Entrepreneurship is often described as a thrilling adventure that entails taking risks, pursuing innovative ideas, and creating something new and valuable in society.
Within this dynamic landscape, however, there exists an exceptional few who take the leap and become serial entrepreneurs, who continuously seek for new opportunities.
However, the path of a serial entrepreneur is not without its challenges. Each venture brings its own set of hurdles, demanding unwavering commitment, and the ability to persevere in the face of adversity. The pressure to succeed can be intense, as serial entrepreneurs constantly balance the desire for growth and profitability with the risks inherent in pushing the boundaries of what is possible.
So what is it like to be a serial entrepreneur? What is it like to walk in their shoes, embracing the challenges and success that come with a life dedicated to perpetual innovation and relentless pursuit of success?
Here is an inside look at the good, the bad, and the ugly of being a serial entrepreneur.
Nobody sets out to be a serial entrepreneur
For many entrepreneurs, starting multiple businesses is not something that they intentionally set out to do. Rather, it is something that develops naturally.
And that is precisely the case for Jeremy Ko, the founder of gym chain Arkkies, indoor fitness and bouldering gym Fit Bloc, physical education equipment supplier Javy Sports, and fitness equipment supplier Movement First — one business eventually led to another.
Jeremy first started Movement First while he was still a student at Nanyang Technological University (NTU), which initially supplied sports tapes. Eventually, he moved into selling a variety of sports equipment, based on customer demand in 2016.
“It’s basically using the same operational systems, just in a horizontal expansion,” he said. Jeremy went on to start up his other businesses in a similar manner, expanding into different verticals within the fitness industry.
Cassandra Riene Tan, the founder of The Well Group — an umbrella company that creates and operates a diverse portfolio of hospitality, lifestyle and wellness concepts — started up her businesses in a similar vein.
She initially intended to launch BOTANY, as her sole F&B concept under The Well Group. However, she soon realised the potential for further expansion, leading her to launch additional concepts, including cafe and bar concept The Ritual and the upcoming Japanese fine dining concept Takahashi, to cater to diverse communities.
Miza Nazili Ghazali, on the other hand, was motivated to start multiple businesses as she believes in diversifying her income sources.
“By having multiple businesses, I reduce the risk of relying solely on one company’s success. This approach allows me to support and sustain other businesses, even if one faces challenges,” she explains.
The 29-year-old initially dabbled in the F&B industry, but she eventually found her passion when she ventured into the e-commerce industry. Today, she runs four businesses, comprising health and beauty platform Beautyfyxed, whitening supplement brand Ivwhite, clothing business Naezily, as well as health and supplement company Shortcutx.
Meanwhile, for some, building something from the ground-up provides them with a sense of satisfaction — which is exactly what drove Federico Folcia, an Italian entrepreneur based in Singapore, to launch multiple businesses.
Driven by his constant dedication to seek out new opportunities, he founded community space Crane and boutique business consultancy service Powerhouse.
Identifying the right opportunities to start new ventures
For Miza, thorough market research is vital before starting a business. “I analyse factors such as customer demand, the likelihood of returning customers, as well as the maximum revenue potential of the business,” she said.
By doing this, she gets to evaluate the feasibility and profitability of each opportunity to ensure that her potential ventures have a solid shot at success.
Similarly, Cassandra shares Miza’s thorough approach to evaluating potential ventures. She emphasises the significance of assessing associated costs, required resources, and potential risks before committing to a new venture.
To do this, she considers the worst-case scenarios in order to make informed decisions about the feasibility and sustainability of her ventures. “This evaluation helps mitigate potential challenges and ensures a solid foundation for success.”
Jeremy’s entrepreneurial philosophy, on the other hand, centres around cultivating competitive advantages and fostering a beneficial ecosystem. He places great importance on having an edge over existing market players and assessing how a new venture can synergistically benefit his current ecosystem.
Movement First, Javy Sports, Arkkies, and Fit Bloc all assist each other in a positive feedback loop. Our equipment design is improved gradually through heavy commercial usage at Arkkies, and we then sell the [improved] equipment to clients at Movement First.
