The Tax Divide: Why Singapore’s Doctors Lost, While Billionaires Win Through Ownership

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Zion Zhao Real Estate | 88844623 | 狮家社小赵 | wa.me/6588844623 |  https://linktr.ee/zionzhao
This post is for general information, education, and market literacy only. It does not constitute financial, investment, trading, legal, tax, accounting, or other professional advice, and is not an offer, solicitation, recommendation, or endorsement. Views expressed are personal, general in nature, and subject to change without notice. While reasonable care is taken, no representation or warranty is given as to accuracy, completeness, or reliability. Readers should conduct independent due diligence and seek professional advice. To the fullest extent permitted by law, no liability is accepted for any loss arising from reliance on this material. 

Singapore Tax Ruling Exposes the Wealth Gap Between Earning Income and Owning Assets

Three Doctors, Billionaires and the Tax Divide Between Work and Ownership

Three Singapore doctors recently lost their High Court challenge against IRAS. The legal issue was not whether doctors may incorporate companies. They can. It was not whether dividends are unlawful. They are not. It was not whether tax planning is illegitimate. It is not.

The issue was substance.

In Tan Chek Jin Adrian and others v Comptroller of Income Tax [2026] SGHC 132, the High Court upheld IRAS’s use of section 33 of the Income Tax Act, Singapore’s general anti-avoidance provision. The doctors had operated through a series of jointly and individually owned companies, paid themselves relatively modest monthly salaries of S$5,000 to S$6,000, and extracted substantial sums through tax-exempt dividends and interest-free shareholder loans. One doctor received more than S$7 million in dividends across related entities.

The court’s core concern was not legal form. It was economic reality.

Where income is substantially generated by personal professional services, especially medical expertise, clinical judgment and specialist labour, the tax authority is entitled to ask whether the corporate structure reflects commercial substance or merely converts taxable professional income into lower-tax distributions. The High Court found that the arrangement, viewed holistically, pointed to tax avoidance or reduction as one of its main purposes (Tan Chek Jin Adrian and others v Comptroller of Income Tax, 2026).

This is where the comparison with global billionaires becomes provocative, but it must be handled carefully.

Elon Musk, Mark Zuckerberg, Larry Page and other founder-billionaires are often associated with minimal salary structures. However, the deeper tax advantage is not simply “low salary.” It is ownership. Their wealth is held mainly in shares, not monthly employment income. If those shares rise in value but are not sold, the gains are generally unrealised. In the United States, unrealised capital gains are generally not taxed until a taxable realisation event, such as a sale. If the founder borrows against those shares instead, the loan proceeds are generally not treated as taxable income because debt must be repaid (Internal Revenue Service, 2025).

That is the architecture behind the “buy, borrow, die” strategy.

First, own appreciating assets. Second, borrow against them for liquidity. Third, hold them until death, where inherited assets may receive a step-up in basis for United States income tax purposes, potentially reducing or eliminating tax on lifetime unrealised gains (Internal Revenue Service, 2026). This is not necessarily illegal. It is often the tax system operating as designed.

That is the uncomfortable distinction.

The Singapore doctors’ income was generated by personal exertion. The billionaire strategy is based on capital ownership, collateralised borrowing and unrealised appreciation. One may be challenged under anti-avoidance rules when the legal form diverges from economic substance. The other often sits inside the basic design of capital taxation.

This does not mean all billionaire tax planning is admirable. It does not mean every professional incorporation is abusive. It means the law draws a sharp line between earning and owning.

Professionals earn income through labour, skill and time. Owners accumulate wealth through assets, equity, leverage and timing. Salary is visible, reportable and taxable annually. Unrealised gains are often deferred. Loans create liquidity without immediate income tax. Estate rules may further soften the final tax bill.

That is why the public senses an asymmetry.

A doctor who earns from patients cannot simply label professional income as capital without scrutiny. A billionaire who owns shares can often access liquidity without selling those shares. The first looks like income conversion. The second looks like balance sheet management.

For Singapore professionals, the lesson is direct: incorporation must be commercially real. A company should have substance, business purpose, proper documentation, real risk allocation, defensible remuneration, and a rationale beyond tax savings. Dividends should reflect genuine equity participation and business profits, not merely a substitute for personal service income. Shareholder loans should not appear to be disguised extraction of profits.

