Applying Military Tactics to Investing

My days are a blur of pitch decks, term sheets, and coffee. I’m a tech entrepreneur. I’m a technology investor. My world is defined by TAMs, CACs, and LTVs. It is, by any definition, a very modern life.

But my operating system isn’t.

My core professional framework wasn’t minted in a Silicon Valley incubator or an Ivy League business school. I didn’t get it from a guru.

It was made in Newport, Rhode Island. In the 1990s. In the back of a brightly lit, windowless classroom at the Naval War College. I got it from Dad.

Dad was a professor there for over a decade.

Before that, he was in the U.S. Navy for 20-years. He retired as a Commander.

He was a serious man. He dealt in strategy, history, and geopolitics.

When I was ten years old, I’d sometimes have dinner with him at the college. “Dinner” was a 20-piece Chicken McNuggets and a Coke. I’d sit in the back row of his night class for officers (or maybe it was aspiring officers, I was a kid I can’t recall) but I will never forget smelling the faint aroma of my nuggets, the stale coffee and old carpet as I pretended to do my math homework.

I wasn’t doing my homework.

I was listening.

I was listening to men with short haircuts debate things like “centers of gravity”. They were playing war games. They were planning campaigns. They were analyzing the “threat doctrine” of other nations.

I had no idea, of course, that I was getting a free MBA in strategic planning.

It’s no surprise that these concepts are now hardwired into how I see the world. When I listen to a founder pitch their startup, I’m not just listening to their story. I’m running a military-grade analysis.

The language of startups and venture capital feels new. But the logic is ancient.

Here are three concepts I absorbed in that classroom. They sounded like rejected G.I. Joe codenames. They are, in fact, the three pillars of how I build companies and invest in them.

IPB (Intelligence Preparation of the Battlefield)

In the military, you don’t just run over a hill and see what happens.

That’s how you get ambushed.

You first perform IPB. Intelligence Preparation of the Battlefield.

It’s a formal, four-step process for understanding everything about the environment you’re about to enter. It’s systematic. It’s continuous. It’s not a “one-and-done” report. It’s a living assessment.

The four steps are:

1. Define the Operational Environment

2. Describe the Battlefield’s Effects

3. Evaluate the Threat

4. Determine Threat Courses of Action

This isn’t just a “know your enemy” maxim. It’s a rigorous framework for deconstructing reality.

And it’s exactly what a founder or an investor must do.

Step 1: Define the Operational Environment

In the Navy, this is literal.

“What is our Area of Operations? What’s the Area of Interest?” They draw lines on a map. They define the physical, political, and informational boundaries of the mission. They analyze the civilian population, the media, the infrastructure.

In business, this is your market.

When a founder says their Total Addressable Market is “everyone with a smartphone,” they have failed Step 1. They haven’t defined their operational environment.

They’ve just pointed at the globe. Can’t plan a war like that.

A proper IPB defines the Serviceable Available Market (SAM). Who, specifically, are you targeting? Where do they live? Not just geographically. What platforms do they use? What informational “terrain” do they occupy? Are they on TikTok? Are they on LinkedIn? Are they in a specific subreddit?

You must also define the “civil considerations.” In military ops, this means understanding local customs and power structures. In business, this is regulation. It’s public sentiment. It’s the cultural environment.

Are you launching a FinTech app? The regulatory environment is your operational environment. Are you launching a social media app for kids? The “civil consideration” is a legion of angry parents and a skeptical Congress.

If you don’t define your battlefield, you can’t possibly win on it.

Step 2: Describe the Battlefield’s Effects

This is where the analysis gets granular.

Military planners break this into “Terrain” and “Weather.”

“Terrain” isn’t just about hills and valleys. It’s about effects. A hill isn’t a hill. It’s “an observation post.” A river isn’t a river. It’s “an obstacle to ground movement.” A dense forest is “cover and concealment.”

In business, “Terrain” is your market structure.

