ArchiveOODA Original

Nate Fick on His Early Career, Writing ‘One Bullet Away’, The Stoics and Dynamic Leadership (Part 1 of 2)

In March 2021, Matt Devost had an OODAcast conversation with Nate Fick, whose career has been eclectic with a throughline of demonstrating superior leadership abilities in a diverse array of successful opportunities. Nate is currently a General Manager at Elastic, having joined the firm with their acquisition of Endgame where he served as CEO. After graduating from Dartmouth, Nate took the unconventional path of joining the military and serving as a USMC officer, leading some of the first U.S. troop deployments into Afghanistan and Iraq after the September 11th terrorist attacks.

His service in the military is chronicled in his New York Times best-selling book, One Bullet Away. The book was also a Washington Post “Best Book of the Year,” and one of the Military Times’ “Best Military Books of the Decade.”  Nate also served as the head of the esteemed national security-focused non-profit think tank, the Center for a New American Security, and has had a ten-year tenure as an operating partner at Bessemer Venture Partners.

We continue our effort to underscore certain patterns and themes found throughout the OODAcast library of over 90 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.

In Part I of this conversation, Matt and Nate discuss lessons learned from leading a non-profit, writing One Bullet Away, Stoicism, and dynamic leadership.

“…servant leadership…focus on mission, vision, values, culture…and…focus on communicating and over-communicating…those are the sort of tenants that I think I will bring to any leadership experience I have from this point forward.”

Matthew Devost: You’ve had a fascinating career, transitioning from the military to a think tank to venture capital to working in cybersecurity and tech in general. Can you step us through your career and how it progressed over time?

Nate Fick: Yeah, I am happy to, with the caveat right up front that the great lesson for me is these things only make sense in hindsight. Looking forward, it has always been very hard to foresee the next step from any point along the line. You look backward and think, okay, that kind of makes sense. But I came out of college in the late nineties. I had gone to Dartmouth and most of my classmates, something I observed in college, and this is probably true of many people, people come in with a thousand interests and seem to get funneled into just a few narrow paths coming out. I was not at the point where I wanted to go to law school or med school or be an investment banker or be a management consultant.

And I wanted to do something different. I like team sports. I like the outdoors. I had this sort of public service impulse. And so, I ended up joining the Marines. It was pre-9/11 peacetime. I spent a couple of years as an infantry officer in the peacetime Marine Corps and then 9/11 happened and by virtue of timing and circumstance I took one of the first American units into Afghanistan in the fall of ‘01 and then into Iraq in the spring of ‘03 and I learned a lot about leadership, high stakes, high-pressure environments in my early twenties in the Marines. And I, I really liked the military because of the real responsibility that it puts on the shoulders of young people.

I freely admit I am one of the lucky ones who came out of it physically and psychologically intact – more or less. The great leadership lesson that I took, from my combat service in the Marines was the opportunity to work for some terrific leaders and to watch them kind of in these very high-pressure, high-stakes environments. And I pulled one of my bosses aside once, and I said, “Hey, sir, like we would follow you through the gates of Hell. What is it that you’re doing that’s inspiring this kind of followership in us.” And he sorts of dismissed the question. But he followed up with me later and he said, “I do not really have a leadership philosophy, but if I had to boil it down, it is this: Officers eat last.”

And it was this idea – that with rank comes responsibility, not a privilege. He was the kind of leader who would sleep less, who would carry more weight, who would expose himself to more danger. And he just did it kind of naturally. And I think we all instinctively recognized it. So, I left the Marines as a Captain, I realized that it was not how I wanted to spend my, the rest of my professional life. If I had three or four lives, I would love to spend one of them as a military officer. I wanted to take that experience of building and leading teams and try to do it in a civilian context.

I went to business school to sort of tread water and figure out how to apply that experience to a different context and ended up again, in a way that you cannot plan, running a nonprofit, the Center for New American Security. Michele Flournoy had started it. She went into the government as the Under Secretary of Defense for policy and asked if I would run the place. And I had not gone to business school to run a nonprofit like that. that was not in the cards for me, but I loved the mission. I love the team. It was a chance to lead something and shape culture from the beginning. And my business school classmates, candidly, looked down their noses at non-profit leadership and management. In hindsight, after having a decade of high-growth tech and larger company experience, I realized that non-profits are a great leadership training ground because you do not have money and stock options to throw at people to persuade them.

