This guy invented blog advertising. Here’s what he’s up to now

Simon Owens
The Business of Content
19 min readFeb 22, 2018

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Henry Copeland. Photo credit: Nicole Bogas

When Josh Marshall launched Talking Points Memo in November of 2000, it didn’t even occur to him that he could make a living off the site, much less that it would eventually grow into a full-fledged media company. “I didn’t really think of it as a way to make money,” he told me. “I think I originally saw it as something that would be a component of my journalism, a loss leader in financial terms to my journalism.”

At the time, Marshall was an editor at The American Prospect, and he soon left that job to pursue a freelance writing career while continuing to blog on the side. In 2002, he used his blog to report on controversial statements from then Senate Minority leader Trent Lott in which Lott lamented that segregationist Strom Thurmond hadn’t won his racist 1948 presidential run. The fallout from that reporting led to Lott giving up his leadership position, and it brought a flood of new readers to Talking Points Memo.

Marshall began experimenting with various forms of monetization, putting up a tip jar and enrolling in the Amazon affiliate marketing program. But there still wasn’t a great way for bloggers, even popular ones, to make a living back then. And then sometime in 2003 he started receiving emails from a guy named Henry Copeland. Copeland was the founder of a recently launched company called Blogads, and at first, Marshall didn’t give him the time of day. “That was in a period when everything was kind of evolving very quickly and TPM was becoming a big deal,” Marshall said. “There were all sorts of people reaching out to me about projects and ideas and I just didn’t focus on it. We finally did grab coffee and he pitched me the idea. And then we kind of started from there.”

Soon afterward, Marshall embedded the Blogads code to his site, and it wasn’t long before he had his first ad — he thinks it was some sort of novelty deck of political playing cards. Pretty quickly, the amount of money he was bringing in via Blogads grew to a sizable sum. By 2004, he was generating $10,000 a month through the blog and was able to turn his attention to it full-time.

Marshall wasn’t the only blogger to make a living from Blogads. For a period between 2004 and 2010 or so, it was rare to visit a blog with any sort of following that didn’t have the distinctive Blogads widget on its sidebar. Perez Hilton. Glenn Greenwald. Andrew Sullivan. Many of today’s most prominent writers were early users of the platform. Copeland, in creating it, not only turned blogging into a viable business, but he was also a huge influence on the media business as a whole. Blogads arguably introduced the first native social ads, the kind that now generate billions for tech platforms ranging from Facebook to Twitter to Snapchat, and it helped give rise to some of the biggest household names in media and journalism.

And yet Blogads today is a shell of its former self. Copeland failed to transition to the programmatic model that came to dominate digital advertising. Or, perhaps more accurately, he chose not to. Why did a guy who was so ahead of the curve decline to ride the wave he helped create? That was a question I set out to answer.

If there’s a consistent theme within Copeland’s career, it’s that he’s able to spot technological waves before they crest and ride them. In the 1990s, he was a print journalist in Eastern Europe, writing for a small business journal. The internet was still fledgling then, but he began to think that newspapers should put their editions online. “So I went out and looked, and everyone said, ‘Well Microsoft Frontpage does that.’ And I’m like fuck Microsoft Frontpage, that’s a page, I want a whole website. There were some solutions and I didn’t like those solutions, so I started to build my own.”

In 1999, he launched Pressflex, an early CMS geared toward news publications. Rather than building a website from scratch, publishers could host them on Pressflex and use all its publishing tools (interestingly enough, the company still exists and is profitable nearly 20 years later). Essentially, it was an early SaaS business before that term even existed.

But despite Pressflex’s early success, Copeland pretty quickly grew frustrated with its lack of scalability. “The thing about those newspapers is I knew they’d be very loyal, I knew if we’d get them they’d be around for a long time,” he said. “What I didn’t know is how slow they’d be. Inside of every newspaper are five decision makers at the very minimum. You have people coming in and second guessing you all the time. It was really bad in the early days when no one knew what a website was and everyone thought they wanted a piece of it.”

At some point, he noticed that some of the journalists he’d worked with — people like Ken Layne and Matt Welch — were launching blogs, a medium which at that point was still nascent. “I was talking to them and they were getting 10, 15, 20,000 readers a month on their blogs. I had a French newspaper [as a Pressflex client] and it had millions of readers in print, yet it can’t get 10,000 readers online and my buddy in LA blogging at midnight drunk can get 10,000 readers a month. What the hell is going on? That’s what woke me up to the vitality of blogs.”

