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

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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.

  1. FEB 1

    #19: Startup vs. Corporate: Navigating Mindsets, Agility, and the AI Shift | The Fire Chat

    Welcome to the first episodes of 2026! In this premiere, we introduce our new "Fire Chat" format, where the three of us dive deep into a single, burning topic. To kick things off, we are debating the age-old battle with a modern twist: Startup vs. Corporate. It is no longer just about team size; it is about mental models, risk appetite, and the impact of AI. Whether you are chasing a "life-changing exit" or seeking the safety of a global brand, the lines are blurring. In this episode, we discuss: The "Zero to One" Grind vs. The Safety Net: We explore the difference between the "don't die" survival mode of startups and the structural protection of big corporates. Slack Emojis vs. PowerPoints: A raw look at working styles—can you execute with a single emoji, or do you need a PowerPoint prepared weeks in advance?. The New Talent Archetype: Why the debate between "Generalist vs. Specialist" is changing into "Star-shaped" talent—professionals with one superpower and AI-assisted general skills. The Corporate Identity Crisis: How traditional companies are flattening structures and adopting AI to survive, and the chaos that comes with trying to act like a startup. If you are at a career crossroads or trying to figure out where you fit in this new dynamic landscape, this conversation is for you. Connect with us: Have a situation at work or a tech topic you want us to talk through? Email us at techbossdiary@gmail.com. Don't forget to subscribe for more raw, honest, and multi-dimensional conversations.

    29 min

  2. 12/30/2025

    #18: Reflections & Tough Talks in a Year of Podcasting | The Hosts Reflect (Founders@Tech Boss Diaries)

    As the year draws to a close, the hosts gather for an honest and candid reflection on their journey into the world of podcasting. They begin by revisiting their original motivations, which ranged from ticking off a "life bucket list" and pursuing a passion for learning to overcoming a deep-seated fear of putting one’s voice out into the public sphere. The conversation dives into the often-unspoken challenges of managing a side hustle with friends, specifically regarding mismatched expectations. The hosts share how they navigated the tension between wanting to create a "masterpiece" and the reality of balancing the show with corporate careers. You will hear how they utilised "tough conversations" to align their goals and move forward as a cohesive team. Listeners will also gain insights into the technical evolution of the show, including: Workflow Optimisation: How they transitioned from high-effort editing to a streamlined process using AI tools like CapCut and standardised templates to reduce "cognitive energy". KPIs and Discipline: Why they prioritised consistency and personal discipline over ambitious growth targets to ensure the project remained enjoyable. Future Shift: A look ahead to 2025 and 2026, with plans to move away from generic interview formats in favour of provocative "spicy questions" and topic-focused deep dives. Whether you are an aspiring creator or navigating a collaborative project, this episode offers a transparent look at the learning curve, friendship, and resilience required to build a platform from the ground up.

    23 min
  3. #17: Navigating Global Bias, AI Startups, and the Power of Unlearning | Aska Kuwabara (Founder @AxarToys.ai)

    10/25/2025

    #17: Navigating Global Bias, AI Startups, and the Power of Unlearning | Aska Kuwabara (Founder @AxarToys.ai)

    Aska is a global entrepreneur and product leader with a career spanning finance, technology, and AI innovation. Born in rural Japan, she began as a self-proclaimed “rebel” driven by problem-solving. Her professional journey includes roles at Goldman Sachs (finance), Rakuten (Senior Product Manager & Vice Group Manager, leading agile transformation), and Twilio (Asia-Pacific Localization Lead). Now based in Abu Dhabi, UAE, she is building two AI-driven ventures: Get it done with AI, automating SME operations through off-the-shelf AI tools, and Maxi, an AI-powered talking toy that seamlessly weaves learning (like math) into children’s play. Key Learnings and Advice on Leadership, AI, and Growth: 1. Gender and Advocacy: Aska highlights the persistent gender gap in tech, noting that women must self-advocate far more actively—“raising my hand five or ten times more than male colleagues” to be recognized. She contrasts Japan’s slow, paper-based processes with the UAE’s globally progressive and inclusive environment that supports female leadership. 2. AI and Business Focus: She warns leaders against the “AI trendy trap”—adopting AI without clear problem definition. The true power of AI lies in efficiency (handling 80% of work faster), but the final 20%—where quality and context matter—demands human judgment. 3. Mindset and Balance: Aska’s guiding framework as a founder and single mother is the mindset of “it’s okay.” By letting go of perfectionism and unlearning rigid patterns, she maintains resilience and adaptability. She believes success comes from embracing uncertainty and staying humble enough to “ride the waves” of life and technology alike. Follow Aska on LinkedIn: https://www.linkedin.com/in/askakuwabara/ Follow TechBossDiaries on Tiktok: https://www.tiktok.com/@techbossdiaries Instagram: https://www.instagram.com/techbossdiary1

