Someone asked this in the Top Builder chat so I thought I'd share my answer more widely:
- I knew this going in but I see a lot of founders make this mistake: don't be full of shit. If you don't know something, say so. The biggest red flag to an investor is an investment being untrustworthy. This includes lying but also being afraid of reality/delusional.
- if you're raising on SAFEs watch this video: https://www.youtube.com/watch?v=Dk6JNTDec9I
- know what you're worth (I've attached median valuations from Q3 of last year), and I don't mean you're worth more than you think. It can go either way - you might be worth way less than you think. The median is made up of many companies with varying levels of potential.
- until they sign, investors haven't invested so continue to treat them as a counterparty and assume they won't invest until they do sign
- investors are a counterparty. bitcoin investors LOVE to say bitcoin companies have lower valuations than the general tech industry does. It does historically, but that's largely irrelevant. It's akin to them saying "I'm used to getting sweet deals. You owe me one too." So again, know what you're worth. Investors will complain about company valuations like we all do our grocery bill. It doesn't change the price of milk.
- few investors will tell you an outright no. The game theory has them maximizing optionality. If it's not a yes, it's a no. Don't waste your time on investors that will only tease you.
- a lot of bitcoin venture investors haven't been investing very long. This is good and bad, but if they haven't been investing very long, don't grant them authority about things only a veteran would know. And again, even if they are a veteran, they are a counterparty.
- at an early stage, all things being equal, favor investors that can provide you more than money and try to put investors that were founders on your cap table (this game is a mess and it'll help to have people who have been in your shoes)
- don't give up. sometimes you can't raise because you suck, you suck at communicating, or your product sucks, but sometimes you can't raise because you only talked to investors that suck
There's a lot in here that might make you suspicious of investors generally. Don't be! I genuinely like all of my investors and are friends with most of them. It's just that all apple orchards have bad apples and when you're farming apples you have to know a lot about apples.