Thiago Da Costa - Serial Tech Entrepreneur and Leader - Part 1

from Authentic Leadership for Everyday People

Today's guest is Thiago Da Costa, a serial entrepreneur with multiple exits and decades of experience building deeply technical companies. His latest venture, Datagrid AI is an enterprise agentic solution that connects data and automates workflows across tools, files, and systems, Thiago brings a rare combination of technical depth, founder instinct, and hard-earned perspective on what it really takes to start, scale, and survive as an entrepreneur. We talk candidly about the realities of founder-led growth, why most early hires fail, how scaling actually works in practice, and why instinct—tempered by experience—often matters more than advice.We also dig into the employee side of the equation: how to evaluate a founder before joining a startup, what questions really matter in interviews, and why effort, ownership, and clarity are the ultimate differentiators in today’s market.Contact Dino at: [email protected]:al4ep.comdatagrid.aiAdditional Guest Links:LinkedIn: linkedin.com/in/thiagocosta2Corporate LinkedIn: linkedin.com/company/datagrid-ai/Authentic Leadership For Everyday People / Dino CattaneoDino on LinkedIn: linkedin.com/in/dinocattaneoPodcast Instagram – @al4edp Podcast Twitter – @al4edpPodcast Facebook: facebook.com/al4edpMusicSusan Cattaneo: susancattaneo.bandcamp.com

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This episode was published on January 5, 2026.

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