PLAYTHROUGH LOG · APRIL 2026 · THE HONEST VERSION
CHARACTER SHEET v1.0 SAVE FILE: KEVIN.SAV
Kevin Chia
KEVIN CHIA
CLASS: SEMI-RETIRED ENTREPRENEUR
LVL 43 · LOCATION: SINGAPORE · STATUS: BUILDING
OPTION TRADER BUILDER CALCULATED RISK TAKER
TRADING
85/100
BUILDING
78/100
CONSULTING
65/100
FAMILY
95/100

My story


I'm Kevin Chia. Singapore born and raised. Failed my A levels after three years in JC. Semi-retired at 41. The path between those two facts is the whole story.

This is the honest version of it.

PLAYTHROUGH TIMELINE · 2007 TO PRESENT
2007 CH 1 2011 CH 2 2013 CH 3 2022 CH 4 2026 NOW
SAVE FILE 01 2003 - 2011

The Rocky Start

PLAYTIME   8 years
DEATHS   1 (A levels)
LOCATION   Singapore
CLASS   Fitness PT
JC & NS

Three years in JC and still failed A levels. Not exactly the start Singapore parents dream of for their kids. Did NS, then enrolled at Ngee Ann Polytechnic for a Business Studies diploma. And this is where something clicked. Scored above 3.0 GPA without really trying. Could just absorb and apply. Graduated around 25. Took longer than most, but I got there on my own terms.

2007 - 2009

Started personal training straight after poly graduation. Genuinely passionate about fitness, not just the job. Built a client base, launched kevinchia.sg as a fitness resource back when Dreamweaver was how you built websites. IPPT prep, fat loss, mobility. Tried to cut through all the bad advice floating around with honest content. Built a small following. Full time PT for those two years.

2009 - 2011

Some people online decided they wanted the top PT slots in a fitness forum badly enough to make it personal. Forum harassment that spilled into real life with spoof SMS, way before all the current scam awareness. Decided it wasn't worth it. Went low profile, took a day job as ops exec at Yami Yogurt at $1.5k starting pay, kept PT going part time at nights and weekends with the boss's blessing. Around 2008 had also started a hair salon on the side with one of my clients. Three things running at once was just normal.

SAVE FILE 02 2011 - 2013

Going Independent

PLAYTIME   2 years
UNLOCKED   First trading club
LOCATION   Singapore
CLASS   Solo operator
2011 - 2013

Hair salon was closing. Felt like the right signal to stop working for others entirely. Became an insurance agent, but on my own terms. Told the manager upfront before joining: I'll do it my way. He said fine. After joining, daily morning meetings and mandatory training started appearing. That was factor one to leave.

Ran simultaneously as a financial fitness coach and set up CC Traders Club, teaching SGX stock trading using a breakout strategy. Had students, had traction, was trading well. Then the Bluemont saga unfolded and the strategy burned out with it. That was factor two.

Around the same time, Sylvia needed help with Vivre Activewear. That was factor three. All three hit together and the decision made itself.

SAVE FILE 03 2013 - 2024

The Vivre Years

PLAYTIME   11 years
PROPERTIES   6 bought, 3 sold at profit, 3 held
LOCATION   Backstage
CLASS   Operator
2013 - 2024

Sylvia started Vivre Activewear. Joined her full time when operations started getting overwhelming. Division was clean: she owned marketing and design, I ran everything else. Admin, ops, tech, website, inventory systems. A ladies activewear brand where the guy stays backstage suited everyone just fine.

Bought three commercial properties across the Vivre years. Sold all three at a profit as we scaled down — that capital didn't sit idle. Closed all retail stores by October 2024 as leases ended naturally; the last property cleared early 2025.

Vivre didn't die. It evolved. Today it runs online with maybe two hours of work a month thanks to automation and software built over the years. Still profitable, de-registered GST, leaner than ever.

SAVE FILE 04 2022 - 2025

The Investor Phase

PLAYTIME   3 years
UNLOCKED   Semi-retirement (age 41)
LOCATION   Anywhere
CLASS   Investor
Oct 2022

Started investing in US equities seriously. The Nasdaq 100 had dropped about 35% from its peak. That was the signal to enter. Not luck entirely. I'd been watching and waiting for the right moment. That entry compounded well from there.

The honest reflection: if I had discovered US equities and IBKR before COVID, I'd be in a very different position today. Better late than never. The portfolio grew to a point where options premium, share lending income, and interest alone cover monthly expenses. At that point the math changes completely.

