Let me be the first to say what a lot of my startup/YC dork friends are only going to say privately on Slack:
If you're not going give Pinboard one of the two HN/YCF slots, because Maciej is HN-famous or too well-established, then just make a third slot for him. This is the cheapest access you will ever get to Maciej Ceglowski.
YC came up with an interesting idea and actually tried it. Something interesting happened as a result. Let's see where it goes!
This is the cheapest access you will ever get to Maciej Ceglowski.
But do they want access to Maciej Ceglowski? They didn't want access to me, even after I promised that I would refrain from providing any marketing advice; and I'd like to think that I could be a helpful member of the community.
(Which, incidentally, is why you don't see Tarsnap on this list. I figured that since YC had decided that they didn't want to award a fellowship, the best possible outcome of submitting Tarsnap here would be that YC gets pushed into funding someone they didn't want to fund... and I want to see Apply HN be a success, so I didn't want to sabotage it like that.)
I think the difference is that you've stated explicitly that you'd rather be King than Rich, while Maciej's response when asked that was "I feel like after seven years, I have a pretty good sense of what bookmarking/archiving needs people have, but am at the limits of what I can personally build. If the votes swing my way, I'd be happy to have a good-faith conversation with you", i.e. as long as YC didn't try to turn Pinboard into something it isn't, he'd be willing to listen to ideas that may help it reach more people. The difference is pretty subtle, but it basically amounts to "Is YC wasting its time with its advice?" It also helps that it's Kevin Hale opening the conversation, and Wufoo was not unlike Pinboard (or Tarsnap, for that matter).
Nothing wrong with being King, BTW, but YC's made it clear that it's not willing to play court jester.
Tarsnap is definitely not suited for YC Core. I applied for YC Fellowship -- and only YC Fellowship -- because I wasn't sure if Tarsnap was suitable or not: I don't know what YC is trying to do with YC Fellowship. (For that matter, it's far from clear that YC knows what YC is trying to do with YC Fellowship.)
Follow up. Kinda bummed you didn't submit Tarsnap.
I understand why some believe that projects like Pinboard or Tarsnap don't "fit the spirit" of Apply HN, and that truly makes me sad.
Software like Pinboard or Tarsnap should embody great "hacker" software, and the sort of software quality that YC companies aspire to build. The concept that these ideas are less "fund-able" because they don't have more attractive splash screens or because they haven't embraced growth hacking is a real shame.
It all depends on what the purpose of YC Fellowships is. If the purpose is "get a direct return on investment", Tarsnap and Pinboard are probably not good companies to accept. If the purpose is "gain information to improve future YC Core admission decisions", likewise. If the purpose is "bring interesting people together who will contribute to the YC community and help other YC-funded companies", then I think they should accept Tarsnap and Pinboard.
But I don't think YC makes many mistakes, so I'm inclined to conclude that the third of those possible purposes is not why YC set up the Fellowship program.
I went back and reviewed the YC Fellowship thread and sama's AMA thread because I got curious about this.
I would like to understand why you are reluctant to take investment. As I see it, there are two possible paths:
1) You take investment from YC, you become part of the community, you get advice, but your desire to remain King is respected. It seems to me that if this were the outcome, moving to the Bay Area for three months and incorporating in the US is a fair exchange.
2) You take investment from YC, you become part of the community, you get advice, AND there is now a perceptible push to make Tarsnap more like a "make-me-Rich" company rather than "keep-me-King" company: they keep on suggesting that you raise more money and start doing things that would increase the valuation of the company but that you would fundamentally disagree with, etc. etc. Certainly this would not seem like a fair exchange.
IOW, what I am trying to ask you is this: is the fundamental reason why you are reluctant to apply to YC Core is that you are concerned that your desire to remain King will be challenged? Or is it something else entirely that I am not seeing? Because certainly incorporating in the US is a schlep, and finding housing in the Bay Area is a schlep, but I can't imagine those being the fundamental reasons for not applying to YC considering the benefits of the community, and getting a bunch of money from YC, if it comes with no strings attached (aside from the moving and incorporation mentioned above), can't be a bad thing, even if you don't need it.
It's partly the king-not-rich bit; but it's also partly that I'm an irrationally patriotic Canadian. Canada is my home, and Canada is Tarsnap's home; my notion of success includes providing an example of a Canadian startup which was successful without moving to the bay area -- because Canada is sorely lacking such examples.
That looks like a strangely self-limiting argument.
No one in their right mind would argue that Canada can't produce a company that has global reach, but that consists of a founder that lives in Canada, and a UI programmer that lives in Romania. It doesn't seem to me that those are the examples that Canada is lacking.
It seems perfectly reasonable, however, to argue that Canada doesn't have the investment ecosystem that is capable of creating a <insert your favorite company whose founders chose rich rather than King> on the same scale as the Bay Area - but it doesn't seem like that's the example you are trying to set anyway.
Sorry, that was a bit incoherent; I was nearly asleep when I wrote it. Probably better to say that I'm pushing back against a pervasive notion that "you have to move to the USA if you want to succeed".
If you're not going give Pinboard one of the two HN/YCF slots, because Maciej is HN-famous or too well-established, then just make a third slot for him. This is the cheapest access you will ever get to Maciej Ceglowski.
YC came up with an interesting idea and actually tried it. Something interesting happened as a result. Let's see where it goes!