As Copeland got further and further immersed in the blogosphere, a few things jumped out at him. The first was that bloggers were forming stronger and more direct bonds with their readers than he’d ever seen with newspapers. The second was that these bloggers didn’t have a good way of making money. He began to think about the classified ads in French newspapers that were formatted so they ran as columns next to the news stories. “I got in the car and was driving somewhere,” he said. “And I started thinking about how blogs had scrolling content, and what if you put ads all down the side of that content. And then it was like that classic moment of combining chocolate and peanut butter. Literally the words were in my head, ‘blog ads.’ And I was like holy shit, I have to do Blogads, I hope nobody’s registered it.”

This was in the Spring of 2002. Copeland diverted some programming resources from Pressflex to rush out a Blogads prototype. He then set about trying to court bloggers and get them to adopt the platform. They weren’t always receptive. “I went around saying to people, ‘Hey I can run ads on your blog, and it was really a lot like saying to somebody, ‘Hey wouldn’t you like to put a big Marlboro sign in your living room,’ because at that point blogs were very personal spaces. There’s always been an anarchist undercurrent to blogging. A lot of people were like, ‘Screw you, no, I have no interest whatsoever.’ But I gradually warmed them over and convinced them that these are going to be cool ads, these aren’t going to be Marlboro ads, it’s not going to be Coca Cola.”

Though Blogads would eventually span across virtually every content category, Copeland initially focused on wooing political bloggers. Josh Marshall was one of them. Another was Taegan Goddard. Goddard worked on Wall Street but had started out his career in politics, working as a policy advisor for both Senator Donald Riegle and Connecticut Governor Lowell Weicker. In 1999, he launched a blog called Political Wire and modeled it off Washington Wire, a weekly Wall Street Journal column that aggregated news in a blog-like fashion.

Unlike Marshall, Goddard grasped the potential for blog advertising almost immediately. “I watched Meet the Press with Tim Russert on Sundays,” he told me. “You’d get great political content, great interviews. And then you’d look at the advertising and it was Lockheed Martin, McDonnell Douglas, Archer Daniels Midland. All these companies that did not sell products to consumers, and yet they were advertising on this show because it was the only way to reach a politically influential audience. They knew staffers at the Senate Armed Services Committee or in the Pentagon or in the White House were watching this show and they were willing to pay huge dollars to advertise on a national TV show just because a small slice of the audience was probably watching. I realized that a site like Political Wire could create a similar niche audience but much more efficiently. I thought that business model could be used on the web, and if you could create a community of politically influential people, that it was a perfect venue for advertising.”

The only problem was that there was no easy way to serve up those ads. If someone wanted to sponsor Goddard’s blog, they needed to reach out to him, negotiate a price, design an ad that fit his blog’s specs, and then have him manually place it on the site. The beauty of Blogads was that it was a completely self-service platform. The blogger set a price for what it cost to advertise for a week, a month, or even a year. The advertiser would pick the run-time, and then upload both an image and text. The blogger was then alerted to the ad and could either accept or reject it. “It became a very significant source of revenue very, very quickly,” said Goddard. “It would be not unheard of to have eight or 10 ads on your sidebar through Blogads.”

Blogads adstrip widget highlighted in red

Once Blogads started showing up on these high-traffic sites, it didn’t take long for other bloggers and — more important — advertisers to take notice. Ad buys started trickling in — $20 here, $30 there — and Copeland would get an email from Paypal every time someone would place an ad. “And then one day in August of ‘03 I was sitting there and all of a sudden I saw a $900 payment come through. And I was like what the living fuck?” he recalled “It was the ACLU of Pennsylvania buying a year long ad on Atrios” — a liberal blog — “And I was like this has got to be a mistake.”

It wasn’t a mistake. Every week the amount of revenue Blogads was bringing in grew. By the end of 2003, the company had generated $10,000. The first month of 2004, it generated another $10,000. By the end of 2004, an election year, it had brought in over a million dollars.

