through the University of Hawaii’s Pacific New Media program. In 2012, MTV’s Rob Dyrdek sought the @Rob handle; TMZ reported how I had already declined a $25,000 offer[2].
- The agency years // ActivityRez
From booking hotel rooms to booking everything around them.
While running my agency, I helped architect ActivityRez, a reservation and operations platform for tours and activities. It brought bookings, availability, and fulfillment together for the people delivering experiences on the ground. Expedia licensed ActivityRez to run its Local Expert operation, connecting that infrastructure with travelers looking to book more than a hotel room. This was the next frontier of digital travel: making local experiences bookable, organized, and accessible.
- Semantic data & enterprise architecture
Recognizing the structure under the surface.
I contributed to Schema.org’s General Automotive Ontology, applying taxonomy, semantic markup, and technical SEO to enterprise information systems. At the scale of millions of URLs, the relationships between things matter as much as the individual pages.
- From 2017 // a quieter chapter
Mostly retired. Thinking about the future.
I had largely retired from running businesses. Instead of starting another company, I spent time at futurist meetups and in interdisciplinary think-tank conversations. Urban planners, community builders, financial analysts, and specialists in other fields brought perspectives I could not have learned from software alone. I brought my experience in technology, marketing, and business, and together we explored what would change, what new needs would emerge, and which assumptions might no longer hold.
During that same period, I mentored startup founders through Alchemist Accelerator, a Silicon Valley venture accelerator ranked Platinum in 2017[3], and through a mentoring program at San Diego State University, near where I lived. I was no longer looking to build every idea myself; I enjoyed helping founders think through the future state of their markets, business models, and products.
- An urgent assignment // Cylance
The favor that brought me back to development.
I was largely retired and, frankly, a little bored. A team building an on-premise platform for Cylance was facing a tight deadline. They knew I could do the work, so I took the project on as a favor. I wasn't looking for another career chapter. But that short engagement led to my recruitment by Boldend.
- Boldend // three months
Hank McCoy. The house on the hill. What I chose to leave.
I joined as employee number six, recruited to architect and develop the web-based interface for a cyber-operations platform. The office was an unassuming house on a hillside overlooking the Pacific in northwestern San Diego County. Everyone used superhero codenames when committing code; the team assigned me Hank McCoy.
I understood the technical assignment when I accepted it, but not the full weight of what the platform was intended to support. Once inside, I recognized that we were developing offensive cyber-warfare capabilities for the CIA. As I understood more of the work and its implications, I walked into our conference room one day and found a Rothschild there. That encounter crystallized a decision I was already considering: I did not want to continue building it. After three months, I left the week my shares vested.
Only years later did I discover Boldend was backed by Peter Thiel’s Founders Fund [1][2]. In August 2024, SIXGEN acquired Boldend in a private-equity-backed deal that expanded its offensive cyber and electronic-warfare capabilities. The purchase price was never disclosed. Looking back, I believe my shares would have been worth a substantial amount. The question that stayed with me was no longer simply what I could build... but what I was willing to build.
- After Boldend // a different investigation
From building systems to questioning reality.
After Boldend, I began an intense search to understand a supernatural personal experience I could not explain. I immersed myself in world religions, examining their beliefs, their sources, and the assumptions on which they rested. I questioned what I had inherited, how people reached their convictions, and whether the claims could stand up to careful examination. I wasn't looking for another project. I was trying to understand what I had experienced... and what was actually true.
- The turning point
The question changed. The ability did not.
That search eventually led me to give my heart and hands fully to Jesus. The skills I had spent years developing did not disappear, but their purpose changed. I no longer wanted to measure my life by what I could accomplish for myself. I wanted those abilities to serve the Father, to help prepare a people for what is coming, and to become personally what I was learning to teach.
The next chapter would not begin with another company. It would begin with a different question: what does He want me to build... and whom am I meant to serve?