An odd couple

At the dawn of the new year, ArtsandTV was tucked into a sublet on Toronto's rapidly growing King Street East district that was just big enough to hold two people and a conference table. The Project Sunblock team presently consists of Lightstone and James Wallace, who takes the lead on the programming. An additional two contract employees work out of Richmond Hill, near Toronto, to tackle any issues that come up with servers; Project Sunblock uses Amazon's data centres to handle heavy traffic loads. On this day, things are busy: The partners are in the process of integrating Microsoft's ad network into their roster of clients - their biggest catch by far, and a big boost for their credibility. Project Sunblock has become an upstart player in a fluid and growing market that's rapidly coming of age, with millions of dollars, and billions of impressions, at stake. The firm travelled a long, tough road to get here. As Internet entrepreneurs, Lightstone and Wallace make an odd couple: the grandfather and the coder. Wallace is a casually dressed young man nestled amid an unfolding array of flat-screen panels, looking every bit the programmer. Lightstone is the businessman, with the blazer, open-collared shirt and buzzing BlackBerry. At 67 years old, with a full head of slightly floppy salt-and-pepper hair, he bounces around the office with energy. Lightstone is a newcomer to Internet start-ups, but he's an old hand at marketing. He was a co-founder and principal of Thompson Lightstone, a marketing research company that, among other things, helped big brands in media and consumer goods keep track of how they were being perceived in the marketplace. In 1998, they sold the company; Lightstone stayed on until 2003 before retiring, joining a hospital board, and doing some consulting.

'A remarkable act of reverse succession'

Meanwhile, Lightstone's son Jeremy was building an Internet company. A headstrong thirtysomething who didn't always see eye-to-eye with his father, Jeremy Lightstone had been trying to make his online business fly. The restless polymath kept tinkering with his business model, meeting enough success to encourage him to keep going, but never reaching critical mass. Then, in 2009, his work in advertising led him to a product that the rapidly evolving online world needed: a tool that would keep online ads, the lifeblood of the new economy, from appearing on pages that would embarrass their brands. With financing from his father, Jeremy roped no smaller a company than IBM into a partnership that made ArtsandTV a real competitor on an international level. And then, just as his business took off, cancer struck - a rare form of brain tumour that left him wracked with seizures. When the tumour in Jeremy's head made it too difficult to go into his office, he kept in touch with his employees over Skype. When his eyesight deteriorated, he had computer code printed off in a big font. When he couldn't type, the caregivers who had moved into his house punched in the code for him. Months later, in January, 2011, he passed away. Succession is a challenging thing for any business, all the more so for a start-up on the threshold of its first major commercial success. Start-ups are all but defined by their founders, and now ArtsandTV's was gone. It could easily have been the end of the story. But what happened instead was a remarkable act of reverse succession. Having lost his only child, Ian Lightstone stepped in to give his son's business a shot.

When 'ad adjacency' goes wrong

For online advertisers, the nightmare scenario is porn. When "ad adjacency" goes wrong - as it did with that unfortunate conjunction of cruise-ship promotion with a cruise-ship disaster - it's a real problem. But that mix-up, at least, has the look of an honest mistake. Even more troublesome to advertisers is the possibility that their ad might inadvertently wind up on a web page next to content that, to put it delicately, does not reflect their brand values. This could leave the impression that not only does the brand endorse the X-rated contents of the page, but that they stand to profit from it. "It's 100% a huge problem," says Andrew Casale, the vice-president of strategy at Casale Media, an established Toronto-based ad technology company with a network that places online ads on a roster of 3,000 digital publishers across North America (including The Globe and Mail). "It's a problem that impacts businesses that are careless in the procurement of the impressions they're ultimately selling." Casale sees an industry in flux, a Web full of dodgy sites, and a spike of unethical practices among publishers and intermediaries alike. As such, he's a big fan of ad verification - Casale Media uses one of Sunblock's more established American competitors. (He'd heard of Sunblock but, as is the way in the Internet world, was surprised to learn that it was based just across town from his office.) The basic problem with online advertising is this: There's more "ad inventory" - the blank spots on web pages where advertising goes - on the Internet than there are advertising budgets to fill them. As the Internet grows, with users clicking blog post upon cute cat video upon news article, ever more blank ad space is created.

