A Candid Look At My 10 Years Of Entrepreneurship Journey In 8 Minutes (Lessons included)

This article first appeared on my blog at Weikiat.NET

My earliest recollection of something resembling Entrepreneurship was when I was 15. I’ve picked up programming for about 2 years by then, and I have created a couple of random apps and tried to sell it online. One of the app was called Wicked’s Developers’ Suite and contains a html text editor, a search engine scraping tool and a tic tac toe game. I tried to sell it for $5.

It didn’t go well.

I had no distribution channel, my app looked like shit, and I had no go-to-market strategy. My app didn’t have a clearly defined addressable market, and there was nothing special. The fact that it was named “Wicked” didn’t help.

At just 15 years old, I’ve basically made every single startup mistakes known to man.

I then continue to make more startup mistakes when I launched SGShoppin, the second or third blog shop directory to launch here. I ran into scaleability problems as the key value proposition of my site was that our expert team (my girlfriend), would manually review every single blog shop submitted to my directory. We counted 2,000 blog shops at our peak. We could not review submissions as fast as they came in.

I also launched SgZap, a URL shortening service (as if there weren’t enough of these already!). The inclusion of “Sg” in the name didn’t make sense and no one wanted another URL shortening service that had less features and reason for existence than any other such services in the market.

I also launched The Wicked, an online puzzle game inspired by the famous Notpron. Despite the lack of features, the horrendous design, it took off. Apparently I did something right in assuming that my alma mater, The Chinese High School (Now Hwa Chong Institution) was the best place to seed my game. Intellectuals like to play ‘intellectual’ games.

This time, naming it “Wicked” served to improve the game’s value proposition, not take away from it. I also seeded on various discussion forums where techies gathered, including SPUG (Singapore Palm User Group), Vr-Zone and Hardwarezone. I also seeded on the most popular content directory at that time, Ping.SG, as well as added my game to a Wikipedia list of prominent online puzzle games. In a nutshell, I’ve done growth hacking before the term became a buzzword. I even got featured on The Straits Times’ Digital Life for my creation.

Opportunities came knocking afterwards and I realized I sucked at business. I licensed my game to STOMP and M1 for a 3 digit sum. Real profitable. I ran Google Ads on The Wicked but my account was banned due to fraudulent clicks. For a game site that enjoyed as much traffic as XiaXue’s blog at that time, I earn a grand total of only slightly more than a grand.

I realized I can build, I can bring stuff to market, but I still can’t continue to do what I love — creating things — if I don’t know how to make money.

So I went to Singapore Management University, the “business” university to learn how to make money.

Week 1, I realized students were buying and selling pre-owned textbooks because the cost of new ones were way too high. There was an existing textbook market place, called “SgTextBook” by the founder of Vodien. I felt that the marketplace sucked because the search box was way too small, so I created a new one overnight. My textbook marketplace, BookINBookOUT, had a giant textbook on the front page that allowed you to buy or sell books quickly just by typing the name in. BookINBookOUT was acquired by the time I was in my second year in SMU for an undisclosed (a.k.a super low) sum.

So I decided that I’ve learnt a few things, but none of these were actual startups or companies. I’ve done lots of random stuff but I had not founded any actual companies. At the same time, I was looking to rekindle BookINBookOUT’s peer-to-peer marketplace mechanisms into something more. I was also fascinated by online social interactions — I even heard of a couple who got together after trading textbooks with each other over BookINBookOUT.

I then decided to start GetFromFriends, a peer-to-peer marketplace that has many social features, such as getting a discount when buying from friends, easily search for items put up for sale by friends first before finding items sold by strangers, and getting notified whenever your friends bought or sold something.

Everything seemed to go well. I had the backing of SMU’s Institute of Innovation & Enterprise. We applied for Ace funding and we got it, after an intensive panel round. Then, bad things happened.

We had 5 co-founders and everyone had equal equity.

There were many overlaps in roles and driving the company along a singular mission became impossible.

We spent 3 months changing the company’s name and designing a logo because we didn’t know better.

I lost control as I couldn’t tell everyone to stop wasting the time on this.

In the end we named the company “Oompr” because we were too tired of trying to think of another name.

