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

4/26/12Follow @jpruth

Like many entrepreneurs, Josh Rosenwald ate a healthy slice of humble pie after his previous startup went under. So he planned carefully before committing to his latest endeavor. This time he believes he found a scalable idea he can monetize. That does not mean Unroll.me, his New York-based startup, is a sure bet, but he is using his prior experience to position his company to seize opportunities.

Unroll.me, founded last September, lets its users unsubscribe from unwanted automated e-mails and newsletters—a pain point co-founder and CEO Rosenwald says others have struggled to address. Many times users of e-mail do not remember when they agreed to receive messages, which can include special offers, newsletters, and general marketing from websites and companies. Getting rid of such automated e-mails can be tricky. The process may be more complicated than signing up, or worse, the sender might ignore the request to stop. “The more friction they add, the less customers they lose,” Rosenwald says. Unroll.me also lets its users discover new newsletters and lists they may want to receive.

The Unroll.me team got some attention last week when it won the best unfunded startup award at the NY Tech Day fair. Rosenwald says the startup—which has thus far been bootstrapped with support from friends and family—is in talks with potential investors. The platform lets users see and control the e-mails they signed up to receive. Unroll.me is expected to emerge from beta in a couple of weeks, Rosenwald says.

Other startups operating in the e-mail sector, he says, tend to address highly specialized problems. For example, there’s technology to tell e-mail senders whether their messages were read. That may be important for marketers concerned about conversion rates, but scaling such technology to a broad audience can be a challenge. “They can’t market [that service] to everybody on Gmail; it wouldn’t be cost effective,” Rosenwald says. Unroll.me, he says, aims to meet a more widespread need.

Though the idea seems simple, Rosenwald says developing the platform led to some issues. “About two months in we said ‘we didn’t think it would be this hard,’” he recalls. The platform had to be tweaked to operate with different e-mail providers. Unroll.me currently works with Gmail, Yahoo, and AOL e-mail clients.

Furthermore, Rosenwald had his own doubts about the business viability. “Nobody made money from the unsubscribe process,” he says. “You can’t charge for it. We had to figure out how to monetize.”

If users only tried the platform once and then never returned, there would be no way 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.”

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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