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.

The reality is, risk is variable. Those in the financial world know it.

Since your company is the product that makes all of your other products, it should be the best product of all. When you begin to think of your company this way, you evaluate it differently. You ask different questions about it. You look at improving it constantly, rather than just accepting what it's become.

Your company is a product. Who are its customers? Your employees, who use it to do their jobs.

If yesterday was a good day's work, chances are you'll stay on a roll. And if you can stay on a roll, everything else will probably take care of itself - including not working from the moment you get up in the morning until you nod off to sleep.

By rationing in-person meetings, their stature is elevated to that of a rare treat. They become something to be savored, something special.

The office during the day has become the last place people want to be when they really want to get work done. In fact, offices have become interruption factories.

The reality is that companies are full of things that are left unspoken. And even when they are out in the open, the CEO is almost always the last to know.

Your employees have lots of opinions about everything - your strategy and vision; the state of the competition; the quality of your products; the vibe in the workplace. There are tons of things you can learn from them.

Nearly every boss has said it. And just about every employee has heard it. Yet it's one of the most meaningless lines ever spoken in the office: 'My door is always open.'

When you spend time with potential customers, you get to hear about their struggles firsthand. You see their eyes light up with excitement or darken with confusion. You learn things you would never find in a survey, database, or questionnaire. You learn why people buy.

Being a salesperson prepares you for just about everything in business: how to listen, empathize, and persuade; when to back off and when to step in; and, of course, how to close.

To say that the grocery business is cutthroat would be a major understatement.

Fix a few things here, improve a few things there, launch a new feature every so often. That's coasting. And I don't want Basecamp to coast.

When something is working well, it becomes too easy to let things run themselves.

Very, very few people actually have long stretches of uninterrupted time at an office.

Like many entrepreneurs, I started out in sales. I began at 14, when I got a job selling shoes and tennis rackets at a pro shop, and I've been selling one thing or another ever since.

I'm not sure a lot of companies know their story, or can explain why they exist and who they are, without just spewing just corporate speech.

Customers buy Basecamp without ever having to interact with us. If they do have a question, we handle everything via email. We've been in the business of automation. We've never really valued full service.

It's easy to forget, as a leader, that when employees don't get the wide view, not only does the point of their work escape them, but it can also lead to real frustration. It's hard to feel pride and ownership when you don't understand where things are going.

These two staples of work life - meetings and managers - are actually the greatest causes of work not getting done at the office. In fact, the further away you are from both meetings and managers, the more work gets done.

When it's all about the work, it's clear who in the company is pulling their weight and who isn't.

I know plenty of entrepreneurs who are numbers first. They tend to be highly analytical people, and before they pull the trigger, all the numbers have to line up just right.

We've never much liked the idea of charging a participation tax, a phrase we coined to represent what it feels like when a software company charges you more money for each additional user. Participation taxes discourage usage across a company.