“Oompr” had zero meaning unlike “GetFromFriends”. We later realized that “Oompr” actually meant Out Of My Price Range. The perfect name for a marketplace startup.

While I was the one who came up with the original idea, I gave up the CEO position to another co-founder because I felt that I should focus more on the tech.

The CEO then came up with 101 new feature requests every day and the tech couldn’t keep up.

We became so obsessed with features that we didn’t bothered with user acquisition and delayed our launch.

Then, Carousell launched first.

When Carousell started going down to maker’s markets and fleas to drive downloads and users, we ran iPad giveaway on Facebook to acquire users. We thought we were smart. We thought Carousell’s founders were stupid. None of our users bothered logging back in again. Carousell’s few but valuable users logged in to their marketplace frequently.

For some reason our second grant disbursement was delayed drastically by Ace, so we had zero cash for close to 6 months. Till this day, nobody knew what really happened. We didn’t receive any explanation. There was an interrogation session where it seemed as if they suspected someone was making use of me to start a business. I don’t blame anyone for this. Just bad luck.

Whatever the case, because of their suspicion, everything died. We couldn’t move at all with no money and we were just freshly harvested meat left on the grass to rot. Time is crucial for any startup. Because we had no money, we had to rely on others. And then we suffered.

In Oompr, we made a ridiculous amount of mistakes that we could never have made and learnt from otherwise.


  • Don’t found a company with friends. It makes it hard to separate friendship and business relationship. It prevents honest review of partnership disputes and only let issues compound. In the end, there was no business. We were lucky that we were all matured adults, so we didn’t lose our friendship. But we came close.
  • Always have clearly defined roles and don’t let any one whom you don’t critically need into the founding team
  • Nobody gives a shit about the name. In most cases, the name doesn’t really matter. Windows? Apple? LOL!
  • Features are frequently not more important than users. In most cases, creating a new feature that others already have will not bring you more users. Focus on 1 or 2 features that can help you communicate your unique value propositions, and grow from there.
  • Try to have the person who came up with the original idea be the same person who guide the company.
  • Don’t rely on cash that you are at the mercy of. E.g. Don’t count on grants to be given on time. Don’t count on being funded. That is one less cause of failure.
  • Sticky users are more important than users who are just here because they want something free.
  • 5 co-founders may be too many.
  • Ask yourself, can the company survive without this person? If yes, the person should not hold equity.
  • Likewise, can the person survive without the company? If yes, the person should not hold equity.

Oompr failed in 2013. We were losing co-founders fast and it ended with only me and the CEO. Even the CEO bailed because he had some highly lucrative job offer somewhere, so I was left to pick up the pieces.

Still, founding Oompr was the BEST thing I ever did because then I decided to do things very differently when it comes to my second company, Originally US, a Singapore mobile app development and marketing company:

  • Most young businesses or startups only really need 2 persons. One to do the tech, and one to do the sales & pitch. Keep it that way and discard unnecessary weight. Originally US started with just two persons.
  • As long as you have some skills, you can make some money. Ideas are cheap. Executing ideas isn’t cheap. So, Originally US started first as a service business (we build award-winning mobile apps for clients) to sell our own skills to build up the cash and expertise before we started exploring our ideas.
  • Use as little money as possible, because I don’t know when I will need it. For a large part of 2014, Originally US’s address was a virtual one that costed $99/year, and we were working from business lounges that costs S$70/month, even cheaper than any co-working space, which I felt are getting overpriced.
  • Quick and dirty wins the game. Our own products were often launched incomplete, before we quickly iterate based on users’ feedback in order to build something that people really wanted.
  • I do not ever want to find myself in the position where I got stuck while executing an idea because of cashflow, so we started building recurring income. Our side project, SG BusLeh, now generates enough ad revenue to pay for our entire operations at our Vietnam Office. With this revenue, we can then focus on executing our startup ideas without worrying too much about money.

We are now moving to the next phase. We have got a few parties who are interested in investing in my companies. Some even offered to acquihire the whole team. It will be a new journey and a virgin experience for me.

I wonder where the future will take me. Can’t wait to find out! Hope that this sharing has been useful to you!

Like what you read? Give Calixto Tay a round of applause.

From a quick cheer to a standing ovation, clap to show how much you enjoyed this story.