Urban Challenge was already in many U.S. cities, but it wasn't in Canada yet. I thought I could create a version in Toronto. But first, I wanted to see how it actually worked.

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My girlfriend, Bronwyn, and I hadn’t travelled together yet. I suggested Seattle for our first trip. We could do the Urban Challenge race and stay with a friend who had moved there from San Francisco.

Neither of us had been to Seattle before. It was late August 2003. The weather was beautiful. We walked the city, hit some bars and restaurants. There was a huge rally for Howard Dean that weekend. Thousands of people showed up. He was running for the Democratic presidential nomination and looked like he might actually win. It was peak Howard Dean, before the scream incident. The energy was incredible.

We showed up on race day. About 250 people were competing. I can’t remember where we placed but it wasn’t near the top. We had fun, though. More importantly, I saw how the race actually unfolded, and how many clues and checkpoints made sense, and what the organizers did before and after the race. I also got a feel for what it was like to compete as a participant, what worked and what didn’t. I took detailed notes on it all.

When we got back to Toronto, I was confident I could create an Urban Challenge of my own.

I didn’t wait. I set a race date for October and moved fast. I built a website with help from former Agency.com colleagues, and secured sponsors. All proceeds would go to the Make-A-Wish Foundation, my father’s favourite charity.

I called it The Experience Running Project.

I tried to keep costs low. Steam Whistle donated the Roundhouse as the venue. I bought digital cameras to lend to participants since smartphones didn’t exist yet, figuring I’d spread the cost over future races. I paid for race bibs, rented a race clock, and hired a DJ. Bronwyn and some of my friends volunteered as staff. I ordered food from local restaurant Jumbo Empanadas to go with Steam Whistle beer for the post-race celebration.

For promotion, I made flyers and distributed them around the city, and submitted the event to free listing sites. But the real boost came from media coverage. CBC did a TV segment. The Toronto Star wrote an article comparing it to Urban Challenge.

75 teams signed up.

Just before race day, I noticed a flyer for something called City Chase. It was a similar concept. I did some digging and figured out the two people who were behind it. Then I noticed they’d signed up for my race. They were doing research, just like I’d done in Seattle. After they finished, I introduced myself. I asked if they’d had fun and wished them luck with City Chase, which was scheduled for a few weeks later. They seemed surprised I’d figured out who they were.

Race day was exciting. The DJ was spinning music at the Roundhouse. There was good pre-race energy. The venue was nontraditional for a running race, which made it feel unique. People were curious and excited to see what this would be like. It was a good mix of participants. There were some runners, and some people who were clearly not runners but who I imagine thought they could be competitive in a race that relied as much on solving clues as on speed.

The race generated about $1,000 in proceeds. I wrote a cheque to Make-A-Wish.

It seemed easy enough to repeat. The next summer, I decided to go national. Nine cities across Canada. Winners from each city would get a trip to Montreal to compete in a championship for $10,000. Top teams from each city would be invited to compete, but only the winners would get free flights and hotel rooms. I got national sponsors like Vonage and Monster Energy. I found a hotel in Montreal to donate rooms, and secured venues in each city willing to host in exchange for sponsorship.

Then I made my biggest mistake.

I rebranded to Navigate the Streets. I thought it was a better name. I spent money on a new logo and website, but I threw away all the momentum from The Experience Running Project including the press coverage, the name recognition, and maybe some of the participants who might come back. All of this was gone because I wanted a different name.

I also had no local knowledge of most of these cities. I’d never been to Halifax, Ottawa, Winnipeg, Edmonton or Calgary before. I had no connections there, no sense of the market, and no local staff or volunteers to help me execute the races.

I spent money on flyers, Google search ads, online banners and print ads in alt-weeklies in each city. Now Magazine in Toronto. Fast Forward Weekly in Calgary. The Georgia Straight in Vancouver. It didn’t translate to enough sign-ups. Press coverage wasn’t as good either. The Toronto Star and CBC had already covered the event the year before. They weren’t interested again. I did get coverage from Explore Magazine, the Winnipeg Free Press, and the Globe and Mail, complete with a photo of me holding a cellphone and a map outside Union Station in my brand-new Navigate the Streets t-shirt.

