Josh Pigford, Creator of

In this episode, Ben interviews Josh Pigford, founder of, 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 - The best app for pair programming - The fintech startup Josh founded
NodeJS - The starting framework for
Ruby on Rails - The new framework for

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.

  • (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

Creators and Guests

Josh Pigford
Josh Pigford
Founder of Maybe, Synth Finance, and Detangle AI
Josh Pigford, Creator of
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