To help his father get out of debt, Mr Deepak Gurnani quit school at the age of 14 to search for work.
There was no point taking the exams, he told his mother, because he would not be promoted to the next grade unless he paid his school fees. His monthly fee was 10 rupees (20 Singapore cents), and he was months behind on the payments.
The son of Pakistani migrants to India, Mr Gurnani found a job with one of the many cloth merchants in the Sindhi community of Vijayawada.
After a few months of being an understudy in the shop, Mr Gurnani convinced his mother to write to a distant cousin, asking him to send money for Mr Gurnani to start a clothes shop.
The money came - 500 rupees by money order - and the adventure of Deepak Clothes Store began.
Best and worst bets
Q What has been your biggest investing mistake?
A During the Lehman crisis, I lost US$1 million (S$1.4 million) across a few banks.
But my worst investment would not be what I lost in 2008, because what I lost in 2008, I gained in 2009 by staying invested.
In 1993, I bought one small apartment in Indonesia. It was marketed as a "condotel", a condo-hotel - called Cocobay Resort. First, the developer we bought from went bust, but I paid all the money and I got the unit. I gave money to one company to renovate it. It also went bankrupt. After that, I gave it to a third party to put on a rental scheme, and they also went bust. So though the property was bought at $66,000, I think I must have lost close to $150,000. And every month, I'm still writing a maintenance cheque.
I could sell the unit for $25,000 and call it a waste, but the monthly cheques keep me rooted to the ground - knowing that I will not make all the good choices in my life.
Q And what has been your best investment move?
A Angel investment. I started because of my background, where somebody helped me in the past, so I am always open to helping. I realise that we have become so risk-averse today, it's difficult for a start-up to borrow even a thousand dollars from a bank for its idea.
This is where I can make a difference. In 2008, this young NUS (National University of Singapore) student Pranoti had an idea for Rotimatic (an automated roti-maker), so two friends and I invested in her dreams, as I call it, which ended up producing a unique product. We put in about $500,000 and, today, Rotimatic is worth a lot more - tens of millions.
[Porta ac consectetur ac morbi leo risus]
First, Mr Gurnani had to scout for a place to set up shop. He found an old man running a sweetmeat shop and proposed to rent half his space.
Mr Gurnani, 54, recalls: "I said, 'I want to be a cloth merchant.' He said, 'Oh, very nice. People will come, and you will be selling towels and this and that?' I said, 'Yes.' (He said,) 'So they will eat my sweets and they will wipe their hands on your towels?'
"I did not know what was meant by sarcasm so I said, 'Yes, yes.' He said, 'Idiot, how can that happen? You have to take the whole shop.' "
The old man agreed to rent the shop to him for 45 rupees a month, promising that he would bend his ear if he failed to pay up on time.
Next, Mr Gurnani went to the wholesalers to stock up on goods.
"They would see a small boy coming to them on a bicycle, asking for credit. They actually used to tell me, 'We don't know you.' I said, 'My name is Deepak, now you know me right? Now you must give me credit,' " Mr Gurnani says. "I must have come across as someone very arrogant. I had no other option. There was no trying to be nice and waiting for somebody to introduce you."
Eventually, one man relented and offered the young boy 200 rupees' worth of credit. He immediately used that as a bargaining chip with the other wholesalers, and soon enough the shop was filled.
On its first day, Deepak Clothes Store made 20 rupees in sales, and a profit of five or six rupees.
"My first business, how much I made, it still gives me more of a thrill than all I can make today," says Mr Gurnani. "I was so happy, I went home to my mother to say that all our troubles have vanished."
Indeed, that small business took care of the family of six for two to three years.
In his late teens, Mr Gurnani went for an interview with a trading company and moved to the Maldives as a manager, where he worked his way up.
He first visited Singapore on a business trip and moved here when he was 31, with his wife and daughter. His son was born here subsequently.
The businessman and angel investor is now a Singapore citizen.
