Matthew Segal
Credit: Tanya Goehring on location at Leisure Center

Matthew Segal, 24


Life Story: What’s an Ivy League economics grad to do? In 2016, Matthew Segal appeared to be headed for a career in investment banking after leaving Yale University, where he rowed First Varsity for four years. But several job offers later, Segal decided his heart wasn’t in it. Back in his hometown of Vancouver, he also chose not to follow in the footsteps of his father and grandfather, prominent developers Lorne and Joseph Segal–for now, anyway.

Instead, Segal got to work on an anonymous messaging app he had dreamed up at Yale because he was too shy to talk to a girl he liked. The result was Lipsi, created with a handful of software engineers in B.C. and Ukraine. The popular free app—65 percent of whose users are female—has many uses, from personal exchanges to feedback on a product or service.

As Segal admits, sending messages anonymously online carries a stigma. “Our mission has been to redefine anonymity and employ anonymity in an empowering and safe manner, and to be the first to accomplish this at scale.” To make its messaging safer, Lipsi has partnered with Perspective API, Google’s anti-bullying software, which deploys AI to learn user habits and jargon. Recently, Segal and his team have been creating messaging software that mental-health and LGBT support groups could use, via Lipsi or elsewhere. For him, retention is more important than cashing in by bombarding users with ads. “Whether it’s Facebook or Instagram or Google, all these massive platforms have started by providing an amazing service, and monetization has always come second.”

Bottom Line: Lipsi has about seven million users in Canada, the U.S. and the U.K., roughly 350,000 to 400,000 of whom access the app every day. The company, which is developing its software in languages other than English, plans to expand into South America next. As of February, Segal was talking to several parties interested in buying Lipsi.


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