Gumdrop is a Boston-based AI meeting assistant that preps you before a meeting and handles the follow-up after it. It pulls context from past meetings, recent emails, and your contact history to build a short briefing that lands about five minutes before you walk in, then runs an AI notetaker during the call that turns spoken promises into a list of action items. Built by Kayak co-founder Paul English, it also handles the boring scheduling logistics through booking links and an email address you can CC to find a time.

Steli Efti is the co-founder and CEO of Close.com, a bootstrapped CRM platform generating $40M+ ARR that he built by accident - he was running an outsourced sales agency for 200+ startups when he realized the internal software he built to manage it all was the actual product. A high-school dropout from Germany with Greek immigrant parents, he moved to Silicon Valley on a one-way ticket, got rejected by Y Combinator 6 times before being accepted, and has since become one of the most respected voices in startup sales - known for the 48-email follow-up that landed an investor, a no-BS philosophy, and a side podcast about philosophy, literature, and inner life that has nothing to do with business.