Ishwin Singh has never been someone who follows a straight line, and that, it turns out, has been his greatest asset.
Born in Singapore to a family with roots in Bangkok, and shaped by years living and working in England, Ishwin’s path has taken him from the police force to the boardrooms of global companies and eventually, to real estate. Today, he brings financial rigour, cross-cultural perspective, and a genuine passion for the places people call home to his work at PropNex.
Masala sat down with Ishwin Singh, who believes that the best decisions in life, like the best properties, are the ones that hold their value long after the paperwork is signed.
“Do not stay at that crossroads, go for it. You only get one chance at life; fortune favours the brave.”
Tell us a little about yourself and your background.
After national service in the police force, I went to university in England to study accounting and finance in Manchester, then worked at Deloitte for three years. I was restless, so I moved back to Singapore to build an e-commerce startup before returning to England to join Amazon for about four years.
Around that same time, I went through a major health challenge that required emergency surgery, which changed my outlook on a lot of things. After recovering, I joined Autodesk and stayed for about nine years before taking the plunge into real estate in 2023.
You grew up in a family business. How did that shape your relationship with work and the idea of carving out your own path?
My family ran Asher Fabrics, a lace importing business that supplied customers across the region.
Growing up around the business taught me a strong sense of ownership. In a family business, there is no such thing as “that’s not my job”. Everyone does whatever is needed to help the business succeed.
That mindset has stayed with me throughout my career. It served me particularly well at Amazon, where one of the company’s leadership principles is ‘ownership’.
At the same time, it gave me the confidence to carve out my own path, applying the values I learned growing up in a way that reflected my own ambitions.
You spent almost two decades in corporate finance before making the leap into real estate. What finally made 2023 feel like the right moment?
After undergoing heart surgery in 2014, I put together a long-term life plan: within 10 years, I wanted the financial independence and flexibility to choose whether I stayed in corporate life or built something of my own.
By 2023, the key milestones had fallen into place. My wife and I had welcomed our second child, bought our family home, acquired an investment property generating rental income, and built a solid portfolio of growth and dividend-paying stocks.
Having launched my first business during the 2008 financial crisis, I was also mindful of timing and wanted to wait until the uncertainty of COVID-19 had passed. By late 2023, the moment felt right.
Moving into real estate in Singapore is far from a casual pivot. What drew you to this space, and what did becoming a licensed realtor actually involve?
I was drawn to this industry because it gives me the chance to guide people through one of the most significant purchases they will ever make.
In Singapore, you need to pass two difficult exams before getting licensed, so it was back to school, juggling weekend classes with work and family commitments.
The biggest change in mindset was that in corporate life, your goals and KPIs are given to you. As a real estate agent, setting the right goals for yourself is the most important part of that process.
Learning to say no to the wrong deals, clients, and goals frees up your time to say yes to the right ones.
You focus on residential property and conservation work rather than industrial or commercial. What drew you to these areas?
I chose to focus on residential property because it is more impactful to my clients’ lives.
It is not purely an investment decision; it is a home where lives will be lived and memories will be made.
I am an old soul, so being drawn to conservation shophouses was natural to me. My family ran their lace business out of a conservation shophouse in Arab Street, and I spent a lot of time there growing up.
These buildings have beautiful architecture of a bygone era, and each one holds so many stories within its walls. It is almost like you are dealing with a work of art rather than just a piece of real estate.
Your finance background is fairly unusual in real estate. Does it give you an edge with clients?
It is unusual, but it is a crucial skill set, especially when working with buyers making the most expensive purchase of their lives.
Being able to distill and explain complex financial information—taxes, stamp duties, mortgage repayments—in simple terms helps to reassure people and enable them to make big decisions confidently.
What kinds of clients do you work with, and how do their motivations tend to differ?
Most of my clients are young families making their first private property purchase in Singapore.
The two broad buckets are investors, who tend to be rational buyers, and owner-occupiers, who tend to be emotional buyers.
Many are lured by the dream home or buying as a status symbol, without paying enough attention to the financial commitment of a monthly instalment over a 30-year mortgage.
In Singapore, the government’s tight lending restrictions help prevent buyers from purchasing dream homes that could turn into a financial nightmare.
With roots in both Singapore and Bangkok, how has that cross-cultural life shaped your worldview and sense of identity?
My wife Pooja, who is from Bangkok, and I found ourselves in a blossoming relationship in Manchester when we were both studying there.
I am in Bangkok several times a year, and I’m drawn to the older parts of the city since my mom grew up in Thonburi, in Wongwian Yai, so there is a sentimental pull there.
Growing up, I absorbed so many Thai words without realising it. I thought thung (ถุง), the word for plastic bag, was Punjabi. Same with sia wela (เสียเวลา), meaning wasting time.
Neither my mom nor my wife ever taught me Thai, so I can speak Punjabi fluently but barely a word of Thai. When they speak it together, I am fairly sure they are talking about me.
If you peel back the layers, though, there are many similarities between Thai, Indian, and Singaporean culture. I try to find the common ground and make the best of it.
What does life outside of work look like for you?
A lot of my time goes to the kids.
My daughter has taken after her mum and loves cooking and food. My son is still young, but I am working on getting him into football…and supporting my beloved team, Nottingham Forest.
You faced a significant health challenge early in life. How did that shape your mindset and priorities?
A bacteria ate up one of my heart valves, and I needed emergency open-heart surgery at 32, an experience that turned out to be a huge blessing.
Before the surgery I was coasting through life a little. Afterwards, I wrote down a clear plan of the goals I wanted to achieve with the second chance at life I felt I had been given.
It taught me how delicate life is and to be grateful for waking up every morning. It is one of those experiences that reminds you things can change very quickly, and that the time you have is not guaranteed.
What has this journey taught you about reinvention and meaningful success? And what would you tell someone standing at their own crossroads?
Success is being able to live life on your own terms.
As Bob Dylan said, “A man is a success if he gets up in the morning and gets to bed at night, and in between, he does what he wants to do.”
In that sense, I feel incredibly fortunate; being with my family, working with clients who often become friends, staying fit, and keeping my mind engaged by continually learning.
For someone standing at their own crossroads: be honest about what you would really want to do if money were not an issue, then save enough to cover three years’ worth of expenses as a safety net.
Once you have done that, do not stay at the crossroads, go for it. You only get one chance at life; fortune favours the brave.
“Success is being able to live life on your own terms.”