For more than 15 years until his early 30s, Mr James Chua had a recurring nightmare in which he failed an exam. "I'd wake up in a cold sweat," says the 44-year-old.

The nasty dream can be traced back to his teens, when his wild and rebellious ways saw him failing his first year in junior college and nearly getting expelled.

"That was the turning point. It struck me that if I wanted to have a better life for myself, I had to start doing something. No one else was going to do it for me," he says.

The fear of failure dogged him for a long time.

"But it also drove me," he says.

He made it to university and after graduating with a degree in psychology, entered the advertising industry. At 29, he became the general manager of local advertising agency Ace: Daytons.

Today, he is the managing director of Germs Digital, which recently bagged three awards from Marketing magazine: Local Hero for Integrated Marketing, and Local Hero as well as Agency of the Year for Mobile Advertising.

A lean, compact man, Mr Chua fits the stereotype of an ad-agency head honcho: confident, articulate and trendily dressed in skinny trousers, sneakers and a sharply cut jacket accessorised with a pocket square.

The self-assurance, he says, was not always there. In fact, he spent much of his growing-up years feeling lonely and ostracised.

He is the middle one among three children.

"My paternal and maternal grandparents both had 14 children," he lets on with a hearty laugh.

His mother is a housewife. His father has worked in a variety of jobs, including as a coffee boy, plumber, electrician, bus driver and taxi driver.

"My grandmother was a gambler. So he and his siblings had to forgo school at a young age and start making money to fuel her habit," he says.

The first two years of Mr Chua's life were spent in a kampung in Chai Chee. His family later moved to a four-room flat in Marine Parade, which they shared with his grandmother and about 10 uncles and aunts.

Growing up, he always felt a bit lost. His elder brother was studious, well-behaved and held up as the hope of the family. His sister was doted on as the youngest child and only girl.

"I felt left out and I guess rebellion was my way of getting attention. My parents and relatives used to say I must have been picked up from the rubbish dump because I was so different," says Mr Chua, who was always on the receiving end of his father's cane.

"My parents love me but didn't know how to show it. And I didn't know then how to appreciate their love in that form," adds the former student of Tao Nan School and Tanjong Katong Secondary Technical.

He was at his most recalcitrant when he went to Tampines Junior College. He smoked, skipped classes, defied teachers and hung out with other rebellious students.

It came to a head when he failed his first year. To make matters worse, he was one of two students put on probational retention: He faced expulsion if his grades and behaviour did not improve.

His father was summoned to the college. "My teacher explained to him the terms of my probational retention: I had to report to the principal every morning and my grades had to improve. The teacher asked my dad: 'Are you agreeable? If not, we will not give him a place here.'"

When his father thundered at him and asked him what his decision was in front of his teacher, Mr Chua said he wanted to continue his studies.

"For nearly two years, my father didn't really speak to me. He probably thought I wouldn't make it."

The episode jolted him out of his complacency. He switched from the science to the commerce stream and took his studies more seriously.

He also met a group of friends who changed his life. They were fellow oddballs who gave him the warmth and connection he craved. These folks, to whom he remains close till today, include two well-known names in the ad industry: Kinetic Singapore's founder Carolyn Teo, and Mr Pann Lim, named the country's most influential creative director in 2012.

"They gave me a lot of self-confidence. It was the first time I felt a real connection with people. We even had our secret hideout, a canal in Kembangan, where we would swim and fish."

His A-level results were good enough for him to get into the National University of Singapore (NUS). It probably surprised his father and their ties improved, says the psychology major who made the Dean's List in his first year.

"In my first year, I had no idea what I wanted to do when I graduated," says Mr Chua. It was Mr Lim and Ms Teo, who had gone on to study art and design at local polytechnics, who opened his mind to the idea of a career in advertising.

He was hanging out at Mr Lim's place one day when he heard his two friends discuss fonts, ideas and concepts for an ad they were doing for Ms Teo's father, who ran a pharmaceutical business.

"I got very interested and started asking a lot of questions," he says.

The fascination intensified when he convinced the owners of a cafe in NUS to let him and his friends handle the advertising and creatives for a pub they were opening.

Breaking into the industry, however, was tough when he graduated in 1998, as the region was still reeling from the effects of the Asian financial crisis. Although several big-name agencies were intrigued by his resume - designed like a book - to grant him an interview, they all told him they were not hiring.

