All my RailsConf keynotes

(Due to a scheduling conflict, I unfortunately wasn’t able to deliver my regular keynote at RailsConf 2016.)

RailsConf 2007: A peak at Rails 2.0

Unfortunately, I’ve been unable to find the video for this. You’ll have to make do with the slides alone, as I couldn’t even find the audio for this.


Bonus: If you’re really looking for some old school Rails fun, checkout the original 15-minute blog video. WHOOPS! If you want to see the application that gave birth to Ruby on Rails, checkout the all-new version 3 of Basecamp.

Capturing memories in the best light

When our son Colt was born three years ago, I found the true purpose to why I had spent the past decade studying and practicing photography: Capturing the arc of a whole new life that I co-created.

Family photography is often relegated to the lowest rung of Serious Photography. And I get that looking at pictures of other people’s kids really isn’t all that interesting most of the time. But if it’s your kid, suddenly it’s the most important and profound subject in the whole world.

Colt just turned three, and already I have a hard time remembering the specifics of his early expressions just by digging in grey matter. But pull up a few pictures, and all of the sudden the memory is jogged, alive in the mind’s eye.

It’s the magic of photography that it can serve as key to unlock those treasures you’d otherwise struggle to access. So thank you to Canon, Fuji, and, since Colt was about 1, primarily, Leica. ❤️📷




















The day I became a millionaire

I grew up lower-middle class on the outskirts of Copenhagen. Anywhere outside of Scandinavia, the socioeconomic label would probably have been ‘poor’, but Danish safety nets and support systems did their best to suspend the facts and offer better.

Me in the middle in home-made clothing to go with home-made ninja weapons… oh yeah!

But don’t worry: This isn’t a rags-to-riches story. I loathe the I-did-it-all-by-myself heroic myth mongering. I got where I am thanks to government-sponsored maternity leave, child care, health care, education, and even cash assistance. I grew up in housing provided by AAB, a union-founded affordable housing association. And my mother was a damn magician at making impossible ends meet without belaboring her tricks (like biking an extra 15 minutes to find the lowest price on milk).

Keep reading “The day I became a millionaire”

I don’t want to be a winner

Is there anything our society exalts more than The Winner? That fiery someone who crushes all competition to stand alone and victorious at the end. A genetic predisposition, I’m sure.

The paradigm of competition is so ingrained as the basic business narrative that we usually don’t even recognize it, much less question it. Well, of course there are winners and losers! What are you, a fucking communist?!

Actually, no. I’m a capitalist who doesn’t like direct competition. Is that an oxymoron? It shouldn’t be. In fact, it’s the profitable, justified motivation I smiled to see affirmed by Blue Ocean Strategy, the business book that explains this non-combative style with case studies like Cirque du Soleil.

I think that’s why I never really liked individual sports or games either. I remember how hard my heart would race playing 1–1 Quake, and how infinitely more shitty it felt losing than winning, and that even the latter wasn’t all that interesting!

Competition is the direct cultivation of stress and paranoia. Tapping fight-or-flight for game and gold. No thank you. Not for me, no siree!

The only competition I’ve come to love is the one against myself, and that’s not really a competition, now is it? The progress of betterment. Playing your part to the best of your abilities in a beautiful whole.

That’s the joy I take away from racing cars for endurance. It’s not so much being faster than the other cars, but striving to perfect your own contribution as part of a team. Pushing against the limits of perfect execution over the long term. 24 hours of testing your capability to avoid mistake and fatigue. Winning is almost incidental to that.

The same goes for making Basecamp the best software and the best company it can be. It’s not about taking out or choking existing or upcoming competition. It’s not about dominating a space to the exclusion of all others. I’m not sipping sour grapes or feeling bad when a competitor hits its stride. In fact, it’s so much more interesting when Basecamp is just one of many, different choices for people to make progress together.

The world is better off when its not being held in the palm of a few dominating winners.


See what we’re up to at Basecamp after twelve years with the brand-new version 3 we just launched.

Small is not a stepping stone


People ask, “How big is your company?” It’s small talk, but they’re not looking for a small answer. The bigger the number, the more impressive, professional, and powerful you sound. “Wow, nice!” they’ll say if you have a hundred-plus employees. If you’re small, you’ll get an “Oh . . . that’s nice.” The former is meant as a compliment; the latter is said just to be polite.

Why is that? What is it about growth and business? Why is expansion always the goal? What’s the attraction of big besides ego? (You’ll need a better answer than “economies of scale.”) What’s wrong with finding the right size and staying there?

Do we look at Harvard or Oxford and say, “If they’d only expand and branch out and hire thousands more professors and go global and open other campuses all over the world . . . then they’d be great schools.” Of course not. That’s not how we measure the value of these institutions. So why is it the way we measure businesses?

Maybe the right size for your company is five people. Maybe it’s forty. Maybe it’s two hundred. Or maybe it’s just you and a laptop. Don’t make assumptions about how big you should be ahead of time. Grow slow and see what feels right — premature hiring is the death of many companies. And avoid huge growth spurts too — they can cause you to skip right over your appropriate size.

Small is not just a stepping stone. Small is a great destination in itself.

Have you ever noticed that while small businesses wish they were bigger, big businesses dream about being more agile and flexible? And remember, once you get big, it’s really hard to shrink without firing people, damaging morale, and changing the entire way you do business.

Ramping up doesn’t have to be your goal. And we’re not talking just about the number of employees you have either. It’s also true for expenses, rent, IT infrastructure, furniture, etc. These things don’t just happen to you. You decide whether or not to take them on. And if you do take them on, you’ll be taking on new headaches, too. Lock in lots of expenses and you force yourself into building a complex businesss — one that’s a lot more difficult and stressful to run.

Don’t be insecure about aiming to be a small business. Anyone who runs a business that’s sustainable and profitable, whether it’s big or small, should be proud.


This essay and many others like it appear in the book REWORK, written by Jason Fried and yours truly. See what we’re up to with our 12 year-old business Basecamp, which just launched a brand-new version 3.

RECONSIDER

#WEBSUMMIT2015

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 Basecamp.com.

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 Basecamp.com.

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.

WTF.

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 Basecamp.com.

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 Basecamp.com.