I think the early-00s was when it started to shift from something stigmatized to something that a person could be into and still be cool—or, at least, not regarded as automatically weird. By 2010 the shift was basically done, and The Great Techbro Wave was washing over the industry.
It's been super weird to watch the common idea of a computer person shift from someone with bad skin and shit posture in a pit-stained button-up and thick-rimmed glasses and who rarely sees the sun, to a trim, decent-looking person who's into rock climbing and wears lots of new, clean clothes from Patagonia. It was a really fast transition, in hindsight.