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/