A market with high regulatory hurdles is “channelizing terrain.” It forces all new entrants down a single, narrow, expensive path.

A market with strong network effects is “high ground.” The incumbent who has it can see everyone else coming and has a massive defensive advantage.

A market with high customer acquisition costs (CAC) is a “swamp.” It looks easy to enter, but it will suck your marketing budget dry and slow your advance to a halt.

“Weather” is the other half of the equation. In the military, it’s simple. Rain grounds the helicopters. Fog provides concealment.

In business, the “Weather” is the macroeconomic climate.

For the last decade, we had “sunny skies and zero wind.” Capital was free thanks to ZIRP policy. It was a perfect day for flying. You could launch any crazy idea, and a VC would fund it.

Today, the “weather” has changed. We are in a high-interest-rate storm. The wind is a 50-knot headwind. Capital is expensive. Visibility is low.

A good founder, like a good commander, doesn’t complain about the weather. They use it. They built their company to be “all-weather.” They know that a storm grounds their competitor’s expensive, cash-burning “helicopters,” while their own lean, efficient “ground troops” can keep moving.

Step 3: Evaluate the Threat

This is competitor analysis. But not the kind you see on a pitch deck.

I’m talking about the slide with four logos on it, where the founder puts checkmarks next to their own name and ‘X’s next to everyone else. That’s not analysis. That’s a marketing graphic.

A real “threat evaluation” is a deep, doctrinal analysis.

In the military, you build “threat templates.” You don’t just list the enemy’s tanks. You figure out how they think. What is their doctrine? How are they organized? What are their preferred tactics? What are their capabilities, and just as importantly, their limitations? What do they value? What is their “High-Value Target” (HVT)?

When I look at a market, I’m doing the same thing.

Don’t just tell me Google is a competitor. Evaluate the threat.

What is Google’s “doctrine”? They are a mass-market, data-driven, advertising-based organization. Their “limitation” is that they are terrible at high-touch customer service. They are slow. They are politically constrained.

A startup’s doctrine might be speed and niche focus. That’s an “asymmetric” advantage.

You have to identify your competitor’s “High-Value Targets.” For a big incumbent, their HVT might be their stock price, their brand reputation, or their relationship with a key distributor.

A smart startup can attack those HVTs without the incumbent even knowing they’re in a fight.

Step 4: Determine Threat Courses of Action

This is the capstone of IPB.

You take the first three steps and you wargame the future. You don’t just guess what the enemy will do. You create a list of their most likely and most dangerous COAs.

“COA 1 (Most Likely): They will ignore us.”

“COA 2 (Most Dangerous): They will copy our core feature and use their distribution to crush us.”

“COA 3: They will try to acquire us.”

When I was ten, I was running my own rudimentary IPB on my brother. His “most likely COA” was to just ask for my fries. His “most dangerous COA” was to create a diversion and steal them while I was looking away. I planned accordingly.

When I invest, I ask founders this question directly: “Walk me through your top competitor’s Most Likely and Most Dangerous COA when you launch.”

A founder who has done their IPB will have an answer.

“Our incumbent’s Most Likely COA is to dismiss us as a toy. Their Most Dangerous COA is to launch a ‘good enough’ version for free. Here is our plan for both.”

A founder who hasn’t will say, “We’re moving too fast for them to notice.”

That’s not an answer. That’s a hope. And hope is not a strategy.

IPB is the strategy.

It’s the single most important analytical tool I have.

If you remember nothing else from this piece, remember IPB.

But you can get MUCH more lethal than that!

2. F3EAD

If IPB is the strategic planning process, F3EAD is the operational tempo.

This is the “Get Stuff Done” loop. It stands for Find, Fix, Finish, Exploit, Analyze, Disseminate.

F3EAD is a targeting cycle used by Special Operations Forces. It’s designed to be fast, relentless, and iterative. It’s how you go from “we think there’s a bad guy somewhere” to dismantling an entire network.

It is the Agile methodology for not getting killed as you take out the baddies.

