The Pioneers

Now that everyone seems interested in blogging again, here’s a list of early and influential bloggers that helped to shape the genre. Maybe you can borrow some pointers.

By Ernie Smith • Jan 04, 2023

Today in Tedium: I think the thing I’ve realized recently is that it’s been so long since we’ve had a fully open online culture that we haven’t really talked about how that is different from what came before, and why it’s something people might want. The reaction when the fediverse, particularly Mastodon, saw a surge in attention was telling. It’s not just the commentary about the platform being confusing or the concern that having to make choices about your digital identity was hard. We have been centralized so long that many of us don’t even remember how it feels to experience online creation on an open plot of land. So with that in mind, given the fresh attention being given to blogging at the moment, I wanted to offer a quick guide to some key early voices in blogging that might give you an idea of what exactly you’re getting into if you decide to start a blog in 2023. This is going to be a listicle style, and I’m going to focus more on historic relevance than fame or authority. For at least some of these, I am specifically highlighting voices you may or may not know so that you dive in a little further. (Folks like Anil Dash and Jason Kottke and John Gruber are hopefully obvious.) The numbers mean nothing in terms of order, other than a rough chronological order. So, with that in mind, today’s Tedium talks blogging pioneers. — Ernie @ Tedium

1. Jerry Pournelle

Blogging genres: Technology, science fiction, conservatism

Known for: Writing books, writing a column for Byte, being the first writer to use a computer

Website: Chaos Manor

When I was 12 years old and obsessed with reading old technology magazines at the library, this man was a legend to me. Still kind of is. A science-fiction author who dabbled in computers at a time when that was unexpected, he found a perch for his interest in computers in the pages of Byte, a magazine that had no real interest in how companies were run or boardroom wheelings and dealings that define modern tech journalism, but rather the technology itself.

Pournelle would write massive, multi-thousand-word columns that were more like journeys than reviews, and were really just him talking about how he experienced the world more than any attempt to do so previously. When I described him in a 2017 piece written upon his passing, I called him “one of the writing world’s greatest early adopters—setting the parameters for how writing and technology would interact.”

As a digital-first writer, his Chaos Manor website predated the term “blog,” and he wasn’t a huge fan of using it, but in many ways, he helped to shape the form in important ways, and if you see some writer going extremely long on a topic, he is the guy who helped shape what that would look like in a digital format.

It should be noted that Pournelle sometimes dabbled in political commentary, especially later in life, making his website a great fit for the blogosphere that grew around him.

2. Justin Hall

Blogging genres: Personal website, lifestreaming

Known for: Being one of the original bloggers

Site: Links from the Underground (Links.net)

If there is something that can be taken away from Pournelle’s “first writer on the internet” stance, it’s that he started in the pre-internet days, sharing on outlets like BIX, only later moving to the World Wide Web.

Justin Hall, on the other hand, started writing in a blog-style format on the web as a college student way back in January of 1994, with arguably one of the best domains on the internet—links.net. He is considered widely to be the first-ever blogger, with a website that feels utterly retro in nature and in its 1994 form reflecting a blast from the past in the best way possible.

Hall was notable for laying everything out on the line in its rawest form, basically using this home base as a place to tell his life story.

Hall, who now works at an online marijuana dispensary startup, went to the trouble of doing a 40-minute documentary on his life as the first blogger seven and a half years ago and it has less than 15,000 views on YouTube. A goddamn shame.

Mirsky’s Worst of the Web, as it appeared in 1995.

3. David Mirsky

Blogging genres: Link of the day

Known for: Starting Mirsky’s Worst of the Web

Website: Mirsky.com

Mirsky’s Worst of the Web was such an influential site for me that I made it the subject of the third-ever issue of Tedium.

Created by comedy writer David Mirsky, the site—a lampooning of cool-site-of-the-day sites like, well, Cool Site of the Day, was deeply influential on the shape of the early web, as it may arguably be one of the first successful examples of shitposting, which is obviously one of the more important elements of online culture. Without shitposting, what would be the point?

Sure, other shitposters took things a lot further than he did—and the later sites Something Awful and Fark were arguably more influential—but his role embracing the bottom of the barrel was novel in 1995 or so.

Admittedly though, it didn’t work out for him in the end. Mirsky tried the creator thing at a time nobody else was in the hopes that it would make him rich, but after failing to have success after 18 months, he ended up quitting, eventually taking on a role as a writer for the animated comedy Futurama.

Pop&Politics, as it appeared in 1996.

4. Farai Chideya

Blogging genres: News, politics, culture

Known for: Becoming one of the first Black bloggers

Website: Farai.com

In 1999, the early online entrepreneur Omar Wasow, a former BBS operator, found much success by creating BlackPlanet.com, a social media network for Black audiences that was one of the first of its kind. A few years prior, Wasow (who is now a high-profile academic at UC Berkley) helped a Harvard graduate and freelance journalist build a presence on the internet for her political and pop-culture writing—and as a result helped create one of the first genre-defining blogs.

