Josh's math: "that new person that you meet for 15 minutes has spent 15 minutes, and you've spent 50,000 hours" — in front of clients, customers, investors. It doesn't mean you're perfect, but no brief meeting should override your accumulated intuition about how the machine operates.
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The trap is that the doubt comes from people you overwhelmingly respect. "The amount of times that I met VCs where I was like, oh my god, that's this person... and they go, your pricing model sucks, I would never invest in that company. And then you go home and you're like, you know what I should do? I should do that." His reality check: "I'm just gonna convince an entire hundred seventy billion dollar machine to just completely change overnight because Josh says so? Because this person says so?" That person is going to meet you for 20 minutes — they haven't had time to understand the industry.
The cost of not trusting yourself compounds. Josh says those conflicts led to some of his dumbest decisions and wrong hires: "when you make the wrong hire, you waste $1 million or $5 million." His conclusion for founders: "there's one thing that you definitely have over everybody else, which is you spend more time on this thing. It's your baby... no one will ever spend more time."