About 12 years ago, I co-founded a startup called Basecamp: A simple project collaboration tool that helps people make progress together, sold on a monthly subscription.

It took a part of some people’s work life and made it a little better. A little nicer than trying to manage a project over email or by stringing together a bunch of separate chat, file sharing, and task systems. Along the way it made for a comfortable business to own for my partner and me, and a great place to work for our employees.

Keep reading “RECONSIDER”

What would it take to prove me wrong?

Good intuition propels progress. Listening to your gut is faster than rigourously exploring all possible options. The more you can get away with leaning on intuition, the more things you can improve in the same amount of time. The best product makers have excellent intuition.

But exactly because intuition on a roll is so powerful, it also invokes a sense of invicibility: Hey, if I was right about the gut take the last twenty times, why wouldn’t I be right about this too?

“Success is a lousy teacher. It seduces smart people into thinking they can’t lose” — Bill Gates

That’s no reason to give up on intuition, but it is cause to consider a fallback strategy. The primary of which should be having answers to the following: What evidence would prove me wrong? Is my gut take falsifiable? Will I have the courage to admit being wrong, if the data proves it so?

Some times there’s simply no way to know before you act. That’s the providence of A/B testing. If the data isn’t there upfront, then let’s just try it and see what happens!

Other times the answers are indeed already there, we just don’t have the confidence to look. It’s so easy to fall in love with an idea that makes intuitive sense. The theory is just too satisfying to give up. We don’t even want to entertain the idea of being wrong, at least not yet.

The golden path is to give almost all intuitive ideas the benefit of the doubt, but then articulate that doubt as clearly as possible. The quicker you determine which ideas are duds, the quicker you can load the next batch.

Check out what we’re up to at

Why I stopped paying attention to industry news

A couple of years ago, I did an experiment: I kicked sugar for three months. I’d have whatever naturally occurred in foods, but I wouldn’t eat anything with added sugar. The goal wasn’t to eat like this forever. I just wanted to know what it felt like to get all that sugar out of my diet. How would I react? What would be different? Would I like it?

The short answer: I felt great. I had way more energy, more balanced days, better mental clarity. But the most surprising outcome came when I reintroduced extra sugar into my diet. During the sugar fast, I wasn’t eating apples, but I tried an apple again. And wow, did I feel it. A sugar high from an apple? That was an eye opener. Even today, with my just-a-tad-of-sugar diet, I can feel the effects of the sweetener in ways I never could before.

I realize this isn’t a health magazine — so why am I talking about sugar? The food detox inadvertently got me to try cutting back on something else I was unknowingly overdosing on: industry news.

Up until about a year ago, I read industry news religiously. I’d load up Hacker News a few times a day, clicking away on the top-voted stories. I’d head over to Reddit and do the same thing on its tech-news subreddit. If I saw something on Twitter linking up a tech-news story, I’d be all over it. Clickity, click click click. I was a tech-news binger.

Then, last summer, I stopped. Cold turkey — just like when I stopped sugar. I had just reached the point at which I could feel an unhealthy level of toxicity piling up inside of me. I felt myself getting too involved, too absorbed, and a bit too anxious about what I was missing, and about what I knew or didn’t know, but thought I should know. I was checking Twitter too often and reloading sites too often. If someone told me about something I hadn’t heard of, I felt like I should have already known about it. Industry news was becoming an addiction.

The first couple of weeks after I cut the cord were challenging. My mind was craving the latest on tech as if it were a substance. While I could steer clear of the tech-news sites, it was difficult not to get hit by friendly fire. I was still on Twitter reading non-tech banter, but then a tech story would suddenly appear in my stream and that uneasy feeling would strike.

Finally, after a few weeks, I began not to miss the news. Whenever I’d see a headline on Twitter, or see people I follow chatting about some new company or technology, I felt a little disgust. It was similar to how I had felt when I saw people gorging on decadent desserts after I’d kicked sugar: It made me sick. So I came up with a new ritual. Every time friends tweeted about tech, I’d use Tweetbot to mute them for 30 days. Eventually my stream was cleansed of all the content I was trying to avoid.

