Stop optimizing for customer 100 when you're at zero

When you have zero customers, your brain immediately jumps to: "How will this scale?" You start thinking about:

• Automated onboarding sequences
• Self-serve signup flows
• Knowledge base documentation
• Pricing tiers and packaging
• Sales playbooks and processes

Stop. None of that matters yet. You're solving problems for customer #100 when you need to be obsessing over customer #1. The reality is brutal: you don't know what your customers actually need yet. You don't know how they'll use your product. You don't know what questions they'll ask. You don't know what makes them successful. Building systems before you have this knowledge is like designing a highway before you know where people want to drive.

Instead of thinking "0 to 100 customers," break it down into distinct milestones:

• 0 → 1 customer
• 1 → 5 customers
• 5 → 10 customers
• 10 → 20 customers
• 20 → 100 customers

Each milestone represents crossing a different type of customer segment. This comes from Geoffrey Moore's "Crossing the Chasm" - one of the most important books for B2B founders. Here's why these segments matter: Your first customer is an innovator - someone willing to take a risk on an unproven solution because they're desperate for it to work. Your fifth customer is an early adopter - they like being first, but they need to see some proof it works. Your twentieth customer is early majority - they want references, case studies, and proof from others that this is actually a real deal and they can trust your product. Your hundredth customer has entirely different needs compared to the first one. Different segments = different strategies = different milestones.

Who they are: Innovators are willing to take a risk on an unproven solution because they're desperate for it to work. They have a painful problem right now and existing solutions aren't cutting it. Where to find them: Your network. Almost every successful B2B company got their first customer from first or second-degree connections. Not from cold outreach. Not from directories. From people who already trusted them. Your strategy at 0→1: 1. List 10 people from your network who have the problem you solve Think friends, family, former colleagues, people from local meetups, online communities. Focus on people who genuinely have acute pain. 2. Have real conversations, not pitches Ask about their current workflow. Understand their pain. Don't pitch your solution yet - just listen and validate the problem. 3. Offer white-glove everything Do the setup. Handle data migration. Build workflows for them. Make it feel instant even if it takes you days in the background. 4. Remove all their risk Use satisfaction guarantees: "I'll invoice you only if you're satisfied. Not happy? No invoice. No questions asked." What success looks like: One paying customer who is actively using your product and getting value. That's it. Nothing else matters at this stage.

Who they are: Early adopters like being first, but they need to see some proof it works. They're not as desperate as innovators, but they're excited about new solutions and willing to give feedback. Where to find them: Still mostly from your network, but now you can start asking for referrals. Your first customer becomes your case study, your reference, your proof point. Your strategy at 1→5: 1. Make your first customer wildly successful Before you even think about customer #2, obsess over customer #1. If they're paying you $20/month or $2,000/month, treat them like your only customer - because they are. 2. Ask for referrals directly "Who else do you know with this problem?" If you did a good job, they'll be excited to introduce you to their friends and colleagues. 3. Start seeing patterns Customer 1 might use your product one way, but customers 2, 3, 4, 5 might all use it slightly differently. Pay attention. These patterns are telling you something important about product-market fit. 4. Keep doing white-glove service Yes, still. Personal onboarding for everyone. Quick responses. Learning from every interaction. Help them migrate data, import data, create workflows - whatever they need. What success looks like: Five paying customers, all actively using your product. You're starting to see patterns in how they use it. You have at least one strong reference willing to vouch for you.

Who they are: Still early adopters, but with slightly more expectations. They want to see that you have other customers and that those customers are happy. Where to find them: Mix of referrals from existing customers and your extended network. You might start getting some inbound interest from word-of-mouth. Your strategy at 5→10: 1. Document what you're learning By now you should be seeing clear patterns:

• What do successful customers have in common?
• What questions do they all ask during onboarding?
• What workflows do they all create?
• What outcomes do they care about most?

2. Start refining your ICP You now have enough data to know who your ideal customer actually is - not who you thought it would be, but who it actually is based on real customer behavior. 3. Build your first case study Document one customer's success story. Specific numbers. Specific outcomes. Specific before/after. This becomes your proof point for the next milestone. 4. Still doing personal onboarding Yes, still. But now you're learning which parts can eventually be documented vs which parts need personal touch. What success looks like: Ten customers with clear patterns emerging. You can articulate exactly who your ICP is. You have at least one detailed case study. You're starting to understand what makes customers successful vs what makes them churn.

