As a startup, you’re an insurgent. Innovation, like revolution, is about replacement. You’re upending the status quo and disrupting incumbents because it’s the only way forward. You have a better solution. But the odds are against you.
As a founder, you’re facing an occupying power with more resources than you. Even if you’ve discovered a “blue ocean” or have a positive-sum offer, you’re up against switching costs, behavioral inertia, and trust issues. You’re up against Goliath.
Fortunately, there’s a playbook for that.
This is Phase 1 of Go-to-Market as Unconventional Warfare. Unconventional Warfare (UW) is about supporting a resistance movement or insurgency to win against an occupying power. Last week I published the setup—Phase 0. Now we’ll get the ball rolling with Phase 1: Preparation.
You need to understand the arena before you get into it. Doctrinally, this would be intelligence preparation of the battlefield.
To gather that foundational intelligence, you need to study the population, the adversary, and the resistance. Study the conditions, the area, the people, and who holds power. Study potential supporters, strengths, weaknesses, agendas, and relationships.
For your startup, preparation is about deep customer research, competitive analysis, and identifying your asymmetric advantage. You need to understand if the landscape is setting you up for success or failure. Richard Rumelt calls this diagnosis “an explanation of the nature of the challenge,” where a good one identifies “certain aspects of the situation as being the critical ones.” Understanding these things helps you determine what you’re going to focus on.
Jake Knapp and John Zeratsky use these questions to open their Foundation Sprint:
“Who, precisely, is your customer?”
“What problem are you solving for them?”
“What’s your advantage?”
“Who or what are you up against?”
Let’s address each of them. Then we’ll cover four more things you need before making Initial Contact: price, supporters, conditions, and what winning looks like.
Your customer
Which customers come first? Start with intensity over quantity. Start with people who really need what you’re making. People who need it badly. Paul Graham says you should choose “something a small number of people want a large amount.” For products that get better the more people use them, in The Cold Start Problem, Andrew Chen suggests finding your Atomic Network, the smallest network that can stand on its own; it’s “probably smaller and more specific than you think.”
In Disciplined Entrepreneurship, Bill Aulet suggests you define your segment by making sure:
Everyone in it uses the same product.
You sell to all of them in the same way.
They all talk to each other.
If you need different products or pitches, then the segment is too broad.
Their problem
Trying something new costs your customers time, energy, money, and even their reputation. Jake Knapp and John Zeratsky suggest you start with “What problem causes enough pain to justify that cost?” Like I mention in Random Acts of Marketing, focus on people in the high-pain quadrants. Make precise, timely offers when urgency demands taking action now. Use low urgency opportunities for branding to stay top of mind.
Paul Graham warns that “by far the most common mistake startups make is to solve a problem no one has.”
Your advantage
April Dunford asks you to consider what you have that the other alternatives are missing. Her approach is at the core of UW. You want to focus on asymmetric leverage to find your competitive power. To do that, Richard Rumelt, author of Good Strategy Bad Strategy, suggests answering:
What do you know that other people don’t?
What do you have that other people don’t?
Richard advises that, as a startup, you might need to narrow your field before you can pinpoint where that power is. You want to be able to pre-bunk your customer’s doubts by having explanations and evidence staged and ready.
What differentiates you only makes you special when you compare it to the alternatives.
What you’re up against
You are competing against opportunity cost and what customers would do without you.
Michael Porter, known for his approach to competitive strategy, asks you to consider the opportunity cost—how choosing your product also means giving up the next-best use of your customer’s money and time.
In Obviously Awesome, April Dunford asks you to consider what your customers would do if your product didn’t exist. She notes that Its worth acknowledging how sometimes they’d do nothing at all—that’s behavioral inertia.
These four basics get you started with who you’ll target, what you’ll offer, and why customers might choose you. But we still need to consider how you’ll reach your customers and what you’ll charge. You’ll figure out how to sell in the Infiltration phase.
You also have to consider pricing. With competitive strategy, Michael notes that your customers will judge price based on how they’re handling the problem right now. Those potential substitutes limit your addressable market’s profit potential “by placing a ceiling on prices.” The juice needs to be worth the squeeze. Your solution needs to be worth the price AND the trouble of switching (and taking the leap of faith).
Your price also needs to (at least eventually) cover the costs of serving your customers so you can stay in business.
Your price needs to pass both those tests, or the market you’ve chosen will drag you down with it. In $100M Offers, Alex Hormozi give us the analogy of the market being either neutral, growing as your tailwind, or shrinking as a headwind.
Paul Graham says that if you have to choose between people who will sign up now and those who will pay most, “it’s usually best to pick the former, because those are probably the early adopters.” Targeting your early adopters is where you start layering your efforts like I describe in Random Acts of Marketing. It’s also how you might...
Identify your supporters
Identifying your potential supporters is what will define your route to influence. These people, organizations, and channels are the gateway to getting discovered, making sales, and getting more users.
Analyze your first customers and partners the way an operator might analyze a resistance force. Learn what they do well, what they’re missing, what they want, and how they relate in their social spheres. Who makes decisions? Who do people listen to? Who gets the job done?
Seth Godin warns against starting at the top. People seek social proof when they’re unsure. If you pitch the CEO and she asks her team and they don’t know you, you just lost your shot. Seth suggests the alternative is to start in the middle.
You want to map out the org chart and the task org to understand how your customer really makes decisions. Even families have them. Bill Aulet calls the people surrounding the sale the decision-making unit. You need to know “who makes the ultimate decision to purchase, as well as who influences that decision.” According to Bill, there are three:
The champion
The end user
The economic buyer
You want to aim for the people responsible for profit and loss, or at least revenue, because they make the most important decisions.
Seth notes how the buyer you first connect with might not even be your customer. The buyer might be spending someone else’s money, and they only care about pleasing the boss.
Those intermediate customers, who might buy your product but don’t actually use it, have leverage. Intermediate buyers are powerful brokers that can strong-arm you on pricing, demand more than you could profitably offer at a given price point, and play you against competitors to get a better deal.
Melody Wilding identified three groups of people you should keep in mind:
Decision makers who control resources and opportunities
Power peers who are rising stars across the organization
Behind-the-scenes operators who make everything actually happen
Read the room
UW analyzes things like living conditions, government services, political, military, economic conditions, and so on. Your customers have budgets, rules, buying cycles, and tools they already use with plenty of procurement friction and switching costs to keep them using those tools.
These conditions are the variables that affect what your customer can realistically do. In The 7-Step Influence Process, this analysis focuses on understanding your supporter’s effectiveness.
Do your supporters have the power, control, and authority to influence the outcome you seek?
Do their conditions prohibit them from saying yes even if they like you?
Define winning
Unconventional Warfare starts planning the final transition phase during this preparation phase. For you, that means planning for what comes after the launch now.
What should your customers gain?
What does your business need to achieve?
Make these two specific, measurable, and observable so it’s crystal clear that you’ve hit your target and know when to begin moving towards the next stage of your venture.
Defining your objective is the first Step in The 7-Step Influence Process where you use Objectives & Key Results (OKR) framework along with other tools to figure out what your goals should be.
Success also comes with obligations you may be overlooking right now. What could they be? How can you set yourself up to manage growth now while it’s easy rather than later while it’s hard?
Once you can:
Describe what winning means.
Name your first segment.
Explain why your improvement is worth it.
Define your advantage over the competition.
Name your supporters.
Define a price people will pay that covers the cost of surviving.
It’ll be time for...



