I probably started reading Kottke.org 5 or 6 years ago, but realise that in its near 17-year history, it has survived through some pretty radical changes on the Internet. Jason Kottke writes about this in a, perhaps inadvertently, revealing blog post on the topic of links—the essence of what makes the Internet the Internet.

I could write a lot about what I think defines Jason Kottke’s website as a go-to site for me. Yes, it’s not focussed on a particular topic-area (what are the liberal arts really, except everything), but generally the content is interesting, intelligent and, as a result, rewarding to read. I also appreciate the commercial direction that Kottke.org has taken. On a podcast-interview some years ago, Kottke said that he can’t have a similar sponsorship model to sites like Daring Fireball, because that site is focussed on a particular popular and profitable area (again, that indefinability of ‘culture’). Recently, Kottke.org took on a new sponsorship model revolving around Kickstarter projects, which seems like an excellent fit for the site and are ‘advertorials’ that I actually enjoy to read.

In the blog post that he entitled “The return of the remaindered links (sort of),” Kottke writes about the importance of links to Kottke.org’s initial growth and the subsequent commoditisation of links as the web evolved:

The links gave the site a velocity it didn’t previously have. I hadn’t really thought about it until I sat down to write this post, but that increase in velocity made it possible, more than two years later, for me to quit my job and do kottke.org full-time. But the web has changed. Sites like Reddit, Digg, and Hacker News and services like Facebook and Twitter are so much faster than this one man band…trying to keep pace is like racing an F1 car on roller skates. So, I’ve traded that velocity for quality (or, if you’d prefer, fussiness). I no longer post 10-12 things per day. Instead I post 4-6 of the most interesting things I can share with you on that given day.

With Twitter, things are changing for him again, but I understand the following sentiment quite well:

As my remaindered links experience shows, going fast without a plan can be beneficial in unexpected ways. With different tools and media delivery channels available to me now, I wonder: how fast can a one-person site go while still maintaining that choosiness?

To translate this into something more innovation focussed, we see phases of Kottke’s development:

  1. One of several blogs on the Internet.
  2. An increase in content and audience through the aggregation of links.
  3. Rise of link aggregators (along with, I believe, changes in the way Google weighs them) leads to a devaluation of the link concept.
  4. Refocus of site on quality over quantity again.
  5. Rise of Twitter as a personal link aggregation site (previous aggregators had much less identity associated with them).
  6. Attempt to reintegrate that into the Kottke.org brand.
  7. Next…?

There is no telling if his experiment will work, but my bet is that as long as he associates it with his unique vision about what goes onto the site, it will be somewhat successful. It’s important to note that his current advertising model (just referring to the sponsorships) is long form and therefore perhaps less suitable for a site that posts short links exclusively, if that is a possible direction he is considering.

In the end there is no such thing as sustainability, at least not in the “stay the same and make money” sense. Everything has diminishing returns as the rest of the “competition” eventually catches on. The key is to balance experiments with opportunity cost analysis (risks of jumping on wrong (technology) bandwagon, of alienating audiences or paying customers).