Almost three years after transitioning from Facebook to a nascent startup with only five employees, the writer reflects on the unexpected learning experience and challenges faced in a smaller, less structured environment. Initially, fears revolved around a lack of technical support and potential catastrophic failures, yet the reality proved different as they discovered that the learning curve at an early-stage startup is more manageable than anticipated. The challenges of attracting and retaining users were significant, contrasting starkly with the vast user base of big tech, while early adopters offered invaluable feedback and support. Technical issues like a problematic database query provided real-time learning experiences, yet these challenges arose later than expected, allowing for gradual expertise development. Ultimately, the journey highlighted that, despite the inherent difficulties of startup life, an eagerness to learn can equip one to handle technical challenges more adeptly than initially feared.