I've seen small businesses turn into terrible midsize or big ones because they let their desire to achieve some arbitrary metric get the best of them. Whatever is compromised as a result doesn't matter anymore, as long as the company is growing.

We don't want to bank all our risk on a small collection of big companies. We don't want to lose 20 percent of our business if one big account goes away.

A diverse customer base helps insulate you; a few large accounts can leave you vulnerable to their whims.

Selling to small businesses and selling to enterprises take two very different approaches with two very different kinds of people.

When we launched the first version of Basecamp in 2004, we decided to build software for small companies just like us.

Remind yourself that other people's jobs aren't so simple.

Respect the work that you've never done before.

Sometimes you get lucky and things are as easy as you had imagined, but that's rarely the case.

In my mind, declaring that an unfamiliar task will yield low-hanging fruit is almost always an admission that you have little insight about what you're setting out to do.

I'm generally risk averse, and most great entrepreneurs I know are as well.