Episodios

  • 🎙️ #57 Is Southeast Asia Finally Investable? AI, SGX & Grab+Gojek & 2026

    🎙️ #57 Is Southeast Asia Finally Investable? AI, SGX & Grab+Gojek & 2026
    Nov 29 2025
    A high-signal, no-filter roundtable with• Hian Goh (OpenSpace Capital)• Alex Dwek (COO, Nas.io)• Michael Smith Jr. (The Generalists)• Raz Kotler (The Generalists)Southeast Asia just had a rare real win — the Hepmil acquisition — and this episode breaks down why it matters, why early backers actually made money, and how this exit finally gives founders a real benchmark in the creator & media ecosystem. From there, the table dives into AI, sovereign compute, Grab+Gojek merger dynamics, the future of SGX, ASEAN as an investable region, and why 2026 may be the most interesting year yet for Southeast Asia.This is the full uncut November roundtable — strategy, insights, debates, predictions, and the occasional spicy jab.📖 What You’ll Learn in This EpisodeWhy the Hepmil acquisition is a meaningful benchmark for Southeast AsiaThe VC behind Hepmil and why his connections matteredReal revenue, real EBITDA, and the fundamentals that drove the dealEarly-stage outcomes: houses, windfalls… and realistic 20× returnsWhy Publicis was the natural acquirer (“fingerprints all over it”)The MCN model & why it died in the U.S. but still works in AsiaHow influencer networks succeed (or fail) across the regionWhy this exit helps agency and creator founders pitch with confidenceThe truth behind “overnight success” stories and multi-pivot journeysThe real state of AI: compute demand, sovereign AI, specialized modelsWhether we’re in an AI bubble and what the big tech earnings revealGrab+Gojek merger logic, regulation, and what consolidation would meanHow ASEAN can produce the next wave of $10B+ companiesSGX’s dual-listing mechanism with NASDAQ and what it unlocksHow India’s IPO boom influences SEA founder psychologyWhat the table is excited about heading into 2026👥 The Table Hian Goh: https://www.linkedin.com/in/hiangoh/Alex Dwek: https://www.linkedin.com/in/alexdwek/Michael Smith Jr.: https://www.linkedin.com/in/smittysgp/Raz Kotler: https://www.linkedin.com/in/razkotler/🔗 Links & MentionsHepmil: https://www.hepmil.comPublicis Groupe: https://www.publicisgroupe.comQuest Ventures: https://www.questventures.comTBWA: https://tbwa.comAsian Food Channel: https://www.asianfoodchannel.comMCN (Multi-Channel Network): https://support.google.com/youtube/answer/2737059Nas.io: https://nas.ioGrab https://www.grab.comGojek: https://www.gojek.com🔔 Subscribe for more founder stories, startup wisdom & entrepreneurial insights.YouTube: https://www.youtube.com/@TheGeneralistsPodcastSpotify: https://open.spotify.com/show/2apfGY403NGr1EyTNkJfG4?si=a25c777a19854616Apple Podcasts: https://podcasts.apple.com/sg/podcast/the-generalists
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    54 m
  • 🎙️ #56 The Future of Work is Fractional: Build a Portfolio Career

    🎙️ #56 The Future of Work is Fractional: Build a Portfolio Career
    Nov 27 2025

    From banking in Sydney and Tokyo to co-founding YOLO, getting acquired by Singlife, and building Mission Plus into a leading fractional-work and tech-delivery company. Nick Martin has lived every chapter of the modern career evolution.

    In this full Episode 56 of The Generalists, Nick breaks down how employment, talent, and technology are changing faster than companies can keep up. He explains why fractional leadership is surging, how startups can avoid classic tech-build mistakes, and how the 8+2 Career Model helps ambitious professionals build career resilience without quitting their full-time roles.

    This is a deep dive into the future of work: portfolio careers, AI-enabled teams, cross-border talent, and why curiosity and autonomy are becoming the most important professional skills.

    📖 What You’ll Learn in This Episode

    • How fractional leadership is reshaping how companies build and scale
    • Why Mission Plus emerged from necessity and why “boring businesses” still win
    • Lessons from building YOLO and selling to Singlife
    • How tech layoffs, remote work, and AI changed the supply/demand of talent
    • The 8 + 2 Career Model and why professionals want portfolio-style careers
    • How startups misuse CTO hires and a better model for early-stage product builds
    • Why enterprises struggle to adopt AI beyond prototypes
    • Why curious generalists are becoming more valuable than ever
    • Why Singapore, the Middle East, and APAC are shifting toward fractional adoption
    • How immigration rules, work permits, and PR status impact fractional work

