that Barak was challenging whether we could do it made us want to do it more.
We also knew that, if they didn’t invest in us, they’d invest in somebody else. At
the time, Blogger hadn’t been bought by Google yet, and we thought, “OK,
Blogger will get the money if we don’t.” (Which was probably true if they hadn’t
been bought.) And we didn’t want that—we wanted a stake in it and didn’t want
to be a footnote.
We always had an ambitious, “we want to win” attitude, but we never had
the stakes so high, because it never occurred to us that we could do it. I think
that’s one of the good things, too: since it never occurred to us that we could do
it, it didn’t occur to us that we couldn’t do it. We just had to put our minds on it.
And that has been really key to what we’ve done. The lack of experience made
us think, “Why can’t this just be done?”
So time flies and we grow the company, and we acquired a couple companies
in between.
Livingston: How much funding did you take?
Trott: Initially it was less than a million dollars—so angel money, really.
Livingston: So you now had the money to hire some people and get an office.
What were some of the first things you did?
Trott: Nothing, that’s the funny thing. We treated the money like it was our
own. We were so concerned about it. Suddenly we had this money and we
couldn’t spend it all because, if we spent it all, we’d need more, and then we’d
need more and then we’d have zero ownership of our company. That terrified us.
As a result, we didn’t hire fast enough and we weren’t in an office. We had
closed in April, but we didn’t move into an office until August. We had one
employee who was working out of his house in San Jose, one in New York, and
our support person was in Minnesota. It was like a remote office and nothing
was really changing because we thought, “We can’t spend this money.”
We bought operations stuff for TypePad—servers, etc.—and we had payroll
for the first time. Five people on payroll. Five people is a lot more than zero.
And Ben and I were never really taking a salary other than what we earned
from consulting, which was just kind of recycling itself.
We were the complete opposite of the things that typified the Bubble. We
saw the Bubble, and we saw people spending too much money on things that
didn’t matter. Then you have us, who didn’t even want to buy a refrigerator for
the office because it cost $150. I think that there’s a middle road that’s a lot
better.
Livingston: Why did you set yourself up as an LLC instead of a C corporation?

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