Tech Boss Diaries: Untold Stories of Asia’s Tech Leaders

Whether you’re launching your first product or diving into the tech world, get practical advice in every episode. We bring you raw, honest conversations with Asia’s top tech leaders who spill the tea on: - Career hacks they wish someone told them years ago - Real struggles/failures that taught them invaluable lessons - How they built apps and products people actually use No fluff, just real talk. Hear about the times they failed miserably, moments they almost gave up, and the pivotal decisions that shaped their early careers. Discover how they got back up, turned vulnerabilities into opportunities, and pushed forward with grit, courage, and hard work.

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Episodes

Friday Jun 20, 2025

🎧A former Google AI researcher turned startup leader shares his unconventional path from Taiwan to Silicon Valley and back to Asia. From launching foundation models at Google to embracing startup chaos in Southeast Asia, he reflects on career pivots, cross-cultural lessons, and why AI won’t replace us—yet.
 
💡 Key Takeaways & Topics:
 
 ✅ Academic Journey and early career at Google
 ✅ Challenges of building and shipping AI in big tech
 ✅ Cultural and career shifts after moving to Singapore
 ✅ Comparing innovation in Silicon Valley vs. Asia
 ✅ Startup life at Tokopedia: unlearning Google habits
 ✅ Future of AI: tool, not threat
 ✅ Career values, personal growth, and advice for the next gen
This one’s for the thinkers, the wanderers, and anyone questioning what success really means.
#TechCareer #AI #Google #StartupLife #SiliconValley #Singapore #CareerAdvice #NLP #LifeLessons #WorkCulture #Innovation #JobHopping #PersonalGrowth #FutureOfWork
🔥 Why People Would Listen
Career Inspiration from a Nonlinear PathListeners—especially students, early-career professionals, or those considering a pivot—love hearing real-life stories of people who left "safe" jobs like Google to pursue something more aligned with their values. It gives them courage and perspective.
Insider Tech & AI InsightsAs someone who helped build Google’s foundation models, the guest offers a rare, firsthand look at what it’s like behind the curtain of Big Tech AI. That credibility makes the episode valuable for AI enthusiasts and professionals.
East vs. West Innovation CultureHis reflections on working in Silicon Valley vs. Southeast Asia touch on globalization, adaptability, and what it takes to lead in diverse tech ecosystems. This resonates with listeners interested in international careers or cross-cultural dynamics.
Relatable Startup ChallengesStories from the trenches at Tokopedia (e.g., "unlearning Google habits") humanize startup life—it's messy, personal, and funny. People appreciate the honesty and learn from it.
Human-Centered View of AIAmidst hype and fear, he brings a balanced take on AI as a tool, not a threat—emphasizing human creativity, context, and ethical responsibility. This thoughtful framing appeals to those skeptical of AI or curious about its long-term impact.
For the Underdogs & "Outliers"His identity as someone who didn’t take the “perfect” path (non-native English speaker, moved across countries, took career risks) makes him deeply relatable to anyone who feels like they don’t fit the mold.
 

Sunday May 25, 2025

🎙️ From debugging video code to leading product strategy—how one engineer broke into PM without a roadmap, climbed up the ladder, and built her own playbook along the way.
In this episode, we sit down with Deepika, a former video engineer who made the leap into PM… thanks to a company bold enough to hire a movie director to play the role of a product manager (true story). From busting the myth that PMs need MBAs, to calling out the biggest lies in the industry (spoiler: you don’t need to be the smartest person in the room), she tells it all.
We spoke about:
✅ Her wild career pivot from engineering to PM—and what triggered the switch ✅ The biggest changes in the PM role over the years (hint: it’s no longer just writing specs) ✅ Whether PMs today need to be data storytellers, fast prototypers, or mini-CEOs (and why that last one’s a trap) ✅ How to handle career conflicts—when to escalate vs. when to walk away
Plus, Deepika gets real about mental wellness, setting boundaries, and why staying present is one of the most underrated leadership skills. She also shares how communities like Women in Product helped her grow—and how you can find your people too.
👩‍💻 Shoutout to Women in Product—a global community supporting women in tech with events, mentorship, and career advice. If you're in Singapore and working in product (or thinking about it), follow them for updates on local events and tips to grow your PM career.

Sunday Mar 23, 2025

🎙 What happens when you leave a safe job at Yahoo Taiwan, jump headfirst into Grab’s wild hyper-growth phase, and end up leading design at a Web3 giant? Rice Lee has lived it—and she’s spilling everything.
In this episode, Rice—now Senior Designer Manager at OKX and author of "我28歲,領世界級薪水:從指考英文20分,到影響6億人日常生活的首席設計師."—gets real about her biggest career jumps. From moving to Singapore without speaking fluent English, to experience Grab’s design team from 10 to 180, to juggling life as a designer, author, and podcaster without losing her mind.
We spoke about:
✅ Why Web3 design is a different beast (and why she loves it)✅ How she wrote a book, launched a podcast, and still found time to have a life✅ What young designers need to know to survive AI (don’t panic—just get curious)
This isn’t one of those sugar-coated success stories. Rice keeps it real about the struggles, wins, and lessons from her career. If you’ve ever wondered how to actually grow in design while keeping your sanity, you’ll want to listen to this one. 🎧

