370: ‘Fine Hypertext Products’, With Jason Kottke

Episode Summary

Executive Summary: Jason Kottke and John Gruber reflect on 25 years of web publishing, tracing the evolution from experimental personal sites and episodic design to blogging, RSS, and modern link curation. They discuss the craft and psychology of writing online, the strain of constant feedback, the decline of the open web, paywalls, dead links, and why sustainable independent publishing now often requires rethinking pace, format, and boundaries.

Main Topics: The origin and evolution of Kottke.org (Priority: 5/5): Kottke explains how his work began with Oscillate, an early episodic site from the mid-1990s, then shifted naturally into a blog because publishing became easier and people responded positively. Blogging, RSS, and the form of web writing (Priority: 5/5): They discuss how reverse-chronological posts, RSS, and titleless short-form writing shaped the blog format and made frequent reading habits feel natural. Design, craft, and the feel of old web publishing (Priority: 4/5): The conversation revisits frames, JavaScript toys, early web experimentation, movable type, and the evolution from playful design experiments to a more stable editorial identity. Monetization, memberships, and the Deck model (Priority: 5/5): They compare old membership schemes, ad-supported models, and modern subscription approaches, with a shared preference for keeping most writing free and accessible. Burnout, sabbaticals, and the cost of relentless online publishing (Priority: 5/5): Kottke describes taking a seven-month sabbatical due to burnout, the strain of constant feedback, and the need to protect personal life and long-term sustainability. The decline of the open web and link rot (Priority: 4/5): They lament dead links, paywalls, and social platforms absorbing writing that used to live on personal sites, making it harder to link to durable, open content. Indie publishing as a durable identity (Priority: 4/5): Both speakers emphasize that their sites are built around personal voice, flexibility, and direct audience relationships rather than platform dependence or corporate structure.

Key Arguments: Chronological, feed-driven blogging became the natural web format because it matched how readers checked sites and how writers could publish frequently without overthinking structure. Hyperlinks are not just references but part of the writing itself; for web writers they function like a core rhetorical device, not decoration. A sustainable independent site often works best when the publisher can keep control, avoid excessive bureaucracy, and retain the freedom to publish in a personal voice. The open web is weakened by paywalls, social platforms, and link rot, which make durable linking and broad access harder for writers and readers. Membership and subscription models can support indie publishing, but many writers prefer to keep content open and monetize in less intrusive ways. Burnout is a real occupational hazard for solo online publishers because the work never fully ends and feedback arrives continuously, both positively and negatively.

Data Points: Kottke.org anniversary: 25 years - The episode centers on the site’s quarter-century milestone. Official anniversary date: March 14 - Kottke notes the site launched on March 14. Daring Fireball age: 20 years - Gruber says his site turned 20 the previous August. Kottke post count: about 40,000 - Kottke says his archive contains roughly forty thousand posts. Daring Fireball post count: about 32,000 - Gruber estimates his archive at roughly thirty-two thousand posts, excluding sponsor copy. Sabbatical length: 7 months - Kottke explains his break lasted longer than the originally expected 4–6 months. Expected sabbatical length: 4–6 months - Kottke says this was his initial expectation. Oscillate start: early 1996 - Kottke dates his pre-blog experimental site to early 1996. Full-time transition: 2005 - Kottke says he began doing the site as a full-time job then. Gruber full-time transition: 2006 - Gruber says he moved to full-time blogging in 2006. New York residence window: 2002–2016 - Kottke mentions his years living in New York before moving north. Google Reader impact: major RSS-era shift - They describe Google Reader as a key factor in making full-feed subscriptions and reader habits central to blogging.

Pivotal Quotes: "I just felt burned out and I had felt burned out for quite a while." — Jason Kottke: Explaining why he took a long sabbatical from publishing. "Hyperlinks are like italics on steroids, on superpowers." — John Gruber: Describing why links are an essential part of web writing. "I feel a genuine responsibility to keep going on that basis to prove that this works." — Jason Kottke: On running a paid-membership-supported site while keeping the content open.

Implications: The episode argues that independent web publishing still works, but only if writers protect their energy, own their platforms, and resist overreliance on closed systems. It also warns that link rot, paywalls, and social-media drift are eroding the original open-web culture.