It’s the startup growth loop. It’s just a cooler acronym.

Here’s the cycle.

Find: Identify a target. This could be a person, a piece of infrastructure, or a network vulnerability. It’s the “start point” for intelligence collection.

Fix: Lock onto the target. This isn’t just finding them once. It’s developing a “pattern of life.” You use multiple intelligence sources (signals, human, imagery) to triangulate their position in time and space until you can act.

Finish: Execute the operation. This is the action. A raid. A capture. A strike. The target is neutralized.

This is where most bad teams stop. They celebrate the “Win”. As if victory is a permanent state.

But the SOF teams my dad talked about knew the mission wasn’t over. It had just begun.

Exploit: This is the most important step in the entire cycle.

After the “Finish,” you “exploit” the site. You grab the laptops. You grab the cell phones. You grab the pocket litter. You collect every piece of data you can. This is where the real value is.

Analyze: The collected data (the “exploit”) is immediately analyzed. You’re not looking for history. You’re looking for the next target. The data on that laptop doesn’t just confirm what you knew. It points you to three new people you didn’t know about.

Disseminate: The new intelligence is immediately “disseminated” to all relevant units. This new intelligence feeds a new “Find” phase.

The cycle starts over. But now it’s faster. And smarter.

This is how modern startups must operate. In loops, moving ever faster.

Find: “Find” a user problem. “Find” a market inefficiency. “Find” a high-value customer segment. This is your customer discovery.

Fix: “Fix” that user’s “pattern of life.” This is your user persona. Your user journey map. You use multiple data sources (analytics, user interviews, heatmaps) to “fix” their location. Where do they click? Where do they drop off? You understand their behavior so well you can predict it.

Finish: “Finish” the problem. Ship the feature. Launch the marketing campaign. Close the sale. This is the “action.” You push the code.

Now, most startups stop here. They “finish” the feature. They mark the ticket “Done” in Jira. They go to the virtual launch party. They move on to the next thing on the roadmap.

They have completely failed. They forgot the most important part.

Exploit: “Exploit” the action. Collect the data.

You shipped the feature. Now, what happened? What’s the A/B test result? What does the analytics data say? What is the user feedback? You must exploit the result of your “finish” action.

The data you get back is the TRUTH that tells you what’s really going on.

Analyze: “Analyze” that data. Don’t just admire it. Don’t just put it in a dashboard. Analyze it.

“We thought this feature would increase conversion. It didn’t. But the analysis shows 60% of people who used it also tried to click this other area. They’re telling us what they want.”

This analysis doesn’t produce a report. It produces the next target.

Disseminate: “Disseminate” this finding. Share it with the whole team. The product team’s analysis is disseminated to marketing. Marketing’s “exploit” from their ad campaign is disseminated to sales.

This shared intelligence feeds the next “Find” cycle.

“Okay, based on that analysis, we’ve ‘found’ a new, more urgent problem. Let’s ‘fix’ the user persona for it. Let’s ‘finish’ it with a new sprint. Let’s ‘exploit’ the data...”

This is the tempo of a high-growth company.

As an investor, I don’t fund “Finish, Finish, Finish” teams.

I fund “Finish, Exploit, Analyze” teams. I fund teams that are addicted to this loop. They run it every week. Not every quarter.

The F3EAD cycle is relentless. And it always wins.

Spin it up in your life and in your orgs.

Now let’s get to the last one. And it’s the one that separates the amateurs from the professionals.

3. Branches & Sequels

In my dad’s world, no commander ever presents just one plan.

That’s malpractice.

A plan is not a linear script. It’s a decision tree. That tree is built from two components: Branches and Sequels.

Branches are contingency plans. They are the “what if” scenarios.

A “branch” is an option built into the main plan. It’s not “Plan B” that you invent when everything goes wrong. It’s a pre-planned, pre-rehearsed, pre-resourced alternative action that is triggered by a specific event.

