People and Blogs: Andy Baio

Let's start from the basics: can you introduce yourself?

Hi, my name's Andy Baio. I'm a writer and coder living in Portland, Oregon. You might know me from my blog, Waxy.org, where I've written for 25 years about the internet. If you've never heard of it, I rounded up some of the highlights from my first decade of blogging in 2012, and the second decade in 2022.

You may also know me from some of my other projects? I ran the XOXO festival in Portland for 12 years from 2012 to 2024, launched (and relaunched) the events community Upcoming.org, and I helped build Kickstarter as a long-time advisor and their first CTO.

Along the way, I coined the term "supercut," produced a chiptune tribute to Miles Davis's Kind of Blue, and got threatened with lawsuits a bunch of times. (I did some other stuff, too.)

These days, I'm mostly helping my wife Ami with her game design studio, Pink Tiger Games. We've self-published seven conversational party games since 2017, with three more slated for later this year.

What's the story behind your blog?

Before I started Waxy.org, I mostly sent links via instant messenger to my friends who had blogs. I knew I was good at finding things online, and after the umpteenth friend told me to start my own blog, I finally did. I wanted a place of my own online, somewhere to experiment and write about weird corners of internet culture, online community, and copyright, as well as a sandbox for new experimental projects of my own.

By the time I launched Waxy in April 2002, I felt like I was late to the blogging trend, which in hindsight, seems ridiculous. I was still pretty early, as it turns out. Within a year, I'd been interviewed by the New York Times and other major papers dozens of times for news stories I'd either broken or somehow found myself tangled up in.

The name, Waxy.org, came from a Perl script I'd written the year before to search for available .com, .org, and .net domains using every dictionary word in the English language. (I also picked up Meaty.org, which I never ended up using, and Upcoming.org, which I did.) "Waxy" didn't really mean anything, but I'd been using "waxpancake" as my alias for years so it seemed like a good fit.

I added a linkblog, Waxy Links, to the sidebar about 18 months after launch, which became a good outlet for quick links that didn't warrant full posts. I redesigned the site in 2008 with a cleaner design and better mobile support.

After 14 years of blogging, I switched from Movable Type to WordPress in 2016, with a new redesign that I slowly improved in the years since. I recently added redesigned archives and search, which I'm pretty happy with.

It's always under construction, a work in progress — like me, you, and the rest of the internet.

What does your creative process look like when it comes to blogging?

I used to do much more investigative journalism, but these days, Waxy is primarily a linkblog where I point to fun or interesting things I find online. Unless I stumble on a story too compelling to ignore, forcing me to pull the string and see where it leads.

Those story ideas and links can come from anywhere. I'm a voracious consumer of information online, and I've always joked that Waxy is the natural byproduct of endlessly procrastinating from doing other things by looking at the internet.

I subscribe to around 450 feeds in Inoreader, my RSS reader, and skim it all nearly every day. I follow another 1,000 or so people each on Bluesky and Mastodon, with custom lists for each so I don't miss particular people. I'm in dozens of Discords, many with people sharing their work or pointing out good stuff they find online, and nearly 100 mostly-niche subreddits covering many of my interests. I use tools like Sill and Scour to find signal in the noise, and even built a link aggregator of my own that I used for years to find good links on Twitter, until Elon shut down the API.

My frequency of posting has waned over the years, first cannibalized by social media and then by larger life and work stuff. I've recently found myself drawn back to it, posting more regularly, trying to wake those atrophied writing muscles. Even if I've slowed down, it's hard to ever imagine stopping entirely.

Do you have an ideal creative environment? Also do you believe the physical space influences your creativity?

I used to be able to work from anywhere, typically a coffeehouse or library, and tune out the rest of the world on my laptop with a good pair of earbuds.

As my eyesight's worsened, I find that working on a large monitor is more of a necessity than a luxury for any serious length of time, especially if I'm coding.

I also used to love working around others, but these days, I tend to like retreating to the quiet of my basement office. No music, no sound. Just a quiet hum of my computer and the sounds of my keyboard.

A question for the techie readers: can you run us through your tech stack?

