When going all in doesn’t pay off: Meet the ex-entrepreneurs who chased their dreams and failed

In 2017, Ms Madeline Toh left a promising corporate career to take over a handmade udon restaurant in Kuala Lumpur (KL), Malaysia.

She had learnt through a friend that the two owners of the restaurant were retiring to return to Tokyo and were looking for someone to take over.

"I had a pretty solid corporate career trajectory that I was actually looking forward to," said Ms Toh, who was then 28 and a management trainee at a multinational company. 

But the draw of running her own business was too strong especially since the restaurant was already up and running, with staff and equipment in place.

It was the opportunity Ms Toh, who had long imagined opening a cafe or restaurant of her own, had been waiting for. 

After taking over the restaurant, Ms Toh and her three investors expanded into two more outlets in KL selling freshly made tamagoyaki (Japanese omelette) – a concept that became popular and drew media attention.

But by late 2019, declining footfall and mounting costs forced Ms Toh and her partners to decide whether to commit more funds or walk away.

By then they had pumped S$150,000 (US$118,000) into the business and in the end they chose to wind up the business.

"Winding the business down seemed like a failure," said Ms Toh. 

Like her, many workers in Singapore feel the need to scratch that itch of venturing out on their own and starting a business. 

A 2026 survey by the Association of Chartered Certified Accountants (ACCA) found that out of 11,389 accountancy and finance professionals across 160 countries, 54 per cent wanted to become entrepreneurs at some point in their careers. 

The survey included 140 respondents in Singapore and found that 46 per cent of them had similar aspirations.

Another 2022 study by the Singapore University of Social Sciences (SUSS) and insurer Great Eastern, which surveyed 2,500 Singaporeans aged 16 to 25, found that one in five respondents under 20 was looking to start a business.

While the appetite for starting a business remains strong, the challenge of launching and sustaining a business has doused the fire of many an aspiring entrepreneur.

Former business owners told CNA TODAY that striking out on their own proved harder than they had imagined, and that failure is the norm, not the exception.

Figures from the Accounting and Corporate Regulatory Authority (ACRA) from January to August this year show this too: While 56,548 business entities were formed in Singapore, 42,741 ceased. 

100-HOUR WORK WEEKS, ENDLESS PIVOTING

The startup formula can seem deceptively linear and simple: have an idea, raise money, scale fast and, if all goes well, become the next unicorn, or a company valued at over US$1 billion (S$1.27 billion).

However, as many founders told CNA TODAY, the reality is much harsher. Hard work, they found, does not always translate into wins – and many were blindsided by unexpected challenges. 

Mr Admond Lee was 27 when he quit a steady job in data science to take the leap into the unknown, even when he "wasn't entirely sure about his business idea". 

In 2021, he joined the Entrepreneur First incubator, a programme that brings aspiring founders together to develop startup ideas. He met his co-founder at this programme.

The pair spent the next two years trying to find a viable business idea, pivoting four times and exploring ideas such as an app for food delivery riders and food and beverage (F&B) recruitment before settling on a financial technology (fintech) product that would help digital lenders access small and medium-size enterprises' financial data.

Even when they finally landed on the idea, it was no silver bullet. 

Looking back, Mr Lee said he and his co-founder had effectively adapted a model they had seen in the United Kingdom without doing enough research into whether it would work in Singapore. 

Since neither founder came from a fintech background, they spent roughly six months understanding the problem and another three months building the product. 

Once they had the product ready, they approached prospective customers, but few were willing to bite. Some raised compliance concerns, while others simply didn't think it was worth paying for. 

The S$100,000 they had raised was rapidly running out with no paying customers to show for it. 

"We spent almost a year building the product and talking to customers, but we ended up with no revenue and no commitment. Eventually we ran out of cash," said Mr Lee, now 32.  

Their final hope, an acquihire deal where a startup is purchased for the skills of employees rather than the product, fell through after four months of negotiations, leaving them with no revenue, no fresh funding and little choice but to shut down.

