Honest Disclosure of How I Built My Portfolio to Where It Is Today

From time to time, people have asked me how I managed to build up my current portfolio size, especially when I often say I have always had a relatively low active income.  More questions actually popped up after I wrote the post where I decide to liquidate my US Growth Portfolio to pay off my mortgage in Malaysia.  To be very honest, the journey was not glamorous, nor was it the result of overnight success.  It was a combination of discipline, patience, keeping expenses low, and a few key decisions (and saddening privileges) along the way.  This post is written with much emotions, as it openly shares my entire financial journey along the way, filled with ups and downs, and scars in life.  Please be kind towards my financial mistakes, as I know very well I am far from being perfect.

Early Days – Humble Beginnings

I started working in 2007 at a Japanese engineering firm with a starting pay of SGD 2,400 per month.  It was not much, but it was the reality of my first job.  At this point, I was literally starting from scratch because I did not have much savings during my University Years.  However, as I started working, I made a promise to myself that I need to start saving and eventually save up enough to buy a house in Singapore (I am not eligible for HDB, so private property was my only option).  That was my first thought when I received my first pay check.  Therefore I would say from the beginning of my working life, I made a conscious choice to be mindful of my spending.  

Expenses were kept as low as possible.  The main unavoidable cost was rent, and for a period of time, that took up a big chunk of my pay.  Still, I knew I had to think long-term.

Early Stock Market Days – Trial and Error

Around 2009, I started dabbling in the stock market.  To be honest, I had no plan.  I did not know of any financial bloggers at that time whom I can learn from.  But luck was on my side with my first few initial trades because a rising tide lifts all boats.  2009 to 2010 was the time when the Singapore stock market was recovering from the 2008's Great Financial Crisis.  I made some profits with the initial trades and managed to slowly accumulate a little more capital.  As how usual stocks trading stories go, the winning trades made me feel that my "technical analysis" was quite good, and that's where failure comes.  There were trades that went wrong and earlier profits were wiped out by a single losing trade (recall Rotary, FJ Benjamin, FSL Trust and Super).  At that time, I thought I was following technical analysis, drawing lines of support and following moving averages and bollinger bands.  However looking back, it was more like gambling than investing.  Still, I managed to save bit by bit, and these experiences planted the seed for what would eventually become a more structured approach in future.

First Property – With My Dad’s Support

In 2011, after much discussion with my dad, I took a leap into property.  In fact, I was hesitant to buy because I have not saved my first SGD 100K at that time (I had about SGD 65K at that time), but my dad, with his clear foresight, told me to go ahead and he will support me when required.  With my dad's financial help for the down-payment, I bought my first 2 bedroom private property in Singapore.  The timing was crucial, as it was just a couple of months before the Additional Buyer’s Stamp Duty (ABSD) came into effect.  

This was a pivotal move, as it meant that instead of paying rent every month, I converted that same outflow into mortgage payments (with a little more cash top-ups).  From then on, I was fully responsible for servicing the loan myself.  Nonetheless, I know I was privileged to have had my dad’s help at the start, and it set the foundation for my financial journey moving forward.

Throughout the years of owning this property, I stayed in 1 bedroom, and rented the other room to tenants, and the rental helped a little to cover a small part of mortgage.

The Turning Point – 2017 to 2018

The real shift came in late 2017, when I decided to revamp my entire approach. I wanted to stop playing around and start investing with a clear plan.  By late 2017, the stocks in my Central Depository Pte Ltd (CDP) account was worth SGD 120K, and I had about SGD 100K in cash.  This is also the time that I decided to revamp and start dividend investing by accumulating shares.  So, I sold all the shares I had and redistribute them slowly into dividend-paying shares.

In January 2018, my total portfolio size was about SGD 30K with only 3 stock, namely Singapore Technologies Engineering (STE), Mapletree Industrial Trust (MIT) and the previously favored Mapletree Commercial Trust (MCT).  It was not much, but it was a clean slate and a solid base to build from.  Although I had a sum of cash at that time, I continued to dollar-cost average into the market, slowly buying into the various shares and building up my portfolio bit by bit.  At the end of 2018, total portfolio value was around SGD 80K and total dividends collected in 2018 was about SGD 2.6K.  It was not much, but definitely a good motivation and indication that I am on the right track.  This spurred me to continue what I am doing, slowly and steadily.

Around the same time, I also laid my hands on my retirement home, a simple 1 bedroom unit in Johor, Malaysia.  It did not require much capital for down-payment as citizens are able to loan up to 90% for first property in Malaysia.  The property was rented out since I collected the keys till now.  This purchase was also the reason why my CDP had SGD 120K in 2017 but 1 year later it has only SGD 80K worth of shares.

