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Gen Y Speaks: I dropped out of school and had brushes with the law. Now I run 2 businesses

Growing up, I always felt out of place among my peers. While everyone was working hard to earn a place in a reputable school, I always thought about making money. I believed that becoming an entrepreneur was my destiny.

Mr Caleb Sim, who dropped out of secondary school and then polytechnic, now runs two consultancy businesses.

Mr Caleb Sim, who dropped out of secondary school and then polytechnic, now runs two consultancy businesses.

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Growing up, I always felt out of place among my peers.

While everyone was working hard to earn a place in a reputable school, I always thought about making money. I believed that becoming an entrepreneur was my destiny.

However, my story didn’t start off as one would expect. I made money, but not through entrepreneurship. I made money dishonestly.

In 2012, when I was 15, I got acquainted with gang members who were 10 years older than me and adopted a lifestyle of vice.

I picked up smoking, abused pills, and learned to scam other people.  

I would purchase game credits from stolen phones and sell them to others. This two-minute process earned me S$180 per transaction, and the idea of such an easy money-making scheme intrigued me.

This went on for some months before the law finally caught up with me.

After I was arrested for a criminal breach of trust, I swore never to run afoul of the law again. But as the saying goes, old habits die hard.

Not long later, I dropped out of Maris Stella Secondary School and spent most of my time in a gang. I visited illegal online casinos, broke into houses, and sold keychains on the streets to purchase drugs.

It is no surprise that I got into trouble with the law once again. I was arrested for stealing perfume at Mustafa Centre while high on pills.

Even after that incident, I continued pursuing my reckless lifestyle, and it broke my parents’ hearts.

The sobering moment came when I was arrested while saying hello to my friends who were dealing drugs at a back alley in Geylang.

I had done nothing wrong but being acquainted with them got me arrested.

As I was locked up in a cell, it dawned upon me that I was mixing with the wrong company.

I had to change the way I was living, and the first step was to go back to school.

Finding a secondary school that would accept a dropout with multiple pending police cases was a tall order.

Fortunately, I was accepted into Peicai Secondary School.

In late 2013, I was given multiple police warnings for my past misdemeanors and told that I would be taken to task should I reoffend within the next 12 months.

I was glad I got a second chance and pledged to turn over a new leaf. I subsequently secured a place in Ngee Ann Polytechnic with my GCE O-Level results.

But just before entering polytechnic, my family went into a financial crisis due to the difficulties my sole breadwinner father faced in his music school business.

We moved to a smaller place and sold our car.

It was a painful but pivotal moment for me, sparking a newfound motivation to make my own money. But this time around, it was in an honest way.

I found a job as a sales representative selling productivity solutions to businesses. I enjoyed what I was doing and thrived at it. At just 17, I became the top salesman among my much older peers.

However, earning S$1,000 commission for a S$5,000 sale wasn’t enough to satisfy me. I decided to quit and start my own software company.

I was selling customer relationship management and human resource management software that was of subpar standard to organisations.

My company got off to a fast start and in no time, I was earning a five-figure salary.

Believing that I was the next great entrepreneur and the next Mark Zuckerberg, I lost interest in studying and dropped out of my diploma course.

But as soon as I did that, my business went downhill.

Mr Caleb Sim (centre), seen here with his parents, said that his reckless behaviour when young broke their hearts.

I was exposed for being in a tech business without understanding technology. My sales pitches were strong, but my products had no substance.

That was my first business lesson as an entrepreneur — a business can only survive and thrive for the long run if it provides real value to its clients.

I was very much just a salesman at that point and if I wanted to find success in business, I had to be an entrepreneur.

My future seemed bleak, as I was left without a business or any academic qualifications.

Thankfully, that was not the end of me.

While serving National Service (NS), I started learning search engine optimisation (SEO) and tested my newfound strategies at my father’s music school.

The results were immediate as new students began pouring in.

In my final year of NS, I founded Genia, an SEO consultancy.

This time around, I resolved to sell only a service of value to businesses.

My hard work and ambition paid off. In my first year of running the business full time, Genia went from zero to S$28,000 in monthly recurring revenue.

While our growth was relatively quick, clients did not come in predictably and regularly.

In Genia’s first year, we were completely reliant on referrals or word of mouth and as a result, in early 2021, we struggled to grow the company’s revenue levels.

We had one client who accounted for almost half of our revenue.

I was supposed to be in the best moment of my life but I was worried every day, fearing that I would lose everything and eventually be left with nothing but a failed business, again.

Unlike my first attempt at business, though, I had no room for failure this time.

I was no longer a teen who could go back to school or a boy in the army who had time to figure things out.

I had taken on bigger financial responsibilities at home and built a team at Genia.

There was too much at stake. The business had to work.

Determined to make it this time, I hired marketing coaches and soon discovered a unique client acquisition system that helps me to grow the business.

People used to tell me that I needed to get a diploma as a “safety net” because, in business, anything can happen. I beg to differ.

As entrepreneurs, our charisma, tenacity, leadership abilities, salesmanship and entrepreneurial mindsets are our safety nets.

If one business fails, we pick ourselves up, learn from our mistakes and go again until we find a winning trade.

Last year, what started as a duo (myself and a freelancer) grew into a team of six full-timers.

I have also founded a second company, Tres, a client acquisition consultancy that helps businesses acquire clients predictably and grow their revenue using the exact steps I use to grow Genia.

My near-term goals would ideally be to move my family into a larger home while having both my businesses flourish in the upcoming year.

As someone who does not come from a wealthy family and has only a GCE O-Level certificate, I’ve gone against the grain and showed that anyone can achieve their dreams and find success in life in a meritocratic society.

Business is the great equaliser, and anyone, regardless of academic or economic background, can succeed as long as they can provide real value to the world.



Caleb Sim, is chief executive officer of Tres, a client acquisition consultancy, and Genia, a search engine optimisation consultancy.

Related topics

entrepreneurship education Technology

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