The incredible thing is that a few months into the industry-news detox, I felt better not only mentally, but physically, too. My mind wasn’t on edge, waiting for the next big thing to hit. I was calmer, I found myself with more time, and I was far more focused on stuff I could control, like my product, my company, my person, rather than stuff I couldn’t, like the next “Basecamp killer” or some hot new startup.

It’s now a year later and I still don’t read industry news. Sometimes I’ll accidentally run into it. Sometimes someone will mention something to me wondering whether I’ve heard of it. I’ll often say no and ask for details. And then he or she will tell me about it in a way that’s actually useful, not sensationalized, as most coverage of new things is. I don’t feel disconnected. In fact, it’s quite the opposite. It’s no longer just empty calories: I eventually hear about what’s really important.

Originally published in Inc. Magazine.

Be sure to check out what we’re up to over at Basecamp.

Remove the stress, pick a deadline

October 20 was the internal deadline we picked for Basecamp 3 back in early Summer. It was computed by the highly scientific method of two-parts sussing, one-part calendar dart throwing, and the full awareness of its arbitrary nature.

The purpose of a self-imposed deadline is to sharpen the edge of your prioritization sword and stake a flag of coordination for the team. It’s not a hill to die on. It’s not a justification for weeks of death marching. It’s a voluntary constraint on scope.

Yes, deadlines are wonderful! They’re the tie-breaker on feature debates. They suck all the excess heat out of the prioritization joust: “Hey, I’d love to get your additional pet feature into the first release, but, you know: THE DEADLINE”.

The opposite of the deadline, the once much heralded When It’s Done, is the oppression of a blank canvas. Unless your system has fewer moving parts than you can count on two hands, objective perfection is impossible. It’s always a trade-off, but one that now needs to happen in the uncharted territory of a team-sized illusion of agreements.

Putting in a good day’s work relies on the knowledge that you just moved a little bit closer to the finish line. If the finish line is constantly moving and constantly in dispute, it’s impossible to reap that satisfaction. Which in turn leads to stress and misery.

Don’t let the self-imposed deadline kill you, let it free you.

Check out what we’re up to at

Poaching is for animals, not employees

The language of hiring is broken. From the cog-like “human resources” to the scalp-trophy chase of “head-hunting”. Yuck. But no term gets me more riled up than “poaching”. It’s shockingly revealing: You’re an animal, our animal, and other hunters better keep their hands off our property.


Employees should go wherever they can get the best deal for themselves. I would! Better deal in the holistic sense of everything that’s involved with working for someone else: Most interesting and rewarding work, most freedom in living arrangements, autonomy/responsibility, and, yes, pay and benefits.

If you can only retain employees by fencing them in with non-competes, hiding them away from your about page, or blocking competitive deals from even reaching their attention, well, then you suck.

All your energy should be poured into making sure you have the better deal. That work aligns perfectly with having a better business in general, so it’s not like you’re taking a detour here.

If you’ve done all you can, if you sleep sound with a smile knowing you’re offering a great deal, then the sting of someone leaving should be manageable too. They found something that was better for them. Be happy! You helped someone get to a better place, and you’ll surely be able to find someone else to fill their shoes.

You can’t keep everyone forever, and you shouldn’t try. That’s called captivity. Some people will want to try something else regardless of how good your deal is. That’s natural, and fighting it is only going to make matters worse.

So stop nurturing your poaching fears with defensive moves and start putting in the work to make your deal better instead.

Check out what we’re up to at

Making money takes practice like playing the piano takes practice

Most of the people I know who are money-making-machines got started really early. Lemonade stands, car washes, lawn mowing, baseball card trading. I think the reason they are money-making-machines today is because they started early. They learned the skills of negotiation, pricing, selling, and market-reading early. They have more practice selling than most people. That’s one of the reasons they’re better at it than most people.

