Founder Magic: Why Your First 100 Users Need the Unscalable Version of You

The Stripe Story: When Patrick Collison Personally Onboarded Users

In 2010, Stripe was just getting started. Patrick Collison, the co-founder, spent countless hours personally installing the payment system for their first users. He would sit with developers, watch them integrate the API, and fix issues in real-time. This "unscalable" approach helped Stripe understand the real problems developers faced with payment integration.

Why Your Early Users Need the Raw, Unfiltered Version of You

Your first 100 users aren't just early adopters - they're your partners in building something people want. When you're personally involved in their success, you gain insights that no analytics dashboard can provide. This direct involvement is what we call founder magic.

The Power of Unscalable Actions

Here's what happens when you get personally involved:

1. Users feel valued and stick around longer (leading to better retention)

2. You spot patterns in user behavior before they show up in data

3. Feature requests come with context and real use cases

4. You build genuine relationships that turn users into advocates

How to Apply Founder Magic

Start with these actions:

1. Send personal welcome emails (not automated ones)

2. Schedule quick video calls with new users

3. Share your personal contact info for quick problem-solving

4. Create custom solutions for early users' specific needs

When to Scale Back Personal Involvement

Watch for these signals:

1. You're spending more time managing existing users than finding new ones

2. Common questions and issues become predictable

3. Users are successfully onboarding without direct help

Making the Transition

As you grow beyond 100 users:

1. Document common solutions and create self-service resources

2. Build processes based on successful manual interactions

3. Train team members using insights from personal user interactions

Remember: The goal isn't to stay unscalable forever. It's to learn enough about your users to build something they truly need. Your personal involvement early on is what makes product-market fit possible.

Extra Tip: The Follow-up Power Move

Two weeks after personally onboarding a user, send them a quick note asking about their progress. This simple action often reveals insights you missed during the initial interaction and shows users you're invested in their long-term success.

Start With Documentation

Create a simple system to document every support interaction. Use minimum viable processes to ensure consistency without overwhelming your team.

Build Support-Development Bridges

Set up regular meetings between support and development teams. Share support insights using customized dashboards to keep everyone aligned.

Test Solutions Quickly

Use feature flags to test solutions with small user groups before full rollout. This reduces risk and accelerates learning.

Measure Impact

Track how your solutions affect support volume and user satisfaction. Implement customer health scoring to measure improvement.

Start With Documentation

Create a simple system to document every support interaction. Use minimum viable processes to ensure consistency without overwhelming your team.

Build Support-Development Bridges

Set up regular meetings between support and development teams. Share support insights using customized dashboards to keep everyone aligned.

Test Solutions Quickly

Use feature flags to test solutions with small user groups before full rollout. This reduces risk and accelerates learning.

Measure Impact

Track how your solutions affect support volume and user satisfaction. Implement customer health scoring to measure improvement.