While I was working at Gilt, my coworker Steve Martocci—something of a serial entrepreneur at the time—would regularly pitch me startup ideas and I’d generally give him critical feedback of the “ehhhh, I don't know...” variety. But when he pitched me the idea for what would eventually become GroupMe, I was taken aback, and responded with something along the lines of, “that’s a great idea, you should do that.” Several weeks later, he took that idea and built it out over the course of a day and a half at the TechCrunch Disrupt hackathon and received enough positive feedback from investors that he gave his notice at Gilt almost immediately after.*

Over the next couple months, I participated in a couple hack sessions on what was then called groop.ly before Steve and his partner Jared Hecht raised a seed round and hired their first three employees, Brandon Keene, Pat Nakajima, and Cameron Hunt. It’s crazy to think about it now, but back then in 2010, there was no way to have a real-time group chat on your mobile phone — SMS was one-to-one only, and iMessage, along with other third-party apps like Whatsapp, didn’t even exist yet. So what was essentially an SMS hac... Read more