I use WordPress with my own custom-written theme, using the Advanced Custom Fields plugin to handle all the special fields necessary for my linkblog. I use a custom bot to cross-post my links to Bluesky, and a plugin called Share on Mastodon to post things there. (I stopped automatically cross-posting to X/Twitter years ago, for obvious reasons.) Everything's hosted on a DigitalOcean droplet along with a bunch of other side projects, with Cloudflare managing the domain and DNS.

Given your experience, if you were to start a blog today, would you do anything differently?

I would have started collecting email addresses from the very beginning. I've never really liked reading newsletters by email, and I read almost every newsletter I subscribe to through my feedreader, which gives me so much control over my attention. But I never considered that people would start to shift their attention away from the web, or that feedreaders would largely go away, so I never tried to build a mailing list for my own projects.

The ability to directly reach the people who care most about your work, outside of the capricious nature of social media algorithms, is essential. It's my one big regret, and I hope to change that soon.

Financial question since the Web is obsessed with money: how much does it cost to run your blog? Is it just a cost, or does it generate some revenue? And what's your position on people monetising personal blogs?

My blog has never cost much to run, and never made much money. I used to have a dedicated server that cost $150/month, but these days, it's running around $50/month on a shared instance with some other projects of mine.

The visibility and reach from writing on Waxy opened a lot of doors for me, though. I met so many amazing creative people through blogging, and it gave me a platform for launching projects that I wouldn't have had otherwise. I met most of my friends, directly or indirectly, through the writing I did on Waxy.org.

I did run ads on my blog for a few years, experimenting with Google ads from 2004 to 2005 and, in 2006, joining as one of the first members of The Deck, Jim Coudal's pioneering unobtrusive, privacy-centric boutique ad network that helped support sites like Daring Fireball, Kottke.org, Ze Frank, The Morning News, A List Apart, and many others. It paid me a reliable $1,000/month for ten years, until shortly before it wound down in 2017. I haven't made any direct income from my blog since then.

I think anything that supports independent writers/bloggers, artists, or other creators on their own terms is a good thing, whether it's through Kickstarter, Patreon, or more commonly, through paid subscription newsletters. I have major issues with Substack's management, but I credit them for normalizing the idea of directly paying bloggers a recurring monthly fee. But please use Ghost or Buttondown instead.

Time for some recommendations: any blog you think is worth checking out? And also, who do you think I should be interviewing next?

Oh, god, too many to list. Off the top of my head, Marcin Wichary's Unsung is probably my favorite new blog, constantly updated with new insights about user interfaces and design. Nobody notices things the way that Marcin notices things.

Matt Muir's Web Curios is like a month's worth of good links crammed into a single post every Friday. I don't know how he's done it so well for so long.

Depths of Wikipedia's Annie Rauwerda isn't a traditional blogger, but spreads her curatorial eye between two Bluesky accounts, two Instagram accounts, TikTok, a newsletter, a touring live stage show, and a very good personal website. She's just so funny and weird and good. I wish she had an RSS feed that combined it all. Maybe I'll make one for her.

I think David Friedman's Ironic Sans is incredibly underrated, moving from a traditional blog to more of a newsletter format, with weird little side projects and games along the way. He's been continuously great for 20 years.

I'd love to see Jason Kottke interviewed. More than anyone I can think of, he's carved out a Kottke-shaped hole for himself on the web, growing it into a sustainable living through direct reader support over nearly 30 years. Even now, he continues to refine and adapt and evolve his site in surprising ways.

Final question: is there anything you want to share with us?

The last project I worked on was the permanent archive for XOXO that launched in April, collecting everything we did related to the festival. The site was a huge undertaking, bringing together every lineup, schedule, recap video, conference talk, and standalone website that we ever made into a single permanent archive, filled with little photos and ephemera from the festival.

XOXO was a huge part of my life for 12 years, easily the most creatively rewarding and emotionally exhausting work of my career, and I'm really proud of how the archive came out. At the very least, go poke through the video archives. The featured tag highlights some of our favorites, like Cabel Sasser's wonderful talk from our final year.