The day I realized money can’t buy happiness.

16 August 2024. The day I realized money can’t buy happiness.

I left my role at Bank of America after a 5-year stint under the Prime Brokerage department. I have been through multiple ups and downs with the team, involving 1 restructuring, toiling through covid as a 1 man army, dedicating personal time to crafting resources and capacity to automate manual tasks and train up the incoming team, and having my personal Steve Jobs Moment - Getting Kicked out of the team I built up after I outlived my usefulness.

Writing this post is not an easy one. It is a story of how a star-eyed analyst whom made a decision to leave an 155 year esteemed custodian bank (founded by one of the founding fathers of America), in search of a career opportunity to grow towards a team lead, and be closer to investment decision making role, to getting disillusioned after all have transpired.

Here is my story. I hope you can glean insights from it.

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One of the major push factors that prompted me to leave Bank of New York, is being presented with the plan to train up the Pune team and offshore my market responsibilities (and coverage of Hong Kong market) to India. The managers attitude towards the analysts is one of hire and fire. They do have any good plan to guide the analyst to navigate through this difficult period or present to them any proposal to protect my livelihood. Their attitude is heads I win and take the credit. Tails you lose and you take the responsibility. From there on, it is a quest to find a new home to be with.

Why I chose Bank of America Merill Lynch
Pull Factors
1) It was a Warren Buffett company. By working in my company (Which I have indirect ownership interest in), I am directly contributing to the profitability of my own investment portfolio.

2) I worked in a contract role at Bank of America and interacted with several high caliber people with great leadership, knowledgeable and willing to teach, and learn with the analyst. The mix of humility, ownership of the tasks, and teamwork is something that really impressed me and inspired me to be like them.

3) I was trying to breaking into an investment management role. Under Prime Brokerage, I am directly working with institutional investors and hedge funds - the smartest and brightest in terms of trade execution. I will be able to identify the best investors and learn from them and invest in them eventually. If all goes well, my knowledge and expertise I gained can equip me to move towards a client facing role.


Cool things I have witnessed and contributed
1) Strategic task allocation in Bank of America
Unspoken to the people outside the walled garden of wall street, the nature of trading in modern investment banks is 90 percent driven by automation and computerization, and success is measured by the (Straight Through Processing STP rate).

Because of the sheer complexity of different trading flows and various legacy systems, dedicated trade instruction teams are set up just to manage the complex flows. As different countries have very different tax structures and variety of corporate action events, the local CA processing team and offshore team is large and there will be unique CA events that need case-by-case analysis.

For Large markets like Japan, the teams are integrated from client servicing to trade processing team to settlements to clearing so that self clearing markets can operate seamlessly without any disruption to the trading flow. For other markets whereby trading volume is lower, the global custodian – local sub-custodian model is employed, whereby the agent (me) needs to ensure the trade execution in the market is correct and complete, while we ensure (and adjust) our books to reflect market reality.

2) My voice to be heard and impact made
Being a follower of Buffet for 8 years, I am keenly aware of Buffett’s description of wall street behavior, whereby short term profitability behavior is common. People wish to break into High finance and do the sexy deals, and no one wants to do the plumbing and flushing of the financial systems. The essence of value investing is to avoid the overheated trade and focus on bringing value to the people around you. So I did the following.

i) Merrill Lynch has NO cash or stock bonuses for junior employees after the 2008 Acquisition by Bank of America, and their model is to actively employ contractors rather than firming up on a long term position. The incentive structure is disincentivizing long term ownership.

Solution => My feedback in the Employee Engagement Proposal to let senior and junior employees be awarded RSUs in Bank of America got the green light after 2021. The vesting period will encourage employees to actually work harder to profit their own coffers, instead of treating it as a temporary home.

ii) Bank of America has legacy systems, and internal security policy only allow very select external automation and robotics tool to be used.

