When Bernard Leong looks across Asia’s enterprise landscape, he sees a widening split between two worlds: companies still experimenting with AI, and those already realizing value at scale.

In the full episode of The Generalists, Bernard Leong, founder of Dorje AI and host of Analyse Asia, joins Michael Smith Jr. and Raz Kotler to unpack the findings from the Cisco AI Readiness Index 2025. The data reveals a striking new divide: while most enterprises are still stuck in pilot mode, a small minority — the “pacesetters” — have mastered data readiness, network architecture, and cultural flexibility to scale AI across their operations and unlock measurable ROI.

📖 What You’ll Learn in This Episode

• Why Asia’s AI economy is splitting into “experimenters” and “value creators”
• How Thailand and Indonesia are leapfrogging Singapore in enterprise AI adoption
• What separates true AI readiness from isolated pilot projects
• Why back-office automation is delivering the clearest early ROI
• How data maturity, network infrastructure, and cultural agility drive scaling success
• The emerging role of AI agents — and the hidden security and workflow implications
• What CEOs should start (and stop) doing to build practical AI readiness

👥 Hosts

• Michael Smith Jr.: https://www.linkedin.com/in/smittysgp/
• Raz Kotler: https://www.linkedin.com/in/razko282/

👤 Guest

• Bernard Leong: https://www.linkedin.com/in/bleongcw/

🔗 Resources & Links Mentioned

🚀 Reports & Research

• Cisco AI Readiness Index 2025: https://www.cisco.com/c/m/en_us/solutions/ai/readiness-index/realizing-the-value-of-ai.html
• Cisco AI Readiness Index 2025 – Full PDF: https://www.cisco.com/c/dam/m/en_us/solutions/ai/readiness-index/2025-m10/documents/cisco-ai-readiness-index-2025-realizing-the-value-of-ai.pdf
• McKinsey Global Survey on AI (2024): https://www.mckinsey.com/capabilities/quantumblack/our-insights/the-state-of-ai-2024
• MIT Report – 95 % of GenAI Pilots Fail: https://www.computing.co.uk/news/2025/ai/mit-report-95pc-corporate-generative-ai-pilots-fail

🧠 Technology & Tools

• DeepSeek-OCR:https://www.deep-seek-ocr.org/en
• Dorje A: https://dorje.ai

From global campaigns and TEDx Singapore to rebuilding life in Southeast Asia at 50+, Christopher Smith has spent three decades mastering the skill machines can’t replace: asking better questions.

In Episode 52 of The Generalists, Christopher joins Michael and Raz to unpack the real advantage humans have in the age of AI — lived experience, cultural intelligence, curiosity, and the willingness to interrogate assumptions. He shares the story of arriving in Singapore “with a chip on his shoulder” and how being publicly called out in a StarHub meeting reshaped his leadership forever.

Christopher reveals why AI isn’t a threat, but a multiplier — if you know how to use it. From launching Rock Paper Scissors, a fully AI-augmented creative studio, to publishing his book Question Is to Answer, he shows how reinvention becomes possible at any age once you realize better questions = better outcomes.

This is a conversation about humility, creativity, and how to future-proof yourself — no matter what technology does next.

📖 What You’ll Learn in This Episode

• The #1 human skill AI can’t replicate: questioning & critical thinking
• How getting humbled in Singapore unlocked cross-cultural leadership
• Why “Asia isn’t one market” and how to actually work here successfully
• How generative AI expands creative depth and pattern recognition
• The danger of binary questions — and how to ask expansive ones instead
  • Why experience becomes a competitive advantage in the AI era
  • The mindset behind lifelong reinvention — especially after 50

👥 Hosts

• Michael Smith Jr.: https://www.linkedin.com/in/smittysgp
• Raz Kotler: https://www.linkedin.com/in/razko282/

👤 Guest

• Christopher Smith: https://www.linkedin.com/in/christophersmithsg/

🔗 Resources & Links Mentioned🚀 Companies & Projects

• Rock Paper Scissors: https://rockpaperscissors.sg

• 50 Over 50 Campaign (Singapore): https://www.a50over50.com

📚 Books & Ideas

• To Question Is to Answer by Christopher Smith: https://www.amazon.sg/Question-Answer-Think-Critically-Thrive/dp/B0DZ2YM6K1/
• Idea Flow by Jeremy Utley & Perry Klebahn: https://www.amazon.com/Idea-Flow-Creative-Businesses-Win/dp/0593239613
• The Algebra of Happiness by Scott Galloway: https://www.amazon.com/Algebra-Happiness-Equations-Meaning-Life/dp/0593084195

🧠 Concepts & Frameworks

• Cross-Cultural Intelligence & Listening Before Designing – Harvard Business Review: https://hbr.org/2015/09/what-is-cultural-intelligence
• The Humility Framework for Global Leaders – INSEAD Knowledge: https://knowledge.insead.edu/leadership-organisations/why-humility-works-for-leaders
• Creative Empathy in the AI Age – MIT Sloan Management Review: https://sloanreview.mit.edu/article/human-creativity-in-the-age-of-ai/

From insurance disruption and billion-dollar exits to rethinking how money should feel, Walter de Oude has spent two decades building companies that challenge the way we think about value, trust, and happiness.

In Episode 51 of The Generalists, Walter sits down with Michael and Raz to unpack the journey from actuary to entrepreneur — from founding Singlife, Singapore’s first homegrown digital insurer that scaled to over $4 billion AUM, to launching Chocolate Finance, a new kind of fintech designed to make money feel good.

He shares how the experience of building — and later leaving — a billion-dollar company reshaped his view of work, purpose, and leadership. Walter explains why meaning and happiness, not résumés or capital, are the true measures of success — and why every founder should wake up and ask one thing: Do I love my life?

📖 What You’ll Learn in This Episode

• Why “Do I love my life?” is the ultimate founder metric
• How Walter built Singlife to fix an industry that “sucked”
• Why Chocolate Finance was designed as a happy place for money
• How purpose and impact outweigh skills or credentials
• The mindset shift from corporate operator to infinite-game founder
• Lessons on balance, family, and designing a fulfilling life

👥 Hosts

• Michael Smith Jr.: https://www.linkedin.com/in/smittysgp/

• Raz Kotler: https://www.linkedin.com/in/razko282/

👤 Guest

• Walter de Oude — Founder of Singlife & Chocolate Financehttps://www.linkedin.com/in/walterdeoude/

🔔 If you’ve ever questioned what success really means — and how to build a life you actually love — this video is for you.

👉 Subscribe Now: https://www.youtube.com/@TheGeneralistsPodcast

🔗 Resources & Links Mentioned

🚀 Companies & Platforms

• Chocolate Finance – https://chocolatefinance.com
• Singlife – https://singlife.com

📚 Books & Ideas

• The Infinite Game — Simon Sinek https://www.amazon.com/Infinite-Game-Simon-Sinek/dp/073521350X

• Adrift: America in 100 Charts — Scott Galloway https://www.amazon.com/Adrift-America-100-Charts/dp/0593540401

🧠 Concepts & Frameworks

• The Infinite Game Mindset — Simon Sinek https://simonsinek.com
• Trust in Fintech — Accenture Study https://www.accenture.com/sg-en/insights/financial-services/fintech-trust
• Founder Resilience — Harvard Business Review https://hbr.org