It really all comes down to mission, vision, values, culture. And so that ended up again, being a formative and valuable leadership experience. I at the same time was an operating partner at Bessemer Venture Partners. I have been an end-user of a lot of security technology as a Marine. Bessemer was building an investment thesis in security. I got to know some of the team there, really liked them, liked the firm and so I spent almost a decade at Bessemer and ended up as the second CEO at Endgame. A company that had raised a Series A, was going through a leadership transition. And so, I showed up on day one in the software business with military experience and an MBA and some non-profit experience, but otherwise kind of a fish out of water.

And what I realized is I think that the core tenants of leadership across all these different contexts are similar. And the big one at Endgame for me was a CEO really is Chief Explaining Officer. Something I have realized, as companies grow especially during that high growth period where you are changing so much that it is a different business almost on an annual basis. The job of the CEO is to build context and build a shared understanding of what is going on. And that requires saying things until you are blue in the face and then saying them again. So, if I look back on it, just to summarize, I think that notion of servant leadership in the Marines, and then the focus on mission, vision, values, culture from the nonprofit world, and the focus on communicating and over-communicating in a startup environment, those are the sort of tenants that I think I will bring to any leadership experience I have from this point forward.

“I had a bunch of journals. I had a bunch of pictures. I had recent searing memories. So, I just sat down and started writing.”

Devost: Excellent. Along the way, you wrote a book, One Bullet Away, which my copy is pretty beat up because both myself and my daughter have read it and highlighted it. So, it’s got the dual format, she highlights a lot prettier than I do with squiggly lines, et cetera. But what was the catalyst for writing the book and what did you hope that folks would get out of it reading it?

Fick: Again, these things seem linear only in hindsight, but I had never written anything longer than a college term paper. And I got out of the Marines in 2004 early in the campaigns after September 11th. I had done my two combat tours and I was getting rotated out to a desk job for a while. And that was not what I wanted to do in the Marines. So, it was time for me to get out. I was in a unit at that time, a reconnaissance unit where we could pick our own replacements, it was sort of a tap system. And the guy I picked to take over for me and take my Marines back to Iraq on another tour was a great infantry officer named Brent Morel.

And Brent was killed in April of 2004 in Fallujah literally doing my job and it affected me deeply because I had essentially put him in the role and I felt like, at that point, we heard from journalists, and we heard from generals and we heard from politicians, but we had not heard a lot from the people who were on the ground. And I thought, maybe I’ll publish it, maybe I won’t. I will stick it in a desk drawer and show it to my kids someday. But that was the genesis of the book.

“I think that a more natural expression of my personality was more in the entrepreneurial ecosystem.”

Devost:  So just to capture a couple of things, one interesting highlight that I’ve found was my daughter’s, I mentioned we both read your book back several years ago, where you talk about being at the risk of dismissal for failure to adapt.  Can you step us through the process of how you learn to adapt because your career, as you described it, subsequently there’s been a lot of adaption to be successful? So, I’d love to get your thoughts on that.

Fick: Yeah. It’s funny. I, I was kind of an unlikely, in some ways, member of the military, or at least I thought I was, and people have this notion of the military is like goose-stepping automatons. my experience was there was a lot of room for free-thinking and innovation and problem solving and creativity. But that all comes later rather than early on, there’s a focus on conformity and like getting you to be a part of this unit and part of this organization. And it was a hard adjustment for me. I mean, you come off, a late 20th-century college campus and you get your head shaved and suddenly you’re a number. But that is an important part, I think, of the psychological transition.

But I, I had a tough time adapting to that. And, even now over the bar at our home, I have a framed letter of reprimand that I received from a boss who pointed out that maybe I had issues with authority. So, there were aspects of military life that were challenging. But fundamentally I made my closest friends in uniform and I am profoundly grateful to have done it, but I think that a more natural expression of my personality was more in the entrepreneurial ecosystem.