Sunday Mar 23, 2025

🎙 What happens when you leave a safe job at Yahoo Taiwan, jump headfirst into Grab’s wild hyper-growth phase, and end up leading design at a Web3 giant? Rice Lee has lived it—and she’s spilling everything.
In this episode, Rice—now Senior Designer Manager at OKX and author of "我28歲,領世界級薪水:從指考英文20分,到影響6億人日常生活的首席設計師."—gets real about her biggest career jumps. From moving to Singapore without speaking fluent English, to experience Grab’s design team from 10 to 180, to juggling life as a designer, author, and podcaster without losing her mind.
We spoke about:
✅ How to build influence as a bilingual designer (even when you’re not sure people understand you)✅ What really went down inside Grab during its craziest years (random desks, last-minute Jakarta flights, you name it) ✅ Her go-to moves when PMs and engineers push back (hint: empathy—and a paper trail)
This isn’t one of those sugar-coated success stories. Rice keeps it real about the struggles, wins, and lessons from her career. If you’ve ever wondered how to actually grow in design while keeping your sanity, you’ll want to listen to this one. 🎧

Tuesday Feb 25, 2025

🎙️ In this episode, we chat with Damiano Tietto, a seasoned tech leader and AI startup advisor, about his journey from Italy to Taiwan, scaling Carousell’s R&D center, and navigating the evolving world of engineering. He shares insights on hiring philosophy, managing diverse teams, and how engineers can adapt to AI-driven changes.
Key Highlights:
✅ Working culture differences across regions and how they shape tech teams✅ Hiring philosophy & people management – spotting and nurturing top engineering talent✅ How engineers can thrive in the age of AI - leveraging AI for software development✅ Career advice and life lessons from a tech leader’s perspective
Tune in for an inspiring conversation with Damiano Tietto on leadership, growth, and the future of tech! 🎧Visit MyMika: https://www.mymika.com.tw/#Leadership #AI #TechInnovation #EngineeringCulture #CareerGrowth #Hiring #TechLeadership

Saturday Feb 01, 2025

🎙️In this episode, we’re thrilled to have Isabella Yamin, Co-Founder of an innovative AI startup focused on revolutionizing product testing and automation. With a rich background in tech consulting, product management, and entrepreneurship, Isabella has a proven track record of leading teams, driving growth, and building impactful solutions across startups and established organizations.
Join us as Isabella shares her fascinating journey:
Transitioning from a career in big consulting firms and tech giants to Silicon Valley startups, and eventually making her mark in Asia’s tech scene.
The motivation behind founding her own startup, driven by a fear of missed opportunities and a desire to fully utilize her potential.
The challenges of unlearning skills from her corporate days and adapting to the fast-paced, resource-constrained world of startups.
Insights into founder-market fit, idea iteration, and the key principles that guided her through pivots and tough decisions.
Her maximizer philosophy—how it shapes her decision-making and drives her to seek the best possible outcomes.
Useful Links from Isabella- Mark Manson’s Engineering your own luck:https://markmanson.net/how-to-make-your-own-luck- Earned Insight for New Product Idea:https://www.reforge.com/guides/pressure-test-a-new-product-idea- ⁠Neither Civil nor Servant- Philip Yeo Story:https://www.stbooks.sg/products/neither-civil-nor-servant-the-philip-yeo-story- ⁠Thinking in Bets by Annie Duke- ⁠Algorithms to Live By - The Computer Science of Human Decisions Brian by Christian and Tom Griffiths- CarbonCopies AI - test your website with AI copies of your usershttps://www.carboncopies.ai

Tuesday Dec 24, 2024

🎙 In this interview with Maitreyee, we explore her inspiring journey from challenging societal norms in India to building a thriving career in market and UX research. Maitreyee dives into the realities of transitioning between fields, managing biases in research, and practical tips for aspiring researchers entering the tech world.
Maitreyee’s Career Journey – From pursuing humanities against societal expectations to establishing a global career in market research and UX.
From Market Research to UX Research – Insights into the differences between these fields and how she navigated the transition.
Challenges in Research – Managing stakeholder biases, adapting reports for diverse audiences, and advocating for users in under-resourced environments.
Advice for Aspiring Researchers – Building empathy, active listening skills, and strategies for navigating remote work challenges while continuously learning from industry leaders.
Don't miss this insightful conversation with Maitreyee, packed with real-world experiences and actionable advice for anyone navigating the dynamic world of research and user insights.

Sunday Dec 01, 2024

🎙 In this episode of TechBossDiaries, Thuya Kyaw shares his journey from rural Myanmar to becoming a tech evangelist, and explores the evolution of the Singapore tech community, the rise of AI, and practical advice for junior developers navigating the future of tech.
Thuya’s Career Journey – Key moments and transitions in his path to success.
Developer Relations Engineer Role – What it’s like to connect developers with companies.
Tech Community in Singapore – How it’s evolved and what’s next.
AI Trends & Tips for Junior Engineers – The latest AI developments and practical advice for newcomers.
Don't miss this insightful conversation with Thuya, packed with valuable advice and real-world tech insights.

Sunday Oct 27, 2024

🎙 In this episode with Valerie Chang, we uncover:
Navigating tough stakeholders with different goals and backgrounds—an inside look at the realities of corporate life.
Smart ways to stay on top of fast-changing tech trends.
The advice Valerie would give her younger self, looking back a decade.
Get real-world insights on managing relationships, staying current in tech, and lessons for a successful career in tech.

Sunday Oct 27, 2024

🎙 In this episode with Valerie Chang, we uncover:
Her leap from running a startup to a product role at Rakuten Viki. What’s different about life in a big company?
The truth about junior PM interviews and what to expect.
Tips on building allies at work to help you overcome weaknesses.
Valerie’s biggest product failed and the lessons that came with it.
Tune in for honest talk on career changes, learning the hard way, and practical tips for surviving as a non-technical product manager.

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