Founder Playbooks

Stop optimizing for customer 100 when you're at zero

The milestone mindset: why getting from 0→1 requires a completely different strategy than 20→100, and how to avoid the fatal mistake of scaling too early

December 2, 2025 · 9 min read

The most common mistake I see founders make: they have zero customers but they're already thinking about scalability, automation, and systems. They're optimizing for level 100 when they're still at level 0. For my first customer at my current company, I manually triggered a Postman API call 400 times. With a stopwatch. 55 seconds between each call because of API rate limits. That's not scalable. That's not efficient. That's not "best practice." But it's exactly what you need to do to get from 0 to 1. Here's why different customer milestones require completely different approaches - and how to avoid wasting months optimizing for problems you don't have yet.

The Fatal Mistake: Optimizing for Scale 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.

From the Video (04:09-04:37)

When you think about your first hundred customers, the most common mistake that I've seen is that people think about scalability, automations, which gets them to the wrong path. People are optimizing for level 100 and they're still at the level 0.

Common Mistake : The Efficiency Trap

The minute you start optimizing for efficiency instead of learning, you stop getting the insights you need to build something people actually want to buy.

The Milestone Mindset Framework

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.

From the Video (05:07-05:36)

If you have zero customers, don't think about 100 customers. Think about the first one. So here is how I approach it. A number of customers, 0 to 1, 1 to 5, 5 to 10, 10 to 20, 20 to 100. So each milestone requires a different approach because you're crossing different types of customers.

Key Takeaway : Key Framework

Innovators (0-1) → Early Adopters (1-5) → Early Majority (5-20) → Late Majority (20-100). Each segment has different motivations, risk tolerance, and proof requirements.

Milestone 0→1: Finding Your Desperate Innovator

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:

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.
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.
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.
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.

Example : Real Founder Example

For my first customer at my current product, I triggered Postman API call 400 times. Manually. With a stopwatch timing 55-second intervals because of API rate limits. Days of manual work so their experience felt instant.

From the Video (05:37-05:57)

Your first customer is an innovator, someone willing to take a risk on an unproven solution because they are desperate for it to work.

Milestone 1→5: Early Adopters Want Proof

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:

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.
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.
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.
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.

From the Video (05:57-06:13)

Your fifth customer is an early adopter. They like being first but need to see some proof it works.

Common Mistake : Don't Automate Yet

There's a big temptation at this stage to start automating. Don't do it. You haven't learned enough yet. Keep doing things manually so you can keep learning.

From the Video (10:06-10:25)

Getting from one to five customers, it's still about relationships heavily, but now you can start asking for referrals. Your first customer becomes your case study, your reference, your proof point.

Milestone 5→10: Patterns Emerge

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:

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?
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.
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.
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.

From the Video (10:25-10:42)

Here's an interesting thing that you start seeing when you go from customer one to five: you start seeing patterns. Customer 1 might use your product one way, but customers 2, 3, 4, 5 all use it slightly differently. So you need to pay attention to these patterns. They're telling you something important about product market fit.

Tip

The feedback loop from your first ten customers is worth more than a thousand website visitors. When you get people actually using the product, telling you all the angles, asking questions, saying how it fits their workflow - that's how you learn the most.

Milestone 10→20: Early Majority Needs Social Proof

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:

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
Create customer success stories
You need at least 3-5 detailed case studies with specific metrics. This is what closes early majority buyers.
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.
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.

From the Video (05:57-06:13)

Your 20th customer is early majority. They want references and case studies and proofs from other people that they experience it that it's actually a real deal and that they can trust your product or service.

Key Takeaway : The Chasm

Moving from early adopters to early majority is "crossing the chasm" - the hardest transition in B2B. You need proof, processes, and social validation. Many companies die here.

Find prospects at the right stage

Dealmayker shows you which prospects are ready to buy now - so you can focus on the right milestone with the right customers.

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Milestone 20→100: Now You Can Think About Scale

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:

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
Optimize unit economics
You should know:
- Customer acquisition cost (CAC)
- Lifetime value (LTV)
- Payback period
- Churn rate by segment
Segment your approach
Different customer sizes might need different approaches. Enterprise vs SMB. Self-serve vs sales-assisted. Monthly vs annual contracts.
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.

