Explaining Steve Gillmor
Nobody I know can understand a thing Steve Gillmor is talking about, mainly because he makes so many obscure references without explaining them. I thought as a public service I would provide a detailed exposition of his latest blog post, Bad Sinatra.
Context & Ripple Effects
Steve Gillmor spent 2006 as one of the most-quoted voices in tech commentary — his February Gillmor Gang episode on Memeorandum and the future of media set the agenda others reacted to. By late December, though, the complaint circulating among readers was that his blog prose had become unreadable: unexplained references stacked so densely that even attentive followers could not reconstruct what he was arguing.
Joel Spolsky, writing on Joel on Software — one of the most widely read software blogs of the period — turns that complaint into a stunt-exposé, publishing a detailed exposition of Gillmor's post "Bad Sinatra" as a "public service." When a mainstream explainer has to be written to decode a fellow pundit, the story stops being about the subject matter and becomes a verdict on insider-allusive tech writing itself.
First-order effects
- Readers of both blogs get a working translation of "Bad Sinatra," which directly tests whether Gillmor's argument survives being made explicit — the exposition either vindicates the substance or exposes the obscurity as load-bearing.
Second-order effects
- Gillmor's standing depends on how he responds: doubling down on allusion risks ceding the explanatory audience to writers like Spolsky, while simplifying costs him the in-group register his regulars value.
Third-order effects
- If the pattern holds across mid-2000s tech blogging, unexplained-reference writing gets recast from a credential into a liability, pressuring prominent commentators toward self-contained prose or confining them to ever-smaller expert audiences.
The trend: Tech blogging is splitting between insider-allusive commentary that presumes shared context and explanatory writing built for general readers, with readability becoming a competitive weapon between prominent voices.