Yep, VA paid for the shirts from the Community groups petty cash fund, much as we paid for events at LUGs and other non-corporate events (my first two years at VA we gave out endless amounts of swag, distro CDs, various and sundry, but the team was almost totally an island unto itself. I just have a view that the events were too community-level to have had much of anything to do with the roadshow (and certainly from a professionalism standpoint would have been a distraction), and MS was already doing FOSS (as well as other *nix vendors, primarily SUN) a bunch of favors with its antics.
I was given the "official" spiel from Hall and it was otherwise not discussed much at VA (other than deciding very shortly afterwards that we all looked largely ridiculous, a position I still agree with - thankfully I'm in it for all of 1.5 seconds), and what I recall was that it was finished shortly after IPO and then sat for a while (because of lack of funds) waiting for final edits. At that stage you can't exactly go back to re-film much if you're already scrambling for cash.
"My only point was to push back on what I perhaps wrongly expected the narrative on HN to be, which is reflexive hagiography that doesn’t bear much resemblance to reality then or now." My feelings on pretty much all coverage of SV in general. But I am very biased, in that I love what I do in tech at the micro level but am ambivalent as to what the industry itself has morphed into. The beginning VA days were full of pre-HN/TechCrunch/Reddit sincere sense of wonder and opportunity to do something for the time radically different; in many ways VA succeeded given where the alumni landed (various key spots at Google, 23andMe, AWS, Samsung, Apple, AMD etc) and I still consider that period to be some of the most exciting of my career, if only for the sheer seat-of-pants ride it was.
I learned a lot and made numerous lifelong friends (and maybe a few lifelong enemies), but it was a helluva ride (cheesy events held in Fry's parking lots notwithstanding).