=> For my direct team, I build different processing documents to concatenate and manipulate different data points so they can do the manual processing on behalf of the analyst. The brain-numbing manual copy and pasting of data between different systems be done by robotics automation. Because different client servicing team and agency teams employ the same systems as my team, the macro is designed to improve time savings and allow them to run the mundane automation processing in the background and do parallel processing on other higher priority tasks.

iii) Huge Manpower turnover during covid period

=> During the covid crash and subsequent hiring spike. all of my local teammates got headhunted to rival firms and decided to left for greener pastures. I myself receive several attractive opportunities, but due to my commitment to see the team through, I decided to assist my manager in his efforts to hold the fort and stabilize the team. When the new teammates and other teams got on-boarded after work in office posture resumed, I volunteered to build up the training resources and capacity and trained up the team. This is in order to build relationships with the newcomers, as well form alliances and collaboration opportunities across different departments.


3) Differentiated trading strategies
In the hedge fund world, the nature of their value proposition is to deliver returns that are uncorrelated with the market. In the midst of the below major trading events throughout my time there, I acted as the invisible hand to move the market.

Nike Shape - Market Volatility amidst the covid frenzy
Stock Market’s Covid Pattern: Faster Recovery From Each Panic - The New York Times (nytimes.com)

Crypto Craze – Bulk offboarding of hedge funds which leveraged and lost money
https://globalrestructuringreview.com/review/asia-pacific-restructuring-review/2025/article/cryptoasset-recovery-and-restructuring-lessons-the-crypto-winter-in-singapore

Market Volatility amidst the WSB frenzy
A Look Back on How R/WallStreetBets Kicked Off the GameStop Frenzy - Business Insider

Some strategies that I executed involved the following. The learnings I gathered from the wins and misses helped me to develop my investment philosophy and deepened my understanding of the diversity of other strategies beyond growth and value investing.

i) ETF creation and redemption in Taiwan market
ii) Leveraged investing – Reallocation of assets to different accounts via re-hypotication
iii) Long short portfolio – Helping client to identify and cover their shorts
iv) Replying queries with respect to direct market access for high frequency traders
v) Navigation internal flows with respect to dark pools allocation for whale trades and cheaper execution
vi) Working with Agency broker – Working with client and counter-party for trade bulking and split trades


Now the big question. If I have worked so hard to built the above. Why did I give it all up?

Push and Pull Factors
1) The very nature of my automation and offshoring tasks is gradually making my own role redundant and shrinking the job pool for future Singapore bankers entering the industry. As I go down for my Sunday youth classes and see the young students aspiring to enter the workforce, or do my self studies at Republic Polytechnic, deep down I wondered if my actions are directly smashing my rice bowl and killing the market for future local bankers. My actions are mostly enriching the middle and senior management and I don’t see a strong purpose in what I am doing.

2) Trust is earned, respect is given, and loyalty is demonstrated. Betrayal of any one of those is to lose all three.
With the quiet firing practices that is undergoing at BAC, some of the more able leaders I worked with and greatly respected left for greener pastures. Even in my own team, there is a revolving door policy whereby the younger managers came in, inspired the junior staff to slog their guts off, get promoted, and use it as a stepping board to move on to other higher visibility roles.

After having trained up different personal and getting them promoted (2 AVP and 1 VP), working under 3 different VP for the past 5 years, but yet getting squeezed by current management and not granted the opportunity that was promised to me, I believed the opportunity cost to learn from better leaders that has a long term growth mentality is too huge to ignore, and I wanted to hone the knowledge and skills I have been practicing to grow and lead a new team.

3) After monthly meetings with members of my Investing group and surrounded myself with businessmen and senior leaders from different industries, I wanted to pivot towards a role whereby I can have better control over my own career direction and remuneration. Using Richard Kiyosaki 4 Quadrants (ESBI) as a base, I was in an employee (E) role to get the prerequisite funding, and trying to Pivot to a management (B) and Investor (I) role and my current trajectory will never allow me to reach there. Fortunately, I was inspired by the right investment gurus and their philosophy and practices, and have the foresight to have invested early and accumulated a sizable net worth. That gave me the courage to increase my negotiating power against the senior leaders, and to walk away when the negotiations went south.

Money Can’t buy happiness, but it can give you the power and courage to decide and change your own fate. I will be stepping out of my organization and moving into a client facing role, whereby I believe I can have a greater impact and improve the financial lives of those that I can reach out to. I will also be experimenting with different social media platforms and explore different forms of content creation. Until then, I will work with my new teammates and aspire to be the best version that I want to be!