With this post I want to lay out a way rap music is going to forever change the world of enterprise IT. Rap will have this impact on IT in many enterprises, but one of the biggest impacts, I predict, will be on the US Intelligence Community and in DoD.

First some background so you can see why I’m so convinced: Enterprises exist because the our biggest challenges require people to come together to collaborate on outcomes. This is true in and out of government. It is how humanity really moves things forward. That is one of the reasons enterprise IT is so cool. The enterprise CTO gets to impact some huge missions.

One of the hardest challenges in enterprise IT today is sensemaking over data. This is a driver of the current “Big Data” movement sweeping the community. But sensemaking is more than just machine analysis and algorithms. Sensemaking requires an ability to tap into institutional knowledge of your workforce. It can also require information collected by distant parts of your enterprise or perhaps collected long ago.

Some of the biggest challenges I’ve seen in sensemaking are in the intelligence community. If you are trying to understand something as complex as adversary intentions you need to tap into every source possible and need to understand the strength and weakness of every source. In the intelligence world, there are no perfect sources. Every source has flaws and must be put into context.  Every source, whether that is a satellite picture or a document translation or a communications intercept or a defector debrief or a report from an agent in a position to observe your enemy, must be put into context if you want to know what is going on.

The need for context over intelligence reporting is not a new concept. It has been part of our tradecraft for years.  Reports from satellite imagery include numbers that tell the image quality. Reports from communications intercept can contain information that provides the error associated with the location or perhaps analyst comments on whether it seemed the speakers were lying. Reports from agents can contain text that indicate if the ultimate source can be trusted or was in a position to observe. There are many other means of providing context. There are related means of capturing context and providing feedback to other elements of the intelligence process, including mechanisms to give feedback to those that plan, collect, process and analyze intelligence. But every means I know of for providing this context is the product of industrial age processes.  Most all of those are in need of modernization.

But how can rap help with this? It is not the music itself, but a capability developed by three fast-thinking rap fans designed to help in sensemaking over rap. The result, a new way to capture the thoughts of people via annotations and assessments. Their company and the sensemaking tool they provide is known as:  RapGenius.

RapGenius is a site that lets users upload lyrics. Then it lets other users annotate and explain the meaning of the words for each song. It has rocketed to the top of lyrics sites and is quickly becoming the top destination for lyrics on the net. Part of the reason why is the incredibly smart way they built their annotation capabilities. It is powerful and easy. Users can upload lyrics (or any other text) and others can very easily comment on that. And then people can evaluate the comments and suggested continued improvements. In building a platform for lyrics annotation they have built a great means to add context to text.

This is exciting for many reasons. They have built something that humans can easily use (and the market is proving that), they have built something that can easily track who made the comments, and they have built something that has been shown to be scalable to millions of users a day.

So you may already be wondering, will they be building an enterprise version?

RapGenius has attracted the attention of VC’s including one of the great investors in enterprise IT, AndreessenHorowitz. And along with the investment is coming advice from a team with a world class record in fielding enterprise grade software.

I had a chance to talk with RapGenius co-founder Ilan Zechory and focused in on this topic of the potential of RapGenius in the enterprise. Here is how the conversation went:

GOURLEY: Thanks for the time. What a great capability you have built.

ZECHORY: Thanks. You into rap?

GOURLEY: Not so much, but you guys have some of my favorite songs in Rap Genius (even American Pie, which I help explain here) and I’ve tried your capability out. I like the Rap Genius interface and ease of use.

ZECHORY:  Thanks. We are excited about our ability to add context and depth to rap and know this same framework can add context and depth over text from many other fields.

GOURLEY: Seems like some clear potentials for this framework as an enterprise IT capability. And with this recent a16z news lots of us are wondering about your future. What can you tell us about that?

ZECHORY: We know enterprises are full of people seeking truth about information. Collaboration and communication over text is traditionally the way most of that truth seeking and sensemaking gets done. But the technology to help do that has not improved much over the years. And once you make sense over data how do you record it for other’s use?  And how do you give feedback to others who have previously provided context? These are challenges faced by enterprises everywhere and they are things we have addressed in our platform.

GOURLEY: How can this help?

ZECHORY: One non-rap example is the Apple iTunes Terms of Service.  Clay Shirky uploaded that to Rap Genius after he saw another document (the Mayflower Compact) had been uploaded.  Apple’s terms of service, like so many others, is long and hard to understand. Shortly after Clay tweeted about his upload people started coming in and annotating it and clarifying that is is you are agreeing to if you accept these terms. Other than just explaining, people are also pointing out places that make these terms potentially voidable and other issues of note. This is turning into a great example of how our platform can help people communicate and clarify meaning and form assessments on action the meaning might compel.

GOURLEY: What sort of things will you add in to make this more enterprise ready?

ZECHORY: We are ready for enterprises now and we are continually adding more of the features that will make us even more attractive, like an ability to tap into the power of enterprise directories and to leverage enterprise PKI. We already, by design, build in significant audit and authorization mechanisms like the enterprise CTO will want out of the box. We also built this in a very open way that will let us work with other enterprise systems out of the box, including your behind the firewall enterprise social media systems.

GOURLEY: Great, we look forward to hearing more. Can we come back with more questions from our readers?

ZECHORY: Absolutely.

Closing comments: We will keep tracking Rap Genius and their progress, and hope to meet with Ilam and his co-founders in person in the near term. Please let us know what is on your mind regarding their capability, and please check out Rap Genius yourself to get a feel for their ability to annotate. Find them at http://rapgenius.com