ARTICLE
18 August 2025

5 Structuring Mistakes Entrepreneurs Make – And How To Avoid Them

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Sentient International Limited

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Entrepreneurship thrives on bold ideas, relentless determination, and the willingness to take risks.
Isle of Man Corporate/Commercial Law

Entrepreneurship thrives on bold ideas, relentless determination, and the willingness to take risks. But no matter how innovative the concept or how committed the founder, even the most promising business can stumble without the right structure in place.

For this year's World Entrepreneurs' Day, we are reflecting on some of the most common structuring mistakes entrepreneurs make and the lessons that can be learned from them.

1. CHOOSING THE RIGHT JURISDICTION

One of the most frequent pitfalls is choosing a jurisdiction without thinking through its long-term implications.

Imagine a technology start-up launching in the founder's home country because it seemed the quickest and simplest route. In the early days, it works fine but, fast forward five years, and the company's plans to attract overseas investment are complicated by rigid local corporate laws and a tax regime that makes international operations expensive.

Instead of focusing on growth, the founder is suddenly dealing with redomiciliation, restructuring, and unpicking the operational issues caused by that initial decision.

Businesses often find that certain jurisdictions, like the Isle of Man and Malta can offer greater flexibility for international expansion, tax efficiency, and redomiciliation options. Planning the corporate structure with cross-border growth in mind can save significant time and expense later.

The right jurisdiction is not just about incorporation; it's about ensuring the business has room to grow, attract funding, and operate efficiently across borders.

2. OVERLOOKING SUCCESSION PLANNING

Another mistake is putting off succession planning.

Consider a family-owned engineering firm, built up over decades by its founder. Everyone assumes that one day the founder's eldest child will take over but no formal plan is ever made. When the founder unexpectedly steps back due to ill health, disagreements arise among family members, key staff leave due to uncertainty, and a major client begins to look elsewhere.

Structures such as holding companies, family trusts, foundations, or even carefully drafted shareholder agreements can formalise succession intentions, ensuring that a business's legacy and operational stability are protected.

The lack of a clear, documented transition plan puts years of hard work at risk. Businesses that think about their legacy from the start, and document those intentions, are far better prepared to handle inevitable change.

3. POOR INTELLECTUAL PROPERTY PROTECTION

Intellectual property protection is another area where lessons are often learned the hard way.

Take a design-led fashion brand that expands into Asia without registering its trademarks there. Within months, near-identical copies of its products appear in the market, sold under a similar name.

Legal action is possible, but costly and slow, and by the time it's resolved, the brand's image and market share have suffered.

Entrepreneurs often use structures such as IP holding companies or regional licensing arrangements to centralise and protect their intellectual property across multiple jurisdictions.

Proactive IP protection, in all jurisdictions that matter, isn't just a legal formality, it's a shield for a business's most valuable assets.

4. NEGLECTING GOVERNANCE

Governance is sometimes viewed as something only big corporations need, but its absence can quickly become a problem.

Picture a high-growth food and beverage company attracting the interest of private equity investors. The product is strong, the figures are promising but when investors ask for detailed governance documentation, risk management policies, and board protocols, none of it exists.

This lack of structure gives investors cold feet, and the funding opportunity slips away.

Good governance is not bureaucracy for bureaucracy's sake; it's a sign of professionalism, stability, and readiness for growth.

Even small and medium-sized enterprises can benefit from advisory boards, clearly defined roles, and formalised decision-making processes, helping to demonstrate stability and preparedness for future investment.

5. NOT FUTURE-PROOFING FOR GROWTH

Finally, there's the matter of future-proofing.

A fast-growing e-commerce business starts with a simple structure that works perfectly in year one. By year three, it's operating in multiple countries, holding stock in various warehouses, and managing different tax and compliance regimes.

The patchwork of entities created along the way is costly to maintain and riddled with inefficiencies. What began as lean and agile is now cumbersome and slow, preventing the founder from responding quickly to new opportunities.

Planning structures with scalability in mind – for example, multi-jurisdiction holding structures or entities designed for cross-border operations – allows entrepreneurs to adapt to growth without being held back by their own foundations.

REFLECTIONS FOR ENTREPRENEURS

Successful entrepreneurship isn't just about having the courage to start – it's about creating the conditions for sustained success. By anticipating these common pitfalls and planning ahead, founders can build businesses that are both innovative and enduring.

From choosing the right jurisdictions and protecting intellectual property to planning succession and governance, the right structures can be the difference between a business that thrives and one that struggles to survive.

The content of this article is intended to provide a general guide to the subject matter. Specialist advice should be sought about your specific circumstances.

 

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