Mapping toward digital success

Bill Kilday opens his tech memoir about the digital mapping revolution with a rumination about angrily getting lost on Boston’s convoluted highways. Now practically unheard of, and inconceivable to the smartphone generation, this was once a daily source of misery for travellers: “Somehow I got turned around on my way home,” Kilday writes in Never Lost Again. “In frustration, I pounded my fist against my car’s dashboard, yelling at nobody but myself, while driving five miles in the wrong direction down Route 2, looking for the next roundabout. Or maybe it was 3A?”

How routine it now is that we can simply swipe open a detailed and updated map of almost any place on Earth, with a bright, blue dot announcing YOU ARE HERE. As with almost every technology that first seemed a miracle before becoming commonplace, GPS navigation followed a tortured and convoluted path to ubiquity. Kilday is well-positioned to recount the story. A very early employee of a company called Keyhole (which, after many twists and turns, is now known as Google Maps), he was present at the creation. Kilday’s memoir shines in its description of the volatile oddities of startup life: the birth of the initial idea that first sounded crazy, the constant cash-flow problems and efforts to keep bankruptcy at bay, and the perplexing search for a sustainable business model.

While Keyhole’s engineers pioneered the unsexy but critical back-end infrastructure necessary to manage terabytes of detailed satellite images — tiling all that data into a seamless mosaic was at the core of the innovation — Kilday waded into the chaos of industry conferences to sell the wizardry. The company’s first big clients unexpectedly were commercial real estate brokers who wanted a simple way to investigate properties. Mapping shopping centres in Nowheresville wasn’t part of the original dream, but the journey had other moments of transcendent grace that kept the mission alive. Keyhole’s technology was so novel — and magical — that every demo of the product immediately created a scrum of awed onlookers wanting to scroll, like gods, across the Earth’s surface. What every new user did, Kilday tells us, was find their own house and see their own domestic life on Keyhole. Then one day, whoosh! As with so many startup stories, the flukiest stroke of luck decided the company’s fate. After 9/11, Keyhole made a deal to provide CNN with mapping software for its coverage of the wars in faroff deserts and cities. Keyhole’s wily CEO, John Hanke, insisted that CNN include a link to Keyhole’s website on any CNN graphic, and as soon as the network went live with coverage, the company was deluged with so much interest that the map servers started crashing (always a good sign for a startup).

That soon snowballed into growing revenue and interest from a still-private search company called Google. Despite some initial skepticism — what was a search company buying a mapping company for? — Keyhole warmed and finally agreed to be acquired, a successful outcome for a very fraught venture.

Much like an entrepreneur’s life, the book settles into a lower (and slower) gear after the successful acquisition and the ingestion of Keyhole into Google. Gone were the days of (almost) bouncing payroll cheques and cheap Costco snacks in the kitchen. Instead, here was a tech utopia populated by armies of smart, motivated engineers and executives where cost or revenue was rarely discussed.

But with all that came a new and foreign spectre: politics. Google was just then going public in a much-watched IPO, and the company had curdled into competing fiefdoms and egos. The Keyhole team, still blinking in astonishment at its wild ride and thunderously successful conclusion, was plopped into a budding corporate battlefield. Kilday spends many pages describing his tiptoeing in and around the internal empire of Marissa Mayer, notable early Googler and later Yahoo CEO with a reputation for prickliness. He watches as his much-respected former chief executive and boss elbows his way into a position of influence so the Keyhole dream will survive the jungle of competing priorities.

Fortunately for Keyhole, its technology had the support of the only two fully indispensable and unquestionable Googlers: founders Sergey Brin and Larry Page. In a memorable early meeting, Kilday, mystified by the lack of discussion about concrete revenue or usage targets, blurts out the question: “Larry, Sergey, ten million dollars or ten million users, what would you prefer?”

Kilday’s writing style is that of the product marketing man with an MBA, not the frenetic, reckless startup renegade we’ve come to associate with Silicon Valley. The personal barely creeps into Kilday’s account and is limited to passing mentions of children and bits of group bonding at college football games. This is tech done by adults: grown men and women with spouses and mortgages and careers they are forging. It’s a necessary reminder that the most important technologies are not cooked up solely by the Tshirt-wearing, late-night-coding, social-media-oversharing, 20-something adult-olescents who populate shows like HBO’S Silicon Valley.

That pulsing blue dot, which now lives everywhere, is the real sort of worldchanging disruption that the unostentatious persistence of Kilday and his associates produced. Thanks to them, every soldier, sailor or just workaday commuter can unfailingly reach their destination. Never Lost Again — the title itself describes our new world. The book, like an orderly set of Google Maps instructions, describes how we got there.