IDs just don’t fly. There’s a stack of about 15 things that I have, a big
list of pitfalls.
Livingston: Can you remember any features from del.icio.us that the users
wanted or really loved that surprised you?
Schachter: There’s always stuff. I tend to be careful about that. I think people
ask for features—they want to do something, but they don’t say, “I want to do
that something.” They translate it into some feature that typically they’ve seen
somewhere else and ask for that instead. I want a feature that does this. “Why...

to my wife though.
Livingston: Did you find you were better at some things than you thought?
Schachter: I could focus on it more and do slightly larger stuff. I’ve always had
a short attention span, so that’s probably the actual limiting factor. The amount
of coffee I can consume to mitigate that and that’s about it.
Livingston: Were there things about del.icio.us that users misunderstood?
Schachter:We named things differently. I wouldn’t say that we had awesome
execution. It was very techy. It bred a strong priesthood, which was helpful in
getting...

that was a fully distributed social network—no central server whatsoever. It
used email as a carrier and could tell people you talked to about other people
you corresponded with in an encrypted and compressed way. If I emailed you,
it would attach a Loaf file. You couldn’t open the Loaf file and read the contents
of it; it just didn’t work that way. It used Bloom filter, so it was sort of a statistical
object. But you could take another email address and see if it was in there.
With 99 percent accuracy, you...

is come up with ideas, how do you know if they are any good? You don’t really
know if it’s a good idea until you’ve executed it. You need to understand the cost
of execution and so on.
Also, where I worked at Morgan, they were not hyper-trustful of MBAs. All
my coworkers were PhDs in computer science, mathematics, or physics.
Livingston: New York City doesn’t seem to be a place where too many startups
flourish.
Schachter: There’s a great deal of technology going on in New York City. In
financial places,...

works. He says they never call you back to say no—they don’t want to close the
door in case they want to open it again, but they don’t want to actually give you
a response. Very few VCs actually said, “Sorry, we’re not interested.”
Livingston: How did the process of starting your own company and then selling
it change you?
Schachter: It pushes you far. You learn a lot. I did a round of funding, I was
writing code, I was hiring people, chief architect designer, negotiator, you name
it. I did all...