Deepak Clothes Store cleared all the debts for the Gurnani family, except for one - the 500 rupees seed money that Mr Gurnani's uncle had sent.
Mr Gurnani says he kept that sum as "lucky money" - a reminder that no man can be successful without someone else's input.
Besides, his uncle had completely forgotten about the money when Mr Gurnani brought it up with him years later. He told Mr Gurnani: "Pay it forward. Help somebody else."
Q Moneywise, what were your growing-up years like?
A I saw good and bad. My real childhood was only in Bombay, when my father was a silk merchant. He would give my brother and me a one-rupee bundle of notes each, and we would watch a movie and compete to pay for the tickets.
Then silk prices crashed during the India-Pakistan 1965 war. My father's business totally collapsed, so we moved to a cheaper place in South India, Vijayawada.
He could not bring it upon himself to find work, so he borrowed from his brothers and his friends.
Today, I am totally against debt because I have known first-hand the humiliation of being a borrower.
(When I opened my shop,) my father would give inputs, but then for him, it was too small a business to come and see. For him, it was a climb-down. He had that mental block. But for me, I have no issue. I don't have a class to retain.
It's all in our hands, how we bring ourselves up.
Q How did you get interested in investing?
A My first foray into investment, when I was in my 20s, was on a 10-acre piece of land in India I purchased back in the early 1980s.
My cost was less than one rupee per square foot. At that time, nobody had thought of marketing a land bank, but the population kept growing and I sold the plot at 100 times that value in about five years.
As this could be a good source of passive income, I slowly began exploring other investment avenues.
Q Describe your investing strategy.
A I start by taking small stakes in an investment, especially if it's liquid, like stocks or bonds. So I first get my feet wet to understand the product, and if I like it - because I already have an interest now - it will give me an incentive to study this company, and I may buy a couple of lots.
My friends and I are always discussing investments so some ideas do come about from there, and I listen to the news to get a flavour of everything. By the time my private banks send me ideas, I'm in a position to make a decision without having to talk to the banker.
Q What's in your portfolio?
A I am invested in the stocks of more than 50 companies across the world. I hold stocks such as Singtel and HSBC.
I've also invested in five start-ups in Singapore, and eight or nine overseas. I still have land. Now I buy near where the infrastructure is developing, like in New Bombay where a new airport is coming up.
I had a portfolio of 50 properties at one time, but I have cashed out some of them. My biggest motto is: Don't fall in love with your investments. That is one mistake which many people make; I refuse to make it.
Q What does money mean to you?
A For me, money, if not spent, is just a piece of paper. But money is there to make a difference in peoples' lives. So make it as widely used as possible - there's no point locking it up.
Q What's the most extravagant thing you have done?
A Actually, not much. If they are shoes I wear, they are ordinary shoes. The shorts I wear are ordinary shorts. And you will not see me flying business class at all. My wife might arm-twist me into buying things sometimes, but that is a different story.
Q What is one of your biggest regrets when it comes to investing?
A Until 2008, I used to have some discretionary portfolios with the banks, which I would not give my time to because I have my businesses to take care of. But after I took a big hit during the Lehman crisis, that taught me that I should have my own hand in every investment.
Now I handle all my portfolios actively myself. I use the banks as a platform, because they give you portfolio loans and leverage options, but I make my own calls. So even if I lose, I don't feel bad, because it's my own call.
Q What are your immediate investment plans?
A Now I focus on investing in Singapore-based start-ups as an angel investor. In Singapore, many people don't have the knowledge of how to put their plans into action, and that is something that angels can help with.
In my experience, the few companies which I have mentored have relied more on my expertise than my capital. Capital is just one way of having an entry to a company.
Q How are you planning for retirement?
A I could retire today if I wanted to. My retirement plan has already been executed. My office in High Street Centre and my home have both been fully paid up.
Q Home is now/I drive...
A I live in an apartment in Amber Road and I drive a Nissan Sylphy.