Although they've succeeded in very different industries—he launched Twitter and Square, she's a clothing designer who built an eponymous empire—Jack Dorsey and Diane von Furstenberg have both struggled with similar entrepreneurial challenges. They discussed them at Fast Company's Innovation Uncensored conference in New York in April.
Jack Dorsey: Who did you look up to when you were growing up?
Diane von Furstenberg: The most important influence in my life has been my mother. And the reason is that my mother, when she was 20, she was a prisoner of war. She was in a death camp; she was in a concentration camp when she was 20. She survived. She weighed 49 pounds, but she survived. And then she married my father after that and the doctors said, ''You can't have any children," and yet 18 months later I was born. So my birth was a miracle.
So she always told me that God had saved her so that she could give me life. That's a heavy thing to have to live up to. But the biggest thing she always told me is that fear was not an option, and that was the best lesson ever. Who influenced you?
JD: My parents as well. My parents inspired me dramatically. I have a funny creation story. My father opened a pizza restaurant with his best friend and they called it Two Nice Guys. And they just loved making pizza. They wanted to delight people.
DVF: How old were they?
JD: They were only 19. They didn't go to high school, they didn't go to college, they wanted to make pizza. The pizza restaurant, in St. Louis, started doing very, very well, and they wanted to preserve the sanctity of their business and also their friendship so they made a rule between themselves, which was they would not date any of the waitstaff. And the first person they hired was my mother. And my father fell in love with Marcia, my mother, and a week later he went to his best friend and said, "I broke the rule, the business is yours." And I was born 10 months later.
JD: So I have always looked up to them.
DVF: And he left the business?
JD: He left the business. They got married, they had me, and we stayed in St. Louis. And they have always stuck by the city. They have always loved the city. They have always taken significant financial risk to do what they love and to provide for their family.
When I was first starting Twitter [with Biz Stone and Evan Williams], we had all this flack about, well, no one really wants to know about what you had for breakfast. And I am someone who tweets about what they had for breakfast. For most of the world it's useless; it's maybe so useless that it's offensive. But it's very useful for one person and that's my mother. She loves seeing every single day that I'm eating breakfast.
DVF: Oh, that's sweet. What's her Twitter?
DVF: Okay, I'll follow your mother.
JD: She will love that, she will love that.
DVF: So Jack, you have invented something that has changed the world and that everybody is using to catch thieves and to make revolution. How does it feel?
JD: It feels humbling. What's been most amazing about both technologies, Twitter and Square, is that people come to them as utilities and they build their own products on top of them. And it's a great thing that the younger folks are out there—they're moving faster—because it pushes us to be better. It pushes us to think in a different way.
DVF: And you know what? A hundred forty characters used to be so little and now it's exaggeratedly big.
JD: So we should cut it in half?
DVF: No, no, no, no. But it just shows how quickly one adapts and how you synthesize the thoughts.
JD: How do you run your company and your brand? What are your guiding principles for running your brand?
DVF: I try to be authentic. You know, people do different things. There are some people who start a business saying, "I am going to start a business," and then they write a business plan. I didn't, and I'm sure you didn't. You just have an idea and you create it and you believe in it. But with the authenticity, there is a bad side too: There is so much human in the way you created it that it attracts all the human faults, right?
DVF: That's always the difference when you have companies that are founder based, you know? It goes to a point, and then it's no longer the founder and then all of a sudden it goes to a different level. So as a founder, you have an authenticity and a human factor that is really special and that gives an enormous amount of energy and fuel. But as a founder, you're also not as cold, maybe, or as pragmatic. Do you feel that?
JD: Oh, absolutely.
DVF: Or have you learned how to be cold and pragmatic? I haven't.
JD: At times. But I think that's exactly right: You have an idea and the company becomes the oxygen for that idea. It becomes the supporting infrastructure. But it's all about making the idea thrive; in these times, a company is the best way to spread that idea. But before you know it, you do have one employee and then two employees and you have hundreds of people working.
DVF: And that is the hardest thing.
JD: How do you continue to reinvent yourself? How do you continue to innovate in the company?
DVF: Oh, I don't know. I used to write in my diaries for years and years and years. And if I go back to my diaries, I always read "I am at a turning point." So it seems like I am always at a turning point. I mean, it's ridiculous. I was so arrogant with my youth. I used to say, "Oh, I will retire by the time I am 30." And now I'm still working. You have two ways to be: You are either an entrepreneur and the advantage is that it's your own company or the disadvantage is that . . . it's your own company. But I mean, I don't think I would be a very good employee. Would you?
JD: No. [Laughs] No.
[Photo by Benjamin Lowy]
A version of this article appeared in the July/August 2013 issue of Fast Company magazine.