Who they are: Early majority customers want references and case studies. They want proof from other people that this is actually a real deal and they can trust your product. They're less willing to take risks than innovators or early adopters. Where to find them: Now you can start experimenting with more channels:

• Content marketing (if you have insights from your first 10 customers)
• Strategic partnerships
• Limited cold outreach (but only to highly qualified prospects)
• Community building

Your strategy at 10→20: 1. Build a repeatable sales process By now you should know:

• What questions prospects always ask
• What objections always come up
• What proof points close deals
• How long your sales cycle typically takes

2. Create customer success stories You need at least 3-5 detailed case studies with specific metrics. This is what closes early majority buyers. 3. Start building self-serve resources Now - and only now - can you start creating documentation, help articles, and onboarding materials. You know what questions people ask because you've answered them 10+ times. 4. Introduce some light automation Things like automated welcome emails, basic onboarding sequences, and data imports can now be partially automated - because you understand the edge cases. What success looks like: Twenty customers. You have a repeatable (not yet scalable) sales process. Multiple case studies. Some self-serve resources. You're spending less time on each new customer because you've documented common issues.

Who they are: Mix of early majority and late majority. They want proven solutions with clear ROI, established processes, and minimal risk. Where to find them: Now you can invest in scalable channels:

• Paid advertising (you know your CAC and LTV)
• Content marketing at scale
• Outbound sales team
• Channel partnerships
• Product-led growth motions

Your strategy at 20→100: 1. Build for scale Now - and only now - should you be thinking about:

• Fully automated onboarding
• Self-serve signup flows
• Extensive documentation
• Customer success team
• Sales playbooks and training

2. Optimize unit economics You should know:

• Customer acquisition cost (CAC)
• Lifetime value (LTV)
• Payback period
• Churn rate by segment

3. Segment your approach Different customer sizes might need different approaches. Enterprise vs SMB. Self-serve vs sales-assisted. Monthly vs annual contracts. 4. Build the team Now you can hire salespeople, customer success managers, and marketing people - because you have a proven playbook to train them on. What success looks like: A hundred customers. Repeatable and scalable processes. Proven unit economics. A team executing the playbook. You're no longer personally closing every deal or onboarding every customer.

At 0→1:

• ❌ Building a perfect landing page instead of talking to people
• ❌ Launching on Product Hunt instead of reaching out to your network
• ❌ Polishing features instead of getting one person to pay you
• ✅ Have conversations with 10 people from your network
• ✅ Remove all risk with satisfaction guarantees
• ✅ Do everything manually to learn

At 1→5:

• ❌ Starting to build automation systems
• ❌ Hiring salespeople
• ❌ Creating extensive documentation
• ✅ Obsess over making your first customer wildly successful
• ✅ Ask for referrals directly
• ✅ Keep doing white-glove service for everyone

At 5→10:

• ❌ Thinking you have product-market fit
• ❌ Trying to scale before understanding patterns
• ❌ Building features customers haven't asked for
• ✅ Document the patterns you're seeing
• ✅ Build your first detailed case study
• ✅ Refine your ICP based on real customer data

At 10→20:

• ❌ Still doing everything manually
• ❌ Afraid to say no to bad-fit prospects
• ❌ Not building any self-serve resources
• ✅ Create a repeatable (not scalable) sales process
• ✅ Build multiple case studies with metrics
• ✅ Start automating the obvious, repetitive tasks

At 20→100:

• ❌ Staying too hands-on with every customer
• ❌ Not investing in team and systems
• ❌ Ignoring unit economics and metrics
• ✅ Build scalable systems and processes
• ✅ Hire and train team on your proven playbook
• ✅ Invest in channels that work for your economics

1. It prevents premature optimization You can't optimize what you don't understand. The milestone mindset forces you to learn before you scale. 2. It matches customer psychology Different customer segments have different needs. Innovators want solutions to their desperate problems. Early majority wants proof. You can't sell to both the same way. 3. It keeps you focused When you have zero customers, your only job is to get to one. Not ten. Not a hundred. One. This singular focus is incredibly powerful. 4. It reveals product-market fit gradually You don't "find" product-market fit at customer #1. You discover it gradually as patterns emerge across your first 5, 10, 20 customers. 5. It aligns with resource constraints As a bootstrapped founder, you can't build everything at once. The milestone mindset tells you exactly what to prioritize at each stage. The best founders don't think about getting from 0 to 100 customers. They think about getting from 0 to 1, then 1 to 5, then 5 to 10. One milestone at a time.