The title of this article is a story of a guy that I tried fund-raising from as a doe-eyed fresh grad. A while ago, he low-key flexed that he had bought himself a plot of land in Tanglin to stay grounded. I think he failed to accomplish his dual-pronged message - to brag and to stay grounded. Here's why.

The obvious guess is that he bought it on a loan which is why it says it keeps him grounded. Well, good for him. But a 3M loan is quite manageable (amongst my peers).

But more importantly, if you need the obligation of a monthly installment to keep you working hard and staying productive. Then, in my opinion, entrepreneurship is not for you.

Entrepreneurship means having the option to fail

Story #1

I started my first startup before I graduated, and I had to take equity deals for $25000 for 25% of my first company, Spawt. Because I was nobody, and they knew I had nowhere else to go if I did not take it. Without the option to fail, it was poor deals or no deals.

Story #2

I was hitched for the longest time, and I needed the cash to pull the trigger. $100k in total. $60k for the house, and $40k for the wedding including the honeymoon. My wife knew I wanted to be an entrepreneur, so I promised her that if I couldn't make money (100k) by the time I was 28, I was to get a real job.

To keep my dream to build a company, I cannot fail. By failing, I mean not making enough money. So I had to do things that guaranteed revenue -- consulting. My second company was a consulting company called Unifide.

Since then, lady luck struck, and a few side products of mine shone the path to product-led businesses (and revenue).

Sapiengraph CCTV

Sapiengraph CCTV is a loss-making product, at least for the first few months. I am funding the entire operations as well as the hardware out of my pocket. And I can do this because this time, I have the option to fail. My house and car are paid off. My son has a comfortable nest egg. If the product fails, I can try again. If it fails, again and again, I guess I have to take up a job in one of the giants in Silicon Valley and make a good Software Engineer salary, like my brother at Amazon.

But when it does succeed, it will be glorious because the ball-game is entirely different. The nature of the product means guaranteed monthly recurring revenue for years to come. And the business model has significant uptick potential for my previous products.

Why do you think the founders of startups that switch-for-the-fence startups such as Grab and Go-Jek are wealthy kids?

I am estranged from my dad, and my mom works at a food court. I had to engineer my risk-negation circumstance before I could take big leaps. And if you do not have wealthy parents like most of us, you owe it to yourself to get rid of obligations.