Most startups raise money at some point.

You should raise money when you need it or when it’s available on good terms. Be careful not to lose your sense of frugality or to start solving problems by throwing money at them. Not having enough money can be bad, but having too much money is almost always bad.

The secret to successfully raising money is to have a good company. All of the other stuff founders do to try to over-optimize the process probably only matters about 5% of the time. Investors are looking for companies that are going to be really successful whether or not they invest, but that can grow faster with outside capital. The “really successful” part is important—because investors’ returns are dominated by the big successes, if an investor believes you have a 100% chance of creating a $10 million company but almost no chance of building a larger company, he/she will still probably not invest even at a very low valuation. Always explain why you could be a huge success.

Investors are driven by the dual fears of missing the next Google, and fear of losing money on something that in retrospect looks obviously stupid. (For the best companies, they fear both at the same time.)

It is a bad idea to try to raise money when your company isn’t in good enough shape to attract capital. You will burn reputation and waste time.

Don’t get demoralized if you struggle to raise money. Many of the best companies have struggled with this, because the best companies so often look bad at the beginning (and they nearly always look unfashionable.) When investors tell you no, believe the no but not the reason. And remember that anything but “yes” is a “no”—investors have a wonderful ability to say “no” in a way that sounds like “maybe yes”.

It’s really important to have fundraising conversations in parallel—don’t go down a list of your favorite investors sequentially. The way to get investors to act is fear of other investors taking away their opportunity.

View fundraising as a necessary evil and something to get done as quickly as possible. Some founders fall in love with fundraising; this is always bad. It’s best to have just one founder do it so the company doesn’t grind to a halt.

Remember that most VCs don’t know much about most industries. Metrics are always the most convincing.

It’s beginning to change, but most investors (Y Combinator being a notable exception) unfortunately still require introductions from people you both know to take you seriously.
Insist on clean terms (complicated terms compound and get worse each round) but don’t over-optimize, especially on valuation. Valuation is something quantitative to …