 

Property Decision 2 – Wrong Investment Decision

In 2019, I made another decision to invest in a resale 3 bedroom property in Malaysia, this time near Mount Austin area.  This was a pure investment decision, as I have no intention to stay there.  Initially I thought I had made a good decision as the purchase price was below MYR 350K, and if rental was above MYR 1.5K, it would be cash flow positive.  However, just 2 days after I collected the keys in March 2020, circuit breaker starts and travel between Singapore and Malaysia was prohibited.  Within Malaysia, travel between states were also prohibited.  Basically lockdown everywhere, and the newly purchased property were left in doldrums.  

Thankfully 1 year later (after bleeding on mortgage payments), the property was rented out but only with MYR 1K rental.  From a positive perspective, I am still blessed as my active income was not badly impacted during the pandemic.  Therefore I could keep up with all the mortgage payments, while keeping my personal expenses low.  

During the similar period, I also received some inheritance, which helped me financially.

Property Decision 3 – Unlocking Capital

In 2020, I made another key decision: I sold my first Singapore property at a profit.  With the proceeds, I bought a smaller 1 bedroom unit, which is where I currently reside.  The best part was that this new unit was at a much lower price compared to the selling price of my first Singapore property.

All the profits from the sale of the first property were channeled straight into the stock market.  That move significantly boosted my capital base, and in turn helped to boost my dividend income.

Property Decision 4 – Attempting to Convert Negative to Positive Cashflow

This year, in 2025, with a relatively substantial equity portfolio accumulated, I decided to face my failed investment and stop the negative cashflow (This negative cashflow occurred because my total income from rental in MYR is insufficient to cover all property related expenses in MYR, but my SGD income is able to cover the difference).  I decided to liquidate my US Growth Portfolio entirely (about 7% of my equity portfolio) and some Singapore Technologies Engineering (STE) shares (about 3% of my equity portfolio) and use the proceeds to pay off my mortgage loan for the property at Mount Austin.  This decision was made after long consideration as personally in my investment journey, I value dividends and cashflow at this juncture much more than capital growth.  Therefore, I am keeping my SG dividend portfolio intact as much as possible, and only liquidating my US portfolio and some STE shares (as its yield is the lowest within my portfolio, thus minimal impact to my dividends income).

When the mortgage is paid off, I will be able to restructure my entire Malaysia property portfolio to ensure total rental collected is more than sufficient to cover mortgage for my retirement property, maintenance fees and taxes for both properties.  There are many naysayers to this move, but I have other plans in mind.  One important reason that I decided to take this move now is simple, I have to admit that I have overleveraged in properties, and if recession hits anytime soon, my financial situation may worsen.  Will recession happen?  That is anyone's guess.  But I think I should hope for the best and always be prepared for the worst.  With the restructuring, I believe the mental boost that positive cashflow brings is priceless.  When the time is right, I will try to sell the Mount Austin property to unlock capital.  

The Journey from 2018 to 2025

Since I started my investment journey, especially with a concrete plan in mind since the beginning of 2018, I stayed the course.  I invested consistently, learned from mistakes, and stayed patient.  Along the way, if I have any spare cash, coming from inheritance, rental, profits from sale of property, additional income that I earn during exam period from the additional classes, I treated most of them as part of my investment capital, and just keeping a small portion of money for some fun and travel expenses as a small treat for myself along the way.

Fast forward to 2025:

• Total dividends collected & reinvested to date: 29.6% of capital invested

• Capital gains (SG & US markets) to date: 30.0% of capital invested

• Annual dividend in 2025: about SGD 31K (projected)

My portfolio is definitely not spectacular, compared to savvy investors who easily more than double their portfolio with strong momentum stocks that helped to propel the portfolio value.  Personally, I know what kind of strategy suits me and though my portfolio performance had been lackluster over 7 years, I am happy with the cashflow it generates compared to the capital gains it brings.  When I look back, the numbers themselves (though significant for myself) are less important than the principles that got me here: persistence, patience, and the belief that long-term investing works if you give it enough time.

Reflections – Gratitude and Next Steps

I am glad my younger self chose to save and stay disciplined instead of chasing flashy spending.  I am also grateful for the financial help I received, especially from my dad, which gave me a head start. Not everything came from my own effort alone, and I acknowledge that.  I thank my dad for inspiring me, molding my financial decisions and way of life through setting an example off himself.  His way of life, outlook in life, financial journey definitely made me who I am today.  Though he is no longer around, I hope to be as financially responsible as he was, and I hope I have not disgraced him.  I hope I can preserve the wealth he left for us, and grow it further to continue his wishes to bring my mum to places she has not been before, and spend more time in future with her.  

Today, I am pleased that my portfolio is not just the result of luck, but also of conscious choices, and the courage to stick to a plan even when it wasn’t easy.  With this foundation, and the financial actions I am making, I hope I am ready to progress into Barista FIRE next year.  The road has not been straight-forward, and not every decisions made has been perfect, but it has been meaningful.  If there is one thing I have learned and would like to promote in this blog to fellow younger investors, it is that slow, steady, and consistent effort really does pay off in the long run.  Construct a plan, and the best time to start investing is now.  Barista FIRE, here I come...!