Category

Founder narrative

48 posts in this category.

Founder narrative

The month I closed my first enterprise deal at $21K MRR

The month my SaaS hit $21,000 MRR I signed my first enterprise deal: one $40,000-a-year contract worth 16% of my revenue. A first-person 2026 diary on the 280-question security review, the SSO build I pulled off the roadmap, net-60 cash delays, concentration risk, and the three rules I wrote afterward.

9 min read100
Founder narrative

Gumroad Revenue: The Failure That Makes $10M a Year

As of 2026, Gumroad's own revenue was about $21 million in 2023 with roughly $9 million in profit, up from $11 million in 2022 (Sacra estimates). The twist in the Gumroad revenue story: the company Sahil Lavingia publicly called a failure in 2019 became quietly, durably profitable, while the eye-catching $142 million figure is what creators earned on the platform, not what Gumroad made.

7 min read855