14. From Coder to CEO: AI Startups, Cross-Generational Leadership, and Building in Asia with Sega Cheng

Episode notes

"I just want to build a company like Google. That was very naive. But that was my passion." Google engineer turned founder Sega Cheng on what happens when you leave the Valley to build an AI startup in Asia — and why the hardest part of the journey was not learning new skills but unlearning the DNA of deterministic code to lead with probabilistic uncertainty. Based in Taiwan , Sega spent six years at Google (Mountain View and Taiwan) working on Android before co-founding iKala in 2012. Fourteen years later, iKala serves over 1,000 enterprises across Asia-Pacific with AI adoption platforms and operates Kolr , the world's largest influencer marketing platform with data on 300 million creators. From cloud infrastructure to AI-powered marketing, Sega has navigated multiple pivots, five funding rounds, and the reality that building a team in Asia with Silicon Valley speed requires finding traits most education systems do not cultivate: adaptability, bottom-up initiative, and tolerance for shipping imperfect products.