    👥 Hosts

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

    👤 Guest

    • Nick Martin: https://www.linkedin.com/in/nicholasrjmartin/

    🔗 Resources & Links Mentioned

    🚀 Companies & Platforms

    • Mission Plus: https://www.mission.plus/
    • Singlife: https://singlife.com
    • Citigroup: https://www.citigroup.com
    • Visa: https://www.visa.com
    • Fireflies.ai: https://fireflies.ai
    • Cold Plunge Singapore: https://coldplunge.sg/

    📚 Blogs

    • The Future Will Not Fit into the Containers of the Past (Rishad Tobaccowala): https://rishadtobaccowala.com
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    54 m
  • 🎙️ #55 Reinvention Playbook: How Generalists Win in the AI Era

    🎙️ #55 Reinvention Playbook: How Generalists Win in the AI Era
    Nov 19 2025
    From airline security shifts in Kyiv to retail entrepreneurship, Malaysian trade diplomacy, Microsoft, Broadcom, and now Cisco ThousandEyes, Elena Lukyanenko has lived five careers in one lifetime - long before she had the language for what it meant to be a generalist.In Episode 55 of The Generalists, Elena joins hosts Michael Smith Jr. and Raz Kotler to unpack how she reinvented herself across industries and continents, how she navigated layoffs twice, and why she believes that generalists thrive in chaotic environments. She explains her framework for “high-level generalism,” the internal work required to prepare for inevitable career shocks, and why identity cannot be built on titles alone.It’s a candid conversation on the realities of layoffs, career pivots, cultural transitions, self-discovery, and what it takes to build a meaningful life across borders. 📖 What You’ll Learn in This EpisodeHow Elena built careers across security, retail, trade, tech, cloud, and AI without a linear planWhy generalists thrive through pattern recognition, adaptability, and skill transferHow to prepare for layoffs before they happen and rebuild identity after job lossThe psychology behind reinvention, momentum, and avoiding the “victim spiral”The surprising story behind launching Graceful Edge and overcoming writing traumaHow dance, strength training, and tea ceremony anchor her mental performance👥 Hosts Michael Smith Jr.: https://www.linkedin.com/in/smittysgp/Raz Kotler: https://www.linkedin.com/in/razkotler👤 GuestElena Lukyanenko: https://www.linkedin.com/in/elukyanenko/🔗 Resources & Links Mentioned🚀 Companies & PlatformsCisco ThousandEyes: https://www.thousandeyes.comMicrosoft: https://www.microsoft.comBroadcom: https://www.broadcom.comPTL Group: https://www.ptl-group.comGraceful Edge (Elena’s Substack): https://www.thegracefuledge.comYammer: https://www.yammer.comPerplexity: https://www.perplexity.aiClaude: https://claude.aiGemini: https://ai.google/ChatGPT: https://chat.openai.com🎬 MoviesHer (2013): https://www.imdb.com/title/tt1798709📚 BooksPSI Book (correct “C Book”): https://psi-book.com🧠 Communities & EventsLean In - Women in Tech: https://leanin.org/circles/lean-in-women-in-tech
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    59 m
  • 🎙️ #54 From Google to Peek: Designing Money for Gen Z

    🎙️ #54 From Google to Peek: Designing Money for Gen Z
    Nov 10 2025

    From swimming lanes to startup lanes, Sherry Jiang has always been a generalist — long before she had a word for it.

    In Episode 54 of The Generalists, Sherry joins hosts Michael Smith Jr. and Raz Kotler to explore how ADHD, behavioral science, and design thinking shaped her journey from Google to Peek - a behavioral-finance app redefining what “money management” really means. She explains why she sees money as autonomy, not accumulation, and how combining psychology, AI, and financial design can build products that actually change habits.

    It’s a candid conversation on cognitive diversity, consumer psychology, and the future of AI-assisted startups - from building a viral Gen Z finance brand to teaching founders how to “vibe-code” with AI.

    📖 What You’ll Learn in This Episode

      • Why being a generalist is a competitive advantage in a chaotic world

      • How ADHD drove Sherry’s obsession with behavioral science and design for emotion

      • What she learned at Google about gamification and the psychology of trust

      • Why Peak frames money as empowerment, not management

      • How AI is transforming product design, founder skill sets, and startup culture

      • The behavioral economics behind “doom-spending” and saving as identity

      • Why personal finance remains one of the hardest categories to build — and why she insists on tackling it


      👥 Hosts

      • Michael Smith Jr. – https://www.linkedin.com/in/michaelsmithjr
      • Raz Kotler – https://www.linkedin.com/in/razkotler

      👤 Guest

      • Sherry Jiang – https://www.linkedin.com/in/sherry/


      🔗 Links & Resources Mentioned

      🚀 Companies & Projects

      • Peak: https://www.peakmoney.app
      • Google Pay - Behavioral Design Team:https://pay.google.com/about


      📚 Books & Ideas

      • Range: Why Generalists Triumph in a Specialized World – David Epstein: https://www.amazon.com/dp/0735214484
      • Nudge – Richard Thaler & Cass Sunstein: https://www.amazon.com/dp/014311526X


