CHRISTOPHER: I don’t know how much your dad has told you but I’m on the verge of kind of a big success; it’s for real this time. I’ve got a company with an actual cash flow, I’ve got employees, I’ve got an accountant, for God’s sake. He wears a tie and says words like “fiduciary” and “ironically”. I mean it’s for real this time, Lor.
This is the Internet start-up business in California that Richard told Lorelai and Rory about in the Pilot episode, approximately six months ago. We now hear more about it from Christopher without ever finding out what exactly the company does, or was supposed to do.
(A fiduciary is a person who holds a legal position of trust in business, typically being in charge of financial assets to either have them in their safe-keeping or to invest them wisely on another’s behalf. Although this would cover many different types of jobs, it is typically used to refer to a trustee who is responsible for the money in a trust fund – it may suggest that Christopher’s accountant is helping him use his trust fund money to pay for his business venture).
Christopher’s reassurance that “it’s for real this time” suggests that he has attempted, and failed, at several businesses previously – or has even flat-out lied about trying to start a business. Little wonder that Lorelai is rather sceptical about it.