He landed a gig as the prop master for the comedy Liang Po Po. The film starred comedian and film-maker Jack Neo in a cross-dressing role as a granny who gets involved in a bank robbery.

The day after the shoot ended, he found himself at a job interview with J. Walter Thompson. Like all the others, the agency told him they had a hiring freeze.

"But I asked them if they took in interns, and if they would hire me on an intern's pay. They said: 'Oh, really?'

"I was paid $500 a month, but was doing account servicing for one of the new accounts, Cold Storage," says Mr Chua, whose pay was doubled to $1,000 the following month.

A friend then told him about an opening at local agency Ace: Daytons Advertising. Because it was a small outfit with no account team head, he found himself thrown in at the deep end.

"It was really tough having to do everything, from account servicing, to strategy planning to traffic to production management. But I learnt to manage things on my own, and that helped to boost my confidence. It was where I picked up the tools of the trade."

His mentor was Mr Adrian Tan, the founder of Ad Planet, Singapore's largest independent advertising group comprising about 10 boutique agencies, including Ace.

The hours and the pace were punishing. But hard work, Mr Chua says, had never daunted him.

Since he was 14, he had worked during every school holiday: clerk, banquet waiter, telemarketer and an assistant in a piling company.

"I wanted my own pocket money and would take any job that came my way. I once worked as a cleaner in a shopping mall, pushing a cart around and cleaning toilets. It builds a lot of resilience," he says.

After 18 months at Ace, he hopped over to Kinetic - another agency in the Ad Planet family - because he wanted to learn about interactive advertising.

A steeper learning curve awaited him. "I realised that I sorely lacked advertising strategic thinking. I could not debate on the same level as my colleagues," he says.

The way to remedy that, he reckoned, was to join an international agency.

DDB was his next port of call.

He handled a big account, Tiger Beer, and lapped up all he could about communications strategy and brand management.

In 2003, when he was 29, Ad Planet's Mr Tan asked him to return to Ace to become its general manager, and to help transform and modernise it.

The proposition excited him but also filled him with trepidation.

"I was only an account manager. What did I know about running a boutique agency? I spoke to good friends in the industry, and one of them told me: 'What's the worst that can happen? If you do it well, you make a mark. If you don't, you go back to being a suit.'"

There was scepticism from colleagues, many of whom were in his age group.

"One of them came up to me and said: 'I'm not sure if you can do it, but since you're here, I'll support you as much as I can.'

"I like to prove people, like my parents, wrong. I also needed to prove myself to my parents, to detractors and to myself," says Mr Chua, who found himself having to learn everything from recruitment to resource planning and business development.

And he did. Within the first year, he grew profits by more than 400 per cent. In the second year, billings doubled and profits went up 800 per cent.

"We also started winning in local and international award shows, including the Creative Circle Awards, The One Show, D&AD," he says.

The shift to digital marketing and the advent of Facebook convinced him that the time was ripe for a new brand focused solely on digital communications.

In 2008, he co-founded Germs Digital with Mr Tan.

His hunch was right. Germs, which has won several awards, was profitable from day one because of the volume of digital projects. Its clients include United Overseas Bank, Income, Clarins and Velocity.

Always on the lookout for interesting work to add to their portfolio, he hatched the idea of inviting Mr Stephen Wiltshire - a British architectural artist who can draw landscapes from memory - to draw the Singapore skyline in conjunction with Singapore Press Holdings' 30th anniversary celebrations three years ago.

Mr Wiltshire was so chuffed with his experience here that he has appointed Germs to be his exclusive representative agent in Asia.

Engaged to a professional show host, Mr Chua says running a successful business has helped him get rid of a lot of his insecurities.

"I used to micromanage a lot but I've learnt to let go. I've learnt not to fuss over the small things and to listen and engage more with the younger generation as they have a whole new way of thinking. They are more vocal, dynamic and enterprising."

He says the ability to change, evolve and stay relevant is imperative in a challenging digital landscape.

"We need to grow laterally rather than vertically," he says, adding that regionalisation - Germs is going to Jakarta - is just one of several things on their to-do list.

"Everyone is feeling the heat of the digital revolution. I've learnt to embrace it, and to enjoy the ride."

In fact, he enjoys it so much, his nightmares have stopped.