That website, called Pop&Politics, was so early to blogging that it referred to the blog as “digitally syndicated columns.”

Farai Chideya was an early digital culture native, something she was exposed to while at Harvard, as Charlton McIlwain’s 2019 book Black Software: The Internet and Racial Justice, From the Afronet to Black Lives Matter makes clear. She joined the WELL at a time when the community was almost entirely white, and was very active in some of the earliest Black-focused online communities, such as AOL’s NetNoir community. But from a blogging point of view, Pop&Politics (which later evolved into a podcast) was perhaps the most groundbreaking part of Chideya’s online presence.

“I saw Pop&Politics as a place where I could be free and say what I wanted without editorial oversight, which again is good and bad,” she recalled in the book. “With solo blogging … most successful bloggers, even ones who are solo bloggers, have someone editing them. I enjoyed the freedom. Newsweek had rules about how much voice you could put into a particular piece.”

Chideya, who used Pop&Politics and NetNoir to successfully launch a book, was also notable in another sense, as her work made her one of the first bloggers to regularly appear on television as a political pundit, something that Wasow also notably did.

Treacle, as it appeared in 2001.

5. Erin Venema

Blogging genres: Personal, diary

Known for: Coining a term that perfectly describes blogging, creating an early online diary

Website: Treacle.net

Venema may not be a high-profile figure in the modern blogosphere, but in 1999, she came up with a clever term to describe the budding space around online journaling, which she shared on the mailing list to the early writing mailing list American Folk:

Well, we could make a Spanish/English half-pun and call oursevles escribitionists. grin Hmm ... I kinda like the sound of that.

In many ways, escribitionist is arguably a better term to describe what personal bloggers do than blogging. It is essentially writing on a tightrope for a digital, public audience. Sure, it is perhaps not as neat and tidy as “blog,” but it captures the glory, pain, and risk of the process. Unlike a handwritten diary, you are putting yourself out there, on days good and bad, and there is a degree of bravery that comes with that.

Venema makes this list partly because of how early she was to the game of online diary-writing, launching well before LiveJournal existed. Her website, Treacle.net, founded in 1997, is still online today, by the way, though it hasn’t been updated since 2016.

Coudal Partners, as it appears today. The site’s design has largely maintained this shape through much of its history.

6. Jim Coudal

Blogging genres: Design, marketing, business

Known for: Coudal Partners, Field Notes, launching an early ad network for bloggers

Website: Coudal Partners

In recent years, the business world has evolved into one that uses blogging as a lingua franca of sorts, a genre of creation called content marketing. Jim Coudal, with his ad agency Coudal Partners, was one of the very first to embrace this general concept in the late 1990s, launching a site that had interesting links and stories throughout.

It put enough of an interest on Coudal’s business that it might have set the stage for the company’s second act, a popular line of notebooks called Field Notes.

If that was all he did, that would be impressive, but Coudal also played a key role in supporting the early blogosphere through his ad network The Deck, an ad network driven by influential bloggers that tried something all too rare—it tried to build a market for advertising without tracking or in-your-face ads, and found success doing so. It wasn’t the first—that was BlogAds—but it was very popular among some of the most prominent voices of the blog era, which makes it particularly notable.

The ad network’s 2017 shutdown was seen as a sign that the blogosphere was declining.

Dooce, as it appears today.

7. Heather Armstrong

Blogging genres: Mommy blogging, lifecasting

Known for: Getting fired for blogging about her job when that was a novel thing

Website: Dooce

In many ways, Armstrong experienced a lot of the negative effects of blogging long before a lot of other people did—but also many of its successes.

Armstrong, a former dot-com employee in the early 2000s, ran her blog (launched in 2001) as something of a satire of startup culture, of which she was part. Problem was, her coworkers found it—and soon she was out of a job, a phenomenon that became known as being “Dooced.”

But in a way, the incident only set her up for success in the medium—in part because of the attention that it afforded her, but also because of her decision after having a child to turn the site into a parenting blog—effectively making her one of the first “mommybloggers.”

She found a lot of financial success as a blogger, but she also faced many challenges along the way, many of which she’s written about. A 2019 Vox profile highlighted how her struggles with depression and divorce from her first husband were likely worsened by sharing her life publicly for so many years.

“The hate was very, very scary and very, very hard to live through,” she told the website. “It gets inside your head and eats away at your brain. It became untenable.”

Despite the challenges, which led to a break from blogging, she maintains the site to this day, with the most recent entry running in November.

Little Green Footballs, as it appears today.

8. Charles Johnson

Blogging genres: Politics

Known for: Being a guitarist, running Little Green Footballs

Website: Little Green Footballs

We can’t talk about the early blogosphere without talking about the rise of political blogs, with sites like Daily Kos, Talking Points Memo, and Andrew Sullivan’s The Daily Dish helping to shape the discourse along the political spectrum.

