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

From matching algorithms and cost optimization to the cultural realities of why companies resist change, Paul Endacott explains how AI and globalization are colliding to reshape how every company builds its team.

In the Generalists Episode 49 with Paul Endacott we unpack how automation is rewriting the economics of hiring, why global talent hubs from Vietnam to the Philippines are transforming access to skilled workers, and what “grit” really means in a world where technology can do most of the work. Paul shares twenty years of recruitment lessons — from launching Grit Search one month before COVID to building Freshly Baked into a cross-border hiring engine — and how founders, employers, and professionals can future-proof themselves in this new talent economy.

📖 What You’ll Learn in This Episode:

• How the Grit Search Talent Platform evolved into Freshly Baked
• Why traditional recruitment models failed to adapt to AI and automation
• The economics behind $20 K placements vs $1 K automated matches
• How companies are tapping Malaysia, Vietnam & the Philippines for talent
• Why the next edge is “borderless recruitment” — and how to leverage it
• How founders and professionals can build career resilience in an AI-driven world

👥 Hosts

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

👤 Guest

• Paul Endacott — Founder & CEO of GRIT & Freshly Baked: https://www.linkedin.com/in/paulendacott/

🔔 If you’re fascinated by the intersection of AI, recruitment, and global workforces — and want to hear how founders are rewriting the rules of hiring — hit subscribe and turn on notifications!

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

🔗 Resources & Links Mentioned

🚀 Companies & Platforms

• Grit Search(Recruitment & Search): https://www.gritsearch.com/
• Freshly Baked (Global Talent Platform): https://freshlybaked.io/
• Deel (EOR Platform): https://www.deel.com/
• Multiplier (Global Hiring): https://www.usemultiplier.com/
• Remote (Global Employment Platform): https://remote.com/
• Squads (Team Extension Platform): https://www.squads.com/

🌏 Markets & Ecosystem References

• Philippines Tech Talent Market Overview – World Bank: https://www.worldbank.org/en/country/philippines
• Vietnam Digital Workforce Report – Google & Temasek: https://economysea.withgoogle.com/
• Malaysia Digital Economy Blueprint – MDEC: https://mdec.my/

📚 Books & Ideas

• Grit by Angela Duckworth: https://www.amazon.com/Grit-Passion-Perseverance-Angela-Duckworth/dp/1501111108

• Atomic Habits by James Clear: https://www.amazon.com/Atomic-Habits-Proven-Build-Break/dp/0735211299

🧠 Concepts & Frameworks

• AI Automation in Recruitment – McKinsey Insights: https://www.mckinsey.com/capabilities/operations/our-insights/the-future-of-recruiting
• Global Talent Mobility & EOR Models – PwC Report: https://www.pwc.com/globaltalentmobility

In Episode 46 of The Generalists Podcast, we sit down with Benjamin “Mr. Miyagi” Lee — pioneering blogger, comedy writer, and Creative Director at Beach House Pictures (a Fremantle company).
From inventing Singlish on the page with Mr Brown, to building stories that cut through censors and land on Netflix, Miyagi unpacks the craft of storytelling that changes minds, policies, and even lives. His journey is a rare look at the evolution of Singapore’s creator culture and how storytelling adapts to new mediums, technologies, and global audiences.

🚀 What You’ll Learn in This Episode:

• How Singapore’s blogging boom kickstarted modern creator culture

• The origins of podcasting with Mr Brown & “Mr. Miyagi”

• Writing comedy under constraints and working the censors

• Building global-ready content at Beach House Pictures

• Why AI is an intern, not a muse, for storytellers

• Fitness after 50, sobriety at 52, and habit engineering

• Parenting and homeschooling a world champion indoor skydiver

👥 Hosts

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

👤 Guest

• Benjamin “Mr. Miyagi” Lee: https://www.linkedin.com/in/miyagi/

🔔 If you love founder stories, creator journeys, and insights for generalists navigating uncertain times — hit subscribe and turn on notifications!
👉👉👉 Subscribe Now: https://www.youtube.com/@TheGeneralistsPodcast

🔗 Links & Resources

• Beach House Pictures: https://www.beachhousepictures.com/

• Mr Brown Blog: https://www.mrbrown.com/

• Perplexity AI : https://www.perplexity.ai/

• The Body: A Guide for Occupants - Bill Bryson: https://www.amazon.com/Body-Guide-Occupants-Bill-Bryson/dp/0385539304

• Burma Sahib - Paul Theroux: https://www.amazon.com/Burma-Sahib-Paul-Theroux/dp/1324076035

• iFly Singapore (indoor skydiving): https://www.iflysingapore.com/

• Kyra Poh: https://www.redbull.com/sg-en/athlete/kyra-poh

• Kai Minejima-Lee: https://www.channelnewsasia.com/today/up-close/world-cup-champion-indoor-skydiving-teenager-kai-minejima-lee-5302251

In Episode 45 of The Generalists Podcast, we sit down with Veli Kattoulas — CEO of Lanturn, former investigative journalist, and founder of multiple companies across Japan, Hong Kong, and Singapore.

