In the first of a multi-part series, Singaporean entrepreneur Choo Yilin opens up about her journey from accidental entrepreneur to founder-CEO to now, finding the right candidates to succeed her

I started my jewellery business in the late 2000s, and growing it has been the most consuming and significant endeavour of my life.  

And yet, I suppose with some irony, when I was growing up, I was certain that I never wanted to be in business, let alone be the CEO of a startup. When I was in the final stage of interviews for a civil service job, I was asked why I was not considering a job in the private sector instead. The interviewer said, “the pay would be better.” 

With the naivete and self-importance of my 20-something self, I declared that “I don’t want to sell my soul to the business world.” 

But life had plans for me despite my youthful convictions.

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The beginning: fumbling with no rule book 

When I was 26, I moved to Bangkok and found myself needing to recreate my professional and social networks from scratch.  That’s when I came across a group of incredibly talented fine jewellery artisans. I decided that I wanted to work with them, and that’s how I became an accidental entrepreneur.  

The first few years of my entrepreneurial journey were a tragicomedy of unforced errors. But there was also an incredible amount of grace: the little company that I founded grew, despite me not knowing things like what a gross margin was, let alone deciding what healthy margins should look like.  

This later led me to pursue an MBA at London Business School in an effort to get a better grasp of business fundamentals.  

At b-school, I was assigned an executive coach. When she studied my profile, she shared that creatives like me would almost never be found in an environment like this. She wanted me to be aware of how the culture in the MBA programme and by extension, a career in business management, might be at odds with my motivations and strengths. I did not disagree.

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The education: dreaming big      

Despite my profile not being an intuitive fit for business leadership or management, b-school was quite precisely what I needed at that time. I acquired the business fundamentals I needed to answer some of the questions I had as an entrepreneur.  

While I missed telling stories with my jeweller’s loupe and gems, there was no shortage of stories of other sorts. 

I learnt the stories of what balance sheets told, and I understood how pursuing good strategy was about saying no to nine possible stories in order to actualise one excellent one.    

But perhaps the most compelling stories I took back with me were the tales of founders, who had built global luxury brands that continued to thrive long after they passed on.

I graduated from the MBA armed with a dream that I, having grown up in tiny Singapore, had a fighting chance to grow my brand, Choo Yilin, globally one day. And that despite my earliest misgivings and my executive coach’s cautionary advice about suitability in business management, I could make a play as a founder-CEO.

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Closures are not always unwanted events, precipitated by tragedy; they are sometimes necessary in order to prepare for the next phase of being

- Choo Yilin -

The quest: being a founder-CEO 

The years after graduating from b-school were a flurry of non-stop doing and trying to grow Choo Yilin to the best of my ability. While my peers marked their lives through external life changes—moving overseas, getting married and having babies—I felt it difficult to offer anything beyond the company’s milestones and leadership gaps that came at me faster than I could address them.  

The media has celebrated our wins and our financial statements told a beautiful story of bootstrapped success—year-on-year double-digit growth and consistent, growing profitability as well; cash flow was healthy. 

Though, for me, time was marked not by these external milestones of achievements, but by how every year seemed like an uphill climb, where the incline kept getting steeper. While my title never changed, my actual work was marked by a constant evolution of skill sets that I felt I had to acquire from scratch again and again, always without a guidebook. 

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I thrived on telling stories about heritage, love and becoming through our intricate pieces of gold and jade, but as we grew, these creative projects gave way to long meetings on financial planning and quarterly KPIs. The days became filled with challenging, often painful, conversations with stakeholders as our organisation became increasingly complex. 

There was never a period of my life as a founder-CEO where I felt I could comfortably cruise, and the feeling of ineptness and drain only grew over time. But it never dawned on me to reflect on the significance of these feelings, because my attention was almost entirely devoted to the company’s well-being, the team, the clients and the products. 

I failed to see the irony that as a founder of a company whose basis of being was about honouring profound emotions and intangibles, my own feelings were irrelevant to the goal of ensuring the health of Choo Yilin, the brand.

The realisation: what’s next?  

In late 2019, we made the unorthodox decision to go on hiatus. This shocked our community because that year, for us, was marked by accolades. In the month leading up to us pausing our retail operations, I spent a lot of time speaking to our community. 

I shared that closures are not always unwanted events, precipitated by tragedy; they are sometimes necessary in order to prepare for the next phase of being. 

In this instance, we realised that while we had built Choo Yilin successfully, we needed to make significant structural changes in order to ready ourselves for internationalisation. While other organisations could pursue both operations and transformation at the same time, we did not have the resources to do that. And so, we chose transformation over operations. 

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“What about the lost revenue?” some asked. My response was that the opportunity cost of that for a number of years would be insignificant as we were looking to preserve long-term brand guardianship. 

In the last three years, while we’ve been in transformation, one of the unexpected realisations I’ve had was that I can no longer be the leader of the company. 

I learnt that the very characteristics that allowed me to drive Choo Yilin’s growth as an early-stage startup, such as the insatiable desire to constantly push the envelope, would become a liability as the company matured. If there was to be a fighting chance to actualise Choo Yilin’s ambitious growth plans, it would be best that the company be led by someone with a different skillset from mine. 

For me, that realisation was simultaneously devastating and relieving all at once. In my next essay, I share the events that led to this conclusion and what it means that I’m going to transition out of the CEO role.


Choo Yilin is the founder of her award-winning eponymous fine jewellery label, which specialises in jade and is modernising this historically significant gemstone for the 21st century audience. She would like to see herself as a storyteller, but instead of words, she uses gold, diamonds and Type A jade to tell these important tales rooted in heritage and history.

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