David is the first to admit that his story is not the typical one you hear when most coding nerds narrate their tech journey. His attempts at programming kept failing, yet he loved computers and video games. His apparent nonlove affair with math didn’t help either, so much so that he at some point concluded that programming was not for him.

The advent of the internet changed that. Slowly.

Through the internet, he grindingly learned HTML and CSS a little bit at a time. He worked with programmers, increasingly getting frustrated when he couldn’t quite get them to do what he needed them to do… at least not fast enough.

This pushed him to learn some more: he took up a little bit of PHP, a little bit of ASP.NET. Over the next few years, he would discover himself as a programmer.

David says that at some point, he realized that building information systems didn’t seem as complicated for him; it felt more like writing than math. For the first time, it felt like there was a chance that he could become a competent programmer, especially when he encountered Ruby.

David’s encounter with Ruby changed the trajectory of his career. He created his first commercial program for Jason Fried, his longtime business partner, in 2001.

Now he is sure:

“This is what I’m going to do for the rest of my life!”

Best at One Thing Versus Great at Many

David’s view of the world is different. Not typical. Yet this might be the simplest way to explain how a kid who didn’t particularly like math would grow up to create Rails: the celebrated development framework that gives developers the structure to write code with ease by abstracting and simplifying repetitive tasks.

DHH, as he is better known, sees patterns where most other people might not. For instance, he is convinced that racing has a host of similarities with programming. These unique perspectives keep him achieving great things—quite a fete for someone who insists that he is utterly disinterested in being the best.

“If you want to be (someone) who becomes number one in their field, you have to, in many ways, give up everything else,” he says, “And we look at that as just such a valiant effort, right? ‘Wow. They’re so brave. They're so committed. They're so dedicated. They're willing to give up everything else. Oh, I wish I could be that person.’ No, you don't. No, you don't. And the people who go down that route are unique individuals who demand our pity as much as our admiration. I was not interested in that!”

This unconventional approach also explains why David doesn’t believe that more is better: that investing more hours into something necessarily results in better output.

“You can have these very intense moments of flow of joy in your work, without it becoming the all-consuming everything,” he asserts. “No one is in a state of flow for 12 hours in a row. You don't need that many hours. The quality of the hours is really what matters. It's not whether you have a hundred of them.”

An Unending Stream of Notifications: Absolute Poison!

You’d have to listen to the podcast to hear David’s passion in his dislike for the electronics takeover that consumes us through unending notifications. Expressing exactly how he feels, he rants in a stream of cuss words that he had, amidst chuckles, promised Tobi to stay away from.

“The number one self-care principle I apply to my electronics is to turn off all notifications. And this is how we built even our new email product: Hey.”

Hey.com is David and Jason’s new email program.

“One of the first features we built in was an anti-feature: a thing that did not exist or does not exist. There are no notifications by default. When you get a new email, there's not a little counter on the icon that tells you how many unread emails you have because that stuff is absolute poison. It is absolute poison for your attention. It's absolute poison for your ability to string together long stretches of uninterrupted time, which is the super fuel of creativity.”

Does DHH have a smartwatch? He says yes, but is quick to add that he only uses it for working out. Beyond that, he says smartwatches are the worst.

“A smartwatch is the perversity of thinking. If they bust your wrist and you could constantly glance at that thing, then you’d truly be on top of things, right? It's madness. And I'd actually say it's worse than madness. The default settings, as most technology ships in terms of notifications are abusive, is absolutely abusive.”

He takes it further, saying that perhaps there should be circumstances where these notifications should be illegal. Comparing smartphones and smartwatches to smoking, DHH says there should, at least, be a label on their packaging warning the buyer that using them could destroy your brain.

“There should be warning labels in the same way. As if you buy a pack of cigarettes and Denmark, you get a lovely picture of a set of black tar lungs. Where are the warning labels on an iPhone box or an Apple watch box telling you, ‘You know what, if you run this wretched machine at its default settings of notifications, you're kind of going to destroy your brain.’”

David’s Perfect Team Size

Tobi also asks DHH about the company culture at Basecamp and his advocacy for small teams and limiting the total number of employees at his company.

David is a strong advocate of limiting the total number of employees at a company. He neither enjoys working at or running large companies. For a long time, Basecamp was made up of just eight people. While it has since grown to 60, David hopes to keep the number largely subdued regardless of how big the company was to become.

“My favorite team size is three people,” he intimates, “That's in my experience, essentially the perfect team size, if you have enough productivity in your tooling and your approach to make three people capable of doing stuff.”

“Now, let's say you become the CTO of Zalando, a company that has, I think, 1,500 engineers and product people,” Tobi supposes, “What would you do?”

“Quit!” David quickly asserts. “I mean that legitimately! I would because that's not a problem I'm interested in solving.”

In any case, even big companies have to create small teams to be manageable.

“If you have a simple team, you'll only need simple principles. You only need simple practices. If you have a very big and very complicated team, and if you have a very big and very complicated company, you need very complicated, convoluted processes and sign-offs, and all the other bullshit that people, rightfully, usually end up hating. So, don't do that?”

Autonomous Teams

Tobi asks David about his take on autonomous teams, specifically the so-called Spotify model.

“The Spotify model, as I understand it is actually bullshit: as in, it does not exist even at Spotify. The Spotify organization does not follow the Spotify model,” he answers Tobi, “The Spotify model to a large extent is a rebranding of existing organizational principles, including functional or matrix structures, and so forth.”

In David’s opinion, autonomy is important, but there are circumstances where it might be essential to have a hierarchy and where teams receive direction. Instead of being caught up in labels that may fall short in defining the setup in your company, DHH recommends specificity when explaining what the teams need to do, the decisions they need to make, and the level of direction they should receive from somewhere else.

“I think to a large extent, self-organizing teams is a great idea, but not universally.”

Jeff Bezos as an Investor at Basecamp

Tobi asks David about Jeff Bezos, who was the only investor to invest in Basecamp. David is quick to clarify, saying Jeff Bezos simply bought a small slice of his and Jason’s ownership stake without controlling how the company is run.

“That’s how we ended up with Bezos as a co-owner at the company, a decision that seemed very appealing and attractive in 2006. 2020? I have some reservations.”

And do they still meet once in a while?

“That’s gone,” David says with finality, “Dude’s the richest man in the world launching literal rockets into space and running a huge conglomerate, big tech monopolist. (There are) other things on his agenda than bothering with this tiny investment he made back in 2006 as a hobby to spend his time.”