From reporting on the Yakuza in 1990s Japan to navigating startup competition and scaling internationally, Veli shares hard-won lessons on resilience, discipline, and the art of “muddling through” when building enduring companies. His story is a masterclass in reinvention and the generalist mindset.

🚀 What You’ll Learn in This Episode:

• How frontline journalism trains you to make decisions under pressure

• Insights into Yakuza–politics connections in 1990s Japan

• Lessons from startup failures and competitors with deeper pockets

• Real-world product validation and pricing strategies

• Why discipline and speed are key for startup growth

• Scaling a company in Singapore vs expanding internationally

👥 Hosts
Michael Smith Jr.: https://www.linkedin.com/in/smittysgp
Razko Kotler: https://www.linkedin.com/in/razko282

👤 Guest
Veli Kattoulas: https://www.linkedin.com/in/velikattoulas/

🔔 Subscribe for more founder stories, startup wisdom & intrapreneurship insights:
👉👉👉 Subscribe Now: https://www.youtube.com/@TheGeneralistsPodcast

🔗 Links & Resources

• Lanturn (company): https://www.lanturn.com/

• Obliquity — John Kay: https://www.amazon.com/Obliquity-John-Kay/dp/1846682899

• Monetizing Innovation — Madhavan Ramanujam & Georg Tacke: https://www.amazon.com/Monetizing-Innovation-Companies-Design-Pricing/dp/1119240867

• Slow Horses (TV show): https://tv.apple.com/us/show/slow-horses/

• Middlesex — Jeffrey Eugenides: https://www.amazon.com/Middlesex-Novel-Jeffrey-Eugenides/dp/0312427735

• Tokyo Vice — Jake Adelstein: https://www.amazon.com/Tokyo-Vice-American-Reporter-Police/dp/0307475298

• Techmeme Ride Home (podcast): https://www.ridehome.info/techmeme-ride-home/

• MarkMonitor brand protection (Clarivate): https://clarivate.com/markmonitor/

• Taobao marketplace: https://www.taobao.com/

In Episode 44 of The Generalists Podcast, we sit down with Gustavo Fuchs — Microsoft Asia Channels, ex Google Cloud leader who’s led teams across Brazil, Turkey, Bahrain, Angola, Dubai, and Singapore. He shares powerful insights on AI adoption, intrapreneurship, and the real advantages of being a generalist in complex organizations.

Gustavo explains why the true generalist advantage—understanding the whole system (P&L, leverage points, structure, and culture)—only works if you keep your entrepreneurial spirit alive. By connecting with startups, outsider communities, and fresh perspectives, you avoid corporate complacency and bring new energy back into your company.

🚀 What You’ll Learn in This Episode:

• The AI value chain: research → models → infra → apps/agents
• Where margins accrue in AI and how to pick high-leverage use cases
• Turning “experiments” into board-level, KPI-tied initiatives
• Build vs. buy decisions for AI and agentic workflows
• The “1%” most teams miss: internal selling & HQ alignment
• Intrapreneurship strategies: creating healthy tension in big orgs
• A practical lens for model builders, digital natives & enterprises
• Cross-cultural leadership playbooks for global GTM success
• Energy management: how to stay “always-on” without burnout

👥 Hosts

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

• 
  

👤 Guest

• Gustavo Fuchs: https://www.linkedin.com/in/gustavofuchs/

🔔 Subscribe for more founder stories, startup wisdom & intrapreneurship insights:

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

🔗 Links & Resources

• The Culture Map (book): https://www.amazon.com/Culture-Map-Breaking-Invisible-Boundaries/dp/1610392507

• Chip War (book): https://www.amazon.com/Chip-War-Worlds-Critical-Technology/dp/1982172002

• XA Network: https://www.xanetwork.co/
• Accelerating Asia: https://www.acceleratingasia.com/