In this essay, I relate my personal journey around the world of startups in Florianópolis, Santa Catarina, Brazil and Silicon Valley, California, USA through a critical analysis of my personal past experiences-first as a startup founder, then as a WebTV series host, and finally as a startup marketing "manager". Using autoethnography as a research method, I present some of the values promoted by the culture of the startups from Florianópolis as well as the difficulties some entrepreneurs might face when building a new business. Supported by critical literature on contemporary ways of working, I portray some aspects of the modus operandi of the technological innovation center once known as "the Silicon Valley of Brazil".