Human Intelligence

What A VC Learned from Interviewing with the CIA

My notebook after I received a mysterious call…

“The poet is of no party. Otherwise, he would be a mere mortal.” — Charles Baudelaire

I interviewed to become a spy with the CIA in the fall of 2006. It started with a phone call. After a short greeting, I remember a disembodied yet firm voice saying, “Michael, we came across your application for the role of political analyst, but we were wondering if you might instead be interested in the clandestine service.”

I can’t exactly recall what I mumbled right then, partly because I was surprised, but mainly because I had never thought of becoming a spy. For all sorts of reasons. But how many times in your life is someone going to call you and ask? So I had to see how deep this rabbit hole could go. I took a dive, “Yes, I would.”

“Great, let’s schedule a preliminary phone call interview for next week.”

During the following week, I had no idea what to expect, let alone no clue how to prepare, so I did nothing. It’s not like a McKinsey interview where you can practice in advance by bullshitting case studies and tumbling through mental math on how many ping pong balls can fit into a 747.

At the time I was renting an attic apartment in a family’s colonial home off Brattle Street — ”Tory Row” — in Cambridge, Massachusetts. Technology Review, MIT’s magazine, had hired me as a writer. I covered everything from quantum computing to ultrasonic backscattering for brewing a better beer. I had dropped out of Oxford University, where I was working towards a doctorate in philosophy. This is not how Casino Royale is supposed to begin. I didn’t own a suit and I couldn’t even pick out an expensive watch.

I took the call in the family’s living room amid a rubble of children’s toys. It was one of those late October afternoons when you notice the days are getting shorter. Reception was bad in the colonial attic and I was afraid the call from this unknown, untraceable number would cut out. On the other hand, being in the living room had its dangers, too. Mom and the kids could walk in.

Short greetings again but a different bureaucratic voice. “I’m going to go through a series of questions and do your best to answer them. Ok? So…” — and recall this was 2006 — ”What are the main motivations and grievances driving sectarian conflict in Iraq between the Sunni, Shi’a, Yazidis, Assyrians, Kurds and Iraqi Turkmen?”

Yazidis? I pace when I have serious conversations on the phone. Hurdling scattered toys, I said, with great weight and authority, drawing on the works of Plato, Nietzsche, and Kant, “Ummmm…”

I did my best to repeat the general analysis I had gleaned scanning the New York Times daily. I probably sounded like the slouch in class who hadn’t done the reading, but raised his hand anyway to get credit for attendance.

He cut me off. “What is intelligence? What kind of information does the CIA want? Just any? Is it the kind that you can Google?”

“Ummm, well of course not,” I offered. “It’s the kind that someone else doesn’t want you to have.”

“Sometimes. But not always. It’s information that is of critical interest to the United States, for its national security, for its foreign policy. That may be the plans and intentions of high-level foreign government officials. But it may be time-sensitive information that these officials don’t even realize is of importance.”

I tripped on a stuffed penguin. “I see.”

He then went on to explain to me the two main entry-level roles in the clandestine service, and that spies typically worked in pairs, one of each role together. On the one hand, there is the “operations officer”, who is more like what you’d think of when you imagine a spy. Undercover abroad, they work to turn non-US citizens who have access to foreign intelligence into sources. This involves building relationships — and also cajoling, persuading, and manipulating — so you can imagine the kind of person who is good at this is the kind of person who can size someone up, build rapport, and make friends quickly. If you’ve met me, you know that someone is not me. They also practice what is known as “tradecraft,” which refers to the bug plants, the dead drops, street surveillance, the secret meetings in safe houses, and so on. Maybe I could do that. I left a key under a rock outside a friend’s house once.

The other role is called a “collection management officer.” If the operation officer collects the jigsaw pieces, the collection management officer is supposed to anticipate how they will fit together, what picture they will form, even though he doesn’t have the puzzle box. With a view to looming trends, this person places the information collected into the wider context of events, backed by research and regional expertise. Together these two solve the puzzle.

“So what role would you prefer to apply for?”

I don’t know how I passed this round of the recruiting process, but I did. I told him I’d probably be better suited to the collection management role, only because it felt more academic to me.

I did not, however, make it past the next round. That included an IQ test, a personality test, a statement of values, a set of essay questions, and a list of the books I was supposed to use as sources. I still have the booklist. Some of the titles, many quite good and largely critical of the CIA’s activities and failures: Steve Coll’s Ghost Wars, a meticulous history of the Taliban and the rise of Osama Bin Laden in the 1990s; the impassioned Imperial Hubris by Michael Scheuer, the former head of the Osama Bin Laden unit at the CIA’s counterterrorism center; strangely, I thought, a spy novel — Agents of Innocence by David Ignatius.

I had to print out my essays and send them to an address in Virginia that disappeared a week afterward. One of my favorite details comes from the personality test. “On a scale of one to five, with one being ‘strongly disagree’ and five being ‘strongly agree,’ this statement is true: When I walk down the street, I feel an aura of power around me.”

What the hell were they tracking for?

I’ll never know why they passed on hiring me; maybe it’s because I didn’t have an aura of power. But ever since I have reflected on the nature of intelligence gathering and the methods that were described to me.

Venture capital has its own information gathering process. You can’t search for it on Google or read it on Twitter. We are trying to obtain time-sensitive information on teams and technologies that no one else seems to think important. The future is present, but invisible on the surface. We have to gather it from a place unseen, where no one is looking.

Like the CIA, 1517 works in pairs. People have called us Mulder and Scully from X-Files. (For some reason they think I’m Scully — the rational skeptic — and Danielle Mulder, enthusiast of the paranormal and mysterious. The truth is the opposite!)

I’m skeptical of investors who work alone. People ask us if we follow technological trends, but we really build jigsaw puzzles using both our strengths, traveling to distant places. Danielle builds relationships and trust just about better than anyone I have ever met. She’s a gravity well for great people and sources of expertise. And she has a keen emotional intelligence that gives her a sound judgment when it comes to assessing character and why people do things. Not to mention she executes more in a second than most in a minute.

I am more of a collection officer. A background of reading, talking to experts, and general curiosity help me bring order to the pieces we come into contact with. The most exciting people we meet are the ones who point the way to the picture forming of a future to come. I don’t have the puzzle box to guide us to the solution. We meet founders and they bring us to the edge of our understanding. What we learn there is not something you’d ever read in a headline. If you did, it’d already be too late.

What is intelligence? “φύσις κρύπτεσθαι φιλεῖ,” Heraclitus says. “Nature loves to hide her secrets.” You can read the CIA’s definition here.

— Michael Gibson