Ep 355 - Stephanie Sy - The Hustle Behind Thinking Machines

EPISODE INTRODUCTION

In this episode of Hustleshare, we chat with Stephanie Sy, founder and CEO of Thinking Machines, to unpack her journey from Stanford and Silicon Valley to building one of the Philippines’ leading AI and data science companies. Stephanie shares how her early startup attempts and time at Google shaped her hustle, why she made the leap back home to start from scratch, and what it took to grow Thinking Machines in a market that was still new to data science. She also gets real about the challenges of building an AI team in a resource-constrained environment, the scrappy moves that helped them thrive, and how purpose-driven projects are helping shape the future of tech in Southeast Asia.

Episode Timeline: 

[00:04:01] – Stephanie’s Hustle: Helping People Make Good Decisions
[00:09:29] – Math & Stanford: Discovering Problem-Solving and Startup Culture
[00:13:58] – First Startup: CTO Lessons and Early Failures
[00:18:04] – Wildfire Interactive: Hypergrowth and Google Acquisition
[00:20:50] – Growing as a Dev: Mentorship and Strike-Team Leadership
[00:25:46] – Life at Google: Big Data and Culture of Curiosity
[00:35:29] – Coming Home: Family, Brain Drain, and Local Opportunities
[00:43:24] – Pre-Thinking Machines: A Freelance Problem-Solver Start-Up
[00:49:26] – Thinking Machines: Early Clients and Breaking In
[00:52:52] – Scaling Differently: Teaching Culture and Going Slow
[00:59:09] – Big Wins: DOH Dashboard and Public Sector Data
[01:04:11] – Data Through History: From Clay Tablets to AI
[01:10:37] – AI 101: Perception, Cognition, and the PH Gap
[01:17:32] – AI as Therapy: Finding Useful Data and Serving Customers

QUOTES
“That’s one thing about innovation. How willing are you to fail? And if they say, “We don’t want to fail. We don’t want to fail at all. We’re just going to innovate and succeed, right?” I should say, no. That’s not right. No. It’s not a straight path. Actually, innovation means you try 10 things and maybe 8 will fail. And it’s really about the 2 that succeed and get you to the next place.”– Stephanie Sy

CONNECT WITH STEPHANIE:
LinkedIn: https://www.linkedin.com/in/stefsy 
Website: https://thinkingmachin.es/

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