From the proverbial pinnacle, he fell off the precipice and had to don the humble uniform of a cook after 15 years as a top insurer.
But Mr Ramesh Krishnan, who was forced to leave the industry after a scathing reference from a previous employer closed other doors to him, is philosophical about the $4 million compensation he was awarded by the High Court last week, noting that "everybody knows, no matter how much you get you won't be happy".
Prudential had declined to pursue the process of hiring Mr Ramesh in 2011 after receiving a letter of reference from AXA Life Insurance Singapore, where he had worked as an agent.
Mr Ramesh, said to be "one of AXA's best-compensated advisers", sued AXA for defamation and lost in the High Court in 2015. But the Court of Appeal in July last year ruled that AXA had breached its duty of care to him and ordered damages to be assessed by the High Court.
The award given out last week to Mr Ramesh was based on what he would have earned from the offer Prudential had conditionally made.
This included a commencement allowance of $675,000, as well as an initial monthly salary of $65,625 for the first 12 months beginning in April 2011 and $43,750 for the following months until July last year. It also included the loss of future earnings between August last year and July next year at a discounted rate.
The Court of Appeal had said AXA's reference would have given the mistaken impression that Mr Ramesh was not competent, and did not square with the evidence that he was one of AXA's best financial services directors, whom it had earlier persuaded not to resign.
When asked by The Sunday Times about his road to insurance career success, Mr Ramesh was quick to caution that it is "a career where you can be crushed as easily as pappadam".
When asked about his road to insurance career success, Mr Ramesh, 47, was quick to caution that it is "a career where you can be crushed as easily as pappadam".
"I saw the financial industry as a platform that was equivalent to being a lawyer, which I had wanted to be in my dreams of being a success," he said. " So what I did was diagnose someone financially like a doctor, and when I received rejections, would litigate like a lawyer. These two things came easy for me."
He was also dogged about team effort, saying "E pluribus unum (out of many is one)", a motto that is tattooed on him. "My life is directly linked to the three Vs - visual, verbal and vibrant - which boils down to having a plan, being a plan and representing a plan."
He said he would get perhaps two rejections out of every 10 pitches, which led him to rise rapidly to the top 1 per cent in the trade. He went from manager to director and senior financial services director. A slew of top insurance awards came his way and he made his first million before 30.
He was brought up by a single mother who, after her divorce, toiled as a car washer. He, too, was known as "car washer" by his friends as he used to help his mum between 7pm and 4am.
"I got excited about insurance by a person whose car I washed, because every year I saw him changing his car, from Datsun to Morris and eventually Mercedes."
When he went to collect the monthly $12.50 car washing fee from the customer one day, the man asked him to join the trade. Mr Ramesh, who was then 24 and ending his contract as an army regular, "jumped into it".
"All along I wanted to achieve something in life because my mum would tell me that to be born is a huge success. Out of one million, only one is born. I didn't understand it then, but did as I grew up."
He sought to be a success in all that he did, including washing cars, where he had a system to make the process efficient. He brought that to the insurance business. His clients ranged from road sweepers to lawyers. "Eventually, I also ended up changing cars every year."
All this came to a sudden end on April 29, 2011, when he was due to attend an AXA event, where his team was to get awards. Instead, he had to resign from the job after meeting the chief executive the same morning.
The circumstances surrounding his departure became the saga of court litigation and scrutiny that eventually led to last week's award.
When he started the lawsuit in 2012, there were "giggles and humiliation for me because I was told there was no way for one like me to challenge a Goliath company".
The five years that followed were "dark years", where he listened to his inner self, drank a bit and cycled a lot to tackle the stress. He credits his wife Sharina and family for their support. He worked in the kitchen of a vegetarian restaurant, supporting its growth. "I did not even know where to buy onions," he said.
Former colleagues lauded his self-made abilities and achievements. Mr Philip Tan, an assistant vice-president in the industry, said: "Mr Ramesh was my mentor and manager in 2005 and he single- handedly changed my lifestyle and that of my family. He is a leader who leads by example with his charismatic character and knowledge, which I personally feel makes him very different from other leaders."
Financial services consultant K. Nayson, who worked with Mr Ramesh from 2005 to 2011, said he was a director who trained his agents to be his peers.
Mr Ramesh, who now drives a van and is still trying very hard to rejoin the insurance industry, said he cried when he received the text from his lawyer in July last year that he had won the case. "I was at a market buying vegetables," he said.