“…something I had in my rucksack the whole time I was deployed in the Marines was a copy of the Meditations of Marcus Aurelius:  the good days are never as good as they seem, the bad days are never as bad as they seem. And there’s a real value in consistency. And being level-headed come what may.”

Devost: It seems also in reading the book, and you can correct me if I’m wrong, that you kind of adopted a little bit of a stoic perspective as well, kind of living in the moment and taking advantage of the moment. Is that a fair characterization or a misreading?

Fick: It’s an astute characterization. No one has made that observation to me explicitly before and I don’t mention this in the book, but something I had in my rucksack the whole time I was deployed in the Marines was a copy of the Meditations of Marcus Aurelius. I think that’s as good a guide to living in combat in the military as any.  Just having a deep sense of kind of peace and equanimity with where you are, because you’re literally facing death every day and even worse. You’re ordering people, exposing people to their deaths every day, and that can be psychologically incredibly corrosive. And you have got to find a way to reconcile yourself to doing that and trying to do it well and trying to do it with a moral sense and a sense of purpose and honesty and transparency. And it’s hard. But in the truest sense I guess there’s nothing new under the sun and the Stoics, the Stoics were there 2000 years ago. So that was very much something that mattered to me. I love that you picked up on it. Thank you.

Devost: Great. Yeah. I always like to think I am a thoughtful reader, so I am happy to kind of pick up on that transition. Do you feel like that kind of guides your life now as an entrepreneur and executive in a technology company?

Fick: I think it is something to aspire to. I’m wildly imperfect at it, but I think every entrepreneur can identify with the emotional ups and downs, right? I mean, it is such a roller coaster. one day you think I’m on building the most important business in the history of my industry and the next day you think I’m on the brink of ruin and embarrassment. You can toggle between these things so quickly. And I think that whether in a military unit in combat or whether you’re in the early stages of building a company, I think as a leader you feel a profound sense of responsibility for the people, all these people who have thrown their lot in with you, all these people who are relying on your judgment and your decisions and their reputations and their livelihoods and their ego. All these things are at stake.

And I think that one of the journeys that, I will not say I went through cause I think I’m still going through it, but I’m a lot farther along than I was before, is taking those ups and downs and like compressing the amplitude, try to be a little bit steadier, a little bit more even and just tell yourself: the good days are never as good as they seem, the bad days are never as bad as they seem. And there’s a real value in consistency. And being level-headed come what may.

You never once said, ‘come work for me. You said, come work with me.’

Devost:  A question from a leadership perspective: what one piece of advice you would give to somebody that is early in their journey on becoming a leader in any of the domains that you have worked in. And I always liked the ones that are backed by some sort of operational experience or something that happened to you. So, is there a short story that you can share that led to a leadership lesson learned for the audience?

Fick: Yeah. Definitely. The pearl for me is the lesson that officers eat last, get in the back of the line, not the front of the line. And that drove home for me the importance, particularly early in your career, of looking at every job interview is a two-way street. You are hiring your boss just as surely as your boss is hiring you. And the people who I can credit with whatever semblance of success and gratification I’ve had in these last 20 years of professional life; it is because I’ve worked for great people. I had a wonderful boss in the Marines who taught me so much. I had a Board Chair, Richard Danzig at CNAS, who taught me so much. A Board Chair, Chris Darby at Endgame who taught me so much, and now at CEO of Elastic and Shay Banon, who is, I hesitate to say a natural because I know how much work goes into making it look natural. But people who make good ethically based decisions and communicate well.

So, I think hiring your boss – and do not be shy about it when you’re 21 years old, or you are 22 years old and you’re sitting there, and you really want the job. It can be so tempting to compromise and say, oh, I got the title. It’s got the comp, I’m not sure about the person I will be working for, but we will figure that out. I would say optimize for who you’re working for and who you will be working with, and that the title, the comp, all that stuff will come later.

