Poker, Stoicism & Startups: Mental Models That Actually Work

In episode 41, we sit down with 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

🕒 Chapters
00:00 Welcome & Introductions
03:57 Reconnecting & Guest Background
07:54 Engineering at WebLogic
11:51 Moving to Thailand
15:48 AI Tools in Daily Life
19:45 Building Language Apps
23:42 Startup Mental Models
27:39 Lessons from Early Startups
31:36 Product-Market Fit & Investment
35:33 Poker & Business Lessons
39:30 Raising Capital: The Dance
43:27 Changing Your Mindset
47:24 Life in Asia & Tech Differences
51:21 Advice to 20-Year-Old Self
55:18 Health, Books, and Final Thoughts

👥 Hosts
Michael Smith Jr.:   / smittysgp  
Razko Kotler:   / razko282  
https://phuk.et/

👤 Guest
George Kassabgi:   / georgekassabgi  

🔔 Subscribe for more founder stories & startup wisdom
👉👉👉 Subscribe Now:    / @thegeneralistspodcast  

🔗 Links & Resources
Bit9 / Carbon Black: https://en.wikipedia.org/wiki/VMware_...
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:   / gk_  
Michael Pollan (How to Change Your Mind): https://michaelpollan.com/books/how-t...
Netflix Documentary (How to Change Your Mind): https://www.netflix.com/sg/title/8022...

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