After nearly two years at an SAP consulting firm in Toronto, I was getting anxious. The dot-com boom was happening all around me, and I was missing it. I was day trading internet stocks and reading everything I could about this changing world, but my actual job barely reflected that I was living through a unique moment in time. Opportunities seemed to be everywhere except where I was.
I needed to get to San Francisco, the epicentre of the dot-com boom. But how?
Someone at my company had the idea of starting an internet group to figure out how we could add web-related offerings to the firm’s portfolio. E-commerce, online stores, that kind of thing. I volunteered immediately. This let me build internet knowledge and skills on my resume. Meanwhile, the company got bought by PwC, so now I also have the brand of a top-five consulting firm on my CV.
I started applying for jobs in San Francisco. When I’d talk to hiring managers, I’d tell them I’d be in San Francisco in a few weeks and ask if I could schedule an interview. I realized it would be easier for them to say yes if I’d already committed to coming to the city. It worked. I ended up getting interviews with companies that had names like Sapient and Razorfish.
I accepted a position with Agency.com. I didn’t have a U.S. work visa, but they agreed to sponsor me under the H-1B visa programme. I packed up my car and headed for San Francisco.
I ended up living with three roommates in Hayes Valley. All my roommates had full-time jobs at internet companies and dabbled as DJs on the side. To fit in, I immediately purchased a pair of Technics SL-1200 turntables and a mixer.
My job title was “Strategist,” and I worked alongside information architects, front-end designers and web developers to create websites and web applications for Agency.com’s roster of clients. My first project was to create a website for Openwave, the company formed by the merger of Phone.com and Software.com. They made the software that powered messaging and browsers in pre-iPhone mobile phones. You can guess how that business turned out.
For another project, I worked with Visa on an animated logo and sound that would play whenever someone completed an online transaction using a Visa card.
Living in San Francisco was fun. Almost every other night, I’d end up at some sort of party for a dot-com company. Free food, free drinks, people talking about their stock options like they were already millionaires. I could order groceries to my apartment using Webvan or Peapod. I could rent movies from Netflix, and DVDs would arrive in the mail. Bike couriers clad in bright orange were all over the city delivering snacks for Kozmo.com, the short-lived Uber Eats of its time.
The money was everywhere. Companies were burning through it faster than they could raise it. Nobody seemed concerned. The conventional wisdom was that you had to grow fast, that profitability could wait, that whoever captured the most market share first would win everything.
I remember going to parties where people would talk about their companies like they were building the future. And they believed it. The internet was going to disrupt everything.
Looking back, it’s easy to see how delusional this all was. But when you’re in it, when everyone around you is saying the same things and the stock market keeps going up, it doesn’t feel delusional.
I enjoyed my job at Agency.com. The work was interesting. I was learning about web development, information architecture, and user experience design. I was working with smart people.
I also took a continuing education class on sales at Stanford. Every week, I’d drive down to Palo Alto for the night class. I’d see Google employees around campus. I considered asking whether they needed someone to help set up Canadian operations. But I never did. I was happy where I was.
And then the bubble burst.
It didn’t happen all at once. It started slowly, with a few companies running out of money and a few stocks dropping. Then it accelerated. By early 2001, it was clear that something fundamental had broken. The venture capital dried up. The IPO market disappeared. Companies that had been valued at hundreds of millions of dollars were suddenly worth nothing.
At first, Agency.com had a small wave of layoffs. A few people, nothing dramatic. We all told ourselves it would be fine. The company had real clients. We weren’t burning through cash with no business model. We’d survive this.
A few months later, we were all called into the lunchroom and told that Agency.com was shutting down its San Francisco office. We should pack up our things. We were all immediately out of a job.
We were shocked. We’d known things weren’t great, but we hadn’t expected this. We all headed to a nearby bar and talked about how quickly everything had turned. People were trying to figure out what came next.
For me, it was simple. I had to leave San Francisco. There were no jobs, and my work visa had expired. The city that had felt like the centre of the universe six months earlier now felt different. Everyone was either leaving or desperately trying not to. The parties stopped. The bike couriers in orange disappeared.
A friend of mine came from Toronto to meet me. We spent two weeks driving across the country until we got back. He was about to get married. I wasn’t sure what to do next.
I briefly flirted with the idea of getting work overseas. I got a job offer from a mobile consulting startup in Singapore that liked that Openwave had been my client. I interviewed for Deloitte in Auckland.
Ultimately, I decided to travel instead. I spent a couple of months learning Spanish in Antigua, Guatemala. I was in Quito, Ecuador, on 9/11. I took the GMAT in Buenos Aires and considered an MBA at NYU, Columbia, or Kellogg. I spent a few weeks learning to kite surf in Tarifa, Spain. I got my CFA Level 1 while living in Barcelona for a brief time. I was trying to figure out what came next.
I eventually returned to Toronto and got a job. I also explored the idea of starting a non-profit water company. I drove down to New York to meet someone at Balthazar who worked for Keeper Springs, Robert F. Kennedy’s bottled water company, which was doing something similar. Nothing came of it.
The San Francisco experience taught me something. Hype and reality can diverge dramatically. When they do, the correction is brutal. The internet did change everything, but not in the exact ways everyone expected, and not on the timeline people thought.
I also learned that I wanted to build my own thing.
I’m glad I went to San Francisco. I’m glad I got to see the dot-com boom up close. I’m glad I was there when it all fell apart. You learn more from failures than successes.
What came next was Toronto. And eventually, building something of my own, but it wouldn’t be blogTO just yet. Instead, I’d start an Amazing Race-style running race called the Experience Running Project.