Though Copeland started with left-of-center political blogs, the platform soon spread to conservative blogs, and then into dozens of content categories. By 2006, it was impossible to visit a blog with any amount of stature and not see the distinctive Blogads widget. Back then I was already obsessed with the business of digital media, and I remember constantly clicking on the “Advertise Here” button and trying to calculate, based on the publicly-listed rates, how much the blogger was pulling in each month. Some bloggers in the more consumer friendly categories — Perez Hilton for instance — were generating tens of thousands of dollars per week.

A hive for gadget blogs

As his platform became ubiquitous, Copeland built up a sales team to help bring in bigger clients. He also rolled out a number of new features. Blogads introduced a series of mini ad networks, called hives, that allowed like-minded blogs to group themselves together and sell ads. This way, an ad buyer who wanted to target, say, mommy bloggers, could go down a checklist of blogs they wanted to sponsor rather than seeking out each one individually.

The company also launched a form of dynamic ads where an advertiser could connect the ad to the RSS feed for its company blog, and every time it published a new blog post the post’s headline would be swapped into the ad. “I would argue we were the first native ad,” said Copeland. “When we started dealing with political campaigns, we’d get ad buyers who would say, ‘I have these banners already made up that I’m going to run on the Susquehanna Citizen Journal, can’t you run my banners?’ And I’d say nope, blogs are different, blog readers are different, you need to communicate in a more intellectual, authentic way. And it’s going to be text, it’s going to be an image. You can put multiple links in your text. All of this stuff you see today, both on Facebook ads or any content marketing ads — I won’t say they grew out of what we were doing, but they’re not any deviation from what we were doing in ‘03.”

It wasn’t just the bloggers who benefited from the platform; advertisers who understood the blogging medium and how to speak to its readers became loyal users. “Blogads was an excellent tool because it wasn’t the bureaucracy that you’d get at a large company like Google,” said Joel Bartlett, vice president of marketing at PETA. “PETA was hosting some provocative content, and it was up to the blogger whether they wanted that to run on their website versus some giant corporation that was trying to set guidelines that work for everyone. It gave us more freedom and really direct access to the bloggers themselves, and I think because of that we were able to get ads on sites that supported the ads we were doing or supported our right to run those ads. And we had amazing results because of that.”

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The advertisers and bloggers I interviewed spoke to the direct relationships that came as a result of bloggers having veto powers over what ads appeared on their sites. “We had bloggers who would mention our ads in their writing,” said Bartlett. “We also had bloggers who, because of their support, gave us discounts. That was something they could decide to do.”

This was a far cry from today’s programmatic advertising, where multiple ad networks are plugged into a website and the publisher really has no idea which ads are being served up because they’re targeted to individual user behavior. “It completely disrupted the relationships publishers had with their advertisers,” said Goddard. “That’s the problem with programmatic ads running on these websites now. The publishers have no relationship with the advertisers, and the ad networks that they’re using really don’t care much about the publishers.”

But though everyone I talked to for this article spoke highly of Blogads and what it did for their careers, the company hardly exists anymore. It still works with a few websites, mostly in the gossip news space, to handle their advertising, but the platform that any website, from the biggest A-list bloggers to the tiny up-and-comers, could sign up for no longer exists.

Why? A few reasons. The first was that working with such a larger number of bloggers was like herding cats and extremely resource intensive. “It is beautiful and fun to sell ads at $20 on a tiny little blog, that is a gorgeous model,” said Copeland. “The thing I’ve learned is that you can spend as much time dealing with a problem on that $20 ad as you do on a $10,000 ad.” Bloggers were volatile and not always advertiser friendly, or sometimes they’d remove the Blogads widget on accident. “We’d have an ad we were running for a book publisher who really, really liked that blog, and yes it’s only $20, but it’s a book about cats in Egypt and this is a cats in Egypt blog, and the blogger takes the ad down, and you pissed off a great client.”

Perhaps the biggest blow to Blogads was that other networks swooped in and began to pick off its largest publishing partners. In some cases this was simply because the competing network was well-funded and could offer the blogger guaranteed revenue. Blogads was a bootstrapped company, and Copeland wasn’t willing to take on that amount of risk. “It just drove me nuts, because you can give someone a guarantee when you have VC backing, because you’re basically gambling that the market is going to continue to go up,” he said. “I was never going to give someone a guarantee because I knew that if the bottom fell out I didn’t want to be holding the bag making someone a $100,000 a month promise.”

