
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.
Unconventional Warfare (UW) is about supporting a resistance movement or insurgency to win against an occupying power. Sound familiar? It’s at the heart of my career working in Special Operations Forces.
To win, your go-to-market strategy needs to be unconventional. You need to turn your constraints and limitations into advantages an incumbent can’t or won’t use.
“In organizing, the major negative in the situation has to be converted into the leading positive.”
— Saul Alinsky, Rules for Radicals
Paul Graham describes one of these tactics as doing things that don’t scale. Early on, Brian Chesky and Joe Gebbia at Airbnb dedicated 30 days to doing what nobody else would do, “30 days of going out and engaging in person with users made the difference between success and failure.”
To win, you need to win the hearts and minds of your customers when they have no idea who you are or why they should care.
Alexa Mateen Abdi at Tinder won over their first customers by throwing a party where everyone had to download the app to get in. She had a simple pitch: Rejection sucks. You’ll only get a match if both people swipe right.
For startups, funded or bootstrapped, Go-to-Market as Unconventional Warfare is how you’ll win.
Special Operations defines UW in seven phases:
Preparation:
You start by studying the terrain; your market, who the incumbents are, the gaps.Initial contact:
Your entry to the market and connection with your first supporters; deeply rather than at scale.Infiltration:
You secure your beachhead—a specific geography, use case, or segment where you can secure your foothold and establish a forward operating base (FOB); and you’ll optimize for Product Market Fit.Organization:
This is team and network development; your atomic network, your auxiliary, cadre, core, referral strategies, and audience.Build up:
Develop capability, capacity, and reach to hit critical mass; make sure you can deliver on your promise and be mindful of the temptation for go-to-market to get ahead of product.Employment:
Deliver and scale.Transition:
Turn your wins into systems, failures into lessons learned, and grow into the next phase of your venture.
This approach is your playbook for engineering the right conditions and building the necessary infrastructure to scale your business.
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