You might be surprised at the responses you'd get. As you probably know web startups are cheaper than ever to build; that's why the YC model works so well. It's not in a startup's interest to raise huge amounts and give up lots of equity early on; it's far better to give up less than 10% (YC typically gets 6-7%). If you saw a company that you could relate to, and which you understood the dynamics of, and furthermore might also be able to contribute your support to then that can be worth quite a lot. The money is just part of what you can bring to the table. You've already built a successful tech app so you obviously have some tech knowledge, which is likely valuable. It certainly doesn't hurt to ask; the YC companies are the same types likely to be on HN, so approach it as more of a community/team aspect than a rigid VC offer. An early YC company might give up another 4-5% for what you could offer, and even that small amount might be worth millions in the not-too-distant future - meeting your criteria.