2024 · Age 41

Declared myself semi-retired. Not because I hit some magic number. Because the income from multiple streams (options premium, share lending, interest, Vivre, property) covered my lifestyle comfortably without me needing to be anywhere or do anything I didn't choose to do.

What that actually looks like day to day: wake up without an alarm. Take my time with breakfast. Gym when ready. The rest of the day is mine. Some days it's Netflix and a long lunch. Some days it's a nap followed by nothing in particular. Aircon runs 24/7. Tesla in the carpark. Can buy what I want without overthinking it. Not ultra rich by any measure. Just cash flow positive, financially unstressed, and answerable to nobody's schedule but my own.

That's the actual goal. Not a number. A feeling.

Spent about a year and a half like that. It was good. Then it wasn't enough.

Late 2025

Started options trading properly. Wheel strategy on US equities via IBKR. Cash secured puts and covered calls on stocks I'm comfortable owning. The premium income, combined with share lending fees and interest on idle cash, makes this the closest thing to genuinely passive income I've found. Built my own tracker to manage positions. Still refining it.

SAVE FILE 05 · CURRENT 2026 - now

The Reboot

PLAYTIME   Ongoing
UNLOCKED   Builder mode (again)
LOCATION   Singapore
CLASS   Builder + investor
2026 · Now

A year and a half of Netflix and gym was what I needed. Full recharge. No guilt about it. But somewhere in early 2026 something started stirring again. Joined a SCTP Lifestyle Entrepreneurship course mostly for the social experiment of it (walk in, see what business ideas surface). That was the plan.

What actually happened was the builder in me fully switched back on.

I used to test as INTJ for most of the last decade. Quieter, more internal, perfectly happy running systems in the background and letting things operate on autopilot. That version of me suited the semi-retirement phase well. But the ENTJ that built businesses in my 20s and 30s didn't disappear. It was just resting.

It's back. But different this time. No desperation. No proving anything to anyone. Just genuine energy for building things that matter, sharing what I've learned, and connecting with people who are somewhere earlier in the same journey I've been on.

Started learning to code properly. Built Snapbook.ai, a SaaS platform for Singapore small businesses. Rebuilt kevinchia.sg from the ground up (twenty-odd years after the first version ran on Dreamweaver). Launched a tech consultancy for entrepreneurs who need real systems built, not templates dressed up as solutions. Started putting my thinking out into the world properly for the first time.

The difference between building now versus building at 25 is everything. The income is already there. The properties are held. The portfolio is compounding. I build because I want to, not because I have to. That changes how you make decisions, what you're willing to say out loud, and who you're willing to help.

What I do now


Semi-retirement for me doesn't mean doing nothing. It means doing only things I choose to do.

// OPTIONS TRADING

Main income engine. Wheel strategy on US equities via IBKR. Cash secured puts and covered calls on stocks I'm comfortable owning. Premium income, share lending fees, and interest on idle cash combine to cover monthly expenses without touching the principal. Built my own tracker to manage positions.

// SNAPBOOK

Built a SaaS platform for Singapore small businesses. Operations management and AI-powered tools. Learned firsthand that building the product is the easy part. Getting people to use it is the real work.

// VIVRE ACTIVEWEAR

Still running, online only. Down to maybe two hours of work a month after years of automation and system building. My wife Sylvia is the face of the brand. I stay in the background. Works perfectly for both of us.

// CONSULTANCY

Supporting entrepreneurs who want to build real systems, not just ideas. From websites and backend infrastructure to thinking through business decisions that actually compound over time. Not a coach. Not a guru. Someone who has built across multiple businesses, made the decisions that led to financial independence, and can walk alongside you as you build yours.

What I actually believe


Semi-retirement is not about retiring early. It's about designing a life where work is optional, not mandatory. You get there by building income streams that don't all require your daily presence, keeping your expenses honest, and making decisions based on what actually matters to you rather than what looks good to other people.

I also use Bazi and Human Design as frameworks for self-understanding. Not as fortune telling. As lenses that help me understand my own wiring and make decisions that fit who I actually am. I built the calculators on this site because I use them myself.

And I'm deeply sceptical of anyone selling a system that promises financial freedom. Not because freedom is impossible. Because the systems are almost always designed to enrich the person selling them, not the person buying.

> Where do you go from here?