Mom, I’m going to be an entrepreneur

“You want to start your own business? Why are you so stupid?” cried Joe’s mother. It was five years ago when I remembered hearing the personal story of an entrepreneur during one of my pro-bono advisories.

Joe (not his real name), was then a recent graduate at a local Singapore university. “But mom, this is really what I want to do. I can make a change in people’s lives with my business,” pleaded Joe.

His mother, who was a saleslady selling traditional medical products for over 25 years, was totally unconvinced. “Change what people’s lives? You have been offered a job by the Ministry of Education to be a teacher. That is an iron rice bowl job! It is stable income. You can pay for your student loans and be assured of getting your future HDB flat. Who would want a man with no financial stability? And where do you think you can obtain any housing loan with no income?” she wailed with intensity of emotions rising.

“You dishonour us with your foolish actions,” sighed Joe’s father, who has been driving a taxi for the longest time. “I have worked so hard all my life to ensure that you get a good education, so that you can get a good job working for the government and take care of us. Are you expecting us to keep working till we die?”

“Dad, I don’t care. This is what I want to do and I am going to do it!” Joe gave the ultimatum. And his father replied, “If you want to pursue this, you are no son of mine and should no longer live here.”

And that was the night where Joe walked out of his home to pursue his dream. He found kind-hearted friends who gave him temporary shelter, until he found a space of his own to live. It was quite heart-wrenching for me to hear his story, but Joe was a determined man who felt that entrepreneurship was his calling. I am relieved to mention that his parents, though still unsupportive of his entrepreneurship career, has since reconciled with Joe.

The Asian tradition of honouring one’s parents

We may all claim that the world is changing, and attitudes towards entrepreneurship is increasingly positive. But when it comes to family support, in particular for traditional Singaporean families, and, to an extent, Asian families, their mindset toward entrepreneurship is still largely negative.

Asian parents, who have toiled hard for many years, used most of their savings to invest in the education of their children, hope to forge a better life for them. Ironically, some of these parents themselves are entrepreneurs in their own right, where they run small-time successful businesses.

They know how difficult it is to run a business, and do not want their children to face these hardships. Rather, they hope for their children to join large corporations or the government for high paying jobs and work-life balance.

They feel that it is a failure on their part when their children do not pursue stable careers. For their children to want to take risks and become businessmen like them, they view it as a persistent cycle of hardship which has yet to be broken.

Significant others wanting stability

Somehow, that mindset also extends to the significant other of the entrepreneur.

I remembered another young entrepreneur who spoke with me in 2014. He co-founded a startup with his long-time buddy, but the bootstrapped startup was not paying him a salary. His girlfriend wanted to get married, and there was the future house to pay for. And in all practicality, he had no income to speak of to contribute his share to the house. It was not easy explaining to his co-founder why he needed to leave the startup and obtain a full-time job instead.

No entrepreneur should be alone

There is a saying that “it takes a village to raise a child.” I would like to extend that saying to “it takes a whole ecosystem, including family and friends, to raise an entrepreneur.” This is why I am highlighting the importance of why an entrepreneur needs the buy-in from his loved ones.

In the last few years mentoring startup founders, I had no lack of cases where I dealt head-on with the issue of family support for entrepreneurs. While other mentors tend to focus on discussing the issues of business and shy away from sensitive family or emotional issues, I would openly talk with founders about their family and spousal support.

To me, a founder with a happy family is a boon for the startup, as he can fully focus on business problems and not be distracted by personal ones.

I even recall once meeting a mother to assure her that if her son didn’t go anywhere in the next two years, I will get him back into the workforce! And she gladly gave him the support thereafter. I sighed with relief when he received his first round of funding and is moving along just fine.

So how does one reveal to their parents and loved ones that they are going to be an entrepreneur?

During my mentoring, I would normally start off by asking simple questions on whether their parents are supportive of the decision of the founder for taking the entrepreneurial track. For more mature founders, I would determine whether the founder has received the go-ahead from his significant other. For those that have not broached the topic, here is some advice I usually give, and with added insights from an entrepreneur who has been there and successfully got his loved one to buy in.

