In this episode, Ben interviews Josh Pigford, founder of Maybe.co, about the company’s journey from VC-backed startup -> closed startup -> open source project -> funded open source project. They discuss JavaScript and Rails trade-offs, the challenges of building a personal finance software, and the operational difficulties of building a business based on open source software.

Links

Tuple.app - The best app for pair programming
Maybe.co - The fintech startup Josh founded
NodeJS - The starting framework for Maybe.co
Ruby on Rails - The new framework for Maybe.co

Key Takeaways

• Choosing the right tech stack is crucial for the success of a project.
• Running out of runway can force difficult decisions and pivots.
• Making a codebase public can generate interest and community engagement.
• Replacing third-party dependencies can be challenging but necessary.
• Rebuilding a software project requires careful planning and decision-making. Building a personal finance app involves challenges such as managing pull requests and issues in open source development.
• Transitioning to Rails can provide a more stable and efficient framework for building a complex application.
• The decision to rewrite the app from scratch allows for better decision-making and faster progress.
• Targeting Mint users with a budgeting tool presents an opportunity to capitalize on a fragmented market.
• Detangled, a project that simplifies legal documents, has the potential for commercial success. Moonshot ideas can be exciting and worth pursuing, even if the specific angle is unclear.
• ChatGPT has the potential to generate usable results, either through heavily massaged prompts or prewritten blocks.
• Tools like detangle can augment conversations with lawyers, providing insights and helping users know what questions to ask.
• There are commercial opportunities in selling services like detangle to companies that don't have full-time counsel.
• Finding the right balance between passion and traction is important when deciding which projects to pursue.

Chapters

• (00:00) - Introduction