👋 Hi, I'm Matt Sly

I live in Boston by way of Oakland (and Williamstown, 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 (with my friend Jay) way back in 2002. FutureMe is a simple web-site where you can write letters to the future. I ran FutureMe as a “side-hustle” as it grew into a global business with millions of users. FutureMe has 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.

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

I recently built The Parent Bank because I decided that the piggy bank is due for an upgrade because it doesn’t teach kids about how saving also means earning. I wanted to be able to (among other things) pay my kids a really high interest rate and teach them about the wonders of compounding.

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

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

I went to Williams College, where I “played” (um, sat on the bench) 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 web-site featuring The Dancing Baby went viral.

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

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