ok, good point. However, based on my experience with HN, I bet the second segment of people you describe are under represented here. I generally see swagger discouraged around here so a strategy like this is not effective, even if it made the frontpage.
He's a no-name designer (not to be too disparaging) in a sea of no-name designers. A tiny percentage of a large (HN) crowd is still going to be a bigger audience for him than he might have got with a plain site.
I have more experience and a broader portfolio, but do you think anyone would have reason to submit my site to HN? Nup.
If the large percentage rubbed the wrong way by this were likely to rain his house with stones, he'd have a problem, but they won't. They'll move on to the next topic and forget him pretty quickly.
On top of that, he will get a more receptive crowd as this moves around Twitter and the like too.
I'd guess that big business or even medium enterprises won't touch him, but anyone needing a freelancer or with a start-up might. Those two groups would be reasonably well represented here.
