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
(01:21) - Making the Codebase Public
(07:21) - Community Engagement and Pull Requests
(12:17) - Ripping Out Functionality
(15:03) - Replacing Data Aggregator
(16:10) - Building a Personal Finance App
(17:39) - Challenges of Open Source Development
(21:08) - Managing Pull Requests and Issues
(23:35) - Struggles with React Next.js
(27:45) - Choosing Rails for Development
(32:40) - Targeting Mint Users with Budgeting Tool
(35:45) - Modular Use Cases
(38:53) - Open Source Contributions and Bounties
(40:47) - Next Steps
(45:16) - Detangled: Simplifying Legal Documents
(48:32) - Exploring Moonshot Ideas
(48:58) - The Potential of ChatGPT
(49:45) - Augmenting Conversations with Lawyers
(50:21) - Commercial Opportunities
(50:53) - Balancing Passion and Traction
(51:20) - Closing Remarks

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