Perhaps the best example of the shift in influence that political blogs had on the discourse came from Charles Johnson, a onetime jazz guitarist whose Little Green Footballs emerged in 2001, in many ways reflects the shape of the blogosphere. Johnson started his site with a relatively apolitical bent, which shifted dramatically after the attacks on September 11, 2001. Johnson helped to use his platform to support the War on Terror, and played an important role in exposing Memogate—the controversy around George W. Bush’s service records that led to Dan Rather’s ouster from CBS News—all because he was observant about how text is portrayed in Microsoft Word.

What’s fascinating about Johnson is that around 2009 or so, he dramatically changed sides and took a more left-leaning stance, denouncing many of his more aggressive anti-Islam stances in the process. These kinds of political shifts are not particularly common—and if they happen, it’s often more gradual than what Johnson did.

In many ways the political blogosphere has largely shifted to social media and Substack, but Johnson’s blog is still operating more than two decades in.

Gawker, as it appeared in 2003.

9. Elizabeth Spiers

Blogging genres: News, politics, media

Known for: Being the original writer for Gawker, editing the New York Observer

Website: Elizabeth Spiers

In many ways, the original form of Gawker, despite the hate it later fostered, represented one of the first true attempts to turn blogging into a business, rather than a purely creative medium. Spiers, who only worked at the position for about a year, maybe a little less, nonetheless helped to shape its early focus on New York City, its voice, and the website’s reputation as a launchpad for important writers.

As the magazine N+1 wrote of the Nick Denton-founded site, Spiers approached her role as an outsider to NYC whose voice wasn’t as aggressive as Gawker would end up being, but whose writing style set the tone for the whole franchise.

“There have been so many incarnations of Gawker,” Spiers told Recode in 2016. “If you read it when I was writing it, it wasn’t really negative — it was gleefully laughing at the notion that the entire world revolves around New York. The alter-ego voice I was using was a persona that had no self-awareness, and that was part of the fun of it.”

This concept was a model that Denton replicated a couple of years later with an even more pointed tone, with the D.C.-focused, Ana Marie Cox-edited website Wonkette in 2004. And of course, Gawker became a dominant part of the internet for many years. But Spiers was first, and accordingly played a key role in shaping the overall voice.

The first image to appear on Soup, way back in 2007.

10. Anthony De Rosa

Blogging genres: Tumblogging, social media reporting

Known for: Working at a number of major media outlets, running the Soup Tumblr

Website: Soup on Tumblr

Tumblr first went online in the winter of 2007, the work of a software consultancy owned by a then-20-year-old David Karp (and developed closely with the help of Marco Arment, an app developer who is also a popular podcaster). In the fall of 2007, an unsuspecting thirtysomething Mets fan named Anthony De Rosa launched a site called Soup on Tumblr with a camera phone photo of a MacBook showing Soup starting Soup while The Colbert Report was playing in the background.

Not that he could have known it at the time but this was the perfect opening bow for De Rosa as a public-facing blogger—less than a decade later, he would find himself working at a version of The Daily Show that was finding its footing after Colbert and later Jon Stewart had left the late-night franchise. He had evolved into a successful digital journalist thanks in no small part to the site he originated on that fall evening.

Anthony’s gift to the medium of blogging was the role of curation—a newshound’s eye that focused less on having a lot to say and more on bringing together a lot of interesting ideas and angles in a single place. It was a skill that grew increasingly important over time, and one that particularly found value on Tumblr and later Twitter. Tumblr, in many ways, was a bridge between blogging and social media, and De Rosa was one of the first people to cross it.

While De Rosa, like a number of vintage Tumblr users (myself included), eventually moved away from the medium, his success in media shows how blogging came to shape the media significantly in the 2010s. During that period, De Rosa spent time at Reuters, The Wall Street Journal, The Daily Show, and at the media startup Circa.

There are lots of different voices and people that could have been on this list. I kept it to 10 and largely tried to pick people who I felt had shaped the nature of the blogosphere in significant ways, whether through technology, writing style, presence, or terminology.

Some of these people were big names. Some of these people had smaller presences. Some were influential because of what they said. Others because of what they built, or what they represented. But all of them did something important in the history of blogging—they decided one day to put themselves out there on the internet, writing voice and all, to just see what might happen.

If you’re thinking about starting a blog this year, you could learn a lot from the stories of any of these people. Their writing, both individually and collectively, shaped a medium, and many of them needed a lot more than 280 characters to do so.

Are there any bloggers you think should be a part of this list? Give me a shout!

Find this one an interesting read? Share it with a pal! And if you decide to start a blog this year, may you find a great topic and the right voice.

And thanks to Important, Not Important for sponsoring.

Correction: An earlier version of this article incorrectly claimed The Deck was the first blog ad network; that honor goes to BlogAds. We regret the error.