Making money takes practice, just like playing the piano takes practice. No one expects anyone to be any good at the piano unless they’ve put in lots practice. Same with making money. The better you practice the better you get. Eventually making money is as easy for you as piano is for someone who’s been playing for 10 years.

This is one of the reasons I encourage entrepreneurs to bootstrap instead of taking outside money. On day one, a bootstrapped company sets out to make money. They have no choice, really. On day one a funded company sets out to spend money. They hire, they buy, they invest, they spend. Making money isn’t important yet. They practice spending, not making.

Bootstrapping puts you in the right mindset as an entrepreneur. You think of money more as something you make than something you spend. That’s the right lesson, that’s the right habit, the right imprint on your business brain. You’re better off as an entrepreneur if you have more practice making money than spending money. Bootstrapping gives you a head start.

So if you’re about to start a business, or if you already have a business and you’re thinking about taking funding, or if you’ve already taken funding and are considering going back for more, consider the alternative. Don’t raise money, raise prices. Sell sell sell. Get as much practice as you can. Force yourself to practice. Force yourself to learn how to make money as early as you can. You may hate it in the short-term, but it’ll make you a great businessperson in the long term.

Check out what we’re up to at

There’s always time to launch your dream

“I’d love to start a company / become a great programmer / write an awesome blog, but there’s just not enough time in the day!”

Bullshit. There’s always enough time, you’re just not spending it right.

Now that’s some tough love, but I’m sick and tired of hearing “no time” as an excuse for why you can’t be great. It really doesn’t take that much time to get started, but it does take wanting it really bad. Most people just doesn’t want it bad enough and protect their ego with the excuse of time.

This excuse is particularly depressing when it comes from students.

“Oh, I have so many classes. Oh, I have so much home work. There’s simply no time to learn outside of school.”

Then you’re doing it wrong!

Never let your schooling interfere with your education, someone clever once said. Being willing to sacrifice at the edges is one of the most important skills you’ll ever learn.

I’ve received plenty of Bs and even Cs for classes that I was incredibly proud of because they came from hardly no time spent at all. Time that I could then spend on reading my own curriculum, starting my own projects, and running my own businesses.

And I did. During my undergrad, I created Instiki, Rails, Basecamp, and got on the path to being a partner at 37signals. Do you think I could fit all that and still get straight As and have lots of time left over for playing World of Warcraft? No.

If you want it bad enough, you’ll make the time, regardless of your other obligations. Don’t let yourself off the hook with excuses. It’s too easy and, to be honest, nobody cares on the other side.

It’s entirely your responsibility to make your dreams come through.

Check out what we’re up to at

Don’t base your business on a paid app

The App and Play stores have turned out to be exceptionally poor places to run a software product business for most developers. They’re great distribution channels for service makers, like Facebook or Lyft or Basecamp, but they’re terrible places to try to make a living (or better) selling software products.

At a buck or few per app, how could it be otherwise? That type of pricing will work for Angry Birds and a handful of other games, but very poorly for most other types of software products. The scale you need, the sustained influx of new customers, well, it’s a place for mega stars, and people who think they can beat the odds at becoming just that.

That’s why I’ve been discouraging people from chasing dreams of a successful, sustainable software product business by pursuing paid apps. Far better be your odds at succeeding with a service where the app is simply a gateway, not the destination.

Watching users of Tweetbot heckle the team for daring to charge $5 for a 8-month upgrade only reaffirms that belief. It’s a sad sight of entitlement, but at this point also entirely predictable.

Apple and Google both benefit from having apps be as cheap as possible. For Apple, that means people will buy an iPhone more readily when the cost to fill it with software is near nil. For Google, it means app makers have to shove ads into products to make them pay. Win-win-lose.

What’s good for platform makers is often not good for those who build upon it. That’s where the whole picking up pennies in front of a steamroller comes from. Yes, a few may be quick enough to pickup enough pennies to fill a jar, but for most, it’s not a wise trade of risk vs reward.

Forget the paid app.