"After I shut down the company, the next four to five months were the darkest period of my life," said Mr Lee, who suffered bouts of burnout during this period. 

"My expectation was that I'd raise money from investors, make money, exit the business, get rich and retire. The reality was very different."

Mr Lee said that if he had stayed in his full-time job, he would have earned at least S$200,000 over those last two years and attained at least a senior or managerial role. 

"I thought I was going to become the next Anthony Tan," said Mr Lee, referring to the co-founder of ride-hailing app Grab. 

"Instead, after two years of building my company, I was back to almost nothing, and some of my friends were mostly senior-level executives, with some already at the C-suite level." 

After shutting down his first startup in 2023, Mr Lee joined a friend’s influencer marketing agency as a full-time chief technology officer and minority shareholder, helping to build its tech arm from scratch. 

The business was acquired about a year later. Mr Lee then started The Runway Ventures, a newsletter that shares failed startup stories and lessons from founders in Singapore and Southeast Asia.

For software engineer Mr Varick Lim, he was taken in by the deluge of success stories about other founders who had set up businesses and made it big. 

With his background in tech, Mr Lim said entrepreneurship seemed like a natural next step, something he "should be" doing.

He left his job in 2023 to co-found a tech startup that used artificial intelligence (AI) to help consumer-facing companies consolidate and analyse customer feedback. 

However, Mr Lim soon realised that being a founder involved far more than building a product. 

"Part of being a business owner is that you have a lot of responsibility. Every question, every decision goes back to you, and I didn't like that," he said.

He also had to take on other day-to-day responsibilities which he neither enjoyed nor wanted to pursue.

"I didn't enjoy most parts of the job, especially sales. It was new and uncomfortable, and I kind of sucked at it."

As a founder, he didn't get much time to do what he enjoyed: building and making products. 

Mr Lim said that because his start-up was venture-backed, there was pressure to become profitable and deliver returns of 20 times or more on investors’ money, something he soon realised was not what he wanted.

"I was spending a lot of time on the business, and I wasn't doing much else that I enjoyed. So even though I'd get some wins in the business, I didn't feel much satisfaction."

He added that he was well aware of the challenges that came with setting up a business, but he hadn't thought it would be that painful.

"I've played sports and used to be a performer, so I'm used to tough rehearsals, training and late nights. That kind of pain can still feel rewarding," said Mr Lim. 

"With the business, I think the difference was that I honestly didn't have a strong conviction about why I was doing it." 

Mr Lim closed the business in 2024 and is now working as a full-time software engineer at an early-stage tech startup.

Despite all the high-profile tech startup success stories, the sector also proved tough going for Ms Lu Mei Ling, who built up an AI health-tech firm, pouring nearly all her savings into the business.

The 35-year-old was no stranger to gruelling hours, having worked 80-hour weeks in management consulting. Even so, co-founding a startup took that intensity to a whole new level. 

With the United States as its main market, she and her co-founder once worked more than 100 hours a week, taking calls early in the morning or late at night and travelling to meet customers, collaborators and other partners.

"I really couldn't take any break. The funding from the venture capitalist was in the bank the week after my second baby was born," said Ms Lu, who gave birth to two of her children while running the startup. 

The company eventually attracted more than 150,000 users globally and developed patented technology, but its business model did not generate enough revenue to keep the company afloat. 

Ms Lu made the difficult decision to step away in 2025, and the company was formally shuttered this year.

"We went really all in. It was really a bitter moment to say that this is where it ends for me," said Ms Lu, who also suffered from burnout from the venture.

BRILLIANT IDEAS CAN'T ALWAYS MAKE MONEY 

Former business owners told CNA TODAY that aside from putting in immeasurable time and effort, what they learnt was that the best-intentioned ideas do not necessarily translate into successful ventures. 

For example, Mr Cedrik Lim, 32, started uWave with three other co-founders in late 2019 as a fourth-year student at Nanyang Technological University. ⁠⁠The app allowed students to track campus shuttle buses, generate their class timetables, check campus crowds, and served as a forum for students.

