Unroll.me CEO on Learning from Mistakes and Striking When the Market is Hot

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to scale up the business, Rosenwald realized. To drive recurring use, Unroll.me offers a free option to receive a daily digest of all the deals, newsletters, and other automated e-mails users choose to keep. Rosenwald says Unroll.me’s daily digest is opened more than 50 percent of the time.

More content curation is in the works from Unroll.me. Rosenwald say the startup is developing a platform to aggregate information from daily deals and discount offers from retailers for users. “We think being able to discover content is going to be a huge play for us,” he says. Rosenwald, 22, believes Unroll.me’s platform could help keep e-mail relevant at a time when some industry watchers believe the medium is a dying form of communication in the face of social media. He does not expect tweets alone to replace e-mail, even among today’s youth. “They will enter the workforce eventually and they will use email,” he says.

But can it make money? Rosenwald admits Unroll.me has not developed a revenue model, though he says adopting an ad revenue stream might be possible.

Rosenwald says he has learned from his previous experience building a startup. In 2010 he founded Sportce, which planned to sell video footage from sports leagues to appear in place of banner ads on sports blogs. But he ran into some tough obstacles. Specifically, the cost of securing such content outstripped Rosenwald’s means. “I reached out to the NFL,” he says. “It [cost] $26,000 per second to license their footage. Very quickly you’d go broke.”

Looking for alternative content he could sell, Rosenwald tried to use audio of professional athletes discussing their game strategy. He developed connections with agencies in the NFL, which he planned to share revenue with, and entered negotiations with a blog network. With a potential $20 million deal on the line, Sportce got ahead of its own technical expertise. “I knew absolutely nothing about Web development,” Rosenwald says.

He tried using third-party Web development companies to get the components he needed to seal the deal. It took more than 10 months to create a product that Rosenwald admits was unsatisfying. By that time, the once-interested parties chose to move on. Sportce shut down last April then he turned his attention to Unroll.me.

This time around, Rosenwald focused on gathering talent in-house to carefully build Unroll.me into a platform that’s ready for primetime. He brought together friends with the technical knowledge necessary to establish the startup and thus far the team has focused largely on development. “I made sure I wouldn’t make the mistake again,” he says. “I got friends who knew how to build websites.”

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