The most dangerous phrase in tax planning is “everyone does it.” The second most dangerous is “my accountant said so.” Professional advice matters, but it must be documented, credible and consistent with actual conduct. Ultimately, the taxpayer remains responsible.

The larger policy question is harder.

Modern tax systems tend to tax labour immediately while allowing ownership wealth to defer, compound and borrow. That does not automatically make the system broken. It shows what the system prioritises: realised income over unrealised wealth, salary over capital appreciation, employment over ownership.

The doctors’ case made headlines because it was visible, domestic and legally contested.

The billionaire strategy rarely looks like a courtroom drama. It looks like private banking, securities-backed credit, estate planning, executive compensation, philanthropy and balance sheet optimisation.

That is why this story matters beyond three doctors and one tax appeal.

It is not merely about tax avoidance. It is about the structural divide between those who work for income and those who own appreciating assets.

In modern capitalism, the tax code does not just collect revenue. It reveals power.

新加坡医生税务败诉背后：为什么打工赚钱被征税，拥有资产却有更多选择？

工作者与资产拥有者之间的税务分野

三名新加坡医生近日在高等法院挑战新加坡国内税务局（IRAS）的裁定失败。法院支持税务局依据《所得税法》第33条，即新加坡的一般反避税条文，行使相关权力。

这起案件的重点，并不在于他们是否可以设立公司。设立公司本身是合法的，派发股息是合法的，合理税务规划也是合法的。真正的问题在于：商业实质。

据案件内容，相关医生每月仅支付自己约5,000至6,000新元的薪金，却通过免税股息和免息股东贷款提取大量利润。其中一名医生通过相关公司收取超过700万新元的股息。法院认为，从整体安排来看，该结构显示其主要目的之一是避免或减少纳税义务（Tan Chek Jin Adrian and others v Comptroller of Income Tax, 2026）。

这也是为什么公众常常会把这类案件与全球亿万富豪的税务安排进行比较。但这个比较必须精准。

Elon Musk、Mark Zuckerberg 以及其他创办人，常被认为采用低薪或象征性薪金结构。然而，更深层的税务优势并不只是“低薪”，而是“资产拥有权”。亿万富豪持有不断升值的股权，避免出售股票，并以这些资产作为抵押进行借贷。由于贷款通常不被视为应税收入，因此他们可以通过债务取得流动资金。若相关资产被继承，美国税法在某些情况下还可能允许资产计税基础在继承时重估，从而有机会减少甚至消除长期未实现资本增值所对应的所得税影响。

这就是结构性的差异。

医生的收入，本质上来自个人专业服务、临床判断、医疗经验和手术能力。亿万富豪的财富策略，则建立在资本所有权、未实现资本收益、资产抵押借贷和遗产规划之上。当形式与实质不一致时，前者可能被反避税规则重新定性；而后者往往本身就运行在税法制度架构之内。

对专业人士而言，真正的启示非常清楚：不要把税务效率误认为税务规避。公司必须具备真实的商业实质，薪酬必须具备合理性与可辩护性，文件记录必须完善，结构设计也必须具备税务节省以外的商业目的。

更大的政策问题则更加令人深思。现代税制往往会立即征税劳动收入，却允许资产型财富继续复利、借贷和递延纳税。这个制度未必是坏掉了，而是在清楚展示它优先保护的对象：已实现收入，而非未实现财富；劳动，而非所有权；薪金，而非资本。

三名新加坡医生败诉，亿万富豪却能借钱生活：真正差别在这里

在今天的市场环境下，房地产决策不应该被孤立看待。

《The Tax Divide》带来的启发很清楚：财富的建立，离不开资产所有权、结构设计、时机判断和有依据的资本配置。

作为一名新加坡房地产销售人员，我的顾问思维并不只局限于房地产本身。我持续研究宏观经济、国际地缘政治、资产配置、股票市场、加密货币市场、新加坡土地法以及商业法。同时，我也在新加坡武装部队（SAF）担任 Officer Commanding（OC）一职，并持有上尉军衔。

我每天都会投入时间进行研究、写作和尽职分析，因为我相信客户需要的不只是销售话术，而是更深入、更全面、更负责任的判断。

无论您是新加坡本地买家、中国内地客户、东南亚或国际投资者、超高净值家族、家族办公室、机构投资者、陪读家长或留学家庭，新加坡房地产都有机会成为投资组合中相对稳健的一类资产，并具备长期资本增值与租金收入潜力。

如果您正在寻找一位具备宏观视野、纪律性分析和跨资产理解能力的房地产顾问，我将非常荣幸为您提供专业、真诚和尽责的服务。

Zion Zhao Real Estate
狮家社小赵
8884 4623
wa.me/6588844623

References

Inland Revenue Authority of Singapore. (2024). Incorporation of companies by medical professionals and relevant tax implications.

