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  Octoboxy Project History

All years and dates should be read with a prefix of ‘circa.’


2010 - 2014

It all began when we wanted a custom photo gallery.

Towards this goal, we rebuilt the same site once each year for five years:

  1. Hand-coded HTML
  2. Adobe Lightroom galleries
  3. Drupal
  4. Wordpress + premium theme
  5. Wordpress + our theme

Making money is good, so on the side we built three versions of an eCommerce site, for a company that made t-shirts:

  1. Wordpress + free theme
  2. Drupal
  3. Wordpress + premium theme

By this point we'd seen that we were solving the same problems on both sites. We started thinking about a digital asset manager that could directly support our web properties.

First Versions

2014 - 2015

We called our project "Moonrise."

v0.5 "Moonrise" - 2014-03
  • 2.5K lines Python
  • rendered photo assets using Photoshop
  • indexed those rendered assets

The first working version was a glorified asset index. At the time we still thought exporters/importers to move assets into a Wordpress front-end was the way to go. But then it hit us: we were already using Django -- a web app platform -- for the developer interface on our glorified asset index. Why not build the whole frontend out of Django too?

We had no idea what sort of a monster project we were getting into.

v1.0 "Sunrise"
  • 12K lines Python
  • photo gallery website

Some experimental projects happened here:

  • Interlude: photo galleries for handoff to a publisher
  • Interlude: color identity explored via Amazon’s Mechanical Turk
  • Interlude: Lightroom plugin to maintain collections in our index

Making Ends Meet

2015 - 2016

The frontend and backend individually worked, but under the hood shared few connections. The next version was all about bringing them together.

v1.5 "Unity"
  • unified codebase: workstation and website
  • taxonomy data structure

After this we began making smaller, feature-add versions, as opposed to megalithic redesigns.

v1.6 "The Doctor"
  • integrity testing
v1.7 "Plug n’ Play"
  • more generalized model for a digital asset
v1.8 "Feature Creep" - 2016-04
  • first version with wallpaper art
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v1.9 "Prose" 2016-05
  • documents are now assets

Starting with v1.8 we have a better idea when versions launched because each release got new wallpaper art, and image files have timestamps built in!



We were tasked to build a new, photo-based app to run lost-and-found operations at Burning Man.

The lost-and-found problem gave us opportunity to explore an excellent real-world use-case. Many parts of our system, most especially our taxonomy models, grew in complexity as a result.

Fiindex went through two versions:

  • Fiindex v1 -- branched from Moonrise v1.9
  • Fiindex v2 -- refreshed with Moonrise v2.1

Now Do It Better

2016 - 2019

Version 1.10 started out as a brush-up on the visual look of the system. Code-wise, it never deployed, but blurred seamlessly into a v2.0 where we rebranded the project.

Project Moonrise was now Octoboxy!

v1.10 "Skin" / v2.0 "Duality" - 2016-12
  • 28K lines python
  • website layer redesign
  • branded: Octoboxy

Our system still had a lot of room to mature in every existing component.

v2.1 "Enchantment" - 2017-08
  • standardized cloud deployment
v2.2 "Shadows" - 2017-12
  • multiple web properties on the same server
v2.3 "Meta" - 2018-01
  • improved background processing
v2.4 "Continuity" - 2018-03
  • better sandboxing of faces
Curecanti Narrow
v2.5 "Crucible" - 2018-05
  • new user model

At this point the core was more or less stable. It was time to tackle some bigger problems:

v2.6 "Kjahiit" - 2018-08
  • eCommerce
v2.7 "Serendux" - 2018-11
  • off-schedule improvements
v2.8 "//~;~//" - 2019-01
  • replication between deployments
* - pronounced: sky
v2.9 "Firmament" - 2019-06
  • performance and stabilization

Third Time’s the Charm


To kick-off the next arc of our story we set out to fix every long-standing annoyance we had with system architecture.

Some of this was simple module renames with few semantic changes. But on another level, some whole modules got rebuilt. This became a megalithic redesign version, perhaps our largest one ever.

v3.0 "Illumination" - 2020-09
  • a purifying light shown to every aspect of the system
  • 36K lines python

New codebase was alive! Now it became time to move in and try out the features.

v3.1 "Honor" - 2020-12
  • "cloudshop" app: devguide and domains for sale

This is now present time, present space. v3.1 is what's running the site you're looking at.

The next version, our work in progress as these words are penned, involves a new dialect of markdown called Rightdown. In short, we've out-grown the standard python markdown library and undertook an effort to make a new one. Not to hoard something so fundamental, it's all open-source!

Check out our open-source spin-off: “OctoBase”

v3.2 "Void" - (in progress)
  • re-integrate our own spin-off
Dante Looks Back

Thanks for walking this journey with us!

~ the Octoboxy crew