Till January, he was a transport tycoon running Five Star Tours, which had eight branches in its heyday.
Today, Ken Lim Cheng Chuan, 55, is like any other odd-job worker, serving drinks at a coffee stall.
For a man who started working at a biscuit factory at 13 and climbed his way to become the boss of the transport group, life has come full circle.
The former managing director was visibly tired, but cordial as he served customers on Sunday morning, Lianhe Wanbao reported.
Mr Lim was declared a bankrupt last month and is trying to settle his financial affairs, he told Wanbao.
He said his business went bust as it was badly hit by the emergence of the integrated resorts.
Since 2010, when Resorts World Sentosa and Marina Bay Sands opened, the number of customers taking his tour buses to Genting in Malaysia fell 70 per cent. It was a huge blow, as the Genting trips accounted for the bulk of the company's revenue.
Instead of scaling down operations, he continued to expand in Malaysia, resulting in cashflow problems. He hung on to the end, he said, and personally made a police report when the company folded.
After resting at home for some time, he decided he needed to keep working, and has been helping out at his relative's coffee stall for about a month.
"I work for more than 10 hours every day, standing next to the hot stove. It is a far cry from working in an air-conditioned office," he said. "I am exhausted."
But he joked that the coffee shop was in a central location, making it convenient for him to visit the court and the Insolvency & Public Trustee's Office.
It is also near the offices of the Central Provident Fund (CPF) Board, which he frequents as he still owes some employees CPF contributions, he said with a laugh.
"My friends from the industry drop by sometimes to say hi," he said. "It's encouraging."
Mr Lim is no stranger to adversity. He worked at various jobs in his teens, and started his first business selling ornamental fish at 20. A storm washed that all away and he lost a lot of money.
In 1985, his father started running an office for a Malaysian tour bus company here and that was how he learnt the ropes.
He set up Five Star with his four brothers in 1990.
In the interview, he indicated that he may be back. "Who wouldn't want to make a comeback? Just give me 10 more years... but, perhaps, not now."