Inland Revenue Authority of Singapore. (2026). Income tax: The general anti-avoidance provision and its application.

Internal Revenue Service. (2025). Publication 525: Taxable and nontaxable income. U.S. Department of the Treasury.

Internal Revenue Service. (2026). Gifts and inheritances. U.S. Department of the Treasury.

Tan Chek Jin Adrian and others v Comptroller of Income Tax, [2026] SGHC 132.

Income Gets Taxed. Ownership Gets Optionality. The Singapore Doctors’ Case Explained

Work With a Real Estate Adviser Who Studies More Than Property

The lesson from The Tax Divide is simple but powerful: wealth is not built only by income. It is built through ownership, structure, timing, risk management and informed capital allocation.

Real estate is not just about buying a unit, comparing price per square foot or chasing the next launch. In today’s world, property decisions are increasingly connected to tax policy, legal structures, macroeconomic cycles, interest rates, currency movements, geopolitics, equity markets, liquidity conditions, family planning, immigration needs and long-term wealth preservation.

That is why choosing the right real estate representative matters.

I am Zion Zhao, 赵峻慷, a real estate salesperson based in Singapore. Beyond real estate, I actively study macroeconomics, global affairs, asset allocation, portfolio construction, equity markets, cryptocurrency markets, technical analysis, Singapore land law, business law, statutes and legislation. I also serve as an Officer Commanding in the Singapore Armed Forces, holding the rank of Captain.

I share this not to impress, but to explain my approach.

Every day, I dedicate hours to reading, researching, writing and analysing market developments. I write these essays because I believe serious property advisory must go beyond sales talk. My clients deserve proper due diligence, deeper perspective and a more complete understanding of how Singapore real estate fits into the broader economy and investment landscape.

For international buyers, China Chinese clients, South East Asian investors, Singapore families, ultra high net worth individuals, family offices, institutional investors, parents planning for their children’s education in Singapore, 陪读家长, 留学家庭 and families considering immigration or long-term wealth planning, Singapore property can be more than a home. It can be a strategic asset in a diversified portfolio.

Compared with more volatile asset classes such as equities and cryptocurrency, real estate may offer relatively lower day-to-day price volatility, physical utility, rental income potential and long-term capital appreciation potential, especially when the entry price, location, tenant demand, holding period and exit strategy are properly assessed.

However, property is never risk-free. Interest rates, taxes, cooling measures, financing rules, rental cycles, vacancy risks, maintenance costs and market timing all matter. That is why careful selection, disciplined analysis and proper professional guidance are essential.

My role is not to promise unrealistic returns. My role is to help you think clearly.

I help clients evaluate Singapore property through a multi-asset, macro-aware and legally informed lens. Whether you are buying for own stay, investment, children’s education, relocation, portfolio diversification, rental income or long-term wealth preservation, the right decision should be based on facts, numbers, structure and strategy.

In a world where people who own assets often gain more optionality than people who only earn income, real estate ownership remains one of the most practical pathways for families and investors to participate in long-term asset building.

If you are looking to invest, relocate, study, preserve wealth or build a Singapore property portfolio, work with a real estate professional who does not only understand property, but also understands the wider forces shaping property.

I would be honoured to assist you with professionalism, sincerity and diligence.

Zion Zhao Real Estate
赵峻慷 | 狮家社小赵
Singapore Real Estate Salesperson
WeChat: zionzhaosg
WhatsApp: wa.me/6588844623

Disclaimer: This post is for general education and market commentary only. It does not constitute legal, tax, financial, immigration or investment advice. Please seek independent professional advice where necessary before making any property, tax, legal, financing or investment decision.