From the Video (06:13-06:39)

Your hundred customer will have entirely different needs comparing to the first one.

Tip

Only after 20+ customers should you think about: automated sequences, self-serve flows, sales playbooks, or hiring SDRs. Before that, you're optimizing for problems you don't understand yet.

Common Mistakes at Each Milestone

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

Common Mistake : The Meta-Mistake

The biggest mistake is doing level 100 activities when you're at level 0. Each milestone has its own priorities. Don't skip ahead.

Why the Milestone Mindset Works

It prevents premature optimization
You can't optimize what you don't understand. The milestone mindset forces you to learn before you scale.
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.
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.
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.
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.

From the Video (05:07-05:36)

Therefore, I want to ask you to embrace the milestone mindset. If you have zero customers, don't think about 100 customers. Think about the first one.

If you're at zero customers right now, stop thinking about scalability. Stop thinking about automation. Stop thinking about systems. Think about one thing: getting to one customer. Pick three people from your network who have the problem you solve. People who trust you enough to have a real conversation. Reach out today. Don't pitch. Listen. Understand their problem deeply. Then remove every barrier for them to say yes - do the work for them, eliminate their risk, make their success inevitable. That's how you get from 0 to 1. Then you obsess over making that one customer wildly successful. That's how you get from 1 to 5. Then you look for patterns in how those five customers use your product. That's how you get from 5 to 10. One milestone at a time. Each milestone requires a different approach. Don't optimize for milestone 5 when you're at milestone 0. The milestone mindset isn't just a framework - it's permission to do things that don't scale. And that's exactly what you need to do to get your first customers.

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Frequently Asked Questions

What is the milestone mindset for getting B2B customers?

The milestone mindset breaks customer acquisition into stages: 0→1, 1→5, 5→10, 10→20, 20→100. Each milestone represents crossing a different customer segment (innovators, early adopters, early majority) and requires a completely different approach. It prevents you from optimizing for scale before understanding your customers.

Why shouldn't I think about automation when I have zero customers?

Because you don't know what to automate yet. You haven't learned what customers actually need, how they use your product, or what makes them successful. Building systems before this knowledge is premature optimization. Focus on manual, high-touch service so you can learn from every interaction.

What's the difference between innovators, early adopters, and early majority?

Innovators (0-1) are desperate for solutions and willing to take risks on unproven products. Early adopters (1-10) like being first but need some proof it works. Early majority (10-100+) want references, case studies, and social proof before buying. Each segment needs different messaging, proof points, and sales approaches.

When should I start building scalable systems?

After 20+ customers. Before that, focus on learning, not efficiency. At 20 customers, you should have clear patterns, a repeatable sales process, multiple case studies, and enough data to know what's worth automating. Building systems too early means you're optimizing for problems you don't understand yet.

How do I know when I've reached product-market fit?

You don't "find" it at customer #1. Product-market fit emerges gradually across your first 5-20 customers as you see patterns: similar use cases, consistent value metrics, strong retention, enthusiastic referrals, and clear ICP characteristics. If customers 2-5 use your product completely differently than customer 1, you haven't found it yet.

What should I focus on at each milestone?

0→1: Get one person to pay you through your network. 1→5: Make customer #1 wildly successful, get referrals. 5→10: Document patterns, build first case study. 10→20: Create repeatable sales process, build social proof. 20→100: Now you can think about scale, automation, and team. Each milestone has different priorities.

Why does Crossing the Chasm matter for B2B founders?

Crossing the Chasm explains why the jump from early adopters to early majority is the hardest transition. Early adopters tolerate bugs and missing features. Early majority wants proven solutions with references. Many B2B companies die in this chasm because they try to sell to early majority the same way they sold to innovators.

Should I still do white-glove service at 10 customers?

Yes, but you can start introducing light automation for obvious, repetitive tasks. You should still personally onboard customers and respond quickly, but you can begin documenting common questions, creating help articles, and automating simple workflows. Full automation comes after 20+ customers.

Aleksa

Founder of Dealmayker

I'm Aleksa, founder of Dealmayker (bootstrapping it solo), building the future of B2B sales through contextual & emotional intelligence. On the journey to be a 1-person unicorn. Previously built Hyperaktiv and worked in B2B sales at SaaS & FinTech companies.