Jesse Pujji explains how to pitch during casual conversations without killing the relationship. Offer a free analysis first, ask directly if they'd buy, and use questions like "why is this not compelling for you?" to uncover real objections. Even awkward pitches can convert later if you follow up after a month.
I think the hesitation was more like, how do I transition this to a pitch? So I had all these people that I knew from 5 years of hosting the podcast. And so I've been reaching back out to all of them. I had the first of the calls from those meetings today evening. I showed him what we were building. And at the end I said, look, if you're interested, I'll give you a free analysis. I'm still struggling in terms of how do I transition that to a pitch? The most aggressive way to do it would be to say like, well, what do you think about this?
Or it's like, is this something you would buy? You'll know because they'll start showing a lot of interest and excitement and they'll start asking a bunch of questions. Or you could do kind of the persuasive speaking version of it. Like, why is this not interesting for you? Why is this not compelling for someone like you? If they feel like you were doing it disingenuously, it'll actually burn the relationship. And sometimes I do that and like a month later they come back and buy it. Or like, I'll come back a month later and I'll go, remember the thing I got your advice on? It's up and running now. I want to pitch you.
