Nate found that contrary to what people think, getting the first investor doesn't make the rest follow — it almost doubles your pressure. Once you've secured, say, 300 K against a 750 target, you don't want to disappoint the people already in, so you have to go even more aggressive.
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Nate pushes back on the common belief that the first investor unlocks the rest: "contrary to what people think, I think people think that you get the first investor and the rest follows. But I think if you get the first investor, you almost double your pressure to get the rest." Even with a VC and an angel secured for 300 K, "it's still not enough" against the 750 target, and "they're also going to be disappointed if I don't hit the 750." It wasn't a contractual contingency — the investors were "very founder friendly" — but psychologically he didn't want to disappoint them, so the first yes meant more pressure to execute, not less.