1. Are you even ready to start up?

Not everyone is suited to be an entrepreneur. There are many articles out there on this topic. There are many issues to think about before plunging into a startup.

Startup founder Brian (not his real name), tells me if he could turn back the clock, he would have done things differently. “Starting a business should be about reducing risk and making money. I did the reverse, and founded a startup by quitting my job and going full-time into entrepreneurship.

On hindsight, I should have stayed in my job and worked on my startup part-time by testing the idea first, until I was absolutely sure of the business’ feasibility. People might say that I would not have focus by doing so. On the contrary, I was very distracted by personal finances, and it was difficult to focus on the business.”

So before you decide to announce to your parents that you want to be an entrepreneur, do some soul-searching first, to decide whether starting up is right for you.

2. Timing of the discussion

Be strategic. As the saying goes, “There is a time to be silent and a time to speak.” Bryan found that his usual dinner time was the best time to break the news to his mother. He felt it was the best moment to speak, as it was a relaxed setting.

From his example, take the opportunity to speak to parents and loved ones when they are positive and receptive. Start the conversation and assess whether they had a good or bad day. If they are upset, it is not wise to add fuel to fire. Wait for a better moment to speak.

3. Plan on what to say and give assurance

Bryan shared what he told his mother, “Mom, I’d like to quit my job and try something on my own. I have a partner in this. He is quitting too, and we are giving ourselves a year or two. If things do not work out, it will be back to the working world.”

When speaking with parents or loved ones, it is always important to focus on keeping it simple and addressing their fears. Unlike Joe, who was more excited on selling the idea of changing people’s lives, by which his parents have no emotional link to, Bryan was straight to the point about leaving his job, and assuring his mother he would return to the working world if things did not work out. Instead of speaking about the business, Bryan first dealt with his parent’s fears.

Only when you have dealt with the emotions while breaking the news, should you move on to the next topic of personal finances.

4. First having money in your personal bank account

The biggest fear that parents have is the lack of money when one begins the startup journey. My suggestion is to save up and ensure you have at least 24 months’ worth of savings.

This will likely be the amount of time needed to raise your seed round of funding and of which you can finally draw a salary for sustenance. Addressing first the issue of personal finances helps parents to be assured that they do not need to sustain you while you are in bootstrap mode.

5. Having the plan ready to present to parents

Parents and loved ones are also considered stakeholders in your company. While they may not have a direct impact to your startup, they are there to understand, encourage and love you during the low periods and provide the much needed emotional support. And respect has to be given to them by showing them what your business is all about, even to a point of presenting something to them as you would to any potential investor, partner or employee.

One entrepreneur once told me, “If startup founders cannot convince their parents to be on board with their plans, then how are they going to convince others to join them full time or convince investors to invest in them?”

To add on, ensure that your presentation is made as simple as you can. Your parents or loved ones are not in the startup scene and would not know the technical terms. Do not try to give complex statements like “My startup is a fintech startup that will focus on banking the unbanked, where we will use our proprietary Finesse algorithm to be an alternative to the banking system.” That alone can confuse and freak parents out with all the complicated terms.

Rather, make it simple, like “There are many people in ASEAN that do not have a bank account. I want to change that by equipping people with an online bank account.”

6. Maturity and level-headedness

Familiarity breeds contempt. And more so when it comes to parents and loved ones. Many have shared how emotional outbursts happen when informing their parents of their decision to start up.

Being an entrepreneur is the mark of controlling one’s emotions, as an entrepreneur deals with many people on a regular basis. Joe’s story is an example of what not to do, in allowing emotions run high. Be mature about the situation. And if emotions run high, back down and call for a time-out until you are ready to speak again.


Despite the advice, do not expect that convincing your parents is going to be an immediate success. It takes time for the news to sink in.

For Brian, his mother was fearful of his decision as it would affect family finances, but when she saw his progress and saw him on the news, she understood his reasons for starting up and finally became supportive.

So prepare yourself before having that discussion. It will help ease unnecessary heated exchanges.

This is the eleventh article of theThis article first appeared on Tech in Asia. ‘Startup Advisory Clinic’ Series.

Originally published at on May 6, 2016.