Generally, you want to raise capital either when you have to or when it's really easy. If the company desperately needs money, and they can't figure out any other way, then they need to raise money. Or if someone's offering you easy money on good terms, you should take it because you can use it for good things.

If you ask a founder how their company is doing, they always say, 'Oh it's great. We're totally crushing it,' and that's almost never true.

I love working with really early stage startups where the outcome is still in doubt. Maybe they'll go on to greatness, or maybe they'll never get off the runway at all.

Sam Altman Quotes