What's the equivalent for comments?
Personally I think articles about how to make more money are nothing to do with the hacker mindset, but I wouldn't even consider flagging them if other people found them interesting enough to upvote.
On-Topic: Anything that good hackers would find interesting. That includes more than hacking and startups.
Startup-related stuff is therefore explicitly on topic. Making more money seems on topic re: startups.
No better than pointing towards a dusty old copy of the Jargon File -- or the New Hacker's Dictionary, the book version I read when I was a teenager, without which I probably wouldn't be here saying this.
Anyhow, the difference in mindsets between the different readers is EXACTLY why I wouldn't go around flagging things as off-topic that other people liked. Viva la difference.