Three years into running my dev agency, I was burnt out from doing everything—sales, accounting, client support, and coding. I had started the agency not because of a burning desire to change the world; I had failed at being a quantitative trader. Turns out that you actually need maths to succeed in that field. Throwing caution to the wind, I did what I knew best: building websites.
So there I was: failed finance guy trying to build a tech company, desperately hiring developers who promised the world and delivered broken code three weeks late. That three-month e-commerce project dragged on for another six. I was also outsourcing work to unreliable contractors I found on Fiverr. I’ll never forget discovering on Christmas Eve that our Boxing Day launch was nothing but an empty code repository. Thankfully, I had Vincent, my crazy French developer buddy, whom I had worked with at an earlier failed photo-sharing startup, to show me the proverbial ropes. When we finally received an acquisition-hire offer, I was ready to throw in the towel. I had realised that I’d been solving the symptom, not the disease.
Startup Fever
That acquisition taught me I needed to understand why smart business leaders keep making the same technical mistakes. However, after a couple of months, I was getting bored. The waterfall cadence masquerading as an agile process often left me sitting on my hands waiting for feedback from the backend or QA team. So I joined StashAway as employee number two, where we scaled from pre-seed to Series D.
During this period, I watched how technical debt compounded at different stages: ‘I’ll fix it later when I have time’ became legacy code that everyone simply worked around. Even years after I left, those patches were still there, quietly draining developer productivity.
With each funding round, the team grew exponentially to tackle larger commercial efforts. As we expanded into four other regions, I became fluent in financial regulatory frameworks—building KYC/AML systems, working directly with regulators to shape new compliance requirements, even figuring out how to scan passport chips for identity verification. The biggest win was launching in Malaysia just six months after Singapore because we’d built our architecture with regulatory complexity in mind from day one. This taught me the difference between building for today’s problem versus building for tomorrow’s growth.
As we scaled, I learnt how to build and manage engineering teams across multiple disciplines: frontend, mobile, data engineering, and analytics. The technical complexity was brutal, but the real challenge was hiring. Some weeks, I conducted interview after interview, trying to identify genuine talent amongst candidates who could talk a brilliant game but couldn’t deliver.
We had a strong brand that attracted impressive CVs, but I needed a systematic way to separate the talkers from the doers. I developed a structured four-step assessment process based on Geoff Smart and Randy Street’s methodology from Who. The framework helped me consistently identify candidates who could actually deliver results under pressure, not just impress in technical discussions.
VC Pivot
In the summer of 2022, the world was still reeling from COVID. Back-to-back Google Meet calls left me with little time to work on solving technical problems. I needed a new challenge. After six years of scaling a hyper-growth startup, I was ready for a different perspective on the startup world. Along came an unexpected opportunity to work on a project to build a data platform for a venture capital firm.
“We’ll utilise AI to revolutionise the industry,” the founder explained confidently as I watched the room of investment analysts fall into a deep silence. We’d seen variations of this pitch countless times. These founders were building features and not a business.
Watching investment money evaporate as teams spent months perfecting features that customers said they needed but would never use, I realised that I’d made similar mistakes throughout the years. I’d been so focused on building impressive solutions that I’d missed the fundamental question: does this technology actually solve a problem worth paying for? The more I advised startups through hiring disasters and expensive code refactors, the more I realised I should get back to preventing these problems rather than just observing them.
The entrepreneurial itch returned. With everything I’d learned—from desperate founder to scaling operator to investment advisor—I could see exactly what was broken in how businesses approach technology decisions. With AI and automation eliminating many of the traditional technical barriers, there’s never been a better time for businesses to make technology decisions based on strategy rather than limitations.
That’s why I founded Superuser HQ: to be the technology partner that ambitious businesses need to build, scale, and win in their markets.