This case describes the journey of Arjun Sagar Gupta, a restaurateur and music lover who brought the worlds of jazz music and dining together. In 2015, Gupta started The Piano Man, Delhi’s first dedicated jazz club. Delhi was already home to a variety of bars and restaurants, but options for live music, especially jazz, were limited. The Piano Man, a food and beverage (F&B) business, operates from two locations: Safdarjung Enclave, South Delhi (since September 2015) and 32nd Avenue, Gurugram (since June 2019). It has two businesses with a symbiotic relationship: an F&B business and an artist management business. The F&B business generates revenue once clients enter the space, and the music line-up and the calibre of performances drive clientele to the location. Gupta faces an urgent need to make the business more profitable to recover losses incurred during the pandemic and show that his model is scalable for investment. In addition to The Piano Man, Gupta is exploring two other business ideas. The first is a ticketing platform built with years (and 7,000 shows) of data on how people discover noncommercial small- and medium-scale live performances (to compete with BookMyShow). The second is a distribution platform in the form of a music application where one can discover independent artists (akin to Spotify for indie artists). Which path should Gupta pursue? Should he remain small and true to jazz but struggle with the challenges of running a small business, or should he grow large and reach out to a wider audience to provide artists with a better platform? Will growth impede the ideology that made The Piano Man unique in the first place?