– Jeremy Ko, founder of Arkkies, Fit Bloc, Movement First, and Javy Sports
That said, it’s not all about reaping profits — a business should not only be financially viable but also align with desired lifestyles and long-term goals of entrepreneurs, offering them a path towards personal fulfilment.
Federico exemplifies this ethos through his ventures, be it revolutionising the travel industry with a peer-to-peer short-term rental platform (Federico’s home-sharing platform Roomorama, which has ceased operations in 2017) or creating opportunities for personal growth and relevance in today’s fast-paced world through Crane.
Finding the right balance
That said, running multiple businesses concurrently is an arduous task — its tough to find the perfect balance between these businesses. This is why Cassandra believes in automating processes whenever, and wherever she can.
To begin with, I focus on establishing effective systems and processes to streamline operations and reduce manual effort. By implementing efficient workflows and harnessing technology, I can automate tasks and optimise productivity.
– Cassandra Riene Tan, founder of The Well Group
With this, the entrepreneur gets to delegate her attention to strategic aspects of the business, and overall business growth.
Aside from this, effective time management is also crucial in managing multiple businesses smoothly. Miza, for one, allocates specific time windows for each business to give each of them dedicated focus and attention.
“For example, I may dedicate the morning to one business and the afternoon to another. However, flexibility is key, as some days may require more focus on one business than the other,” she explains.
Another important aspect of managing multiple businesses effectively is to remember how to delegate tasks and rely on others. Founders often feel the pressure to handle everything themselves, which can lead to burnout and hinder overall productivity.
In fact, they are more susceptible to mental fatigue, with 50 per cent of them being more likely to suffer from mental stress.
That was the case for Miza, before she learnt how to better manage her time and entrust her staff to shoulder certain responsibilities. She used to work herself to the bone for 20 hours a day in her early days of running her previous F&B ventures, Deli Cakes and Iceburnz.
Another approach to this is to outsource tasks that require specialised expertise to external partners — this is one of the key components of Cassandra’s management strategy. “By leveraging their specialised expertise, I can expedite execution and enhance efficiency. This allows internal resources to be allocated to other essential priorities.”
Similarly, Federico also has “a select group of external collaborators”, who contribute their expertise to both his businesses. “This approach allows for a smoother learning curve, and streamlined communication,” he explained.
Leveraging the interconnectedness of multiple ventures
While managing multiple businesses is a challenging ordeal, the resources and networks from one business can be leveraged to benefit another, enhancing the overall manageability of the whole endeavour.
For instance, when Jeremy decided to start up Fit Bloc, he leveraged the fitness equipment from Movement First as well as his general sourcing expertise to start and manage the business at a lower cost structure. As a result, Fit Bloc managed to breakeven faster as compared to traditional climbing gyms.
Subsequently, in 2021, with the experience of running a consumer gym successfully, Jeremy went ahead to establish Arkkies, which currently has 11 gyms, with three more locations coming later this year.
Federico also leverages shared resources and networks to maximise the efficiency of his businesses. Across both his businesses, Powerhouse and Crane, he utilises the same accounting service and task management set up, allowing for cost optimisation.
Meanwhile, Miza leverages the interconnectedness of her businesses to support and stabilise her businesses. The success in one business provides additional resources and opportunities that accelerate the growth of another, while challenges prompt resource reallocation to support the affected business.
This interconnectedness allows for strategic adjustments and ensures a cohesive trajectory across my business portfolio.
– Miza Nazili Ghazali, founder of Naezily, Shortcutx, Beautyfyxed and Ivwhite
Additionally, Miza capitalises on shared marketing and promotional channels to cross-promote her products and services, expanding the reach and customer base for multiple businesses.
Cassandra takes a similar approach when it comes to growing and expanding the reach of her businesses.
We absolutely make the most of our resources and connections across all businesses in our portfolio. For instance, we have found that BOTANY serves as an excellent location for product launches. We debuted some of Naked Blend (the Well Group’s beauty and wellness concept)’s offerings there, showcasing our new products to media colleagues and friends.