      🧠 Concepts & Frameworks

      • Behavioral Science & Decision Design: https://en.wikipedia.org/wiki/Behavioral_economics
      • Cognitive Diversity & Rare Complementary Skills: https://hbr.org/2018/07/the-case-for-generalists


      🎬 Cultural References

      • K-Pop Demon Hunters (Netflix): https://www.netflix.com/title/81462921
      • Headspace: https://www.headspace.com
      • Duolingo: https://www.duolingo.com
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    1 h
  • 🎙️ #53 Asia's AI Divide: "The Experimenters" vs "The Value Creators"

    🎙️ #53 Asia's AI Divide: "The Experimenters" vs "The Value Creators"
    Nov 6 2025

    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
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    28 m
  • 🎙️ #52 The One Skill That Beats AI Every Single Time

    🎙️ #52 The One Skill That Beats AI Every Single Time
    Oct 29 2025

    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/
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    1 h
  • 🎙️ #51 What Happens After a $4 Billion Exit - Walter de Oude’s Next Chapter

    🎙️ #51 What Happens After a $4 Billion Exit - Walter de Oude’s Next Chapter
    Oct 23 2025

    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
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    42 m
  • 🎙️ #50 From Microsoft to Microphones - Borko’s Leap from Corporate to Creator

    🎙️ #50 From Microsoft to Microphones - Borko’s Leap from Corporate to Creator
    Oct 20 2025
    From live studios and community building to the software stack powering a new generation of creators, Borko Kovacevic shares how leaving corporate life at Microsoft led him to build Poddster—a company redefining what it means to create and scale in the modern media economy.In The Generalists episode 50, recorded live at Poddster Singapore, we unpack how one founder turned a dusty construction site into Asia’s most influential creator hub — and then evolved it into a global SaaS platform now powering over 100 studios worldwide. Borko reveals how community replaced advertising, how operational discipline became a moat, and why podcasting is no longer a niche but an infrastructure layer for the creator economy.He takes us behind the scenes of Poddster’s growth story — from SOP-driven studio operations to partnerships with Stripe and Microsoft, and an upcoming global creator summit in New York — showing how discipline, community, and product thinking can scale even the most analog businesses.📖 What You’ll Learn in This Episode:How Poddster grew from a single Singapore studio into a 100-studio global networsWhy “community over capital” became Poddster’s strongest growth engineThe operational systems (SOPs) that turned creativity into scalable processHow Stripe and Microsoft helped accelerate Poddster’s global SaaS platform PodyxWhy video-first storytelling defines the next wave of the creator economyLessons from leaving corporate life and building from zero in a new industryHow consistency and founder-led iteration drive durable, compounding growth👥 HostsMichael Smith Jr.: https://www.linkedin.com/in/smittysgp/Raz Kotler: https://www.linkedin.com/in/razko282/👤 GuestBorko Kovacevic — Founder & CEO, Poddster: https://www.linkedin.com/in/borko-kovacevic/🔔 If you’re fascinated by how creator infrastructure, community, and technology intersect — and want to learn how one founder built a global media platform from scratch — hit subscribe and turn on notifications!👉👉👉 Subscribe Now: https://www.youtube.com/@TheGeneralistsPodcast🔗 Resources & Links Mentioned🚀 Companies & PlatformsPoddster (Studios & Creator Platform): https://poddster.comPodyx (Rev Ops for Podcast Studios): https://www.podyx.com/Stripe (Commerce Infrastructure): https://stripe.comMicrosoft (Cloud & Productivity): https://microsoft.comDiary of a CEO (Podcast & Live Tour): https://thediaryofaceo.comModern Wisdom (Chris Williamson): https://www.youtube.com/@ModernWisdomPodcastAll-In Podcast (Technology & Venture): https://www.allinpodcast.coWPP (Brand & Media Group): https://www.wpp.com🌏 Ecosystem & Community ReferencesCreator Economy 2025 Outlook – SignalFire: https://signalfire.com/creator-economy-2025Southeast Asia Digital Economy Report – Google & Temasek: https://economysea.withgoogle.comPodcast Industry Trends – Spotify for Podcasters: https://podcasters.spotify.com📚 Books & IdeasRange: Why Generalists Triumph in a Specialized World – David Epstein: https://www.amazon.com/Range-Generalists-Triumph-Specialized-World/dp/0735214484Show Your Work! – Austin Kleon: https://www.amazon.com/Show-Your-Work-Austin-Kleon/dp/076117897X🧠 Concepts & FrameworksCommunity-Led Growth – HubSpot Insights: https://blog.hubspot.com/community-led-growthOperational Excellence in Creative Studios – Harvard Business Review: https://hbr.orgCreator Infrastructure Stack – Andreessen Horowitz (“The Creator Economy 2.0”): https://a16z.com/creator-economy-2-0
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    26 m