Of Risks and Failures – Why we should take the leap and embrace the fall

Failure has always been something harshly drilled in us to be taboo in our Singaporean education system. One small failure along your path and it’s over, you’re done. But, I personally believe that when one fails, just fall forward. Don’t waste all the sweat and effort you put into whatever task it was.

In light of this, I decided to embrace one of my biggest failures- my first startup failure. My colleague Joshua Chua, our acting CFO for my previous startup and I co-wrote this article which detailed the insights of our startup failure. 

“We took the risk, ran the race, and fell brilliantly.”

Our three man team from OpportunitySG. Courtesy of Author.

It Started with a Problem

The problem that we had identified was the internship. Was the internship an extension of the undergraduate’s learning, an opportunity for organisations to invest in new blood, or simply a steady flow of cheap labour? From our personal experiences as well as feedback from our peers, many skewed towards the last point – where experiences seemed to be filled with menial tasks and unmeaningful work. Interns felt underappreciated and that they had chosen the wrong organisation to intern at.

And so, OpportunitySG began with this problem. We researched and found out that there wasn’t an existing service that catered to the problems we identified, and hence felt that we could do something about it. This was when we began to analyse the problem carefully and formulate our strategy.

Unexpectedly Complicated

In a sentence, when we broke down the initial problem, it wasn’t as simple as coming up with one solution. Each smaller segment to the main problem had their own individual problems and respective solutions, and each solution, in turn, had their own problems of viability, sustainability, and speed.

In order to solve the complicated problems, we needed people who were equipped with the necessary skills and expertise to know what should be done and how it should be done. Although our current selves were simply lacking and insufficient, we were willing to learn. From sales and marketing to learning about the internship landscape, business development, project management, and a lot of networking to outsource for help, we did it all as a three-man team.

That being said, we couldn’t fill the role of the IT specialist, so we recruited our fourth member Saif Anasri.

Startups are Slugfests

We worked like mad. Almost every waking hour not spent on school or important relationships was spent on our start-up. The more we did, the more work came up. The more we worked, the more problems came up. Countless hours in each other’s houses and whatever free room we could find on campus was spent on our baby, but it was a problem that grew bigger each time we looked at it.

Balancing our commitments and work was a constant battle with a reward that seemed so far away. For close to 8 months, our goal of making the internship better suddenly turned from an idealistic dream into a monster that we unleashed upon ourselves. We realised then – start-ups are no joke. This is true especially when you’re starting from the bottom.

Small team, Big team.

How can such a small team accomplish much if anything at all while balancing work, school, and everything else in-between? The answer lay in maximising our firepower-per-unit, where every single one of us was in charge and responsible for a distinct and crucial role, yet accountable to the entire flow of work done.

Like a well-oiled machine, communication, hitting deadlines, and simultaneously sourcing for whatever help we could find, was what made our small team pack a punch. As unlikely as it was, there were many willing to help us – be it mentors, friends, parents, or strangers, we networked, connected and presented our ideas consistently to build upon our lack of individual expertise.

Yet, we kept our integrity as a small start-up fueled by our passion for the internship.

Harsh Realities

The more we built up our start-up, the more we had to consider one thing: our unique value proposition. What separated us from the competition. This was essential to marketing our services and forming our identity, our competitive advantage.

Our plans were based on the normalcy of the economic and social situation in Singapore. It would be a lie to say that Covid-19 wasn’t one of the factors that caused our plans to crumble. However, more than affecting us directly, it exposed the great weaknesses we did not see in our start-up.

In the face of a tanking economy, would our service be considered essential? Were our perceptions of our services somewhat not realistic or viable? Did we really have the capacity to pull this off?

These were hard questions we asked ourselves while the world stood still in quarantine and panic. To be honest, at this point we were extremely tired after pushing and pivoting and adapting constantly, yet we tried to hold on. After investing so many hours and a portion of our savings into the business, it was not easy to let go.

The decision had to be made when we reached the critical point. We had talked with over 800 companies and only 20 or so of them were willing to pay for our service – we had officially failed our validation stage.

The Exit Strategy

It was something we never considered – meeting a brick wall, a dead end. Everything we did so far was done in order to push forward. Every obstacle was a challenge to be overcome for us. We did not plan our exit strategy.

At what point in time do we give up and cut our losses? When is it time to pack up and call it a good fight? Looking back, we believe that this was something start-ups learnt through experience. This unsaid point was unsaid precisely because it’s filled with bitterness, slight regret, and uncertainty.

As the late Steve Jobs once said, we can only connect the dots backwards – Only in hindsight, we saw our folly, weaknesses, and the signs that we missed. Remember to plan your exit strategy

We’ve always acknowledged that the entrepreneurial lifestyle is a risk every time. Not just for the first try but for all the chances that will come after. We knew this, yet we took the risk, ran the race, and fell brilliantly. But it’s okay because we’re still young and foolish.

Like a child that is learning to ride a bike, the glory isn’t in succeeding the first time, but getting up each time and persevering. So, to end off, we encourage those who might tread the path less walked, to do it with vigour. Look forward when you try and backwards when you learn. Because that’s what we’ve learnt.


Being a passionate entrepreneur, Ryan Siah had previously co-founded a startup OpportunitySG and is now the co-founder of gaming keyboard startup Wraek(Follow them on Instagram). He specializes in marketing design and business development with a keen interest in the gaming, education, and human resource industries. He is also keen to explore the consulting industry in the future.

Disclaimer: This article was written by a contributor. All content is written by and reflects the personal perspective of the writer. If you’d like to contribute, you can apply here

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