For years I've been toying with making a start-up board game. This essay could easily serve as the basis for that.
Slight disagree with the line:
"For example, if a reputable investor is willing to invest on a convertible note, using standard paperwork, that is either uncapped or capped at a good valuation, you can take that without having to think."
A good valuation means you're going to have to think anyway and if you don't need it you don't need it so then you're just going to have an obligation + temptation to use the funds. There is no such thing as 'free money' and a convertible note is simply deferring a part of the process and you'll need to take care of it sooner or later by going for funding (or paying back the loan). So if you are not sure if you are going to do a follow up round just yet I'd advise against getting a convertible loan, you now have a good chunk of the hassle of having an investor without having properly gone through the process required. Of course you could simply bank the money and pay back the loan if you are still of the same opinion later on but this rarely happens. It's the start-up equivalent of easy credit card debt, and if the valuation turns out to be low you could end up regretting taking the money (for instance, you could lose control like this). Better to negotiate it when you're strong or if you feel very secure about your future valuation.
Having seen a lot of this from the other side of the table quite a few of the passages strike me as extremely negative about investors, I'm sure Paul has a ton more experience than I do so this carries a lot of weight with me but I don't recognize the behaviours he sketches with the investors that I normally work for. Maybe they are the exception (I'm sure they'd like to think that :) ), but I can't imagine it is this black.
Investors look at the process of investing mostly as risk elimination, and as a second best as risk reduction by enumerating the risks. If an investors bails at the last moment (for instance after you've already agreed on terms) that would either reflect very bad on the investor, or more commonly on the party invested in. It's not as clear-cut imo as it is sketched here that all start-ups are angelic and innocent and investors are all sharks to a man and employing dirty tactics to get you to sign on the dotted line.
Again, it's clear on which side my bread is buttered but I simply wouldn't work for investors deploying such tactics, but have yet to see this sort of behaviour in any VC of some stature. Otoh I've seen plenty of trickery by companies about to be invested in (and lots of good companies too).
Just to add a common misunderstanding - a convertible note is debt and raising capital is equity. Debt means you owe something (in this cause equity at a later time), and equity means you own something. I know this is probably "Fundraising 101" but often its the basics that people get wrong.
Slight disagree with the line:
"For example, if a reputable investor is willing to invest on a convertible note, using standard paperwork, that is either uncapped or capped at a good valuation, you can take that without having to think."
A good valuation means you're going to have to think anyway and if you don't need it you don't need it so then you're just going to have an obligation + temptation to use the funds. There is no such thing as 'free money' and a convertible note is simply deferring a part of the process and you'll need to take care of it sooner or later by going for funding (or paying back the loan). So if you are not sure if you are going to do a follow up round just yet I'd advise against getting a convertible loan, you now have a good chunk of the hassle of having an investor without having properly gone through the process required. Of course you could simply bank the money and pay back the loan if you are still of the same opinion later on but this rarely happens. It's the start-up equivalent of easy credit card debt, and if the valuation turns out to be low you could end up regretting taking the money (for instance, you could lose control like this). Better to negotiate it when you're strong or if you feel very secure about your future valuation.
Having seen a lot of this from the other side of the table quite a few of the passages strike me as extremely negative about investors, I'm sure Paul has a ton more experience than I do so this carries a lot of weight with me but I don't recognize the behaviours he sketches with the investors that I normally work for. Maybe they are the exception (I'm sure they'd like to think that :) ), but I can't imagine it is this black.
Investors look at the process of investing mostly as risk elimination, and as a second best as risk reduction by enumerating the risks. If an investors bails at the last moment (for instance after you've already agreed on terms) that would either reflect very bad on the investor, or more commonly on the party invested in. It's not as clear-cut imo as it is sketched here that all start-ups are angelic and innocent and investors are all sharks to a man and employing dirty tactics to get you to sign on the dotted line.
Again, it's clear on which side my bread is buttered but I simply wouldn't work for investors deploying such tactics, but have yet to see this sort of behaviour in any VC of some stature. Otoh I've seen plenty of trickery by companies about to be invested in (and lots of good companies too).