Embarking on a second startup journey can be a thrilling yet daunting experience, especially after the roller-coaster ride of founding the first venture.

This sentiment was profoundly echoed by Ooi Hann Liew, a seasoned fintech entrepreneur, during his speech at “The Fintech Frontiers Conference 2023“.

But Hann Liew’s keynote, aptly titled ‘Start, Scale, Repeat: The Second Startup Journey’, was more than just a walk down memory lane. Instead, it was a candid exploration of his evolutions and a treasure trove of insights for budding entrepreneurs on the nuances of embarking on a second venture.

Starting from the beginning

Born and raised in Malaysia, Hann Liew’s career trajectory led him to the United Kingdom, where he pursued his studies and embarked on a career in the bustling city of London during and after the financial crisis.

In 2010, he decided to dive headfirst into the world of entrepreneurship. Many in the audience may have known him as the co-founder of Jinerxu and RinggitPlus, where he spent over a decade helping people improve their financial literacy and access online financial products,

Hann Liew’s entrepreneurial endeavours also extended to policy advising for the government. His significant role in the National Economic Action Council attested to his influence and impact in shaping financial policy in the nation.

Most recently, he has assumed the role of CEO and founder at Halogen Capital, a pioneering Digital Asset Fund Manager in Malaysia.

When to take a step back

A crucial question often perplexes startup founders is determining the opportune moment to embark on a new venture after their first. Hann Liew underscored the importance of acknowledging when the daily grind of startup life becomes overwhelming.

While every entrepreneur faces challenging days, he said that prolonged difficulties should trigger introspection.

Hann Liew posed the question,

“When is it the right time to take a step back?”

He added that enduring occasional tough days while passionately pursuing a startup’s mission is normal. However, it warrants consideration when those tough days become a persistent challenge.

A framework for self-reflection

In his presentation, Hann Liew introduced a framework for categorising startups into three stages. This classification aimed to help founders assess their personal feelings and their startup’s position when contemplating a step back.

The first stage of a startup is akin to infancy. This phase typically involves a small team of about five to ten people, with the company just post-product launch and beginning to generate some revenue.

In this stage, if a founder is not actively involved in day-to-day operations, it can be challenging to consider it a true startup.

The second stage, the “adolescent” phase, involves more systems, processes, and a larger team of approximately 20 to 50 individuals. Revenue generation is consistent, and there is moderate growth.

However, if the founder steps back from day-to-day operations at this stage, it might lead to some sacrifices, such as slower growth.

The third and final stage, which Hann Liew called the “independent” stage, represents a more mature and stable startup. This stage is characterised by significant senior employees, substantial revenue, and steady, if not explosive, growth.

In this phase, the founder’s role may become less critical to daily operations, and the company can continue to thrive even without their direct involvement.

His framework encouraged startup founders to assess how they felt about their ventures and in which stage of the journey their startup resided.

Roadmap for founders

When contemplating a transition from a startup, Hann Liew emphasised the importance of a well-thought-out plan. He offered a roadmap for founders considering such a move.

Founders should initiate discussions about their intentions with co-founders, leadership, and the team. Gaining support and approval for transition plans is essential. Transparent and honest communication is vital to a smooth transition.

Detailed planning is crucial to ensure a successful transition. Founders should outline how they will delegate authority and responsibilities over a specific period. The transition should be gradual and well-managed, allowing the founder to maximise their impact during part-time involvement.

Even after stepping back from the day-to-day operations, founders should remain accessible to co-founders and employees. They should be supportive mentors and advocates for the company’s continued success.

Hann Liew spoke of the importance of stepping away and actively supporting and championing the team from the sidelines.

The second startup

Venturing into the world of crypto with Halogen Capital as his second startup, Hann Liew shared insights on dealing with challenges.

Learning from past mistakes and striving to avoid repetition is crucial for personal and professional growth. Experience is a valuable teacher, and second-time founders have the advantage of hindsight to make more informed decisions.

Keeping one’s ego in check and remaining humble and adaptable is essential for continued success. While previous successes can bolster confidence, staying open to new ideas and approaches is vital.

Founders must view their second startup as an addition to their identity rather than a replacement. This perspective allows personal and professional growth while embracing new challenges and opportunities.

Insights from a second-time founder

Hann Liew’s journey as a second-time founder provides a valuable roadmap for those contemplating their second startup journeys.

His insights emphasise the importance of recognising the right moment to step back, effective communication and adapting to new challenges.

Ooi Hann Liew’s story is an inspirational tale of personal and professional growth, illustrating how founders can leverage their experiences to navigate the uncharted waters of a second startup with confidence and resilience.

Watch the full “Start, Scale, Repeat: The Second Startup Journey” at the Fintech Frontiers Conference