Devost:  It’s interesting. I think it’s also the turn map perspective:  it is important for the bosses to realize, right? That is the importance of them being interviewed. I always like to share a story about someone I was trying to pursue to come and join the Terrorism Research Center team. And we had lunch together with somebody that I knew from past work. And she turned the job down, she had turned the offer down. And then a couple of weeks later, she called me up and said, “Hey, I’ve decided to take the job.” And she said, “There’s something that stuck with me about all the conversations that we had. You never once said, ‘come work for me. You said, come work with me.’ And that always resonated for me, that as part of that interview process, you’re building a team, and in a perfect world, you’re building a team of leaders because, as the organization grows you must have people that step into that leadership potential and run different projects, et cetera. So that is important too. 

Fick: Absolutely.  

Additional Reading:

Nate’s book One Bullet Away

Meditations by Marcus Aurelius

Turning the Map in Cyber

Elastic Security

ElasticON Public Sector 13 April

The original OODAcast

OODAcast:  Nate Fick on Dynamic Leadership and Adapting to Change

Other recent OODAcast thematic posts 

John Robb on Hyper-networked Tribes, Digital Sovereignty, Digital Identity, Digital Rights and “The Long Night” (2 of 2)

John Robb on the Early Internet, Frameworks to Drive Decision Making, Network Tribalism and Emerging Threats (1 of 2)

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

Related Reading:

Black Swans and Gray Rhinos

Now more than ever, organizations need to apply rigorous thought to business risks and opportunities. In doing so it is useful to understand the concepts embodied in the terms Black Swan and Gray Rhino. See: Potential Future Opportunities, Risks and Mitigation Strategies in the Age of Continuous Crisis

Cybersecurity Sensemaking: Strategic intelligence to inform your decisionmaking

The OODA leadership and analysts have decades of experience in understanding and mitigating cybersecurity threats and apply this real-world practitioner knowledge in our research and reporting. This page on the site is a repository of the best of our actionable research as well as a news stream of our daily reporting on cybersecurity threats and mitigation measures. See: Cybersecurity Sensemaking

Corporate Sensemaking: Establishing an Intelligent Enterprise

OODA’s leadership and analysts have decades of direct experience helping organizations improve their ability to make sense of their current environment and assess the best courses of action for success going forward. This includes helping establish competitive intelligence and corporate intelligence capabilities. Our special series on the Intelligent Enterprise highlights research and reports that can accelerate any organization along its journey to optimized intelligence. See: Corporate Sensemaking

Artificial Intelligence Sensemaking: Take advantage of this megatrend for competitive advantage

This page serves as a dynamic resource for OODA Network members looking for Artificial Intelligence information to drive their decision-making process. This includes a special guide for executives seeking to make the most of AI in their enterprise. See: Artificial Intelligence Sensemaking

COVID-19 Sensemaking: What is next for businesses and governments

From the very beginning of the pandemic, we have focused on research on what may come next and what to do about it today. This section of the site captures the best of our reporting plus daily intelligence as well as pointers to reputable information from other sites. See OODA COVID-19 Sensemaking Page.

Space Sensemaking: What does your business need to know now

A dynamic resource for OODA Network members looking for insights into the current and future developments in Space, including a special executive’s guide to space. See: Space Sensemaking

Quantum Computing Sensemaking

OODA is one of the few independent research sources with experience in due diligence on quantum computing and quantum security companies and capabilities. Our practitioner’s lens on insights ensures our research is grounded in reality. See Quantum Computing Sensemaking.

The OODAcast Video and Podcast Series

In 2020, we launched the OODAcast video and podcast series designed to provide you with insightful analysis and intelligence to inform your decision-making process. We do this through a series of expert interviews and topical videos highlighting global technologies such as cybersecurity, AI, quantum computing along with discussions on global risk and opportunity issues. See: The OODAcast

Daniel Pereira

Daniel Pereira

Daniel Pereira is research director at OODA. He is a foresight strategist, creative technologist, and an information communication technology (ICT) and digital media researcher with 20+ years of experience directing public/private partnerships and strategic innovation initiatives.