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 outdoors.
I’ve worked at Microsoft (Bing, XBox), Amazon (Alexa) and as an executive at several Boston-area venture-backed startups: (EverTrue, Upserve and BetterLesson).
I also created FutureMe (with my friend Jay) way back in 2002…and then ran it as a “side-hustle” as it grew into a global business with millions of users. FutureMe has been featured in many publications (New York Times, Wired, CNN, LA Times, Oprah(!)…) but my favorite bit of press is an interview that I did with Scott Simon on Weekend Edition.
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 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.