A fixture of local tech scene looks to stand out

David L. Ryan/Globe Staff
Wayne Chang has always been obsessed with taking the latest technologies for a spin to test capabilities and create something new.

According to the 21st century blueprint for entrepreneurial success, Wayne Chang has done everything right.

He wrote his first computer game while he was in elementary school, and at Haverhill High he was ducking into the boys bathroom to make business calls. He told the Globe in 2000 that his goal was “to become a millionaire by age 26.’’ In college, he started a file-sharing network that provoked the wrath of the recording industry before shutting down.

He then became a business partner with the Winklevoss twins, the Harvard alums who assert that Mark Zuckerberg stole an idea from them that became Facebook. And he was present at the creation of a Cambridge start-up called Dropbox, which last month raised $250 million in a funding round that valued the company, now in San Francisco, at $4 billion.


Chang is the Zelig of Boston’s technology scene, peripherally involved with an astonishing number of companies, popping up for brief brushes with fame. But at age 28, he is still looking for the first big score he can call his own.

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Chang recently took a big step toward that dream, announcing last month that his latest venture, Cambridge-based Crashlytics, had raised $1 million, the first time outside investors have backed one of his companies. It seemed like a good time to tell the story of one of the local tech scene’s most fascinating - and mysterious - figures.

Chang has always been obsessed with taking the latest technologies out for a spin - to test capabilities, create something new, and sometimes push the boundaries. His side project while studying at the University of Massachusetts Amherst, for example, was built on top of Internet2, a high-speed network intended to foster collaboration between universities. Called i2hub, it was created as a peer-to-peer service for swapping large files, but many students used it to trade copyrighted music and movies, which led to lawsuits against several hundred users. The service shut down in 2005.

When a service called AllAdvantage started paying Internet users for viewing ads while surfing the Web, Chang wrote software called MyAdvantage. It allowed you to turn off the ads, and still get paid. MyAdvantage could also make it seem like you were using your computer even while you slept, so you got paid even more. After threatening Chang with a lawsuit, AllAdvantage hired him as a security consultant to help the company track down copycats.

Around the time he was leaving UMass, in 2004, Chang says he entered into business partnerships with Cameron and Tyler Winklevoss that gave him a chunk of two companies, ConnectU, a social networking site for college students, and the Winklevoss Chang Group. Part of the deal, according to Chang, involved integrating i2hub features with ConnectU.


Chang now says he is due between 15 and 50 percent of the $65 million settlement the Winklevoss twins reached with Facebook, and has filed suit in Suffolk Superior Court to try to get it. A lawyer representing the Winklevosses didn’t return phone calls.

Members of Boston’s start-up community praise Chang for his technical insight. Reed Sturtevant, who helps run the TechStars Boston program for fledgling companies, where Chang has served as a mentor, says, “He is extremely quick at prying apart both business models and strategic technology issues.’’

Chang likes to be evasive, perhaps to cultivate the aura of a savvy, behind-the-scenes player who keeps things close to his vest. How did he obtain the Twitter username @Wayne, the equivalent of getting a low number license plate? Chang says he wasn’t the first person to register for it, but won’t explain how it landed in his possession.

At times, Chang has a tendency to burnish his reputation, perhaps a bit too enthusiastically. Chang’s personal website claims that he led “the online community initiative’’ at Napster, the controversial music-swapping network.

When I asked Napster founder Shawn Fanning about Chang’s involvement, Fanning responded, “I don’t believe Wayne was ever an employee of the original Napster company or associated in any formal capacity.’’ Asked to clarify his role, Chang says, “It was completely volunteer, but looking back, I totally should have been paid.’’


Chang was involved with Dropbox founder Drew Houston in 2007, as Houston was thinking about how to make it easier for people to exchange large files like photos or architectural drawings online. But Chang didn’t stay with the company. He won’t explain why, but a Dropbox spokesman said via e-mail, “Wayne had other projects he was working on and could not commit.’’ (At the time, Chang was working for Boylston Technology Group, a consulting firm he cofounded.) Dropbox now boasts more than 45 million users.

About Boylston Technology Group, Chang says only that the firm had “a lot’’ of employees and revenue “in the millions.’’ But Boylston disbanded early last year, and its founders, Chang and Ben Sack, went their separate ways. The firm was sued by a group of independent contractors it hired, who said they were employees and thus due vacation time, overtime pay, and other employee benefits. That case was settled in 2009, but terms were not disclosed.

Chang says the lawsuit was unrelated to his decision to close the firm: “I didn’t want to do consulting anymore.’’

Several angel investors in Crashlytics told me they didn’t know much about Chang’s earlier career. “He doesn’t volunteer a lot of information, and I don’t like to pry,’’ says Jennifer Lum of Apricot Capital. Another investor, Ty Danco, said, “I think he should remain a man of mystery, keep his head down, and focus on Crashlytics.’’

When I asked Chang who in his life knew him best, his answer: “My attorney.’’

Chang says he is now “150 percent’’ focused on Crashlytics. He and cofounder Jeff Seibert aim to build a simple software package to help people who write software for iPhones and iPads identify and fix bugs. (Eventually, the company plans to support the Android operating system as well.) Chang, says David Aronoff of Flybridge Capital Partners, the main investor in Crashlytics, “is a guy driven to be an entrepreneur. He has smelled and seen and been close to the success. I think he’s learned a bunch of lessons around what makes a good company and what doesn’t. So far, it seems he’s applying the lessons pretty well with Crashlytics.’’

Scott Kirsner can be reached at Follow him on Twitter @ScottKirsner.