A good mechanical keyboard, 3 decent screens, a stand to mount them up high and make room on my desk, and a few other smaller things.
Those parts have done more for my career and sanity than anything else I could have spent my money on at the time.
I spend 40+ hours a week at or around this desk, I want it to be comfortable and work well for me. Not to mention that even if something makes me 1% more productive, it's worth it to spend $1000 a year on it and still "break even" in terms of cost (in theory)
It was a great investment for the financial return alone, but I also learned a lot about business, marketing, and the technical skills needed to run the website.
Not that I'm interested in finding it, I don't care, it's pure curiosity now.
Don't worry about it, I'll take your word for it. The world is more interesting than I thought!
I've made enough bad stock calls that I don't regret putting only $1000 in those, though. Those just happen to be my winners. We might need an Ask HN on our worst $1000 developments :)
That or my cat.
The reduction of hours might cost more than 1000$ though... but it is well worth it!
The subtext is more unpleasant...
At least that's unpleasant to me.
Monetarily, not massive returns, but as a percentage that was by far my biggest return on any investment.
Risk free investment:-)
This question is actually quite hard because so many things cost <=$1000, but it is hard to pick one that is the best.