How many ways are there to say 'the ultimate assistant"? There's "Concierge", but it's a bit boring and can't be trademarked for this application. Then of course's there's "Watson", but IBM would do a bit more than send a letter if you tried to use it for an app. That leaves "Igor" and "Accomplice"... But doesn't Accomplice invoke a criminal activity? Sure, just as Hotwire means one thing, 'to steal a car'. But like Hotwire, Accomplice maps to the positioning of the service. Hotwiring a car is a hack, Hotwire.com is a travel hack. When a name maps to a company's positioning, consumers process the name in kind. No one thinks Hotwire.com or Accomplice is involved in criminal acivity. Nor do they think Slack will produce lazy work. Hotwire, Slack and Accomplice all have a 'negative' side that makes them instantly memeorable, and they all make perfect sense in context.