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

In Episode 36 of The Generalists Podcast, we sit down with Shiyan Koh, Managing Partner at Hustle Fund, for a full-length conversation on how geography shapes entrepreneurship—and why the East-West divide isn’t as wide as you might think.

From Silicon Valley to Southeast Asia, what really sets these startup worlds apart?

What You’ll Learn:

• The cultural and operational differences in startups across regions
• How founders approach risk, fundraising, and growth in the East vs West
• Why local context matters for product-market fit and scaling
• Common misconceptions about global startup strategies
• The “density advantage” of Silicon Valley vs generalist talent in SEA
• Democratizing entrepreneurship via Hustle Fund’s Angel Squad
• Stack-ranking opportunities across emerging markets
• The generational shift in risk tolerance and ambition

Hosts:

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

Guest:

• Shiyan Koh: https://www.linkedin.com/in/shiyankoh/

Resources & Links:

• Hustle Fund: https://hustlefund.vc/
• Reap: https://reap.global/
• Jan Health: https://jan.health/
• CharterSpace: https://charterspace.co/
• Angel Squad: https://www.hustlefund.vc/squad
• A History of the People’s Action Party: 1985–2021: https://nuspress.nus.edu.sg/products/a-history-of-the-peoples-action-party-1985-2021
  

Sau Sheong Chang—Chief Technology Officer and Deputy Chief Executive of GovTech Singapore, and bestselling author of two Go-language books—drops by to code-switch with Michael & Raz on the future of technical leadership. From writing his first lines of C to shipping SingPass Mobile for five million citizens, Sau Sheong reveals how hands-on coding sharpens executive judgment, why GovTech runs like a startup inside the state, and how AI-augmented teams will rewrite the engineer’s career map over the next five years.

What You’ll Learn:

• Why he still writes code as a CTO

• Data-driven leadership lessons from GovTech, PayPal, & SP Group
• AI’s impact on software-engineering careers over the next 5 years
• Building “startup culture” inside government
• Counter-intuitive takeaways for building products
• The one thing he’d tell his 20-year-old self

• 
  

00:00 Introduction02:00 Writing and Publishing Books on Code02:24 Early Coding Journey and Java Era04:36 Transition to Ruby and Go09:31 Career Path and Opportunities12:43 Leading Engineering and Business Teams20:35 Singapore's Unique Tech Journey31:28 GovTech's Role and Responsibilities31:50 Smart Nation Initiative and Govtech34:15 The Role of AI in Software Engineering38:59 Impact of AI on Various Professions49:33 Advice for Startups and Engineers54:58 Reflections and Personal Insights

Hosts:

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

Guest:

• Sae Sheong Chang: https://www.linkedin.com/in/sausheong/

Resources & Links:

• GovTech Singapore: https://www.tech.gov.sg
• SP Group: https://www.spgroup.com.sg
• Temasek: https://www.temasek.com.sg
• Yuu Rewards: https://www.yuu.sg
• Codeium: https://www.codeium.com
• Revenge of the Tipping Point (Malcolm Gladwell): https://www.amazon.com/Revenge-Tipping-Point-Overstories-Superspreaders/dp/B0D5RFG8KQ/

Kevin Brockland, CFA, founder & managing partner of Indelible Ventures, sits down with Michael & Raz to map out what it really takes to build—and fund—tech-enabled B2B startups that can scale internationally. From choosing Malaysia as a launchpad to running a lean, AI-driven fund, Kevin shares the operator tactics and investor discipline that turn regional bets into global wins.

What You’ll Learn:

• Why Malaysia? Kevin’s contrarian thesis for basing a seed fund there—and the flywheel it unlocks
• Fundraising mastery: data-room hygiene, crisp narratives, and the art of saying “no”
• AI for VCs: specific automations Kevin uses to source, screen, and support deals
• Customer support = revenue: why most founders under-invest and how to fix it
• Building global-first B2B companies out of Southeast Asia—step-by-step guidance
• Well-being hacks: Kevin’s mental & physical regimen for sustainable performance
• One thing he’d tell his 20-year-old self that every emerging manager should hear

00:00 Introducing Kevin and Indelible Ventures04:06 Challenges of Raising a Fund in Malaysia09:31 The Role of AI in Emerging Markets19:18 Importance of Data Rooms for Startups23:44 Why We Invest: Decision-Making Insights30:01 The Importance of Saying No31:12 Tech-Enabled B2B Startups31:56 Understanding Consumer vs. B2B Markets32:58 The Evolution of Tech Ecosystems36:48 Customer Support as a Revenue Generator43:44 Challenges and Opportunities in ASEAN54:25 Advice to My 20-Year-Old Self56:13 Maintaining Physical and Mental Health58:17 Recommended Podcasts and Books

Hosts:

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

Guest:

Kevin Brockland: https://www.linkedin.com/in/kbrockland/

Resources & Links:

• Indelible Ventures: https://indelible.vc/
• Portfolio: https://indelible.vc/portfolio
• Kinetix Pro: https://www.kinetixpro.ai/
• K-Link: https://www.klink.cloud/
• Shoppable Business:https://shoppable.ph/
• The Next Big Idea podcast: https://podcasts.apple.com/us/podcast/the-next-big-idea/id1482067226
• Blinkist (book-summary app): https://www.blinkist.com/
• Lightspeed Venture Partners “Southeast Asia: Resetting Expectations” report: https://lsvp.com/stories/southeast-asia-resetting-expectations/
• The Big Bang Theory (TV series): https://www.warnerbros.com/tv/big-bang-theory