Jack Dorsey's Advice On Raising Funding

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Today at TechCrunch Disrupt in New York, Square co-founder (and Twitter creator) Jack Dorsey took the stage to demonstrate Square working on the iPhone. He also sat down with our own Michael Arrington and Erick Schonfeld to talk a bit about his success. And Dorsey had some advice for new entrepreneurs looking to raise money.

Mike noted that Dorsey is sort of a celebrity in the tech community now so raising money for Square was pretty easy. That’s true. Dorsey said that he took two weeks and scheduled 25 meetings in Silicon Valley and New York to talk to venture capitalists about Square. This resulted in Square being valued at $40 million before it even launched.

But Dorsey said his past success (with Twitter) was also a bit of a detriment. He wasn’t sure if people were actually interested in Square, or if they were just thinking about Twitter and his past success. It was important to him and his new co-founder that Square was the focal point.

Dorsey then went into a bit of history with the Twitter funding, and had some advice for new entrepreneurs: “You wanna see that engagement.”

What he means by that is that some of the early Twitter funding meetings were “terrible” because they weren’t questioned hard. The VCs didn’t really seem interested in the product or didn’t get it — so Twitter knew they weren’t the right fit.

The one who was? Fred Wilson, Dorsey took no time saying.

Fred was one of the only people we saw that was a user of Twitter on a daily basis. 20 times a day in some cases,” Dorsey said. Mor e importantly, Wilson asked the tough questions about the long-term goals for the company. He wanted to know the product plan, he was agressive in his questioning, but he got it.

I want someone on the board that will push the company in ways that I’m not thinking about. They need to guide us,” Dorsey said.

Another bit of advice: “Get something you can demo.”

Dorsey said that while most people go into VC meetings with a PowerPoint presentation, that should only be a back-up to what you’re presenting. Instead, you should show the site or the product. And it has to be something you’re proud of, he noted.

He said that they had been using Square for seven months on a day-to-day basis before they hit the road for the funding. They were ready. “We could go into a meeting and take money from someone,” Dorsey half-joked.

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