– Cassandra Riene Tan, founder of The Well Group
Additionally, she also leverages the customer base of her existing ventures to generate awareness for new endeavours. For the launch of the Well Group’s pet wellness concept, A Pet Story, she tapped on the pet-friendly environment at their Japanese-French F&B concept, Well Collective, to draw in its community and generate awareness for the new venture.
That said, Miza cautions against wholly relying on one business to support another. Proper fund management and financial independence for each business are vital, to reduce the risk of one business negatively impacting the other.
Staying passionate about each business over the long-term
Entrepreneurship is a challenging and demanding journey that requires persistence, resilience, and a strong drive to succeed, so it is natural for motivation levels to fluctuate over time. However, it’s crucial to find ways to rekindle motivation and regain focus to ensure that the venture succeeds in the long run.
Cassandra believes that the key to this lies in seeing each business “as a living entity that is constantly evolving”.
It is an intriguing process to continuously refine and shape each venture, and watching it mature into something that is both optimally functional and aesthetically pleasing in its own unique way. This ongoing process of transformation and growth fuels my passion and keeps me motivated for the long haul.
– Cassandra Riene Tan, founder of The Well Group
For Jeremy, he draws his motivation from the positive impact his businesses have on society. “I believe the businesses I create have a net positive to society. Being in the health industry, by making our equipment and gyms high quality yet affordable, being healthy can be accessible to everyone,” he adds.
The same goes for Miza — her products solve common issues faced by Singaporeans. She also wears and consumes the products herself, fuelling her drive to continuously improve and innovate for the long term success of her business.
Meanwhile, Federico adopts a unique approach by allocating dedicated time and empowering individuals who possess expertise and passion for each business venture. He surrounds himself with talented individuals, empowering them to infuse their enthusiasm and expertise into his businesses.
By fostering a collaborative environment and entrusting capable individuals, Federico ensures that each business receives the love and attention it deserves, nurturing motivation and driving long-term success.
“I try to allocate enough love time for each business, and I try to empower smarter people than me to add more love to my ventures,” he said.
Do you have what it takes to become a serial entrepreneur?
Anyone, and everyone, can start up and run multiple businesses. However, it takes certain skills and qualities to successfully manage and sustain these businesses over the long term.
A fundamental attribute that serves as the bedrock for the success of serial entrepreneurs is adaptability. The business terrain is constantly evolving, hence, it’s important to stay receptive to fresh opportunities.
For Cassandra, adaptability has been an integral part of her entrepreneurial journey, particularly during the challenging times brought about by the COVID-19 pandemic. As the pandemic ravaged her F&B businesses, she embraced a solutions-driven mindset to overcome these obstacles and find new avenues for growth and success.
Tenacity also plays an integral part in ensuring the success of businesses, as it enables entrepreneurs to persevere to trials and maintain their determination in the face of adversity.
I would like to emphasise that success is seldom immediate — it took me years to reach my current position. Regrettably, impatience often leads many to abandon their entrepreneurial ambitions prematurely.
– Cassandra Riene Tan, founder of The Well Group
Hence, it’s important to remember that managing a business, or even several, is a marathon, not a sprint. It is about sustained effort and balance, not burning out in a frenzied dash to the finish line.
Jeremy echoes the same sentiment. He said that there is no “magic sauce” to successfully launch multiple businesses, but there needs to be constant hard work and dedication.
When one business is stable, you will logically start looking for your next opportunity. There might be brilliant entrepreneurs like Elon that thrives in chaos, but we are probably not one of them.
– Jeremy Ko, founder of Arkkies, Movement First, Fit Bloc and Javy Sports
When taking up multiple ventures, there is no doubt that entrepreneurs would have to deal with various uncertainties and failures. However, Federico emphasises that it is vital to embrace these failures as stepping stones to success, as each setback provides valuable lessons and growth opportunities
Ultimately, no entrepreneurial journey is the same — but what’s certain is that the path to the long term success of business ventures is paved with challenges.
It is the combination of adaptability, tenacity, and a growth mindset that allows entrepreneurs to not only start multiple businesses but also sustain and thrive in the long run, just like Jeremy, Cassandra, Miza and Federico.
Featured Image Credit: Jeremy Ko/ Cassandra Riene Tan/ Federico Folcia/ Naezily