Square Founder Jack Dorsey and Union Square’s Fred Wilson Chat at NYU

Jack Dorsey, the CEO of Square and Twitter’s executive chairman, made his way back to New York University for a fireside chat Friday with Fred Wilson, the co-founder of Union Square Ventures. Dorsey, an NYU alum, talked about his early startup days and how his latest endeavor is evolving. “Where we’re going with Square is not about payments as a revenue model but more around the data and the experience,” he said. “We don’t know exactly what that looks like yet.”

Square’s initial business model, providing a platform for merchants to accept payments through mobile devices, was a natural start, but there is more to come, according to Dorsey. “We have some ideas, the same way we had a ton of ideas around Twitter,” he said, “but we’re not sure where it’s going to land.”

Dorsey and Wilson, who was an early investor in Twitter, closed the first half of the two-day NYU Entrepreneurs Festival for students, entrepreneurs, and investors. They offered lessons that the students and even seasoned entrepreneurs can learn from. Finding startup people who question everything, Dorsey said, is important to encourage new ways of thinking. He said one of the reasons Twitter chose to work with Wilson was because he used the platform while also putting it under scrutiny.

Fred Wilson “was the only one that really asked the right questions,” Dorsey said. “We left a lot of pitch meetings and no one would ask us questions.” Twitter turned down potential investors, he said, who offered to write checks yet really did not try to understand what the startup wanted to accomplish. “Fred had that aspect of being questioning and thinking about the company and the idea,” Dorsey said.

The NYU festival also featured founders such as Dan Porter of OMGPOP, Alexandre Douzet of TheLadders, and Paul Berry of RebelMouse. Rachel Stern Haot, chief digital officer to Mayor Michael Bloomberg’s administration, spoke about various initiatives underway in New York to cultivate local technology talent for the city’s innovation community.

For his part, Dorsey was candid about his academic career at NYU. “I was a really bad student,” he said. He studied computer science and mathematics, though he admitted to skipping many classes and eventually dropped out. “I did not give it the attention it deserved,” he said. Dorsey did not outright champion the idea of quitting school to found startups, but he did encourage the audience to tap into their entrepreneurial energies. “I don’t believe an entrepreneur by definition needs to start a business,” he said. “You can have an entrepreneurial attitude within a company, or even within school.”

Twitter emerged from an idea he had around 1999 while building a Web-based dispatch firm that ultimately failed. Dorsey wanted to capture what people were up to in a way comparable to updates from black cars, couriers, and emergency services to dispatch systems. He sought to create a way to visualize where people were going and what they were doing. “I tried to build this with a RIM 850,” he said. “It was a little, tiny, snub e-mail pager.” He wrote code for a simple service that sent e-mails from the device to a list of his friends. However, his idea did not immediately impress others. “I quickly learned that no one cared,” he said. “No one else had this RIM device. It was just way too early.”

He later shared his ideas at podcasting company Odeo with Evan Williams, Biz Stone, and Noah Glass, which would eventually led to the development of Twitter.

Founding the mobile payments company Square was not simple, in spite of Dorsey’s prior experiences. Creating a platform and technology for taking credit card payments through mobile devices was only part of the challenge. The banks could have prevented the company from launching the payment transaction system. “We took the pain on of not being in the market for nine months while we worked with the banks,” Dorsey said.

As he wrapped up the chat, Dorsey tried to quell the typical competitive chatter that comes up between the East and West Coast innovation scenes.

“Why do we have to fight?” he asked. “There are a lot of amazing things happening in New York. We almost started Square in New York.” He said the company could not amass the engineers it needed in the city, though.

Dorsey still has a bit of Manhattan in his blood. Last October, Square acquired New York-based design firm 80/20. He believes it is not necessary for New York to try to rival Silicon Valley. “We can have both,” Dorsey said. “Both offer very different perspectives and will be additive to the world.”

João-Pierre S. Ruth is the editor of Xconomy New York. He can be reached at jpruth@xconomy.com and followed on Twitter @jpruth. Follow @jpruth

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