Entrepreneurs love to view risk as binary. The more you put on the line, the greater the potential for reward.

Meetings should be like salt - a spice sprinkled carefully to enhance a dish, not poured recklessly over every forkful. Too much salt destroys a dish. Too many meetings destroy morale and motivation.

If working remotely is such a great idea, why isn't everyone doing it? I think it's because we've been bred on the idea that work happens from 9 to 5, in offices and cubicles. It's no wonder that most who are employed inside that model haven't considered other options, or resist the idea that it could be any different. But it can.

Great people want to work on things that matter. Inevitably, a great person working on imaginary work will turn into an unsatisfied person.

Whenever you need something from someone else before you can move forward, it's a dependency. We believe dependencies slow people down. We want people to be more independent, because that will keep them moving forward.

That's the great irony of allowing passionate people to work from home. A manager's natural instinct is to worry that her workers aren't getting enough work done. But the real threat is that they will wind up working too hard. And because the manager isn't sitting across from her worker anymore, she can't look in the person's eyes and see burnout.

One of the secret benefits of using remote workers is that the work itself becomes the yardstick to judge someone's performance.

The risk of relying on a handful of customers is not just financial. Your product also is at risk when you're at the mercy of a few big spenders. When any one customer pays you significantly more than the others, your product inevitably ends up catering mostly to that customer's specific needs.

We like to bully deadlines. Pick on them; make fun of them; even spit on them sometimes. But what a terrible thing to do. Deadlines are actually our best friends.

A lot of people relate leadership to formalities. They believe that leadership is about being professional and strong and always right and being a booming voice. I just don't buy that. I think that leadership is a soft skill; it's a people skill.

You have to live with your decisions every day. Why live with one you're uneasy with? 'Because it'll make you money' is a common reply. But I don't think that's good enough.

Sustained exhaustion is not a rite of passage. It's a mark of stupidity.

It's like, the front door of the office is like a Cuisinart, and you walk in, and your day is shredded to bits because you have 15 minutes here, 30 minutes there, and something else happens, you're pulled off your work, then you have 20 minutes, then it's lunch, then you have something else to do.

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

It's incredibly hard to get meaningful work done when your workday has been shredded into work moments.

It feels good to be productive.

A large user base helps shield us from things we can't control. You can spend years catering to a major corporation, for example, only to see your contact there move on.

Practice quality, and you get better at quality. But quality takes time, so by working solely on quality, you end up losing something else that's important - speed.

If you ask people where they go when they really need to get work done, very few will respond 'the office.' If they do say the office, they'll include a qualifier such as 'super-early in the morning before anyone gets in,' or 'I stay late at night after everyone's left,' or 'I sneak in on the weekend.'

The owner of a company with supertight margins - say, a restaurant, retailer, or producer of commodity goods - would be a fool not to keep a close eye on the numbers. But when I make big decisions, numbers are seldom, if ever, the tiebreaker.

When time, money, and results are on the line, it's easy for tension to build.

I think that sleep and work are very closely related - not because you can work while you're sleeping and sleep while you're working. That's not really what I mean. I'm talking specifically about the fact that sleep and work are phase-based, or stage-based, events.

It may be irrational, but if you're local, the client often feels that, if worse comes to worst, they can knock on your door. They 'know where you live.' But when you're remote, they're going to be more suspicious when phone calls go unreturned or emails keep getting 'lost.' Stay on top of communications, and you'll reap the benefits.

I think what really people want is just a few things done really, really well. And if you think about ever day of your life, the things you really appreciate aren't the complicated things. They're the simple things that work just the way you expect them to.

Deadlines are great for customers because having one means they get a product, not just a promise that someday they'll get a product.

Respect the work that you've never done before.

When you can't see someone all day long, the only thing you have to evaluate is the work. A lot of the petty evaluation stats just melt away.

You cannot ask somebody to be creative in 15 minutes and really think about a problem. You might have a quick idea, but to be in deep thought about a problem and really consider a problem carefully, you need long stretches of uninterrupted time.

If you tell your story well, it can help attract customers; it can help people understand your business better, and you are more approachable as a business and a company.

I casually advise a few young companies, and I'm always surprised when I see them overthinking simple problems, adding too much structure too early, and trying to get formal too soon. Start-ups should embrace their scrappiness, not rush to toss it aside.

In almost every case, cutting things back is a way of favoring what is left.

Lots of business owners spend their lives trying to land the whale - the single, massive, brand-name account that will fatten the top line and bestow instant credibility. But big customers make me nervous.

Bottom line: If you can't spare some time to give your employees the chance to wow you, you'll never get the best from them.

Who you work with is even more important than who you hang out with because you spend a lot more time with your workmates than your friends.

When meetings are the norm - the first resort, the go-to tool to discuss, debate, and solve every problem - they no longer work.

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.

As the number of people who work at Basecamp has grown, I've noticed places where we could use more features, like management, structure, and guidelines. I've also noticed places where we've overengineered ourselves and should pull back.

Many of the things we do at Basecamp would be considered unusual at most companies: paying for employees' hobbies, allowing our team to work from anywhere, even footing the bill for fresh fruits and veggies in our staff members' homes.

Most work is not coming up with The Next Big Thing. Rather, it's improving the thing you already thought of six months - or six years - ago. It's the work of work.

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

I've run into a lot of companies that invent positions for great people just so they don't get away. But hiring people when you don't have real work for them is insulting to them and hurtful to you.

What's bad, boring, and barely read all over? Business writing.

Even companies that do big business online struggle to be noticed by Google users. The Web, after all, is home to some 120 million Internet domains and tens of billions of indexed pages. But every company, big or small, can draw more Google traffic by using search-engine optimization - SEO, for short.

Meetings should be great - they're opportunities for a group of people sitting together around a table to directly communicate. That should be a good thing. And it is, but only if treated as a rare delicacy.

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

We think of computers as smart and powerful machines. But your goldfish is smarter.

I like to think of myself as a leader whose door is always open. But I recently learned that an open door isn't enough.

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.

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.

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