How credible does the founding team have to be Thomas? While I might not be as well known here on HN as Maciej or yourself, I think I have more than enough of a track record to be credible.
This somewhat implies that the ApplyHN experiment is at least as much about performance art and entertainment as it is doing any sort of real entrepreneurship.
That's fine and all, but let's be honest with ourselves about why we're here.
Do I love his writing, sense of humor, and most importantly his sarcastic Twitter? Yes I do. But I voted for him because I do honestly believe that he would leverage this opportunity better than any of the other candidates in order to positively grow his site into something that could see significant growth.
I undoubtably expect that Maciej will not compromise on his values and vision for the site, even if that's a bit more difficult with investment money. But most importantly, I do think that there are many ways that Pinboard could grow without the need to compromise. That's why he got my vote.
My issue instead is with the reasoning GP gave--that it'll be fun to watch.
Many of the biggest companies founded in the last 3-4 decades have been because somebody thought "Wouldn't it be interesting if...?" In Apple's case, they explicitly thought of themselves as artists, and I doubt they're unique in that.
In fact, if part of the point of this exercise is legitimizing the use of HN as a sort of decorrelated "wisdom of the crowd" hedge for YC's ordinary selection, then including someone with great odds of doing something impactful with the YCF money is a good thing. YC will profit from it, and HN will have allowed that to happen.
Since none of the other startup ideas posted to Apply HN have especially credible founding teams (not a ding!), there's also something to be said for an Apply HN that tries it both ways, both by surfacing an unknown and also by admitting to YCF a company with an established track record. We can then see what YCF does for both kinds of companies.
And, finally: YC's got more than enough money to casually try this out, and one thing I am certain of is that YCF funding Pinboard via an application Maciej Ceglowski posts for Pinboard on Hacker News is going to bring a little bit of joy to my life. It will be fun to watch, for a lot of us, and that's worth something.