Online ad networks

An upmarket website - say, your preferred national newspaper - might go out and sell online ads to clients who want to be associated with a good brand. But it will almost certainly still have ad spaces it can't sell. The website is left with either an awkward placeholder or a big blank space. This quandary led to the creation of online ad networks, which means that advertisers now have a choice: For a reduced rate, networks will unload their ads across a roster of websites. Instead of promising that an ad will run in a specific publication, they promise that the ad will reach a certain demographic. So they'll tell an advertiser that, for instance, its ad for shaving cream will reach 100,000 men between the ages of 18 and 35, but the online ad network will find the target audience across a variety of websites. Some networks only place ads on a well-vetted roster of client sites; other networks reach more eyeballs by being less diligent about potential ad destinations. It's not always cut-and-dried: Think of uncensored blogging sites like Tumblr or Blogspot, where people post pictures about everything from recipes to fetishes - sometimes using similar keywords, albeit in wildly different contexts. (Whipped cream, for example.) Moreover, sometimes networks will sell inventory to each other, in an attempt to get the ads placed on web pages within the time frame they've promised. Before an ad actually appears, it might have changed hands several times, from one network to the next. The advertiser can only hope that wherever its ad has finally appeared, everybody's got their clothes on and nobody's saying nice things about war criminals.

'Jeremy had a lot of chutzpah'

James Wallace found Jeremy Lightstone on Craigs-list in 2005. "It was one of those 'I'm gonna conquer the world but I can't pay you much right now' posts that you always see," says Wallace, who's sitting across the office from Ian Lightstone. "Those are mostly terrible people with bad ideas." But the younger Lightstone had an idea that was actually pretty good. A self-taught programmer with artistic ability (he was an avid oil painter) and a degree in sociology, Lightstone had already launched a kind of proto-social network for artists and creators under the ArtsandTV banner. Now, he wanted to use this assemblage of sites to create an ad network that would give big brands access to a niche audience. "He knew where the young people are going, in terms of artists who have their own sites," says his father. "All kinds of weird stuff. Edgy stuff, I guess I should call it." "It wasn't too edgy," Wallace prompts, gently. "But edgier than what you'd get elsewhere." Jeremy Lightstone brought Wallace and another prospective hire over to his home office, where he laid reams of source code printouts on the table: They were going to dissect the workings of an open-source ad-serving application until they knew it inside and out, and could rewrite it to do their bidding. After a week of this, the other job candidate headed for the hills. Eventually, however, Lightstone's idea found its mark. He and Wallace were able to sell advertising space to enormous brands, including Sprint and Dell, whom Jeremy aggressively courted. "I have to say, Jeremy had a lot of chutzpah," says his father. "He had no fear of calling people."

A close but complicated relationship

All the while, the headstrong dad who'd built and sold a company - and done well by it - and his son, a budding entrepreneur at the start of his own journey, were negotiating their own partnership. Ian had invested in Jeremy's business, but perhaps not as much as Jeremy would have liked. "We had some debates about that," says Ian, drily. "I come at this like any father - you want to help your children, but you have to get on your own two feet. He used to feel I was a hard-ass, in that sense." According to family friends, the two had a close but complicated relationship. "Jeremy loved to argue, and Ian loved to take him up on it," says Scott Poole, who first met Jeremy when they were in kindergarten. By 2008, the ad network Jeremy was running had made him aware of the promising field of ad verification. He discovered that online networks were exchanging ads with one another - that is, until the phone would ring, and an irate advertiser would be on the line, demanding to know why their ad was running on a site that featured people in a state of undress. What's more, trade associations in the United Kingdom, where Lightstone had contacts, were starting to demand that these exchanges be audited. Jeremy Lightstone saw an opportunity, and Project Sunblock was born. At first, the system Lightstone devised was a simple blacklist of sites and pages to avoid. But that wasn't a workable solution - the Web is too big, and changes too quickly, for a small start-up to catalogue it in real time. To get a read on whether any given web page was kosher for an ad, Sunblock needed access to a fresh catalogue of the entire Web.

