Well, there's more where that came from...
I really enjoyed my time at Picdar. I joined the company in 1998 and it was my first exposure to proper enterprise systems. I got to play with Sun Microsystems servers, fibre-channel storage arrays and HP magneto-optical jukeboxes that could store >1TB (that was a lot in the late '90s).
I once went to a customer site to check a server that kept having problems and discovered that it was located at the downstream end of a row of big IBM boxes. The first IBM box sucked in air, spat it out the other side slightly warmer, where it got sucked in by the second IBM box, which warmed it up a little more, and so on until it eventually got blown out onto our poor little Sun server, like it had a fan heater pointed at it. We got them to move our server and the problems abated.
My boss (technical co-founder Andy Heather) was a proper hacker. Picdar had its own SCSI drivers for HP's jukeboxes, its own image format (based on lossless JPEG, if I recall correctly, but wrapped in a file format that included the photo's metadata), and they eschewed SQL in favour of their own in-house database and query language called NACAS (for Named Access Control And Search). I learnt a huge amount from him, largely because he had infinite patience.
For a long time, my answer to the question "What's the biggest mistake you've ever made?" was "I ftp'd a bunch of large files from a production system on top of themselves, resulting in each file getting truncated to 1024 bytes. The client hadn't kept backups." The files in question were tar-style media archives containing preview images for a major newspaper's photo archive. Andy and another developer had to stay in the office until about midnight to fix my fuck-up by re-generating the preview images. I went home at about 7pm because there was nothing I could do. In hindsight, I should have stayed. :-/
Picdar was the first opportunity I had to work with serious software engineers, one of whom introduced me to the Apple Human Interface Guidelines, which has shaped my approach to UI/UX ever since.
There was a framed cheque on the wall for >$1m from a large database company. Said database company had won a contract with one of the big UK newspaper groups to provide a system that indexed their article archive and allowed them to do free text searches. Unfortunately, it didn't work too well (they loaded the article archive in, and ran a test query; after half an hour with no response, they decided to switch the system off), so the newspaper group asked Picdar if they could provide an interim solution. They did, it worked (the same query took just 6 seconds), the "interim" solution became a permanent solution, and the newspaper group forced the large database company to pay Picdar for the solution.
One of the reasons they hired me was because I came from an Internet background. Part of my role early on was to write a strategy white paper outlining the opportunities the Internet offered for the company. I remember doing a lot of research into e-commerce and online payments (in the context of allowing our clients to licence their image archives on the web). I completely failed to recognise the opportunity to offer image hosting to the masses or the potential of online advertising. Picdar could have been Flickr/Picasa/ImageShack/500px. Deeply embarrassing for me, in hindsight.
I once deployed a demo system (running on Linux, with a RAID setup that was a complete bastard to set up because nobody had documented how the Linux RAID tools worked) at a big magazine company. For some reason, the technology guy's office was on the same floor as a bunch of fashion magazines. He was one of two men on the entire floor (there were about a hundred girls). His office was glass-walled and there was a constant stream of models walking past, on their way to castings and photoshoots. That was a memorable couple of days.
In late 1999, I was approached out of the blue and offered the CTO role at a funded startup. I agonised over leaving but it was an offer I couldn't refuse. The right decision in hindsight but it was a real wrench at the time.