In Episode 41 of The Generalists Podcast, we sit down George Kassabgi (GK) — a two-time CEO, angel investor, technologist, and philosopher — to explore the art of fundraising, leadership, and startup strategy.

GK shares why raising capital feels like a ritualistic insect mating dance, highlighting the rhythm, back-and-forth, and delicate courtship between founders and investors. Drawing from three decades of experience across software infrastructure, NLP, ML, quant trading, and conversational AI, he offers practical and philosophical lessons every founder can apply.

What You’ll Learn in This Episode:

• How the Parent–Child analogy shapes founder decision-making
• Spotting hype vs. true paradigm shifts in software
• The most effective and damaging boardroom behaviors
• Why the CEO role is the loneliest job
• Poker analogies for investing discipline and risk
• Why raising capital is like an insect mating dance
• GK’s MoneyTime framework and how it guides life choices
• Why most AGI proclamations are nonsense
• How to master timeless skills despite technological revolutions
• Philosophical lessons from Stoicism, Vitae, and changing your mind

👥 Hosts:

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

👤 Guest:

• George Kassabgi: https://www.linkedin.com/in/georgek/

🔔 Don’t forget to subscribe for more founder stories, startup tips, and global tech trends.

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

🔗 Links & Resources:

• Bit9 / Carbon Black: https://en.wikipedia.org/wiki/VMware_Carbon_Black
• Real-time AI practice in English & Thai: https://phuk.et/
• Spoken Press: https://www.spoken.press
• Mendix: https://www.mendix.com
• Exuma Systems (Incubator): https://www.exuma.systems
• George on Medium: https://medium.com/@gk_
• Michael Pollan (How to Change Your Mind): https://michaelpollan.com/books/how-to-change-your-mind/
• Netflix Documentary (How to Change Your Mind): https://www.netflix.com/sg/title/80229847/
  

In Episode 40 of The Generalists Podcast, we sit down with Grace Clapham—fractional executive, community builder, former Meta director, and serial entrepreneur—to explore her multidimensional career journey. From launching fashion brands across Asia to shaping global community strategies at Meta, Grace shares insights on generalism vs. specialization, building sustainable communities, and rethinking leadership for the next generation.

What You’ll Learn in This Episode:

• How Grace pivoted from fashion marketing to social innovation after personal loss
• The mechanics of building thriving communities and why monetization isn’t taboo
• Lessons from leading global community partnerships at Meta
• East vs. West: how collectivism and individualism shape community-building
• Challenges and solutions for women’s entrepreneurial networks in Southeast Asia
• How the dynamics of wealth are shifting with more women as primary earners
• Redefining success beyond money, status, and traditional markers
• Why generalists and “neo-generalists” are the future of work
• Parenting, self-awareness, and raising confident kids in the AI era
• Grace’s advice to her 20-year-old self: embrace uniqueness and start earlier

👥 Hosts:

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

👤 Guest:

• Grace Clapham: https://www.linkedin.com/in/graceclapham

🔔 Don’t forget to subscribe for more founder stories, startup tips, and global tech trends.

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

🔗 Links & Resources:

• Meta (Facebook): https://about.meta.com
• The Change School: https://thechangeschool.com
• Gorman : https://www.gormanshop.com.au
• ConvertKit: https://convertkit.com
• ActiveCampaign: https://www.activecampaign.com
• Insight Timer: https://insighttimer.com
• The Psychology of Wealth: https://www.amazon.com/Psychology-Wealth-Understanding-Investing-Performance/dp/0470481593
• The Psychology of Money by Morgan Housel: https://www.morganhousel.com/the-psychology-of-money
• The Neo-Generalist by Kenneth Mikkelsen & Richard Martin: https://www.neogeneralist.com
• Ramit Sethi – I Will Teach You To Be Rich: https://www.iwillteachyoutoberich.com