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The Story of an Investment Banker Turned Startup CEO

An accomplished professional in the finance world, Oi-Yee Choo has experienced different working cultures in the Investment Banking Industry. Her years of experience have culminated in her joining ADDX, a startup in Singapore looking to democratise the private markets, in 2020. She was appointed Chief Executive Officer in 2022. Join us in conversation with Oi-Yee as we dive deep into her journey from her days at Nanyang Technological University (NTU) to an Investment Banker and now a CEO of a Pre-Series B startup.


As a young student, what were your interests?

As a student in junior college, I tried to be involved in everything. A friend broke it down: one has to be a straight-A student or do something to stand out. Being a straight-A student was challenging. Therefore, I tried to compensate by becoming involved in everything, from sports CCAs to hall committees and choir.

You studied Accountancy at NTU; what were your aspirations back then?

I chose Accountancy out of necessity, without having a clear aspiration. I was not going to dive into science or the arts, so accountancy was a simple choice in the middle. My mindset at university was to enjoy and to graduate as quickly as possible. The assumption back in my days was that accounting students would most likely enter one of the Big 5 (now Big 4) accounting firms. As such, I tried my best to follow the path.

What lasting impact did your first job have?

I learned a lot of things in my first job out of accounting school. Business automation software was non-existent during my time, making my job mostly menial and repetitive. Being an accountant meant I had to obtain all necessary financial documents from other departments. With such a requirement came the need to hone my soft skills. Making friends with everyone, from the janitor to the tea lady, was crucial. However, arguably the most important thing I took away was that perhaps auditing was not for me.

What made you enrol in the MBA course?

The auditing stint showed me that I did not wish to feel stuck in a batch of 80 people performing the same task. Instead, I wanted to enjoy what I do and to feel part of something important simultaneously. Taking the MBA was a way to expand my horizon outside what I learned in university before choosing the next step in my career.

Why the UK for your MBA?

The location always had to be outside of Singapore. Studying overseas would allow me to step out of my comfort zone and make friends globally. Having to settle your accommodation and doing the chores by yourself daily would help you grow as a person. These factors also apply to undergraduate studies, which I strongly recommend students consider.

Investment Banking

Given your extensive experiences in banks of different cultures, how do you navigate the differences?

Indeed, the culture of a Swiss bank is vastly different from that of a Japanese or American bank. Each has its own unique culture and sub-culture. The uniqueness also depends on which departments you are sitting in. Therefore, the cultural fit within each team has to be near perfection. One will suffer in banking if they are not well-fit for the sub-culture of their team. A particular ethos I try to live by is to be friendly and sincere to everyone, even the tea lady. I have rejected highly qualified candidates who were rude to staff in our offices.

What is the difference between Investment Banking and Startup World?

The primary work ethic is similar in both environments. The dynamics of colleagues and stakeholders are different. The startup space is less formal without compromising on professionalism. Details such as messaging tools in the startup space differ from the banking communication system.

The intrinsic motivation level differs too. In the startup space, the people are typically more aligned with the company’s overall vision since everyone is more incentivised to make it successful. On the other hand, the most prestigious banks have become too large for everyone to feel the same motivation. Depending on one’s motivational needs, either environment would suit them better.

Startup Phase

What motivated you to jump from Investment Banking into the Fintech world?

The emergence of blockchain technology and its fast-paced development caught me with great interest. At the same time, the investment landscape was evolving too. I saw this as an opportunity for Singapore to pioneer the change in the private market.

The idea of participating in this new movement was slowly brewing within me. I concluded that I had accumulated sufficient years of experience to make this crucial leap. I also had several pillars of support from friends and family. Above all, ADDX was at the forefront of the democratisation of capital markets. In the end, every component aligned for me to make the jump.

What are the sources of stress in the startup world?

When building a company in its startup phase, the pressure could come from everywhere. For instance, we must be aware of any new potential technological development that could prove helpful for our product. As we work on our solutions and expand our offerings, there is always room to do more and to do better. To survive, we must keep looking at what our competitors are doing in the space. Listening to what our stakeholders say and gathering actionable insights are crucial. However, as the CEO, it is arguably most stressful to manage and retain our talent at the company. Incentivising talent to maximise their potential in the startup space might be intrinsically easier, but creating “skin in the game” is still a tough act.


In your opinion, should students follow one’s passion?

I think one should focus on their strengths when they are young. Unless the intensity of the passion is so strong that it translates into results, short-term interests can often be mistaken for passions. These are more likely to fade as time passes. A sense of accomplishment drives an individual forward, which, akin to a video game, is often achieved through honing your strengths to the next level.

How relevant is a university degree in today’s job market, specifically for your industry?

I like that universities are evolving and providing ample space to incorporate real-life work experience into students’ degrees. Many of my current interns are from universities in Singapore like SMU. In my opinion, working in real life is vastly different from the academic journey. While each semester is structured into modules with deadlines and limited deliverables, the experience at work is usually non-defined in scope, with a heavy emphasis on problem-solving. Hence, students should focus equally on familiarising themselves in these different environments.

Within the accounting industry and, to some extent, the broader finance world, I believe robots and machines would automate most roles. However, the soft skills will likely remain relevant for longer, as employees are increasingly required to collaborate in cross-functioning teams.

Last but not least, what are your highlights and lowlights from your time so far at ADDX?

Assembling a team of talented individuals who get along well and understand one another has been a blessing. It was a slow process with many ups and downs, especially when we had to build remotely during the lockdown. We have overcome the initial challenges and are now all on one another’s wavelength, to the extent we could finish people’s sentences.

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