Taking Calculated Risks and Building with Purpose with Tsai Chi-Yu

In this episode of Brazil (is not) for Beginners, Isaac Matzner sits down with Tsai Chi-yu, Founder and CEO of Stay, to discuss his entrepreneurial journey, the lessons he learned working on scaleups in the early Brazilian tech ecosystem and, and why he is dedicated to building with meaning.Taiwanese by birth and Brazilian by heart, Tsai's trajectory goes from banking in the US and France to entering the early tech ecosystem in Brazil. He shares lessons from the early days of scaling operations at Uber Brazil and recounts his experience as part of the team orchestrating 99's impressive turnaround from single digits to nearly 40% market share. Tsai shares key insights gained at each stage: from understanding market dynamics and the demands of high-stakes operations, to his focus on hiring for drive and his view on taking calculated risks.He also delves into the hard-won lessons from past ventures, notably the 2022 shutdown of Hash despite the significant capital it raised, and the importance of resilience and strategic thinking when innovating in Brazil. The conversation highlights how these experiences ultimately led him to focus on Brazil's private pension system with Stay. Driven by a mission to address the country's demographic shifts and an unsustainable system dominated by legacy providers, Tsai emphasizes how his continuous search for big problems and meaningful impact drives his approach to building and running Stay.Other key topics include:- Growing up Taiwanese in Brazil — and finding freedom in being multi-cultural- What Uber and 99 taught him about talent density, ambition, and risk-taking culture- One-way vs. two-way doors — and why most people are more conservative than they need to be- His experience at Hash and what the macro environment of 2022 exposed about cash-intensive business models- Brazil's demographic shift and the structural crisis facing the public pension system (INSS)- The opportunity Stay is pursuing around private pensions - less than 10% of Brazilians have private pensions and five big banks dominate 90% of that market- Building a direct, high-performance culture that blends Brazilian warmth with international efficiency- And lots more!