👋 Hi, I'm Matt Sly

I live in Boston, by way of Oakland (and Williamstown, Vermont, San Francisco, Philadelphia, New Haven and Providence). I enjoy making software, playing sports, hanging out with my family (#girldad x 2!) and exploring the world.

I created FutureMe way back in 2002 and ran it as a “side-hustle” for almost twenty years as it grew into a global brand and business with millions of users. FutureMe had several viral moments and has been featured in the New York Times, Wired, CNN, LA Times, Oprah(!)… My favorite bit of press is an interview on NPR’s Weekend Edition. I sold FutureMe in 2021 and recently recorded a podcast where I told the extended story if you’re interested.

I’ve also worked as an executive at several Boston-area venture-backed startups: EverTrue, Upserve and BetterLesson. And I’ve completed tours of duty at Microsoft (Bing, Xbox) and Amazon (Alexa).

These days, I’m mostly being a driver-I-mean-Dad. And gardening. I’m also doing a bit of consulting/advising/investing and building software when inspiration hits. A few recent projects: The Parent Bank because the piggy bank is due for an upgrade and QuarterlyGems as an experiment to rethink social media and online recommendations.

I used to be a pretty decent basketball player even though my high school team’s shorts were too small. Now I’m way over the hill, but I still enjoy playing hoops, as well as tennis, soccer and cycling. A long time ago I coached high school basketball and took a small charter school without a gym deep into the state playoffs. Also - you should “shoot the two” when playing “winner’s outs” half-court hoops.

I went to Williams College, where I played on a really good basketball team that twice went to the Division III Final Four. I also sang in The Springstreeters with some famous people and crashed the college servers when my first-ever website featuring The Dancing Baby went viral.

I’m a testicular cancer survivor, which you can read about in an essay I wrote called “The Year I Went to War with My Body”.

If any of this resonates or you want to learn more, feel free to reach out!

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