I know angels who can cough up more money than most venture firms, but with few exceptions, angel investors lead a startup to the only place where angels live, in the heavens of fantasy.
I say that because:
1/ Most angel investors have not made their money in venture. Otherwise they would still be doing it, and thus have a feeble understanding of the unique and unprecedented risk it takes to cross the chasm (from Geoffrey Moore’s book Crossing the Chasm) armed with the dissent from a new normalization of truth that is poised to break the norm. They tend to invest in downstream sub-optimizations of an existing truth they recognize from their past, highly unlikely to produce venture style returns.
2/ Early-stage funding for a venture-style startup (say, 7x return in 7 years), as the most likely phase for angels to enter, due to size of their checks, demands smooth transition of cap table valuations and founding ownership control to fund the entire runway of the startup towards the upside. Few angels who play with accumulated cash have meaningful connections with the handful of venture firms that can be trusted to produce repeatable venture-style returns to limited partners. Hence a cherry to an angel is by no means a cherry to a reputable VC.
3/ Angel investors spread their money around more vicariously than VC firms as they have no one but themselves to be accountable for. That could be a good thing, were it not for how most angels made their money. Generally, in the bosom of a corporate cash-cow, having sucked their life up to its fullest teat. That history does not lend itself well to the alignment of dissidence and foresight with an entrepreneur willing and able to break the norm.
For brevity, I will conclude here. I have seen, on many occasions, how angels become the kiss of death to outliers because the foresight of unprecedented upside can seldom be achieved from the hindsight of downside.
