Jack Dorsey & Harlem Small Business Owners Discuss Entrepreneurship

A different kind of show went on stage at the Apollo Theater in New York on Tuesday night.

Square CEO and Twitter co-founder Jack Dorsey kicked off a conversation with small business owners in Harlem about their goals and needs. It was the final “Let’s Talk” chat for the year, a series of panels sponsored by Square and held across country.

Sharing their stories were Marva Allen, co-owner of online bookseller Hue-Man Bookstore; Erika Dilday, executive director of the Maysles Documentary Center; Seven Brown, founder of Harlem Skin Clinic; and Emmanuel Pena, co-owner of Astor Row Café. The talk hit on a variety of issues entrepreneurs in the neighborhood face—and it also drew a visit from Democratic Congressman Charles Rangel.

Though the conversation was not heavy on technology, the panel mused about the influence tech is having on their respective businesses. Of course, that’s exactly the kind of conversation Square was shooting for with this promotion—the San Francisco company has raised more than $340 million in its attempt to connect high-tech payment processing innovation with small, locally owned businesses, a notoriously tough market to break into.

“We’d love to see more sellers in our neighborhoods connect [with each other],” Dorsey said. “More frequently, with more support, with more mentorship.”

He pointed out that collectively, independent coffee house in New York outnumber the Starbucks Coffee and Dunkin’ Donuts shops in the city. “There’s a trend towards more of this energy and more people doing it,” he said.

Building a successful business, though—whether that’s creating technology or running a brick-and-mortar location—requires a fair amount of forethought. Dorsey mined the experiences of the panelists to help their peers in the audience. “Making a business plan in reverse is probably the worst thing you can possibly do,” Brown said.

Jack Dorsey asks small business owners to share lessons learned.
Jack Dorsey asks small business owners to share lessons learned.

Strategic planning is important, Dilday said, to at least give a venture some sort of framework to start from. Naturally those plans can change, she said, when put into practice.

Many businesses and organizations fight to attract and retain audience, and Dilday said trying to deal with this quandary consumes her thoughts at the Maysles Center, which is a nonprofit. “There’s no way we’re going to be able to grow until we get to a critical mass of word of mouth,” she said.

That can be hard to do on a tight or nonexistent budget. Allen said she wanted to market Hue-Man as a brand but had no money to put toward a formal campaign. So she leveraged celebrity book signings in her physical store to get the word out. “The day that President Bill Clinton came, I think everybody knew our brand,” she said.

In spite of her marketing efforts, Hue-Man closed its real-world doors in 2012. The company endures on the Web at Huemanbookstore.com. For Allen, the shift to the Internet was somewhat like starting over with customers. “When you move from brick-and-mortar to online, people don’t automatically come,” she said. “We’re ready to play in a territory that is dominated by high technology and we aren’t there yet.”

Rangel seized the opportunity—and a microphone—Tuesday night to stump for Harlem’s growth and federal political issues, such as immigration reform. “We in Harlem are going through one of the most fantastic, historical experiences,” Rangel said, “and we need your help, Jack, and we need the technicians’ help.”

Harlem has long sought to reinvigorate itself, but so far, the historic neighborhood has yet to fully join New York’s current innovation movement. While biotech incubators are setting up shop in this part of the city, the full force of the local tech scene has yet to reach 125th Street and the surrounding blocks of Harlem.

A question arose from Tuesday night’s audience about what needs to happen to change that trend. Community and economic development in many urban areas often focuses on building up more local retail and nonprofit outreach groups. Such activity does not necessarily lead to an influx of tech startups, yet it does not preclude it either.

Rangel believes bringing more technology to Harlem while leveraging the community’s character and history can revitalize the neighborhood. “We have to encourage people like Jack to recognize that we’ve got more love, affection, and culture than we can use right now,” he said.

Author: João-Pierre S. Ruth

After more than thirteen years as a business reporter in New Jersey, João-Pierre S. Ruth joined the ranks of Xconomy serving first as a correspondent and then as editor for its New York City branch. Earlier in his career he covered telecom players such as Verizon Wireless, device makers such as Samsung, and developers of organic LED technology such as Universal Display Corp. João-Pierre earned his bachelor’s in English from Rutgers University.