In June of 2020 and again in October 2021, Matt Devost spoke to former Air Force pilot John Robb. John has worked successfully in a variety of domains, including the special operations community, as an industry analyst, successful start-up founder, and national security expert.

John Robb has distinguished himself with a career of critical analysis on a variety of security, technology, and cultural issues throughout his career, in his popular book “Brave New War”, as well as his current Global Guerrillas content community and the GG Report.

We continue our effort to underscore certain patterns and themes found throughout the OODAcast library of over 80 conversations with leaders and decision-makers, on topics such as leadership, clear decision-making while operating in a low information environment, future threats, and strategic action.

This conversation cover topics such as the early history of the commercial internet, frameworks for organizing information in fast-moving environments,  network tribalism, decision-making scenarios during the pandemic, and the emerging threat environment.

Matt Devost: So, John, why don’t we start off by you giving a little bit of background. Where did your career start and what are you up to today?

John Robb: Oh, wow. Okay. A short version: Air Force Academy, Astronautical Engineering, pilot training followed by a couple of years in C1-30’s – and then five years in Special Ops. I got drafted into a tier-one counter-terrorism unit. That was interesting. I got out, went to Yale, got an MBA to kind of reboot, and ended up as an analyst at Forrester, which happened to be in 1995. So, I was their first internet analyst. I ended up lucking out. I got a lot of coverage in the papers for a couple of years, as every internet company came through my doors. Then started my first company with some friends, Gomez Advisors, which became Gomez. It was a performance testing network that tested the performance of transaction systems at banks and brokerages that ended up selling for $295M [to Compuware, now Dynatrace, in 2009]. It is kind of nice to build something that had some lasting potential.

Then I got involved in 2001 in trying to build social networking, based on a report I wrote back at Forrester and ended up as CEO of UserLand software. And we did the first RSS. We open-sourced that, and then we built the first kind of blogging network where you blogged and then you subscribed. And it was an open blogging network back in 2001.  And then I ended up doing a bunch of other different companies, a global printing company, doing software for the military in social networking.

I wrote a book after the Gulf War kicked in: A Brand New War – that looked at how warfare was changing and how we are seeing open-source networks applied to warfare – and that ended up being pretty prescient in terms of describing how Iraq was operating. Since then, I have been doing a variety of different writing. I have been doing a blog on warfare called Global Gorilla since 2003. That became the Global Guerrillas report three years ago. I put that on Patreon to kind of winnow the crowd down to kind of make sure that the people that were interacting with me on this were high quality and it is proven to be such – and I have been tracking the intersection of politics, technology, and warfare, and it seemed to be right on the mark because the stuff I have been writing about is exactly what we are dealing with today.

“…what I tried to do is develop frameworks…that would help people get their heads around the emerging situation to allow them to act.”

Devost: Excellent. So,  working with tier one folks on a counter-terrorism mission into an MBA program. What lessons allowed you to go from the military experience to transition into the business world?

Robb: Well, I mean, being in a Special Ops role is different than the standard military experience. You operate as an outsider and, I mean, no one is given an aircraft and a bunch of cash to go out and do stuff in the regular military. It’s just very controlled. You have to call before you take off and after your takeoff, and then you get in route, you get a call, and then after you land, you know? Not the case in Special Ops. So that made the transition to kind of entrepreneurial thinking and entrepreneurial life much easier. It was looking, always looking at business opportunities as an outsider that worked out when I got to cover the internet because I was already thinking as an outsider and so much of what was happening in the internet space between ‘95 and ‘97 was all about trying to break things from the outside. Disrupt. And every company had a disruption message and startup fever was definitely up my alley. Things that transitioned over: commitment and the same kind of work ethic that you have in the military applying to business, worked out fine.

Devost:  Being at Forrester in 1995, are there some things that strike you as interesting, that represented a groundswell, that you thought were going to be really important? Because that is really early days in the commercialization of the internet.

Robb: Yeah. I didn’t have a background in IT, which made me kind of an outlier at Forrester, and Forrester had been going sideways as about $20 million company for many, many years focusing on those core IT subjects. So, they allowed me to be creative in terms of trying to synthesize frameworks for understanding how this fast-moving situation was developing. And these frameworks, it is an interesting thing when things are changing so quickly. There really is not any time for a considered analysis, where you build this extensive analysis with 70-page reports and really digging into all the details.

What you need is a framework. And I found that decision-makers at virtually every company during that period, ‘95 through ‘97, were floored. They didn’t know what to do. They were paralyzed by the internet and what was happening, what was coming. And what I tried to do is develop frameworks. What I’m trying to do now at the Global Gorillas report is develop frameworks for understanding or parsing the news as it’s developing, like pigeonholes where you can put different news items in.

