E185: The Challenges with Monetizing Open Source with the Creator of Rich + Textual

E185: The Challenges with Monetizing Open Source with the Creator of Rich + Textual

Author: Robby (MTF); Tim (Essence VC) November 5, 2025 Duration: 34:02

In our latest episode, Robby and Tim talk with Will McGugan, creator of the Rich and Textual open source projects and founder of Textualize and Toad (not yet released), about the challenges of turning beloved open-source projects into real businesses. Despite Rich and Textual's huge adoption in the Python community, he says he waited too long to monetize, focused too much on technical perfection, and tried to build infrastructure before a killer product. He also burned himself out and wishes he had simplified and hired earlier.

McGugan believes the terminal is a neglected but essential interface, prized for speed and flow. Rich and Textual modernized terminal output, but monetizing open-core dev tools proved difficult.

His new project, Toad, aims to be a universal AI front-end for the terminal - open-source, protocol-driven, and able to plug into different agent back ends like Claude and others. The goal: seamless workflows and modern UX in the environment developers already live in.

Big takeaways: monetize early, ship a killer app sooner, don’t overcomplicate structure, and avoid grinding yourself into the ground.


Building a company around open source software is a unique and often misunderstood path, full of specific challenges and rare opportunities. The Open Source Startup Podcast digs into that journey directly with the people who have navigated it, moving beyond theory to the practical realities shared in conversation. Hosts Robby and Tim bring their distinct perspectives from MTF and Essence VC to these discussions, creating a space where founders speak candidly. You’ll hear from the architects behind names like HashiCorp, MongoDB, and Vercel, as well as leaders from Chronosphere, DBT, and mobile.dev, as they unpack their experiences. This podcast focuses on the pivotal decisions around community building, monetization strategies, and maintaining project ethos under the pressures of scaling a business. Each episode serves as a detailed case study, revealing how these companies turned publicly available code into sustainable, impactful enterprises. The dialogue naturally explores the tensions between open collaboration and commercial needs, offering a real-world blueprint that is both instructive and nuanced. For anyone curious about the intersection of community-driven development and venture-scale growth, this series provides an essential and unfiltered resource.
Author: Language: English Episodes: 50

Open Source Startup Podcast
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