    47 min

  4. 09/26/2025

    #16: The AI Singularity: Agentic Code and the End of the Iron Rice Bowl | Jordan Dea-Mattson (CTPO@Jurin AI)

    Jordan D. Matson is a Technology and Leadership Expert with 40 years of experience, including 13 years at Apple (leading the Power PC transition) and building Indeed’s engineering center in Singapore. He views the current AI shift as fundamentally larger than the PC, web, and mobile revolutions combined. He anticipates the Technological Singularity (2035–2040), where the rate of technological change becomes undefined. Key Learnings and Advice on Business and Technology: Disruption: Agentic Coding has effectively "wiped off the map" the entry level of the career ladder. The guarantee of stability known as the "iron rice bowl" is gone, making employment a highly transactional thing due to companies' "zero loyalty". Adaptation: Individuals must adopt a continuous learning mindset. Professionals must pivot from the technical "how" to focusing on the business "what and why". Critical Skills: Success requires AI fluency and mastering human skills: the ability to ask questions, frame problems, and evaluate output. The ideal model is collaboration, maintaining the "human in the loop". Career Structure: Mid-level professionals must become more generalist, rather than specialized, to broaden their understanding. Follow Jordan Dea-Mattson on Linkedin Follow TechBossDairies on Tiktok: https://www.tiktok.com/@techbossdiaries Instagram: https://www.instagram.com/techbossdiary1

    38 min

  5. 07/31/2025

    #15: Don't Be Boring: Communication That Gets You Promoted | Laura Camacho (Executive Presence Coach)

    Laura Kamacho is an executive coach specialising in communication and executive presence, leading her own company and a popular podcast -Speak Up: Develop Your Executive Presence & Leadership Communication Style Her diverse background in business, economics, and science surprisingly enhances her communication expertise, as she believes improving communication can transform one's career outlook. Key Learnings and Advice on Business and Communication: When hiring, prioritise hungry and self-taught individuals and calibrate the role to their strengths, rather than solely focusing on academic degrees. Laura's business motivation stems from the "dopamine hits" of listeners finding her message useful, prompting her to proactively invest in her podcast's growth, even during economic downturns. The primary struggle for introverts and tech professionals in communication is a lack of confidence and knowing what to say. A core strength for introverts is their ability to think before speaking. Shift your mindset to consider yourself a "trusted advisor" whose duty it is to speak up to help the company succeed. Practically, thanking the questioner buys time and reduces stress, improving your response. Aim to provide an informed opinion that is "directionally accurate" rather than an exhaustive response. Utilise the "rule of three" to structure your messages effectively, making you sound competent and clear. Employ phrases like "This is important because..." to "sell it before you tell it" and capture your audience's attention. Follow Laura Kamacho on Linkedin  &  Apple Podcast Follow TechBossDairies on Tiktok: https://www.tiktok.com/@techbossdiaries Instagram: https://www.instagram.com/techbossdiary1/

    56 min

  6. 06/20/2025

    #14: The Outlier's Journey: From AI Research at Google to Asian Startups and Beyond | Angus Kong (AI Lead @Arta Finance )

    🎧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 Path Listeners—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 Insights As 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 Culture His 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 Challenges Stories 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 AI Amidst 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.

    47 min

  7. 05/25/2025

    #13: How Product Roles Are Changing, and What It Takes to Succeed as a Leader. | Deepika Rudra Murthy (Head of Product @ Gojek)

    🎙️ 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.

    49 min

  8. 03/23/2025

    #12: Web3, side hustles, AI tools— how Rice designs and hires for the future | Rice Tseng (Senior Design Manager@OKX)

    🎙 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. 🎧

    28 min
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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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