Toronto numbers stayed flat. About 25% of participants from the year before came back. Vancouver's numbers were slightly lower than Toronto's. Calgary, Ottawa, Edmonton and Winnipeg weren’t great. Halifax and Quebec City numbers were so low that I cancelled the events. People who showed up still had fun, but the races felt much smaller than Toronto. I was embarrassed by the turnout. Even with ineffective marketing and low press coverage, I still thought more people would register through word of mouth.

I was losing money, and I still had to pay for the winners to fly to Montreal and compete for the $10,000 prize.

Before the championship, I sent everyone their flight and hotel details. I also told them I was lowering the prize to $1,000. I couldn’t afford more. People were disappointed but understanding. A free weekend in Montreal and the chance to compete again and be recognized as the national champion still had a lot of appeal.

The other problem was City Chase. They’d also gone national, hitting almost all the same cities, sometimes twice. They had sponsors like The Running Room, who would market the event to their huge database of runners. They promoted the event at other running events in each city.

After that summer, I was done. Navigate the Streets had been a lot of work, and I was feeling defeated. Having to cut the prize amount in Montreal was embarrassing.

Navigate the Streets taught me things I needed to learn.

Execution matters. The concept was simple. What mattered was whether I could pull it off. First year in Toronto, I did. Second year, trying to scale, I didn’t.

Rebranding threw away momentum for no good reason. This lesson stuck with me. Years later, when I was running blogTO, people would occasionally suggest rebranding. blogTO wasn’t a perfect name. But I remembered what happened when I rebranded The Experience Running Project. There are real costs to rebranding, even when you think a different name sounds better.

Local knowledge matters. I knew Toronto and Montreal. I’d been to Vancouver before. I didn’t know the other cities.

Competition changes the equation. Year one, I was first. Year two, City Chase was doing it better. Navigate the Streets was no longer unique.

But the most important thing: I liked building things. Even when it failed, even when I lost money, it was still a fun experience. People showed up and had a good time because of something I created. That mattered.

One more thing: I’d added a blog to the Navigate the Streets website. I posted updates all summer, photos and highlights from different cities. When Eye Weekly ran their Best of Toronto Readers’ Choice poll that year, I submitted it for best local blog. I asked my friends to vote. It won. They sent me a plaque, which I still have in my home office.

It reads: 'Navigate the Streets - Toronto’s best local blog.'

A few months later, I’d start blogTO.

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.

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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.

This was three years before AOL bought Time Warner, the owner of CNN, in what is still widely seen as the worst business deal in history. Back then, CNN had a sterling reputation and was the unquestioned worldwide leader for breaking news.

I was hired to work in the PR department on the 19th floor. My primary job was to read through a stack of newspapers each morning and physically cut out any article that mentioned CNN. It was two hours a day with scissors and newsprint. The clippings were filed in folders and given to my boss, who passed along anything interesting to her boss. It was the kind of work that would eventually be automated.

On my third day, I wandered down to the 18th floor, where CNNfn was based. CNNfn was CNN’s dedicated financial news channel, now called CNN Business. They filmed live all day. There were cameras, lights, and producers with clipboards. It was considerably more interesting than the 19th floor.

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I started spending most of my time down there.

CNNfn had a show called “It’s Only Money” that featured young entrepreneurs building dot-com businesses. It was mostly people in their twenties who had started e-commerce sites and had theories about how the internet would change everything.

I was given the job of pre-interviewing the guests. I’d call whoever was scheduled to appear and ask about their business and their background. I’d take notes and pass them to my producer and host so they’d know what to ask during the live segment.

It was the closest thing to journalism I’d ever done, and I found it thrilling. You’re trying to figure out whether someone will be interesting on camera. You’re looking for the specific details and stories that make a segment feel real rather than rehearsed. Most guests were happy to talk. They were getting free airtime on CNN to promote their startups. They didn’t care that I was an intern.

I don’t remember most of the companies or founders. They’ve blurred together. A few probably survived what came next, but most definitely didn’t.

I made one notable mistake. I pre-interviewed a guest whose business was interesting but who was painfully dull on the phone. His voice was monotone, he had no energy, and his answers went nowhere. I should have flagged this for my producer. I didn’t. The segment aired, and the guest was a disaster. There were awkward pauses, one-word answers, and the host struggled to salvage it.