For instance, I wrote a report on what I called “navigation hubs” in early 1995, just before the portals went public. And I said, okay, these guys, and I ranked them from Yahoo on down, are going to be the centers of the internet. And every content provider is going to need to slot into their hubs in order to make money on the internet. And that would help people get their heads around the emerging situation to allow them to act.  Some cut deals with Yahoo or different portals, which allowed them to gain a foothold on the internet. So that’s what I try to do. Sometimes it’s long-term or something short-term for decision-makers – to unfreeze them, unparalyze them – so they can act and interact with a fast-changing environment.

“We are developing this open decision-making system and it is messy and it is loud, and there are so many dissenting voices…”

Devost: That dynamic of leaders not being able to act because the environment is changing too quickly, or they feel like they don’t have the data points. Do you think that the pace of change has been increasing steadily over time? Are we seeing today the same types of paralysis that you were seeing back in 1995 to ‘97?

Robb: I think it’s worse now. We are getting a rapid technological change and in addition to that, we are getting rapid social change, rapid political change. It’s paralyzing, and not knowing what comes next makes it impossible to plan. If every bit of news that you get is a surprise, your natural tendency is just to sit there and wait until the news settles down, until you could start to make sense of what’s happening before you act. And no one wants to act – and then find out the next day that they’re taking the wrong path. It would be fatal in this situation. You can be mobbed and swarmed.

Devost: Are there some frameworks for what we’re seeing today that you think are useful to help people decipher the global environment that we’re in?

Robb: One thing I’ve been working on is I’ve taken the open-source framework that I used in warfare and moved it to protest. We saw that happen in the Middle East almost a decade ago – but it’s also being proven useful in this current context. It’s changing the way we conduct politics in the United States. And what we’re seeing right now is the emergence of a new decision-making system, you might call it network tribalism. And it’s proving to be very powerful. A network forms online and it is open-source in the sense that there is no set leadership, and there are lots of people contributing to it and they get focused on a single idea and they push it forward. They make it happen. I mean, we saw it just recently with the shut down of the economy in response to COVID. I mean, it was the individual actions of tens of millions of people that really did the heavy lifting on that more so than what the states did with their shutdown orders.

So that is kind of this network tribalism that is very powerful. When it gets focused on an issue, it can take to the streets. And we’re seeing that around the country focusing on getting control of police forces and kind of equalizing the power balance between the public and police. That is network tribalism.  To put it into a larger frame I use David Rosenfelt’s site, David Rosenfelt’s of Netwars. He was at RAND for many, many years. He came up with a framework for understanding how things are changing over a longer time period since, in the last 500 years, is that we have these big social decision-making systems, which is right up our alley with OODA. Big social decision-making systems. Before the printing press and the reformation, it was feudalism in a universal church.

What we had since then is, is a nation-state and bureaucracy and markets. He says, okay, there are three decision-making systems that we currently use in society, and we refine them and made them viable. It was bureaucracy, which is great at mobilizing. It’s great at executing and planning. We have markets, great for allocating and discovering information. And then tribalism, which became nationalism, which gives us cohesion because we must have a certain level in order to operate as a unit. If you don’t have that cohesion and you treat your countrymen are now enemies, you don’t trust anything they say. And what we are adding now is a network layer a fourth [big social decision-making systems]. What I think is happening is that the network layer is now replacing what was tribalism, what was nationalism and patriotism, supplanting it.

And it’s putting pressure on bureaucracy because it’s making decisions faster. It makes decisions faster in terms of COVID than the bureaucracy does. The bureaucracy seems to be flailing. And that it is more powerful than markets. Network tribalism is more powerful than markets because it was able to shut down the economy through the actions of tens of millions of people changing their demand for products and services, not flying, not taking vacations, not purchasing things not going to restaurants network action is proving more powerful than the market decision-making system in that regard.

We are seeing it with the COVID responsive.  Initially, it was good. It blunted the spread of COVID in the U.S. but getting out of it on the backend, whether it is the right time to do it, is getting people to re-engage with the economy and get out of the siege mode. The bureaucratic tools are just not available. I mean, thinking in terms of maybe giving people a stipend of money over a course of a year or two, a thousand dollars a month to get them to start spending and spark re-engaging. But our bureaucracy could not even get their heads around something like that. It is just too outlandish. Just does not work for them.

So, learning to understand that, and there are lots of nuances and lots of interesting things that can be added to that. I have plenty of reports that I wrote looking at it from the international stage too. How does this networking concept apply to places like China? In China, where the state is taking control of this network decision-making system and then enforcing its use from the social credit system that they are doing to getting all the companies and everybody to express publicly online, that they are all aligned with the state’s actions. It is a framework for understanding. Once you start to read it and start to get it, then every bit of news that you start to get now starts to fall in place and you can put it into the right categories. It makes it easier to make sense of it. And then it makes you feel better because at least you have some knowledge of where things are going.