In other cases, Blogads was just too generalized, and niche-specific ad networks would lure blogs away. For instance, one of the company’s largest and most lucrative contingents was mommy bloggers, but in 2005 a group of these bloggers teamed up to launch a BlogHer conference, the success of which led to the formation of an advertising network of the same name. “I would almost argue that was the beginning of the end,” said Copeland. “And there was no way to fight it.”

There were also a number of structural and technological issues that made it hard for Blogads to compete with these new entrants. The first was that it was never really IAB compliant, making it difficult for the network to make inroads with the Fortune 500 companies and the Madison Avenue agencies that serviced them. In the company’s early days, online advertising was still the Wild West, so its “fuck the IAB” approach worked in its favor. But once publishers started pulling in serious money from digital ads, advertisers needed better analytics and something that would scale more effectively.

While all this was going on, Blogads was also having problems maintaining its infrastructure. The software had been rushed to market and wasn’t built to scale properly. “Blogads would have been a lot bigger and the world might be a little different had I not rushed and panicked and basically put a prototype on the market,” said Copeland. “Because when things really started taking off in ‘05 and ‘06, it was architected so you could only have it on one server. And that’s not bad engineering; that’s people building a prototype. It took us literally three years and a quintupling of revenue to get around to fixing it, and we were still just rebuilding and trying to get to system 1.0.” In retrospect, Copeland wishes he had waited to launch the platform. “Had I not panicked in ‘02 and had I just said, ‘Let’s take another six months and get this right and then take it to market,’ it could have been that BlogHer would have never have happened. [Federated Media] wouldn’t have happened.”

Most of the above problems may have been avoided if Copeland just had access to more capital. But other than accepting some investment back when he was starting up Pressflex, he eschewed VC funding. “There were plenty of VC folks who said, ‘We should really meet, we should talk about what Blogads is up to, we think it has potential,’ and I knew it would be a colossal waste of time,” he said. He’s never had a particularly high opinion of VCs, and he didn’t want to hand over decision making power to a bunch of “numbskulls and boobs,” as he called them.

But still, Copeland recognizes that, despite building revolutionary advertising technology, he’s not as famous or widely heralded as a Jonah Peretti or a Shane Smith — much less a Mark Zuckerberg or Larry Page — in part because he was unwilling to take on funding and hit the scale button. “There are a number of entrepreneurs out there like me who are moving along in a fairly low key, under the radar way and they’re doing stuff that’s pretty cool and interesting,” he said. “But they’re never going to be giant because they haven’t rolled the dice with the VC who might push 20 million bucks at them and say, ‘Let’s really roll this out big and let’s buy a booth at CES or let’s do a takeover of the loft in downtown Austin.’” Ultimately, however, Copeland has no regrets. “It’s more fun not to have to deal with those dickheads.”

Either way, by the turn of the decade Blogads’ top earners were leaving in droves. “We didn’t really leave Blogads,” said TPM’s Josh Marshall. “It was sort of a long period of just working together less.” He started by joining some early programmatic ad networks and then eventually brought direct ad sales inhouse. Taegan Goddard left Blogads when he struck a deal with Congressional Quarterly that would allow the publisher to sell ads on Political Wire. “I allowed them to sell all of my ad space because they had great access to this market of policy advertisers,” he said.

These days, Blogads is a shell of its former self. I never encounter its platform anymore. Meanwhile, the digital advertising landscape looks completely different than it did when Blogads came of age. Online publishing is dominated by programmatic advertising, with each publisher plugging multiple pieces of ad tech into their pages at a time.

This has created a few problems. The first is that neither the publishers nor the advertisers themselves have any idea of what ads are running on individual pages. This is why over 2,900 companies were surprised when they were alerted that their ads appeared on white nationalist site Breitbart, or why major corporations threatened to abandon YouTube after their ads were shown along white supremacist content. Users have also grown annoyed by how much ad tech slows down websites, and that’s why 40 percent of laptop users have installed ad blockers on their browsers.

Meanwhile, publishers continue to struggle to generate sustaining income through ads, in large part because Facebook and Google are vacuuming up nearly every ad dollar that’s migrating online. It’s probably not a coincidence that the two former Blogads users I interviewed, Marshall and Goddard, have recently launched paid membership platforms for their sites. It’s becoming increasingly clear that publishers can’t scale their way to lucrative advertising revenue.

So perhaps it’s a good thing that Copeland didn’t try to adapt Blogads in this changing climate. It’s pretty evident at this point that trying to build an advertising company, at least one that isn’t Facebook or Google, is a losing proposition.

