Dan grew up in suburban Atlanta in the 80’s, and his options were kind of join the military, or work at a feed store. His dad retired from the army, and was involved in the intelligence community. When he was old enough to need to pick a direction, Dan’s dad told him to join the Navy or Airforce because they were the most technical (despite having been in the army himself). Dan’s first step to joining the Navy was taking the ASVAB test (the ASVAB is a standardized test that reveals areas of strength and ability in science, math, and language), and he actually scored pretty high. He was in the gifted program in school, and even though he had undiagnosed ADD he did well on tests.
Dan started in a very technical field, and because he scored really high and showed his intelligence they put him in a communications position, but gave him a clearance to go along with it. He started as a radioman sending classified documentation back and forth. Dan was in the navy for 8 years, but the first five years were just technical communications from point A to point B.
His last duty station was NIOWA (Naval Information Warfare Activity.) When he got there in ‘96 they didn’t have him doing communications, but started teaching him things about computers, Windows NT, and networking. He was the first person in that command to go from MS Mail to Windows RT, to Microsoft Exchange. At the time they were actually using the literal thick instruction manuals for computers and development. Dan was there for three years, the Navy got him certified, and he got his MCSE (Microsoft Systems Engineer Certification), and in his last year in ‘99 he had a taxable income of $19,000, and was getting job offers for like $50,000. The Navy asked what they could do to keep him, and he said, “Nothing.”
At the end of his contract he got an honorable discharge, but kept his clearance, and became a contractor for the National Security Agency. Basically, he just transferred from being a government employee to being a contractor. He was stationed in DC at the time, which was perfect for when he got out because there were a lot of intelligence community agencies and contracting companies that just plucked people from the government and put them into a contract. As a contractor he got paid an obscene amount of money because of his clearance, and he felt bad, because he knew what software developers and freelancers in the WordPress space were making. He was getting job offers from some big WordPress companies, but he just couldn’t justify the pay cut. He was frustrated because he knew the government was over paying his company, but at the same time, who doesn’t like money?
Dan was doing that from 1999 until 2021, when he got fired for “reasons”. Basically he made people unhappy by pointing out hate speech, and other illegal things they were doing. However, he said getting fired was probably one of the best things to ever happen to him.
The last contract he had was his longest contract he ever had, reaching up to 12 years, and he was working on the PHPBB (PHP Bulletin Board). The group that he worked with was called Intelink, they basically mimicked everything that was popular on the internet, and they either Acquired, Bought, or Copied (ABC), and they brought it up to what they called the “high side” (high side being the top secret side with no connectivity to the internet). They basically recreated every popular brand on the internet (YouTube, Twitter, etc), and since blogging was so popular they downloaded WordPress, copied it to the high side, and ran WordPress multi-user.
Since PHPBB had a security flaw they said they needed to take it down, but the WordPress guy at the time had just put in his two weeks, so they gave it to Dan and said “Alright, Dan, you’re the new WordPress guy.” This was around February of 2010. The version of WordPress they were running was way behind the current version (they were only running something around 1.9), and it was even WordPressμ, so it was before they branched the two code sets together. Dan didn’t know anything about themes or plugins, and he only had about four days to debrief with the other guy to figure out how everything was built.
When Dan left Intelink in 2021 they had 200,000 users in the database and over 50,000 sites in this multi-user database, so it was huge. His superior was so confused, because to them it looked terrible, but Dan explained that that’s just how WordPress works. Coming from his background, his first thought is to change the entire database, but Dan quickly learned that you really just can’t. It is what it is.
His first WordCamp was in San Francisco in either 2012 or 2013. He met Matt Mullenweg at a bar of all places and showed him on his phone how they were using WordPress. They were still using the original theme and everything, and Matt’s reaction was, “Holy sh*t spies are using it?!” Needless to say he was very impressed, and very excited by Dan’s project. Dan never got into the actual blogging portion of WordPress, but there were some people on his team that put out some really good content. In some cases there were some issues between the different agencies. Now Dan’s group Intelink falls under DNI (Director of National Intelligence), which was created after 9/11.
9/11 was a giant kick in the intelligence community’s butt, and it basically shone the light to the world that the CIA doesn’t talk to NSA, and NSA doesn’t talk to DIA (Defence Intelligence Agency). There are 17 agencies in the intelligence community, but the CIA and NSA have congressionally mandated jobs, so they literally have one job, and for the most part they do their jobs pretty well. No one can say that if they had talked to each other 9/11 wouldn’t have happened, but Dan thinks there’s a good chance it wouldn’t have happened. So DNI was created by congress, and at the time Intelink was a part of NSA. When congress got wind of what Intelink was doing they said, “Okay Intelink you’re now part of DNI, and DNI you tell Intelink to help everyone talk to each other”. So now their whole job became to make the Intelligence Community elaborate, and they were pushing back on the “need to know” concept. They agreed that in some form that needed to exist, but communication needed to coincide.
With their form of Twitter (Chirp) and the blogging platform they created, they were able to bring the whole Intelligence Community together, to the point that people were even having meetups together after work. Unfortunately through politics (and one side of the government) there was no policing of hate speech, and no filter for negativity, so from 2015 on this whole amazing community Dan had worked to create had turned into a dumpster fire, and that’s basically what got him kicked off the contract. Unfortunately, because he was a contractor and not a part of the actual government project, he didn’t have any power to make big changes or try and improve what he helped build.
At the time (around 2010), when Dan was basically handed WordPress and told “Here make something,” he would go out on his lunch breaks and buy whatever random WordPress related book he could from Borders. He said he really envied people that worked in a WordPress office, because he was the only WordPress person in the IC. The IC generally frowned upon anything open source, because anybody could put anything in open source (and they had so many contracts with Microsoft because it’s easier, and it’s what they’ve always done). The people in power also didn’t understand WordPress at all. Something really powerful Dan said was,
“When you have people in power that don’t understand something, they make bad decisions.”
They had to explain that yes WordPress is secure, yes anyone can add anything because it’s open source, but once we have it on a hardened server it’ll be okay. It was tricky too because Dan was on a development team, but everyone was doing something different, so no one understood his work. He’d put things on a test server and hope it worked, and he would test it, but they didn’t have a tester for about 10 years. And once they did get a tester it took him a while to appreciate their work. He had just spent so long working alone that it took time to learn how to work with people again. He knows how to break things and then fix them super quick, but it’s a lot harder to fix something someone else has broken. Long story short, they didn’t have a real development team for a long time. He said he had a lot of fun working on the project, but he’s glad he’s not doing it anymore. Right now Dan is running a new company called Dancy Wood.
Dan Gilmore’s story is quite the thing, and we really didn’t want to cut anything out (i.e., the original article was much too long). In order to save our brains from information overload, we decided to break it up into two parts. Keep an eye out in the next couple weeks for part two!