9 S’pore Startup Founders Reveal Their Craziest (Almost Illegal) Business Ventures

Entrepreneurs challenge and disrupt the status quo, and that takes a lot of creativity and a heck of an enterprising spirit to pull through.

As we get into the Monday blues, we decided to do something fun, so we reached out to a couple of our local founders with one question:

“What was the craziest business venture that you have ever embarked on?”

Willis Wee of Tech in Asia used to catch and sell insects to his schoolmates. Here’s what these founders did.

1. Karl

Serial entrepreneur at heart, Karl has quite a few stories to share. At 17 when most of us were buried in our books, he would be managing his journal blog buying and re-selling used phones.

“I eventually started buying and selling Seiko watches on eBay too, but this came to an end when I sent a whole batch of watches to someone, who turned out to be a Nigerian con artist.”

Image Credit: techweez

“Later at 18, I co-founded a men’s T-shirt blogshop with my JC mates but margins were low and hours were long, I think we made $500 for 6 months of hard work split amongst 3 partners.”

During university, Karl also shared that he was in the real estate sector as a broker and somehow ended up becoming a relocation consultant for MNCs.

“The companies would pay me to take foreign senior execs around Singapore to show them how life would be like here and convince them to relocate into Singapore.”

2. Jacky

“I studied in China for a couple of years and when I returned, I brought home with me boxfuls of knock-off Oakley sunglasses. I then resold them in Singapore at hiked up prices, turning almost a few hundred dollars in profit.”

“I managed to pass many of them off as genuine, but I did meet some buyers who really knew their Oakley brands. They were able to identify them as fakes.”

“Those meetings didn’t go so well.”

3. Melissa

“I used to be a party promoter and sold entry tickets into clubs back in Switzerland.”

The founder shared that she got started whilst fundraising for the biggest annual student party on the year.

“It was awesome because it taught me skills on how to hustle and the importance of networking. I built my networking skills from there. I stopped because I graduated and then passed on my Rollerdex to someone else.”

4. Kiren

Kiren shares that he once created an application modelled after ‘Who Wants To Be A Millionaire’ and put it on his personal website. It ended up going viral, and many people began downloading it.

“One entrepreneur was very interested in it and licensed the software from me to run a local version of the game in his city.”

On another note, he also created a simple but “very cool” Cricket fantasy sports league in university.

“I used to collect bets from the students and get them to create their sports teams,” he laughs.

5. Joshua

Joshua shares that he once sold Polo sweets that he bought at NTUC.

“3 tubes for $2.20 or something, and I sold per Polo sweet at $0.20 – broke even with the first tube. I feel like such a con man now,” he adds sheepishly.

He also sold country flag erasers in Primary school when “eraser battles” were still hot, but the business was not as successful.

“I blame that on the Uncle who cheated me when I bought a box of country erasers only to find out that they were all Singapore Flags. I was too scared to go back and ask for a refund.”

Image Credit: mtradenoveltystore

6. Gilbert

“Back in JC, my friends and I went to Sheng Siong to buy canned drinks to sell at an Expo event and we camped at a spot where the traffic would be the greatest i.e. near the MRT.

The staff from the 7-11 store nearby came out to berate and chase us away because we had no license and also cause we were selling them cheaper than 7-11.”

After the event, Gilbert shared that they received surprised reactions from the attendees about their makeshift stall, but at the end, they still turned a profit and got praised for their entrepreneurial spirit.

7. Daniel

“Back in Malaysia, my friend and I had this idea to create mix-tapes for our friends at school.

I had a huge amount of blank CDs and a CD burner so we created forms for people to fill in with their favourite tracks. My friend would download them, and I would burn the CDs and design custom-made CD covers and stickers.

We earned a fair amount of profit because I already has the CDs and we were never caught, but we stopped cause people found out how to download songs and realised they could do it themselves.”

8. Dinesh

“We had this thing called Entrepreneurship Week in secondary school. My “business partners” and I decided to sell potato chips as one of us had a ‘lobang’ to get them at a cheaper price. But this was before entrepreneurship got cool, so none of us had much interest in it.

In the end, we disappeared to play soccer or go to our CCAs, and there was no one left to take care of the chips and money.

Our Discipline Master decided to take us to task by hiding the money, and then punishing our entire group.”

9. Alphonso

“Well I wouldn’t say it’s the craziest but I was once a children’s entertainer twisting balloons, being a clown, magician and a ventriloquist. 

It started out as a personal hobby, but then I had opportunities to perform for community centres and events so that’s how I started. Props-wise, I made some of them but bought the others to ensure quality.”

Image Credit: bbsballoonowl

“It was good money but I couldn’t seem to automate it so I stopped. That plus my hobby had become a drag.”


Do you know someone who has a wild business adventure to share? Let us know!

Disclaimer: This article is solely for entertainment purposes. Vulcan Post is not endorsing any illegal business ideas. 

Featured Image Credit: Samantha Tay / Vulcan Post

Subscribe to our newsletter

Stay updated with Vulcan Post weekly curated news and updates.


Vulcan Post aims to be the knowledge hub of Singapore and Malaysia.

© 2021 GRVTY Media Pte. Ltd.
(UEN 201431998C.)

Vulcan Post aims to be the knowledge hub of Singapore and Malaysia.

© 2021 GRVTY Media Pte. Ltd.
(UEN 201431998C.)