The producer asked me afterwards if I’d picked up on this during the pre-interview. I froze. Either answer was bad. If I said yes, I should have warned him. If I said no, I was incompetent at the one task I’d been given. I mumbled something about not having noticed. I don’t think he believed me.

At the end of the summer, I found out they were cancelling the show. The producer lost his job. I still wonder if this was partly my fault.

On the 20th floor, Lou Dobbs filmed “Moneyline,” the flagship business show that had made him one of the most recognizable faces at CNN. Dobbs had the kind of casual authority that came from being really good at your job and knowing everyone knew it. I was intimidated by him. He had no idea I existed.

Larry King also filmed at 5 Penn Plaza. He was someone who’d built a career on being curious and letting famous people talk. He was good at it. His questions sounded simple, but gave people room to say interesting things.

The elevators at 5 Penn Plaza were always interesting. The building’s hierarchies temporarily dissolved in there. I’d ride up with producers, hosts, executives, and other interns, and occasionally with someone famous who was there for an interview. The unspoken rule was to pretend not to recognize famous people. Everyone acted like it was normal to share an elevator with someone who’d been on a magazine cover or run a Fortune 500 company.

I rode the elevator with Donald Trump on July 23, 1997. He was there for Larry King. He didn’t talk to anyone. We all pretended not to notice him. You can still read the transcript of the interview online.

I didn’t think much of it at the time. Trump was famous for being famous. In 1997, that meant he was famous for having money, putting his name on buildings, and occasionally going bankrupt and recovering. He wasn’t politically relevant. He was a tabloid fixture, someone who’d married models and built casinos and had a cameo in “Home Alone 2.” The idea of him becoming president would have seemed ridiculous.

The other celebrities I saw in elevators have faded from memory. There were lots of them. 5 Penn Plaza was a high-traffic spot for anyone doing media in New York, and Larry King’s guest list was eclectic. I maintained my policy of studied nonchalance. I never tried to start conversations and never asked for autographs. I treated famous people like they were regular people who happened to be in the elevator, which is probably what they wanted.

The internship was unpaid, which was standard for the industry and completely unsustainable unless you had a second job or, in my case, a cousin with a spare bedroom. The apartment was small and overlooked a highway, but it was free, and I was grateful for the place to stay and the opportunity to experience a full summer in New York.

There was one unexpected perk at CNN. Boxes of review copies from book publishers were always lying around the office, sent to various shows in the hope of coverage that would almost certainly never happen. The books were free to take, so I started taking them.

Barnes & Noble had a generous return policy in 1997. You could bring back books without a receipt and receive store credit equal to the cover price. I realized that this policy, presumably designed for unwanted gifts, worked equally well for free review copies acquired from a CNN internship.

I got strategic about it. I’d rotate between different Barnes & Noble locations around Manhattan, never hitting the same one twice in a row, walking in with a stack of hardcovers and walking out with store credit that I’d immediately spend on whatever I actually wanted to read. I must have visited every Barnes & Noble in the city that summer. This was before Amazon reshaped the book business, when bookstores were still everywhere.

I read more that summer than any summer since.

My time at CNN ended because I didn’t have a work visa. I returned to Toronto and landed a job at a consulting firm specializing in implementing SAP software for clients like Nokia, Panasonic and JVC. SAP is enterprise resource planning software, which is a boring way of saying it’s the plumbing that makes large corporations function. It was technical and tedious, but paid way better than any media job would have.

I was competent at it. Not passionate, but competent. The work was project-based: several months embedded with a client, long hours, then on to the next one.

I kept thinking about CNN, but not because the internship had been glamorous. I thought about it because it was the first time work had felt interesting. Calling entrepreneurs, figuring out whether they’d be good on camera, looking for the details that made a story worth telling. That had engaged me in a way that enterprise software never would.

I didn’t know yet that I’d end up back in media or that I’d start a publication and spend two decades building it.

CNNfn no longer exists. Lou Dobbs went on to become a far-right commentator before CNN cut ties with him. Larry King continued his show for another 13 years. We all know what happened to Donald Trump.

And I went back to Toronto, worked in enterprise software, and then moved to San Francisco just as the dot-com boom was getting overheated.

That’s the story for the next post.