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 onTiktok: https://www.tiktok.com/@techbossdiariesInstagram: https://www.instagram.com/techbossdiary1

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/@techbossdiariesInstagram: https://www.instagram.com/techbossdiary1

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 onLinkedin  &  Apple PodcastFollow TechBossDairies on Tiktok: https://www.tiktok.com/@techbossdiariesInstagram: https://www.instagram.com/techbossdiary1/

🎧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.  

🎙️ 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.

🎙 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. 🎧

🎙 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. 🎧

🎙️ 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

🎙️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

🎙 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.

🎙 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.

🎙 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.

🎙 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.

🎙 In this episode with Tina Huang, we uncover: The soft skills junior designers really need and how to handle feedback from different stakeholders. Navigating tricky situations at work—how to escalate issues and the softer ways to manage things afterward. Performance reviews: Does taking on more responsibility lead to a promotion?  Tina’s advice to her younger self and what keeps her motivated to continue pursuing the designer pathway.

🎙 In this episode with Tina Huang, we uncover: Her journey from navigating different education systems to thriving in her career How to assess job opportunities and know if your manager is the right fit. What to do when you’ve lost interest in your field—and when it’s time to move on. Key hard skills for junior designers, including her "2 Diamond Process."

We're back with Cathy Chang, the amazing General Manager at ASUS AICS Singapore. She's leading a diverse team in AI research, machine learning, software engineering, product management, design, and business development—all working on cutting-edge medical software and AI products. With over 20 years of experience across the US, China, and Singapore. Today, we're talking about a hot topic for fresh grads: Should you join a startup or a big multinational company (MNC)? And how important are those FAANG (Facebook, Amazon, Apple, Netflix, Google) companies really? In this conversation, we'll cover: How to decide if a startup or an MNC is the right fit for you Whether FAANG companies are crucial for your career What specific skills you need to thrive in both environments// Join our Facebook discussion group to ask Cathy your questions directly. // FB Group: https://www.facebook.com/groups/821267593465298

In this episode, we have an amazing guest, Cathy Chang, who's currently the General Manager at ASUS AICS Singapore. Cathy leads a diverse team in AI research, machine learning, software engineering, product management, design, and business development, all focused on creating medical software and AI products. With over 20 years of product experience in both B2B and B2C sectors across the US, China, and Singapore, With over 20 years of experience across the US, China, and Singapore, Cathy's got some amazing insights to share. In this conversation, we'll cover: The cultural and workflow differences between startups and big multinational companies (MNCs) The challenges Cathy faced adapting to different work environments—like the fast-paced hustle of startups versus the structured world of MNCs If you're just starting your tech career and wondering whether to join a startup or a big company, this episode is packed with tips to help you decide what's right for you.// Join our Facebook discussion group to ask Cathy your questions directly. // FB Group: https://www.facebook.com/groups/821267593465298