Jack Dorsey offers practical advice to founders raising venture capital: always approach investors with something tangible to show (working prototype or actual users) and treat taking money like hiring a permanent team member—choose investors who ask tough questions and will add ongoing, constructive value. He cites Square having a working prototype with seven merchants when they raised funds and notes investors like Vinod who check in weekly with probing questions and introductions.
Questions this video answers
Seven merchants.
Once a week.
Chapters
First and foremost, I always want to go to anyone that I want to work with with something to show. And it was really important to us before we talked to any investors on the Twitter side that we actually had people using the service at some scale. And on the square side that we actually had a working prototype square, we had really seven merchants when we actually went to raise money, but we had a working prototype that people were actually using. And if people can't see it and feel it, it's very, very hard to sell. And I don't want to just go and tell people, this is going to be the biggest thing ever. I want to be able to show that and have them feel it and walk away feeling that as well. So that's first and foremost is have something to show. And then second is the realization if we take money from someone, this is kind of like hiring someone that we can never fire, we can never get rid of. So that means, do we really want to work with this person? Is this person going to be someone that really pushes us in the way that we need to be pushed? And you can tell that fairly quickly. In that first week of Pitching, Square got a lot of people who said, you know, okay, great, we don't have any questions. We'll get back to you in about 30 minutes, probably with a term sheet. And I said, I don't want a term sheet, especially if you're not asking any questions, because they ask no questions during the pitch. And that means if they're on our board, that they're actually not going to be all that constructive in terms of really asking the tough questions. That is, the role of the board is to look outside and bring all their insight and wisdom to us so that we can help guide the company. And that second week, we got a lot of tough questions. And that's what I love, because I know if I'm getting tough questions in the pitch, I'm going to get tough questions in the boardroom as well. And not just the boardroom, but every week. I mean, Vinod emails me once a week about, have you thought about this? Are you doing this? And, you know, I know this person. Can I make an introduction here? It's just very, very useful. So I'm looking for someone who I just love working with. And I think you have to set a very, very high bar. It's not just about money or the firm. It's about the individual that you're ultimately going to work with. And people ask me all the time, what firms would you suggest I go pitch I'm like, find the people that you really want to work with in those firms, and if there's someone that just really resonates with you and you love the idea of working with them, focus on them. You have to treat it as like, I'm adding this person to my team.