At its peak, he said about 90 per cent of NTU's student population was using the platform. The company later expanded to the National University of Singapore, where it attracted several thousand more users, and raised US$260,000 in an early funding round.

"We realised that we cannot just focus on getting students to use the app. How are we going to make money?"

He added that while students thought uWave was useful, they were not willing to pay for the app. Furthermore, student activity also fell during term holidays, making usage seasonal.

The company later tried selling uWave directly to universities and eventually secured a paid pilot. But getting the pilot off the ground took about nine months – a punishing sales cycle for a young company that was continuing to burn through cash in the meantime.

Ultimately, the business wasn't viable. He decided to close it in 2023. 

"You build something that's helpful for people, but if you can't earn anything out of it, then there's no business in it. It's just a project," said Mr Cedrik Lim.

For other fledgling businesses, securing investment can feel like a major breakthrough. But funding is only one part of building a profitable company.

Ms Lu's health-tech company raised more than US$1 million in venture funding, but she said some aspiring founders, including herself, fail to appreciate the discipline required in spending capital and facing the challenge of turning that investment into revenue. 

"If the money is not revenue, it's borrowed money," she said, adding that founders should build leanly towards clear revenue targets.

She added the other challenge was timing. While AI and AI-related products are now all the rage, Ms Lu said the company entered the AI space when the technology was still relatively nascent and unfamiliar to many consumers.

People weren't used to AI in their healthcare products, so the team had to spend considerable effort educating the market.

"Being too early in the game sometimes is just not really that fun," she said.

PICKING UP THE PIECES 

As painful as shuttering their business was for many founders, deciding their next move after closure was equally daunting. 

Some founders said that their time as business owners had forced them to wear many hats. As such, they later found it hard to fit into corporate roles that demanded more specialised skills. 

Mr Admond Lee and Ms Lu said this made their return to full-time employment after their business ventures particularly challenging.

"I was a tech guy, but I also did product, business and sales," Mr Lee said. 

"I've always been a generalist, so it was difficult for me to fit into a job market that, most of the time, is looking for specialists." 

For some, it was a relief not to have to call the shots anymore. 

After winding up her F&B business in 2019, Ms Toh started an assistant manager role in e-commerce. 

"I was quite happy to go back (to corporate life) because ... that meant I still had somebody else to guide me and coach me," she said.

"For once I felt: 'Okay, I'm not doing this entirely alone'," added Ms Toh, who is still in e-commerce.

Mr Varick Lim, too, returned to full-time work as a software engineer at another tech company in Singapore. 

"As an employee, even (when) I've been given a lot of work, I know that if I can't handle it, there's someone else above me to handle it. That gives me a lot of relief," he said.

Others haven't ruled entrepreneurship out, but would approach it more cautiously after experiencing failure.

Mr Cedrik Lim is more cautious about growing too quickly. After uWave ended, he moved into full-time employment, joining dating app Tantan as its head of product for two years.

Rather than quitting immediately, Mr Cedrik Lim built a new product, Hopper.so, on the side for about a year, working after hours and on weekends with a lean team. Hopper.so is a platform for online educators to sell courses and host their community.

Once the product was ready, he left his corporate role in May this year to work on it full-time. But he's now more measured about what he wants for his current venture.

"You have to accept that startups are high-risk. But I'm not aiming for my startup to become a unicorn –  my target is now different," he said, adding that he will focus on growing Hopper’s customer base, before he will even entertain thoughts of scaling up.

While some former business owners have no plans to venture into the entrepreneurial space again, others weren't set on ruling it out. 

Even after facing all the bumps along the way, Ms Toh said she enjoyed the problem-solving process, and the immediacy of her decisions was a major plus.

"The flexibility was something I enjoyed. If I thought we should sell something the following week, we could just do it," she said. "In (the) corporate (world), launching a new product could take a year."

Unlike some of the other founders, she also finds that recruiters and employers value her entrepreneurship experience when she applies for new roles.

"I'm glad I made the decision (to run my own business). Even though it didn't work out in the end, it's still a very solid part of my career progression."