In May 2022, Praneet Agarwal, Shashank Patidar and Shaurya Joshi—founders of WeSkill, a live, online “extracurricular” learning platform for children below the age of 14 years—were contemplating ways to sustain their business going forward. The venture, which had been launched in September 2020 when the entire world was fighting COVID-19, had traversed multiple twists and turns. The team had worked hard and enjoyed some success during the COVID-19 pandemic. However, as the impact of the COVID-19 pandemic waned, challenges began to mount. The case documents multiple issues that arise when creating a platform start-up and sustaining it over a long period. It also examines why start-ups that experience initial success may not sustain operations as time progresses.