'A Boss Shouldn't Dictate My Success': Entrepreneur Rejected £2,300 Salary — Built $75M Property Career

Claire Tan was barely out of polytechnic when she turned down multiple job offers paying between SGD $3,500 and $4,000 a month (£2,025-£2,300 / $2,625-$3,000) to bet on a makeup business she had started at 17.

That bet has paid off. Tan, the founder of Ladyy Claire Makeup, one of Singapore's first standalone bridal makeup companies, has since pivoted into luxury real estate and transacted over SGD $100 million (£58 million/$75 million) worth of property, according to the Asia Real Estate Summit.

She won PropertyGuru's Home Run: Singapore reality competition in 2024 and returned as a judge for its second season.

In an episode of the EDIT HISTORY podcast hosted by Cheryl Lau released on 25 January 2026, Tan spoke candidly about the corporate experience that drove her toward entrepreneurship and the financial gambles that followed.

Shanghai Internship That Broke the Camel's Back

Before makeup became her livelihood, Tan studied accounting at polytechnic and juggled freelance marketing gigs on the side. She completed internships in tax and audit across Singapore and Shanghai, each reinforcing a growing discomfort with corporate life.

The Shanghai posting proved to be the final straw. Her supervisor made a personal remark that crossed a line. 'Claire doesn't communicate very well because she's from a broken family,' the boss said, according to Tan. She broke a scholarship bond and returned to Singapore.

'My work could only grow as much as someone dictating it,' Tan told Lau. 'No matter how good I was, no matter how smart I am or talented at my job, I'll never be able to grow unless the leader approves of it.'

A school teacher challenged her after she returned, questioning whether she could survive without a boss dictating her success. Her response was blunt: 'If this is like the real world, then I don't really want to be a part of it.'

So she built something of her own.

From Bridal Makeup to Multimillion-Pound Property Deals

Ladyy Claire Makeup started as a one-woman operation. Tan handled everything from client bookings to tax filings. The bridal beauty industry in Singapore was fragmented at the time, with most makeup artists working under wedding studios for a small cut. Her company was among the first to offer bridal makeup as a structured, standalone business.

The early grind was punishing. Tan told Lau she practised three hairstyles every single day to compensate for a skill gap. Hair styling in Singapore's humidity did not come naturally. 'I just tell myself, push it through,' she said. 'And then I just do. And then I cry. And then I do.'

Her logic was financial. 'If I'm not good, the opportunities won't come,' she said. 'And even if the opportunities come, I may not be able to grab them.'

The pivot to real estate came during Singapore's COVID-19 circuit breaker in 2020, when a friend in the industry suggested she sit the licensing exam. She failed it twice and only passed after roughly 18 months of study. But having invested that much time, walking away felt worse than committing fully.

According to her ERA Realty Network profile, Tan became a Rising Millionaire and consistent Top Achiever within two years. She now works with high-net-worth clients and has managed property portfolios for more than 80 families in Singapore.

The competition is steep. Singapore had over 36,000 registered agents as of early 2025, according to the Council for Estate Agencies. 'You either have to outwork everyone or be damn talented at what you do, but you still have to outwork everyone,' Tan said. 'That's why the turnover rate is so high.'

Despite leading teams across both businesses, Tan describes herself as '99.99 per cent introvert.' Her team jokes she hides behind the curtains at parties. But she views it as an advantage. 'Introverts can connect the best with people one-on-one because they really listen,' she said.

What she is still working on is learning not to hold her team to that same standard. 'I can work the whole day without eating and then just feel faint and then survive on a bit of gummy bears,' she said. 'But I know a lot of people cannot do that.'