The Pain Cave Escape Plan: Moving from Building to Selling

The Truth About Building vs. Selling - A ConvertKit Story

Nathan Barry, founder of ConvertKit, spent his first year building features he thought email marketers wanted. Despite his technical skills and market research, ConvertKit only made $2,000 monthly revenue after a year of dedicated development.

The turning point? Nathan switched from building to selling. He started doing manual sales calls with potential customers, specifically targeting professional bloggers. Instead of adding more features, he focused on understanding what made customers stick around.

This shift led to ConvertKit growing from $2,000 to $625,000 in monthly recurring revenue within two years. The key wasn't better code - it was better customer understanding.

Why We Get Stuck Building

As technical founders, we often fall into the trap of endless building. It feels productive, but it's actually a form of hiding. We're comfortable writing code, but uncomfortable with the uncertainty of selling.

This building-first mindset leads to what I call the "pain cave" - where you're constantly working but not moving toward real success. The symptoms include:

- Constantly adding "just one more feature"
- Perfecting the tech stack instead of talking to users
- Avoiding customer conversations because the product isn't "ready"

The Escape Route

Here's how to break free from the pain cave and start moving toward real success:

1. Stop Building, Start Selling

Your first goal is to find one customer who gets genuine value from your product, even if delivering that value means doing things manually. Use demand-driven development to guide what you build next.

2. Embrace Manual Processes

Start with a manual MVP that delivers value, even if it's not scalable. You can automate later when you know exactly what needs building.

3. Focus on Customer Success Stories

Your goal is to create one solid case study where a customer is thrilled with your solution. This becomes your blueprint for finding similar customers.

4. Let Customer Behavior Guide Development

Watch what makes customers stick around and what causes them to leave. This is more valuable than any feature request. Use customer-driven refactoring to guide your development.

Practical Steps to Make the Switch

1. Set a concrete sales goal: Aim for 5-10 sales conversations per week
2. Create a simple case study template:
- What problem did the customer have?
- How did your solution help?
- What specific results did they achieve?
3. Track customer retention indicators before adding new features

Signs You're on the Right Track

- Customers are succeeding with your current feature set
- You're spending more time on customer calls than coding
- Feature requests come from successful customers, not prospects
- You can clearly explain who your product helps and how

Extra Tip: The Two-Week Rule

Don't build anything that takes longer than two weeks to complete. If a feature would take longer, break it down into smaller pieces that each deliver value. This keeps you focused on quick wins that you can immediately validate with customers.

The path out of the pain cave isn't about building more - it's about selling what you've already built to the right customers. Start today by scheduling your first five sales calls, even if your product isn't "ready."

Common Questions About Moving from Building to Selling

Recommended Approaches for Escaping the Pain Cave

1. Start with a "One-Day MVP": Build something you can show to customers within 24 hours. Use simple tools like Google Sheets if needed.

2. Create a "Manual First" Version: Deliver your service by hand to your first 5 customers. This helps you understand what really needs to be automated.

3. Set Up a Simple Sales Process:

• Use LinkedIn to find potential customers
• Send personalized outreach messages
• Schedule 15-minute discovery calls
• Document what works in each conversation

4. Focus on Learning: Each customer interaction is a chance to improve your understanding. Keep a log of insights and patterns.

5. Build a Support System: Connect with other founders who are also making this transition. Join communities of like-minded builders.

Measuring Your Escape Progress

Track these key indicators to ensure you're moving in the right direction:

1. Weekly Sales Activities:
- Number of customer conversations
- Quality of customer feedback
- Clear next steps from each call

2. Customer Success Metrics:
- Time to first value
- Customer retention rate
- Expansion opportunities

Building Your Sales Confidence

Many technical founders struggle with the transition to sales. Here's how to build confidence:

1. Start with curiosity rather than pitching
2. Document successful customer conversations
3. Focus on understanding problems before offering solutions

Creating Your First Case Study

A strong case study includes:

1. The customer's initial situation
2. The specific problem they needed to solve
3. How your solution helped
4. Measurable results they achieved
5. Direct quotes about their experience

Common Myths About Product Development and Sales

Your Next Steps

1. Schedule 3 customer conversations for this week

2. Document your current manual processes

3. Create a simple case study template

4. Set specific sales activity goals

5. Join a community of founders making similar transitions

Remember: Every successful product started with one customer getting value. Focus on making that happen this week.

Join Our Community of Builders

Ready to escape the pain cave? You're not alone. Join our community of founders who are making the transition from building to selling:

1. List your MVP on BetrTesters to get feedback and early users

2. Join our X Community to connect with other founders on the same journey

3. Share your progress and learn from others who've successfully made this transition

The sooner you start selling, the sooner you'll find the path to product success. Take that first step today.

Common Questions About Moving from Building to Selling

Recommended Approaches for Escaping the Pain Cave

1. Start with a "One-Day MVP": Build something you can show to customers within 24 hours. Use simple tools like Google Sheets if needed.

2. Create a "Manual First" Version: Deliver your service by hand to your first 5 customers. This helps you understand what really needs to be automated.

3. Set Up a Simple Sales Process:

• Use LinkedIn to find potential customers
• Send personalized outreach messages
• Schedule 15-minute discovery calls
• Document what works in each conversation

4. Focus on Learning: Each customer interaction is a chance to improve your understanding. Keep a log of insights and patterns.

5. Build a Support System: Connect with other founders who are also making this transition. Join communities of like-minded builders.

Measuring Your Escape Progress

Track these key indicators to ensure you're moving in the right direction:

1. Weekly Sales Activities:
- Number of customer conversations
- Quality of customer feedback
- Clear next steps from each call

2. Customer Success Metrics:
- Time to first value
- Customer retention rate
- Expansion opportunities

Building Your Sales Confidence

Many technical founders struggle with the transition to sales. Here's how to build confidence:

1. Start with curiosity rather than pitching
2. Document successful customer conversations
3. Focus on understanding problems before offering solutions

Creating Your First Case Study

A strong case study includes:

1. The customer's initial situation
2. The specific problem they needed to solve
3. How your solution helped
4. Measurable results they achieved
5. Direct quotes about their experience

Common Myths About Product Development and Sales

Your Next Steps

1. Schedule 3 customer conversations for this week

2. Document your current manual processes

3. Create a simple case study template

4. Set specific sales activity goals

5. Join a community of founders making similar transitions

Remember: Every successful product started with one customer getting value. Focus on making that happen this week.

Join Our Community of Builders

Ready to escape the pain cave? You're not alone. Join our community of founders who are making the transition from building to selling:

1. List your MVP on BetrTesters to get feedback and early users

2. Join our X Community to connect with other founders on the same journey

3. Share your progress and learn from others who've successfully made this transition

The sooner you start selling, the sooner you'll find the path to product success. Take that first step today.