James Cham argues founders should pitch a small number of aligned investors, not many. The real work is two-way: you assess if they're a good partner while they assess you. Taking money from the wrong investor damages you more than raising nothing.
I think at the core, a pitch is not— like, the pitch is the wrong way to think about it, right? It's not as if you're going out selling a product and trying to get someone to— getting 50 people to buy something. You're trying to get 2 or 4 people to actually make a real connection, right? And so In some ways, it's not about whether you successfully quote unquote pitch your business. The real question is do you make that kind of connection with someone in which you believe that they'll be a good partner to you and they believe that you're someone who represents the future. And so I do think that the hard part for an entrepreneur, of course, is that you're going to be talking to not 3 people, not 10 people, 10 people, like 50 to 100 different people, and with each one of them you're going to be not just sort of telling— you're going to want to say similar things, but like your real goal is to suss out the other guy to figure out whether they're a fit for you and also whether or not they're willing to fund you. And I think that sometimes folks forget that first part, right, that getting money from the wrong source oftentimes is just as painful— is far more painful than getting no money at all.
