In this episode of The Next Next, host Jason Jacobs interviews Sahil Lavingia, founder and CEO of Gumroad and the newly established company, Antiwork. They discuss Sahil's journey from being employee #2 at Pinterest to founding Gumroad, and now venturing into promoting flexible work arrangements and leveraging AI to automate business processes. Sahil shares his insights on the transformative impact of AI in the software industry, his approach to building and scaling companies, and his vision for the future of work. The conversation also delves into how AI is altering traditional employment structures and what this means for venture capital, enterprise software, and individual productivity. Tune in for an enriching discussion on embracing change, optimizing for efficiency, and staying adaptable in a rapidly evolving tech landscape.

00:00 Introduction to Sahil Lavingia

00:31 Sahil's Early Career and Gumroad's Evolution

00:59 The Shift to AI and New Business Models

03:58 Personal Reflections and Work-Life Balance

10:00 The Impact of AI on Software Development

21:04 Future of Work and AI Integration

36:48 Project-Based Work and AI Efficiency

40:22 AI's Superiority in Software Engineering

40:59 The Efficiency of AI in Learning and Documentation

42:17 Understanding Tokens and AI Context Windows

44:09 The Future of AI in Software Development

44:25 AI's Impact on Different Professions

47:38 The Role of AI in Sales and Marketing

53:37 The Evolution of Software and Open Source

55:05 The Future of Venture Capital and Software

01:00:01 Building Efficient Workflows with AI

01:14:29 Concluding Thoughts and Future Directions