How We Work

Below you'll find an internal memo (2021) that explains a little bit why work the way we do, and why we use the tools we use today.


In the past year or so that you all have worked with me, I’ve changed a lot of tools and processes. Thanks for adapting to whatever I’ve thrown your way.

I promise there is a method to my madness. 

I’ve spent the last decade working in government and tech. Both industries are plagued by bureaucracy and bogged down in processes. 

All these things I used because someone else before me used them. I assumed it was the way, unquestioning.  Now when I had the chance to have my own company, I got to question assumptions. And test.

Starting with naming schemes. File organizations. We worked with Microsoft Teams. JIRA. Asana. Slack. Every VC-funded company designed tools to “increase productivity” and unite a distributed team.

We gave them all a good run, believing that the people would make the tool work and not the other way around.

Except it didn’t. I felt more distant. We spent too much time making the tools work together. 

The tool was shaping how we work.

The glorified project management software needed a dedicated human to manage projects.  This is why the last big company I worked for had a project manager for every. single. team. Their job? Turn meeting outcomes into JIRA tasks. 

What I’ve found is that these tools are not a place where work happens, but a place to check off that you did work.

Now to Slack. It’s the central hub for our stuff. Chat rooms force us to think in linear back and forth messages. Slack tries to thread them but then conversations get hard to follow. And it makes you feel like your missing out until you kill time scrolling through to confirm you're not. I made it worse by turning ours into a nonstop notification stream for every subject.

I reject the arrogance of these big tech companies. This is not what work looks like. A thing doesn't need to be a task, assigned to a person, who then gets a ping on a chat, has to get a ping on the project to see it on the chat, three different times, and then goes back and marks it done, ad nausem.  All of them do one little thing well. But they also force us to switch back and forth to keep up. Redundancies are good in software and electrical grids. Not so much in intra-team communication.

More efficient ways to use these tools you say? I thought so too. But not if Asana and Slack have their way. There's a huge market of API connections for each company to source out feature requests. Why have a chat room in Asana when you can have Asana its own Slack bot and charge for it?  

For a small monthly fee per user per tool, you can do everything you think you need to do because of productivity. Is this what hell looks like?

Sure, this is good for a Fortune 500 with 10,000 employees. Or a government agency using carrier pigeons and legacy tech stacks. 

How about a startup whose motto is to build things? Hell no.

That’s why starting this week I’m bringing us all into Basecamp. I admire their founders. And their philosophy. But most importantly, their tech is doesn't get in the way. See for yourself:

See y’all around the campfire.

May 28, 2023