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.

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

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

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.

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

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.

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.

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.'

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.

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.

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.

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

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.

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

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.

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

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.

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

I've found that nurturing untapped potential is far more exhilarating than finding someone who has already peaked.

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

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

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.

I believe if you start a business with the intent of making it huge, you're already prioritizing the wrong thing. Size is important, but it's a byproduct of a whole bunch of other things that are worth way more of your mental energy - customers, service, quality.

Success isn't about being the biggest. It's about letting the right size find you.

I'd love to see more businesses take this approach - intentionally rightsizing themselves. Hit a number that feels good and say, 'Let's stick around here.'

Whenever I speak at a conference, I try to catch a few of the other presentations. I tend to stand in the back and listen, observe, and get a general sense of the room.

People pulling 16-hour days on a regular basis are exhausted. They're just too tired to notice that their work has suffered because of it.

When you're short on sleep, you're short on patience. You're ruder to people, less tolerant, less understanding. It's harder to relate and to pay attention for sustained periods of time.

Give your employees a shot at showing the company a new way, and provide the room for them to chalk up a few small victories. Once they've proved that their idea can work on a limited basis, they can begin to scale it up.

If an employee can demonstrate results produced in a way that the company didn't think possible, then a new way forward can begin to take shape.

I used to think that deadlines should be ignored until the product was ready: that they were a nuisance, a hurdle in front of quality, a forced measure to get something out the door for the good of the schedule, not the customer.

A fixed deadline and a flexible scope are the crucial combination.

I think the story is important in every business. Why do you exist, why are you here, why is your product different, why should I pay attention, why should I care?

A company gets better at the things it practices.

As businesses grow, all sorts of things that once were done on the fly - including creating new products - have a way of becoming bureaucratized.

When it comes to making decisions, I'm not what you'd call a numbers guy.

Statistics rarely drive me. Feelings, intuition, and gut instinct do.

I live in Chicago but own some property up in Wisconsin.

I'm a designer, but I rely on programmers to bring my ideas to life. By learning to code myself, I think I can make things easier for all of us. Similarly, I want to be able to build things on my own without having to bother a programmer.

Unlike a goldfish, a computer can't really do anything without you telling it exactly what you want it to do.

A computer doesn't have a mind of its own - it needs someone else's to function.

Hiring people is like making friends. Pick good ones, and they'll enrich your life. Make bad choices, and they'll bring you down.

If you could taste words, most corporate websites, brochures, and sales materials would remind you of stale, soggy rice cakes: nearly calorie free, devoid of nutrition, and completely unsatisfying.

When you write like everyone else and sound like everyone else and act like everyone else, you're saying, 'Our products are like everyone else's, too.'

If you care about your product, you should care just as much about how you describe it.

It's not easy to sit down and open yourself up and say, 'This is how much I love you,' you know? It's scary to do that.

The fact that I have a Southern accent and write about a lot of rural things leads people to put me in the country category.

The idea of growing up in the South and being a man is an interesting thing; there's a lot masculinity involved, with hunting, fishing, and playing sports that rural people take pride in, but at the same time, I grew up really not wanting to hate anybody.

Songs like 'Outfit' and 'Decoration Day' and 'Dress Blues,' those were good songs, but the output wasn't as consistent in those days.

I have modes, mental modes that I get in, and when I'm on the road, I focus very much on doing the work. On playing the show, on being good every night. And part of me just gets switched off. The part that's very private and very personal and very intimate. That especially, that part of me gets shut off.