Devost: Do you have to have the awareness with regards to how adversaries might try and impact that network tribalism  If I went to a town meeting, it was my neighbor sitting next to me. Now, if I am participating in this networked version of it, there are also adversaries and folks that do not share the same geography that might try and influence that. So how do you protect against that external influence component?

Robb: It is hard, but in the case of the U.S. and the U.S. is probably alone in this I think the volume of what we produce internally is so great that it overshadows anything that China and Russia can do. They are lost in the noise. Now, if I was a smaller country, boy, it can make all the difference in the world. Manipulate Facebook the right way and you get places like the Philippines with 90% of their news they get through Facebook. I mean, that is like a place where you could really have a serious amount of influence if you are an external player with some smarts. Here in the U.S. not so much, you know? We are developing this open decision-making system and it is messy and it is loud, and there are so many dissenting voices, and is so hard for anyone outside to even be heard. They could spend a hundred times what they are spending now, and it would just be dropping the bucket compared to what we produce as just a by-product of our internal discussions.

“…you could end up as a target of this network and they can take you down.”

Devost: So, there are two divergent threads I want to pull on there. You talked about individual decision-making on the network. I would say kind of the next year of decision-making was in the corporate domain. And then the last was in the government space. We had a lot of corporations that were acting before the governments. If we put it a sci-fi hat on it, like Cory Doctorow, where you have a tribe associated with the time zone that you are in, or a Bruce Sterling or Neal Stephenson, where you start to have more affiliation for a particular company than you do for a country, organized in a national construct. Do you think that issues like COVID help reinforce or drive us more towards that kind of corporate affiliation? Or is that just a science fiction pipe dream?

Robb: I am seeing it more at the macro-level macro tribes at the national level, we are seeing tribe development. I have not seen developments at the corporate level, where the primary loyalties are now to companies. Yeah, I would have thought it would be something that would pop up because of this, but I am not seeing it. People are more focused on what we are doing at a national level and trying to align their actions with everybody else. One of the ways that it changes the way we think, becoming part of a network, is that we have become pattern matchers more than solitary, literary thinkers. We used to get a book or read an article, and we read it in isolation. And then we acted based on that. We formed our opinions based on considered reflection.

Now we are pattern matching, we are grabbing bits and pieces of data as it flows over us, we are letting most of it just float past us. And then we are making, setting up patterns. And the more dominant patterns that we are working on are the big national patterns. Occasionally there are pattern matches that kind of cleave off like Q Anon and others who create those kinds of conspiracy patterns. And they never really get that big, but they become very tightly woven and interconnected, and everyone spends their entire day grabbing bits and pieces of data to stick into that pattern. Is it possible that companies could do that? I think [companies are] more focused right now on whether they are aligning with the national pattern, the national tribal consensus of sorts.

But you see it in China where there are looking for alignment. You know, the big challenge of the 21st century for nations is to stay cohesive, given how complex and chaotic the environment is with will tend to rip you apart. As we are seeing. They do it by having the state-run the network and forcing companies to all align. In the states, we do not have the government dictating that. And what we have is this tribal network emerging online, and it is trying to get all these companies to align and express that kind of fealty towards the network and enact, in the case of the big platforms, censorship of the platform in the way that conforms to the needs of the tribal network, enacting policies that align with it. If you do not, then you could end up as a target of this network and they can take you down.

“An orientation crisis requires new frameworks. And that’s what I’m trying to build.”

Devost: I do want to talk a little bit about COVID.  You talked about surprises and predicting surprises and having a framework for how to deal with it. Post-September 11th, there are quite a few that were looking at these issues of biological disease spread and responses to that and kind of how it would play out. Yet, fast forward 15 years later, and we seem to have lost the needle on understanding the risks and the responses and being able to make decisions.  Is that just a failure to sustain the cognitive infrastructure behind some of those things that we studied or how can we best enable future leaders to be able to make decisions based on past analysis?

Robb: That is, how do we improve the decision-making capability of the bureaucracy? In a complex world, in a complex environment, we are getting hit by complex threats that leverage these networks and leverages that complexity. You must rework your models. You must look at which factors are most important and find those factors and then build a new model based on those or update all the assumptions that go into the existing model based on your experience. And it must be done quickly, or you are going to be left without any forecasting capability.

Devost: So, I remember calling for the dynamic decision-making right, the essence of the OODA loop. It is not “make a decision and you are done.” It is:  “make a decision, reevaluate, make a decision, reevaluate.” We saw a lot of attempts at very static decision-making, you know: this will be the truth. This will be the plan for the next six weeks when maybe, in reality, we could have been working at a little bit more accelerated cycle?