Mellow, mutual respect

So, according to his father, Lightstone cold-called IBM. "I don't know how he got to them," says Ian. "They sort of said, 'Who's this guy?' But lo and behold, they said, 'Let's talk.' " The fact that the giant corporation was serious only hit home when the team gathered around the table for a conference call with the Texas-based director of IBM Security Systems. At the appointed hour, the director strode through Sunblock's door instead - without having announced his presence in Toronto. They hammered out a deal. IBM had built its database as a tool to keep employees from surfing troublesome websites, but Lightstone was proposing a whole new way for the company to monetize its data. Today, IBM provides Sunblock with access to its catalogue of web pages, which it has the resources to keep constantly refreshed and categorized by content type. When a request comes in to Sunblock, it relies on its knowledge of what the advertiser would like to avoid, and double-checks the ad placement against IBM's scan of the destination web page. The ad runs only if the site checks out. By the time Project Sunblock was set up in 2009, Lightstone's brain tumour had been detected. At first, though, the prognosis wasn't so bad. "The doctors said, it looks low-grade, we're not going to touch it; carry on," Ian recalls. So they did. For a year, work on Sunblock continued, IBM was recruited, clients were lined up; Jeremy got married and, in short order, became a father-to-be. But Ian stepped up from his role as investor and took an active role in the business, nominally as CFO. It was a change in more ways than one. "I realized that Ian was following Jeremy's vision, and not the other way around," says Scott Poole. The head-butting between the two gave way to a mellower mutual respect.

Tragedy strikes

The company struck up agreements with clients like AdBrite, an American ad exchange, which employs Sunblock as one of the tools available to advertisers to verify websites before bidding on ad space. Meanwhile, Arts- andTV kept working on the big fish: a trial contract with Microsoft's U.K. ad network, which runs advertising on non-Microsoft websites. It was a deal that would ultimately send more than a billion impressions a month through Sunblock's servers. In mid-2010, Jeremy suffered a major seizure. The cancer took hold, knocking him out of the office, and throwing him into punishing chemotherapy treatments. He tried to keep up with office work from home, but the disease progressed quickly enough to stun everyone. By the 2010 Christmas holidays, he was in Princess Margaret Hospital. IBM wanted to make a promotional video; Ian sat and spoke for the camera, as enthusiastically as he could, as his son lay dying. On Jan. 29, 2011, Jeremy Lightstone passed away. That February, Project Sunblock was set to present in a breakout session at a Las Vegas conference attended by thousands of IBM partners and clients. Weeks after Jeremy died, Ian flew across the continent and spoke in his stead. Afterwards, a throng of attendees approached to ask questions, and Ian could only think that he wasn't the one who should have been there. Lightstone feels the generation gap, the peculiar experience of working in a field dominated by thirtysomethings, not sixtysomethings. To help him through the process, he pulled together an advisory board of friends and experts in related fields - law, online advertising, marketing - to give guidance and advice; most of them are his contemporaries. Many start-ups run by hot-to-trot youth go through a phase of requiring "adult supervision," as seasoned guidance is slightly patronizingly described. Project Sunblock's came in an unexpected and poignant way. In early 2012, Lightstone inked the Microsoft deal, which started pouring billions of impressions' worth of verification checks to Sunblock's servers. (Sunblock charges clients a monthly fee for a set number of impressions.) By the spring, the trial had expanded to Microsoft's European ad-network traffic, with Canadian and American pilots to follow. Sunblock has established a U.K. sales office and is looking to raise money there, before it expands into the more competitive North American market.

Bittersweet tenure

Ian Lightstone doesn't want to run the company forever. "It's not something you'd expect to be doing in your life, at this stage of your life." His deferred retirement waits; Lee, Jeremy's son, is now almost three years old and just learning to swim. "Bittersweet" is the word Lightstone keeps coming back to when describing his tenure with Sunblock. In discussing the loss of his only child, he is frank but to the point. You get the sense that he uses that one word where he could use many more. "It's sort of bittersweet. I enjoy it. I enjoy working with James," he says, smiling across the small office. He expects to be involved for a few years more, but is keeping his eyes open for a successor. (Indeed, Lightstone recently bought a house in Florida, turning Sunblock into a virtually-headquartered firm, for now.) What he wants more than anything is for the company that his son spent so long building to succeed, as a legacy. He's built and sold businesses before, but, then, this is no regular business. "I have an emotional stake in it, too. I want to make sure we go in a proper direction. I know the business now. How do you pass that on to somebody, and make sure they pick it up?" In the office, Lightstone's phone goes off regularly. He apologizes, and pauses to take a call and check his e-mail. Later, ignored on the corner desk, his computer screen goes black, then fades into a slide-show screensaver. It's all pictures of Jeremy.

Lessons in advertising