Military example: “Our main plan is to assault the bridge. If we hit the ‘trigger’—say, resistance is heavier than expected then we will execute Branch Plan Alpha, which is to bypass the bridge and use the northern route. The second element will already be in position to support this. Our QRF is able to respond across all paths.”

Sequels are the “what’s next” scenarios.

A “sequel” is the operation that follows the current one. And you must plan for all possible outcomes of the current operation: victory, defeat, or stalemate.

Military example: “The ‘sequel’ for victory is to establish a defensive perimeter and prepare for a counter-attack. The ‘sequel’ for defeat is to fall back to Rally Point Charlie, consolidate, and await air support.”

You plan all of this before you even leave the wire.

Now, think about the average start-up pitch.

The average pitch is a single, beautiful, linear-to-the-moon plan:

“We will do this. Then we will do this. Then we will be billionaires.”

This is not a plan. This is a fantasy novel.

A professional entrepreneur, like a professional commander, plans in Branches and Sequels.

As an entrepreneur, my plan is full of Branches.

“Our main plan is a direct-to-consumer, paid-acquisition model. Branch Plan Alpha, which is already mapped out, is a B2B channel-partnership model. The ‘trigger’ to execute Branch Alpha is when our blended CAC exceeds $100 for two consecutive months. When that trigger is hit, we don’t have a ‘come to Jesus’ meeting. We execute the branch.”

As an investor, I am listening for this. This is forward-looking and grounded in reality.

I will ask a founder: “What is the external, observable ‘trigger’ that would make you abandon your current go-to-market strategy? And what is the pre-planned alternative strategy you will execute when that trigger is hit?”

A blank stare is a $250k ‘no.’

A quick, confident answer: ”Ah, you mean our ‘Branch’ for a failed enterprise sales cycle? If our sales cycle for that segment exceeds nine months, we trigger our ‘Freemium Branch’ aimed at product-led growth. We’ve already got the wireframes for it.” tells me I’m sitting across from a professional.

And then, there are Sequels.

“What’s next?”

A founder will pitch me their “objective,” which is usually “Raise a Series A.”

I ask, “What is the ‘sequel’?”

The sequel for victory (raising the round) can’t be “hire a bunch of people and hope.” It has to be a detailed “Phase 2” plan. “The sequel to our successful raise is our European expansion. We’ve already identified the first three markets, analyzed the regulatory ‘terrain’ (IPB), and have a short-list of Country Managers.”

More importantly, what is the ‘sequel’ for defeat?

This isn’t pessimism. It’s professionalism.

“If we fail to raise our Series A after a 6-month campaign, our ‘sequel’ for that stalemate is Plan R. ‘R’ for ‘Runway.’ We will cut our burn by 40% using this pre-planned budget. We will re-orient the company around a single, profitable customer segment. And we will drive to break-even.”

That is a founder who is in control of the situation, even in failure. They are not a victim of circumstance. They are an executor of a plan.

Living in New York is a daily exercise in Branches and Sequels.

My “main plan” is to take the L train. The “trigger” is the sound of a garbled “sick passenger” announcement. That immediately triggers Branch Alpha (the M14 bus). If the bus is also delayed (a new “trigger”), I execute Branch Bravo (a $35 Uber that I will complain about).

My Sequel to finally arriving home, victorious, is ordering from the good taco place. It’s all pre-planned.

Amateurs are surprised by reality. Professionals have already planned for it. They have built frameworks to address it.

But here’s the thing about frameworks.

Most people treat them like a buffet.

They pick one. They use it. They get really good at “Agile” or “OKRs” or whatever the airport business book of the month is.

They never connect them.

The military concepts my dad taught aren’t a checklist. They’re not three separate ideas.

They are a system. An operating system.

One is the strategy. One is the operation. One is the failsafe.

Using just one is like having a map, but no car. Or a car, but no map. Or a car and a map, but no plan for what to do when you hit a roadblock.

You need all three. This is how they lock together.