Check out what we’re up to at

The Obvious, the Easy, and the Possible

Much of the tension in product development and interface design comes from trying to balance the obvious, the easy, and the possible. Figuring out which things go in which bucket is critical to fully understanding how to make something useful.

Shouldn’t everything be obvious? Unless you’re making a product that just does one thing — like a paperclip, for example — everything won’t be obvious. You have to make tough calls about what needs to be obvious, what should be easy, and what should be possible. The more things something (a product, a feature, a screen, etc) does, the more calls you have to make.

This isn’t the same as prioritizing things. High, medium, low priority doesn’t tell you enough about the problem. “What needs to be obvious?” is a better question to ask than “What’s high priority?” Further, priority doesn’t tell you anything about cost. And the first thing to internalize is that everything has a cost.

Making something obvious has a cost. You can’t make everything obvious because you have limited resources. I’m not talking money — although that may be part of it too. I’m primarily talking screen real estate, attention span, comprehension, etc.

Making something obvious is expensive because it often means you have to make a whole bunch of other things less obvious. Obvious dominates and only one thing can truly dominate at a time. It may be worth it to make that one thing completely obvious, but it’s still expensive.

Obvious is all about always. The thing(s) people do all the time, the always stuff, should be obvious. The core, the epicenter, the essence of the product should be obvious.

Beyond obvious, you’ll find easy. The things that should be easy are the things that people do frequently, but not always. It all depends on your product, and your customer, but when you build a product you should know the difference between the things people do all the time and the things they do often. This can be hard, and will often lead to the most internal debates, but it’s important to think deeply about the difference between always and often so you get this right.

And finally are the things that are possible. These are things people do sometimes. Rarely, even. So they don’t need to be front and center, but they need to be possible.

Possible is usually the trickiest category because the realistic list of things that should be possible will often be significantly longer than the list of things that should be obvious or easy. That means that some things on the possible list might be better off off the list completely. Instead of making them possible, maybe not making them at all is the right call.

Coming to know the difference between obvious, easy, and possible takes a lot of practice, deep thinking, critical analysis, and, often, debate. It’s a constant learning process. It helps you figure out what really matters.

But once you’re able to see the buckets clearly, and you begin to think about things in terms of obvious, easy, and possible instead of high, medium, and low priority, you’re on your way to building better products.

Check out how we’ve balanced the obvious, the easy, and the possible in the all-new Basecamp 3! There’s a whole lot of each in there!

What’s more important: An extra gig of RAM or 3D Touch?

The hardware engineering and software coordination behind 3D Touch in the iPhone 6S is impressive. It’s such an Apple feature. Executed with exquisite diligence because they control the whole stack. Marvelous.

But you know what, it’s not my favorite feature of the 6S. That honor belongs to the low-tech, behind-the-curve addition of an extra gigabyte of RAM. Something that probably cost Apple just a few extra dollars per phone and almost no engineering prowess. (Compare that to the probably hundreds of millions in revised tooling, advanced development, and more needed for 3D Touch.)

Doubling the RAM means apps aren’t constantly being swapped in and out. Which means switching between them is super fast more of the time. Which in turn makes the whole phone feel much better over the course of a day.

It’s been repeated ad nauseam, but it’s still so hard to internalize for most product people: Speed is a feature.

Usually, it’s one of the most important features. Yet it’s also one of the hardest to get right. Chiefly because every other feature is generally at war with speed. Any excess CPU cycles are quickly captured by new, advanced, and ultimately slowing features. Extra cycles are like a surplus government budget: The constituency is going to have a thousand ideas for how to spend it.

It’s not easy to get this balance just so. You have to be fast at what people want and expect. Being the fastest phone running iOS5 or Window OS isn’t going to get you any business.

Comparing this RAM apple and that 3D Touch orange, though, is also a worthwhile reminder that good product design doesn’t deal in distinct categories. It’s all a fruit salad! Customers just want it to be delicious and nutritious.

Check out what we’re up to at