I have one quick tip. If you regularly read the typical startup press, like TechCrunch, GigaOM, The Verge, etc (or heck, even Hacker News): STOP. Stop reading

I have one quick tip. If you regularly read the typical startup press, like TechCrunch, GigaOM, The Verge, etc (or heck, even Hacker News): STOP. Stop reading about other startups. Instead, turn your news consumption to general news topics, or better yet - news about your industry & your customers. (If your customers are other startups, then, well, sorry...) It sounds like a few of the ways you are measuring yourself are by raising money, being in the press, and whatever you define as "real success". I would argue that the first two are inconsequential, and ironically, you know that too, because you haven't announced your fundraising. If you cut out the inconsequential news from your news diet, you may find yourself feeling a bit better. It may not resolve your feelings entirely, but it may help. I know because I've been there, and this worked for me.