We hit publish in October this year with a simple goal: have honest, operator-level conversations with founders building real businesses across Asia. Today’s episode is a rewind of the moments that stayed with us: building through pivots, the realities of raising money, hard decisions, and what it takes to scale across markets and time zones. Expect standout takeaways on AI learning and product validation, global payments and stablecoin rails, business lending, automotive marketplaces, and closing protection gaps through embedded insurance.
💡 What You’ll Hear About
AI education before the hype, and what “AI” actually meant when most people were not paying attention
Personalized learning at scale, including why tailoring to each student matters when resources are tight
Building through constraints and pivots, from adoption friction to making tough resets when the model has to change
AI in eye health and clinical trust, and what it takes to win over conservative medical stakeholders where safety is non-negotiable
Fintech execution in Southeast Asia, and why business lending is an on-the-ground operating problem, not just a product thesis
Scaling a car platform beyond classifieds, including how financing and insurance become real growth levers
Payments infrastructure and stablecoin rails, built for real-world merchants without the “crypto experience,” plus operational realities
Lessons learnt: leadership under pressure, including the hardest calls founders make, the emotional cost, and how teams rebuild and grow
⏱️ In this Episode
0:00 – Introduction
0:36 – Joleen Liang - “AI” before it was a buzzword: adaptive learning and scalable education
2:07 – Kevin Choi - Eye health + AI: earning clinician trust when safety comes first
2:54 – Kelvin Teo - Harvard-to-Southeast Asia: why fintech opportunity is real, but execution is everything
7:02 – Aaron Tan - Building in an “unsexy” category: why cars can still be a massive business
10:48 – David Isaac - From idea to real business: validation, A/B testing, and scenario thinking
14:48 – Rob Schimek - The future of insurance: protection gaps, distribution, and what actually scales
18:07 – Joleen Liang - Going global in edtech: the US market, localization, and teacher capacity constraints
21:44 – Eric Barbier - Stablecoins without the crypto experience: global merchants, time zones, and real use cases
26:17 – Aaron Tan - Scaling into new countries: team first, local realities, and avoiding expensive mistakes
28:39 – Kevin Choi - Fundraising reality check: “money is cold” and what that teaches founders
30:07 – Eric Barbier - How VCs think: incentives, expectations, and the founder–investor mismatch
31:12 – Kelvin Teo - Timing and conviction: raising when it matters, and what investors look for
32:32 – Rob Schimek - Proving you are worth backing: partners, differentiation, and defensibility
36:47 – Neo Zhizhong - The hardest leadership decision: letting people go and living with it
37:56 – Kevin Choi - Hiring and HR mistakes: what Kevin regrets and what he learned
39:34 – Aaron Tan - Expansion lessons: what did not go to plan and how to recover fast (Aaron)
41:36 – Joleen Liang - “Rising from the ashes”: regulatory shock, revenue collapse, and the pivot
48:00 – Eric Barbier - Leadership style: autonomy vs micromanagement, and what teams need
49:25 – Aaron Tan - Talent and culture: why people should come and go, and what that signals
52:38 – Joleen Liang - Female leadership: strength, softness, and how influence actually works
53:43 – Managing Work-Life Balance📚 References (Mentioned in the Episode)
People
Miro Lu — https://www.linkedin.com/in/mirolu
Aaron Tan — https://www.linkedin.com/in/aarontan/
David Isaac Mathews — https://www.linkedin.com/in/davidisaacm/?originalSubdomain=sg
Neo Zhizhong (Neo) — https://www.linkedin.com/in/zzneo/
Dr Joleen Liang — https://www.linkedin.com/in/joleen-liang-70b11ba4/
Derek Haoyang Li — https://www.linkedin.com/in/derek-haoyang-li-076432173/
Kevin Choi — https://www.linkedin.com/in/kevinchoi-mediwhale/
Kelvin Teo — Co-Founder & Group CEO, Funding Societies | Modalku — https://www.linkedin.com/in/tkelvin/
Reynold Wijaya — Co-Founder, Funding Societies | Modalku — https://www.linkedin.com/in/reynoldwijaya/
Eric Barbier — CEO, Triple-A.io — https://www.linkedin.com/in/ericbarbier/
Rob Schimek — https://www.linkedin.com/in/rob-schimek-59b37a1/
Peter Thiel — https://thielfoundation.org
Companies and Organizations
Carro — https://carro.co/sg/en
AIPath.one — https://www.aipath.one/
Geniebook — https://www.geniebook.com
Squirrel Ai Learning — https://squirrelai.com/about/
Mediwhale - https://mediwhale.com/
Funding Societies | Modalku — https://fundingsocieties.com
Triple-A.io — https://triple-a.io
bolttech — https://www.bolttech.io
Trip.com — https://www.trip.com
Lego — https://www.lego.com
Harvard Business School — https://www.hbs.edu
Cambridge International Curriculum —https://www.cambridgeinternational.org/
IB Programme (International Baccalaureate) — https://www.ibo.org/
Singapore Ministry of Education: PSLE (Singapore National Exam) https://www.moe.gov.sg/microsites/psl...
Singapore Ministry of Education: Education in Singapore —https://www.moe.gov.sg/education-in-sg
Vietnam Ministry of Education & Training — https://en.moet.gov.vn/
Swiss Re Institute (Protection Gap research) —https://www.swissre.com/institute
McKinsey (Embedded Insurance) https://www.mckinsey.com/industries/financial-services/our-insights/
EY (Insurtech Landscape) — https://www.ey.com/
IAIS (Global Insurance Regulation) — https://www.iaisweb.org
Ironman Triathlon — https://www.ironman.com
Sequoia Capital / Peak XV Partners — https://www.peakxv.com
Concepts and Topics
GPT / ChatGPT — https://openai.com/chatgpt
DeepSeek - https://www.deepseek.com/
China tutoring ban - https://www.scmp.com/news/people-culture/social-welfare/article/3150726/chinese-parents-turn-black-market-after-school
PSLE (Singapore national exam) - https://www.moe.gov.sg/microsites/psle-fsbb/psle/main.html
Singapore education system - https://www.moe.gov.sg/education-in-sg
The Lancet Digital Health – https://www.thelancet.com/digital-health
Glaucoma — Mayo Clinic Overview: https://www.mayoclinic.org/diseases-c...
Retinal Imaging (Fundus Photography) —https://my.clevelandclinic.org/health...
Cardiovascular Disease (CVD) — WHO Fact Sheet: https://www.who.int/news-room/fact-sh...
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