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5 Common Pitfalls Serial Entrepreneurs Should Avoid

5 Common Pitfalls Serial Entrepreneurs Should Avoid

  • 01 October 2021
  • By OCBC Business Banking
  • 10 mins read

Being a successful serial entrepreneur not only requires you to look out for golden opportunities to help your businesses grow, but also to watch out for potential pitfalls which may pose obstacles to your growth ambitions. Having multiple businesses also gives you a unique set of challenges that can be managed, as long as you watch out for them. Here are five common pitfalls to keep in mind.

Pitfall 1: Adopting the same ideologies and strategies across all ventures

When you have experienced success in your existing businesses, it can be tempting to expect the same results from replicating the same tried and tested business model. However, with an ever-evolving and highly competitive market, there is a need to ensure relevance to your customers.

As a serial entrepreneur, adopting a nimble and forward look attitude is crucial to giving your businesses an edge over the rest. Especially in the light of the COVID19 pandemic, being able to swiftly adapt to the evolving market landscape can help your businesses to succeed, even in difficult times. Adopting new technologies or innovations to optimise your business productivity, or reaching out to a wider base of consumers via online platforms with novel marketing strategies, will give you a competitive edge against competitors.

Pitfall 2: Micro-management

It is common to want to have full control over all your businesses to attain the quality you seek, but knowing when and what to delegate to your trusted team is also crucial if you want to continue expanding your businesses. When running multiple businesses at the same time, it becomes increasingly difficult to maintain equal focus over each of them. As a business owner, being required to be personally involved in every business decision could signal a lack of trust in your team.

This brings you to a two-sided problem, where you may become easily overwhelmed with work while facing an unmotivated team. While it is good to be meticulous, delegating decisions to your employees that are within their expertise empowers and recognizes them as part of the team, which in turn facilitates their feelings of being a valued team player. It is also a good experience for your employees to handle the less critical aspects of the decision-making process so that you can nurture the talent and retain them in the long run.

Pitfall 3: Complacency

Having a successful track record is often a marker of good business management and strategy. This, however, can also cause you to become overly optimistic about your next venture. Classic psychology suggests that people tend to attribute previous successes with their hard work even as they tend to blame mistakes on external factors which they have no control over.

This creates a dangerous cycle for serial entrepreneurs as it may lead to complacency and oversight. In contrast, it is a good practice to remain pragmatic and flexible as you may encounter new issues which you might not have experienced in your previous businesses.

Pitfall 4: Burnout

Serial entrepreneurs are always juggling multiple hats at any one time. Managing multiple businesses comes with its own share of stress and responsibilities. The World Health Organization (WHO) describes burnout as “a syndrome conceptualised as resulting from chronic workplace stress that has not been successfully managed”. You may experience physical or mental exhaustion that can negatively impact your business and relationships.

It is important, as a serial entrepreneur, to manage your time well and know when to take a rest before burnout happens to you. You can avoid burnout by taking a step back and delegating some work to your team, leaving you with important downtime that you can use to reflect on your business practices and issues.

Pitfall 5: Losing sight of your business cash flow

For all serial entrepreneurs, ensuring sufficient cash flow is pivotal for carrying out daily business activities, with additional financial capital coming in the form of equity or debt financing. Instead of seeking loans during difficult times, it would be prudent for you to plan ahead and manage your cash flow while business is flourishing and take up working capital facilities during this time. By working out your financial cycles ahead of time with the advice of a trusted banker, you will be better able to pinpoint exact areas of your business that you wish to grow, as well as gaps that require bridging support.

A common issue experienced by serial entrepreneurs is raising funds when starting out a new venture or scaling existing businesses. When your business is expanding rapidly, there may be a lack of necessary infrastructure and technical knowhow to keep up with increasing demand for your goods or services. At the same time, you might anticipate a cash flow crunch as you plan to onboard new employees or implement more streamlined digital solutions.

At OCBC, we want to support your entrepreneurial journey and growth ambitions. By evaluating your business history across your existing businesses and your personal track record, we can provide working capital that will help with your next start-up ventures or business expansion plans. For example, T Medical group benefited from our financing support to grow their business.

“The willingness of the bank to assess us as a group benefited us greatly. It ensured that we were able to obtain loans despite that at the individual company level, we may be too young or our sales turnover too small. This provides us with the firepower to embark on new opportunities that arise to further expand our business.”

Dr Tan Yuan Zi, T Medical

Let us walk with you on this journey

With OCBC, starting your next business venture or scaling your established businesses, be it locally or overseas, is easier than you think. Instead of being assessed as an entity on its own, we consider your entire portfolio of businesses to gauge your financial stability and credibility. It is possible for serial entrepreneurs with strong track records to have their new loans approved even before the incorporation of their next start-up. To find out more, contact us and we will get in touch.


The serial entrepreneurial journey entails working with different business partners from different industry verticals. This gives them the opportunity to tap on their expertise, glean best practices and expand their network, possibly opening doors into niche sectors.


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The information provided herein is intended for general circulation and/or discussion purposes only. Before making any decision, please seek independent advice from professional advisors. No representation or warranty whatsoever in respect of any information provided herein is given by OCBC Bank and it should not be relied upon as such. OCBC Bank does not undertake any obligation to update the information or to correct any inaccuracy that may become apparent at a later time. All information presented is subject to change without notice. OCBC Bank shall not be responsible or liable for any loss or damage whatsoever arising directly or indirectly howsoever in connection with or as a result of any person acting on any information provided herein. Any reference to any specific company, financial product or asset class in whatever way is used for illustrative purposes only and does not constitute a recommendation on the same.

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