That’s not to say that Copeland has retreated; he’s just continued to launch products, often on the bleeding edge of new technology trends. The last time I spoke to him in person, it was at a conference in 2010, and he showed me a new tool he’d developed. Called Twiangulate, it allows you to plug in the Twitter handles of several popular Twitter users and then shows you the users they follow in common, ranking the accounts from least to most followed.

Why would this be valuable to someone? Well, while it’s incredibly hard to reach celebrity accounts, it’s much easier to get through to the people who influence the influencers. If Rihanna, Taylor Swift, and Drake all follow an account with only 1,500 followers, then chances are that that person is some kind of behind-the-scene player who is much more influential than their Twitter following would let on. Copeland essentially foresaw the rise of social media influencer marketing, which has become a multi billion dollar industry.

Another nascent industry Copeland is tackling: augmented reality. In 2014, years before it became a buzzword and we started to see mass hits like Pokemon Go, he launched an app called Racery. He had become fascinated by a mobile running app called Zombies, Run! It lets you listen to your favorite music as you run, but then it’ll interrupt the music with reports of a local zombie outbreak. You’re suddenly thrown into a world of the app’s making, and it’ll tell you when zombies are chasing you (causing you to run faster) and will steer you to where you can “collect” items that’ll help you survive.

But Zombies, Run offered only a single, non-customizable world. What if you were in, say, a Harry Potter fan community and wanted to craft a running experience that somehow mirrored that world? And what if you wanted to race with people who didn’t live in your physical location? A colleague of Copeland’s lamented to him that he wanted to run virtual races against his brother in Sweden, but at first he couldn’t come up with a solution. “And then six months later he came back and said, ‘I’ve got it. The app will take your daily miles and add them up over the course of a month, and then will overlay them on a Google Map,’” Copeland recalled. “We looked at the Google Maps API, and we were like, ‘Holy shit this is possible.’ So we began to experiment with it.”

Racery, which launched in 2014, pretty quickly amassed a small, but devoted fanbase. And while there are other running apps that have been more widely-adopted (Strava, Runkeeper, etc…), Copeland was able to target a specific niche in which the app has carved out a profitable business: nonprofits.

Charity runs and walks are among the leading fundraising tools for nonprofits and causes, which have traditionally been restricted to a single location to conduct these races. But with nonprofit members often spread out over different geographic areas, Racery provides an opportunity to increase participation, all without members having to leave their hometowns. “What they’re getting out of us is the whole platform, the ability to say, ‘Hey I want to launch a race tomorrow and I have a thousand people,’” said Copeland. Within 24 hours, those racers can log into the app, pay to participate, and begin logging their miles. “The Harry Potter Alliance ran a virtual marathon in London, and you could do multiple loops, and as you hit certain mile markers, you’d get a notification that here’s the bridge where this scene got filmed and a postcard would get triggered and go out to people.” Copeland has essentially created a CMS for augmented reality experiences, and he’s charging organizations upwards of $25,000 to create their own customized experiences.

Speaking to Copeland, it seemed evident that he no longer gave much thought to digital ads. He’d invented an entire platform, conquered an online medium, and then moved on once the scene got crowded. Augmented reality was the new shiny object, the industry that was young enough to where he could stake his claim.

But once again he’s eschewed venture capital funding, and the augmented reality space is starting to get crowded. Pokemon Go became an instant global sensation, and Nintendo has many other AR games on the way. An AR company called Magic Leap has raised $1.4 billion and is on the verge of releasing its first products. If there’s one lesson that can be drawn from Copeland’s past pursuits, it’s that being first to a scene doesn’t necessarily mean you’ll continue to thrive.

But he didn’t seem too concerned when I brought this up. Staying away from investors means that he never has to stay tied to one business, and, in his mind, the decline of one business just means he gets to pursue something new that interests him. For Copeland, the unforgiving and sometimes harsh economics of technology industries are a feature of entrepreneurship, not a bug. “You keep moving forward, make sure you have great people, and you keep on testing stuff,” he said at the end of our interview. “And you don’t get too locked into anything.”

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Simon Owens is a tech and media journalist living in Washington, DC. Follow him on Twitter, Facebook, or LinkedIn. Email him at simonowens@gmail.com. For a full bio, go here.

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