The setup
So I was recovering from having a broken hand repaired at the county hospital. I had been spending some time working for another guy’s little business. With some help from my parents, I had built my first PC, my very own hand-built PC, mind you. I was applying for jobs, and CitySearch offered me a job as their IT manager. The office was growing like mad. With a bunch of new funding they were going to make San Francisco their real highlight startup. The company had originated out of North Carolina, and during my time there, in 1996, it bought MetroBeat, a startup based in New York City. When I joined, the office was probably about 25 to 30 people and growing fast.
I reported to Yen Lee, who reported to Thomas Layton, under founder and CEO Charles Conn. Layton was the CTO, and he started the same day I did.
From the public record, CitySearch was founded in September 1995 as an Idealab-backed company seeded on Bill Gross’s idea and capital, with Charles Conn recruited to lead it. Its city guides launched across 1996, New York came in via acquisition, and San Francisco was a flagship market. Corporate was in Southern California.
What I owned
All technology within the San Francisco office: the central server that ingested and processed the images and content the ops team gathered while onboarding new customers through sales; email; internet connectivity; the firewall; VPN; backups; laptops; domain-controller integration; and DHCP and network configuration. If it had a plug or a packet, it was mine.
Signature work
Over my time there I wrote the Ops Tome. It documented every step of standing up a CitySearch office from nothing: acquiring internet service, configuring the network and VPN on Cisco hardware, DHCP, requesting an internal IP block, setting up firewall rules and internal DNS, bringing up the VPN back to HQ, who to contact, what to order, and what would be delivered. It read like “you are one of the first hires for our new CitySearch office, here are the steps to follow to be successful.” Corporate took it to HQ and distributed it as the standard guide for new offices as the company expanded rapidly and globally. They flew new IT managers to LA to be trained on my tome.
For the sales force, we were very early adopters of Ricochet wireless internet, which let the sales staff run live demos and onboarding in the field, with a few shared units for the ops team to populate content on-site with clients. From the public record, Ricochet, from Metricom, was a novel 900 MHz frequency-hopping wireless mesh with streetlight-mounted repeaters at roughly 28.8 kbit/s, and the Bay Area was among its very first markets in 1995 to 1996. Live internet from a laptop in the field then was genuinely ahead of its time.
CitySearch also hosted a live online Q&A with San Francisco Mayor Willie Brown, run over the Ricochets from inside the Mayor’s office, and another with a sports broadcaster. I was present to make sure each went flawlessly; they ran about an hour. Live, public, internet-based celebrity chats in 1996 were close to unheard of.
The launch: Yerba Buena
The go-live culminated in a celebrity-populated event at the Yerba Buena Center. CEO Charles Conn and Mayor Willie Brown plugged in a giant ethernet cable to bring the site live, with kiosks around the perimeter where attendees could use and see the live site. Behind the scenes it was a scramble: I had to get ISDN into the space, swap out a faulty router on the day of the event, and haul in and set up the monitors and PCs. It went off cleanly.
Outcome
My office playbook became the company-wide standard for expansion. CitySearch went on to grow nationally and internationally and merged with Ticketmaster Online in 1998, after my time. For me, the lasting part was getting to watch an early-stage startup packed with an enormous amount of talent grow internationally and, after I left, go public. It was the first time I saw, from the inside, what that whole arc looks like.
People
- Yen Lee, my manager.
- Thomas Layton, CTO, started the same day I did and went on to become CEO of OpenTable and a well-known tech executive and investor.
- Charles Conn, founder and CEO, later became an author and venture investor.
Tech & craft
Cisco networking with routers, firewall, and VPN; DHCP and internal DNS, domain-controller integration, ISDN provisioning, Ricochet wireless, a server-side image and content ingestion pipeline, backups, and end-user laptop and desktop support.
The story
I came in off a broken hand and a PC I had built by hand, and walked straight into a 25-to-30-person rocket in the earliest days of the commercial web. The through-line of the whole run was making things work under pressure: getting ISDN pulled into an event space, replacing a dead router hours before the mayor arrived, and running a live public broadcast off streetlight radios from inside the mayor’s office.
A couple of moments that stuck. The staff took to calling me “the doctor” or “the professor,” a kind nod to the intellect I brought to the work. And on my first day I was introduced to the SF staff in the same all-hands where they introduced Thomas Layton as the new CTO.
Throughline
The instinct that shows up here and never leaves: make it work under pressure, then write down how, so anyone can repeat it. The Ops Tome was the first time I turned my own operational knowledge into a reusable standard the whole company ran on. That same “the platform carries the playbook” instinct runs straight through to the governance and org-as-code work decades later.