If Lee Kuan Yew Had a Companion AI: Would He Ask About Your Feelings While Building a Nation?
A National Day reflection on building things that last — and why I sometimes wish I had an AI coach with LKY’s conviction
Recently, I had the chance to conduct some very deep, very unpaid research into the Companion AI sector — you know, those AI boyfriends, therapists, and anime husbands that will never ghost you unless the server crashes.
It was... enlightening.
Naturally, after spending hours reading about emotionally intelligent LLMs that whisper sweet nothings and send you good morning texts, I balanced that out with something a little lighter: Lee Kuan Yew’s memoir. Because nothing says “self-care” like the political autobiography of a man who built a nation from a swamp.
I was reading it in honour of SG60 this weekend, but also to remind myself what actual productivity looks like.
This man:
Built the SAF
Created EDB, JTC, Port of Singapore Authority, DBS and many more
Turned Singapore Airlines into a global brand
Attracted multinational investments
All before most of us can finish one Notion board
Meanwhile, I’ve been “between milestones” for three years and still haven’t figured out how to schedule my dentist appointment.
Which got me thinking: if LKY were still around today, what would he do about current trade wars, new tariffs, or watching our digital banks get memed on Reddit?
And more importantly, can we build a Companion AI version of him?
Yes, I’m pitching CompanionAI: Founding Father Edition™. Imagine booting up your phone and hearing:
🧓 “Stop whining. Build the port.”
🧓 “Cry less. Execute more.”
🧓 “You want an AI boyfriend? Marry productivity.”
Honestly, I want to build this. Investors, DM me.
1. From Solace to Strategy: Companion AI Isn’t Just for the Lonely Anymore
Let’s kill the stereotype that Companion AI is just for people crying into their boba at 2am.
What started as digital comfort pillows (Replika, Character.ai, etc.) is now quietly evolving into life strategists in disguise. These AIs aren’t just here to ask how your day was — they’re:
Coaching creators through burnout
Talking teenagers out of doomscrolling
Helping founders survive rejection while pretending to be “still super bullish on the vision”
It’s emotional UX for the always-on generation. Therapy? Too slow. Productivity apps? Too cold.
Companion AI hits that weird middle: emotionally warm, always available, and secretly useful.
LKY wouldn’t have had time for “mental health awareness” — or so we thought. But turns out, he played golf 1–2 hours every day. That counts, right? Self-care, but make it elite.
He just didn’t call it “mental wellness.” He called it swing practice.
And you can bet he’d approve of anything that makes citizens more resilient, focused, and slightly terrified into action.
2. CompanionAI: Historical Figures Edition™ — History Repeats… as a Chatbot
New business idea: AI versions of historical figures to help us survive late capitalism.
Hear me out.
Van GoghGPT: Reacts to modern NFT art with quiet despair and asks if your JPEG has “soul.”
Marie CurieAI: Answers all your radiation questions and reminds you your boyfriend isn’t that smart.
GenghisGPT: Gives career advice like “Conquer. Then network.”
MachiavelliBot: Coaches you through office politics and ex situations with suspicious accuracy.
Princess DianaAI: A soft girl feminist coach with immaculate style.
And of course, LKYGPT. Every time you complain, he sends you a shipping manifest and tells you to build a nation.
Why does this work? Because character + context = emotional resonance. We don’t just want information — we want point of view. Wisdom with a tone. Support with seasoning.
These AI figures don’t just help us think — they help us feel more understood, even if by a dead French philosopher.
3. The Emotional OS Race: Why This Is Bigger Than You Think
The real play here isn’t just quirky chatbots. It’s the next interface for how humans relate to tech — an emotional operating system.
Apple gave us design.
Google gave us knowledge.
Companion AI? It might give us empathy on demand.
And it’s monetizable as hell:
Subscriptions for exclusive characters
Custom avatars for fandoms, celebrities, influencers
Enterprise versions for coaching, leadership, and therapy
We're talking the Pixar-fication of AI — turning personalities into platforms. And unlike humans, these companions scale beautifully, never sleep, and never raise a Series A.
In a way, we’re all building our own inner board of directors. Who’s on yours?
Personally, I want a trio of LKY, Beyoncé, and Confucius yelling at me to send the deck.
🎯 So… What Would LKY Do?
As Singapore turns 60 this weekend, I’ve been thinking a lot about what it means to build something lasting — a company, a country, or even just a sense of personal direction that doesn’t unravel every Q2.
Lee Kuan Yew didn’t have AI copilots or Notion dashboards. He had conviction, a few civil servants, and what I assume was an absolutely terrifying calendar.
If he were alive today, I wonder what he’d think of Companion AI.
Would he invest in one? Would he build one? Would he tell me to stop theorizing and just execute?
Maybe what we all need — in this time of economic volatility, endless pivoting, and LinkedIn humblebrags — isn’t another AI that tells us “you’ve got this.”
Maybe we need one that tells us:
“Stop whining. Build something.”
“Think 50 years ahead, not 5 minutes.”
“The plan doesn’t need to be perfect. Just make sure it ships.”
As a female Asian VC, I’m not here to rewrite history.
But I do wonder: what kind of Companion AI would we build if we stopped chasing virality and started channeling vision?
🧋XY - sipping boba & trying to build my own founding story