Robb: In a complex environment everything, the tendency of the whole network, can change overnight. You think you’re doing one thing and then suddenly, the world changes and you’re out of step or based on the way you have analyzed the current environment, your plan should have this result, but it doesn’t. So, what you need to do is you have to do a lot of probes. You have to do a lot of trials, find out what works based on hidden factors that you had not considered, and then reinforce the one that works and build upon that. The tinkering approach that we see so often and the open-source that works nicely in this environment. And then there is a more formal process for doing that within companies, which is pretty useful.

And then also being willing to be flexible, revisit your assumptions, revisit your models, look for new factors, look for new patterns.  That new framework for understanding what was going, what is going on.  What is really plaguing people if you boil it down from an OODA perspective, is orientation. And I always thought orientation is the key to OODA.  It is the most important piece. It is everything that you are points you in one direction or another, and what we are having right now, given the pace of change in the way things are changing, you are entering a completely new environment.  That is our orientation.  It is an orientation crisis.  All our experience and all our training and all our organizational structure are geared in one direction, but the reality is pointing us in another.  The opportunity space is in a different direction. And you have to orient to what the environment demands. It’s not “orient to what history taught you.”  An orientation crisis requires new frameworks. And that’s what I’m trying to build.

“If you want to censor the private communications of a billion people, you have to have an AI.”

Devost: Given that you’ve been so prescient on kind of emerging threat environments, what do you think are some of the emerging threats that we face over the next five to ten years?

Robb: Externally or internally?

Devost: Either.

Robb: Yeah. I, I think we’re, we’re going to be focused on the internal dynamics and getting this right. I mean, hammering out how to use network decision-making, it’s going to be traumatic. It is already traumatic. It is going to get worse. I mean, just think of going from feudalism in the universal church. In that way of thinking, it is a completely different switch when you start to go to the nation-state and you start to use markets and you start to use nationalism as a mechanism, and those did not happen overnight. That switch out of that old mindset to the new mindset ripped apart Germany with the 30 Years’ War, the bloodiest war in European history. And yeah, that could be traumatic. So, I think most of the stuff that we are going to deal with is internal. Hopefully, it does not end up like during the 30 Years’ War. But there is always an outlier or a situation where that could happen.

Externally I think most countries are going to be dealing with something similar or they are going to go through a kind of a lockdown phase like China’s doing. They are locking everything down, using networks. The end state of that, when you start using social AI’s, which are the biggest AI that we have developed so far and put into play to enforce social cohesion, could end up becoming what I call “The Long Night” if that propagates, if China is able to export that or people copy that. And that becomes the dominant approach. We will have a kind of a long night of oppression because it will not just watch what you do publicly. I mean, it can get into every single private communication and change that, alter that, or censor that and use that against you. And then you have sensors, and you have all this other stuff that we are surrounding ourselves with. It becomes the ultimate nightmare.

Devost: Interesting. So, you invoke AI because AI is the only thing that is going to have the processing power to put all the pieces together?

Robb: If you want to censor the private communications of a billion people, you have to have an AI. We are going to train them. I mean, we are constantly finding the exceptions, the things that pop up, running it by human filters, they are training AIs and that is a constant process. So much of what will constitute new jobs in the future will be that human fields the new thing, they develop a response to it, and that goes into the AI. Just like an Uber driver, their response goes into their AI. And we can do that with every profession. It is like everything that we do is going to be set up in that same situation or that kind of process.

The original OODAcasts:

OODAcast: OODAcast: John Robb on Global Guerrillas and Frameworks to Drive Decision Making

OODAcast:  Digital Self Sovereignty and Avoiding the Long Night with John Robb

Other Resources:

John’s Full Bio

Global Guerrillas Report

Brave New War Book

Covid-19 Sensemaking

Mitigating Risks To America’s Cognitive Infrastructure

10 Red Teaming Lessons Learned Over 20 Years

The Five Modes of HACKthink

Other recent OODAcast thematic posts 

Chet Richards and the Origin Story of The OODA Loop (Part 1 of 2)

Chet Richards on Applying OODA Loops in Business (Part 2 of 2)

Dan Gerstein and Lance Mortlock on Technology Futures and Scenario Planning

Ellen McCarthy and Kathy and Randy Pherson on Intelligent Leadership and Critical Thinking

Richer and Becker on Domestic Terrorism, Cyber, China, Iran, Russia, and Decision-Making

Omand and Medina on Disinformation, Cognitive Bias, Cognitive Traps and Decision-making

Clapper and Ashley on Joint Ops/Intel Operations, Decision-making, the History and Future of Intelligence and Cyber Threats

OODAcast 9/11 Perspectives 

Decision-Making Inside the CIA Counterterrorism Center Before, During, and After 9/11

A CIA Officer and Delta Force Operator Share Perspectives on 9/11