At the Art Stage art fair in Marina Bay Sands last year, Mr Ken Tan stopped by the Marc Straus Gallery and fell in love with several pieces by New York-based artist Antonio Santin.

The paintings were gloriously detailed and looked like photographs of lush Oriental rugs with bodies hidden beneath.

Mr Tan, 35, bought two at $36,000 each.

"Marc was like, 'Who the hell is this kid who just walked in here and bought these paintings?'," he says, referring to gallery owner Marc Straus, who is also a celebrated art collector. "Anyway, we went for dinner, we talked, and he found out that I knew my sh**."

He bought more pieces and a firm friendship developed between the two. A few months later, Mr Straus invited him to New York, showed him his gallery, took him to private museums and introduced him to artists and collectors.

"When I came back, we Skyped, and then he offered me a job," Mr Tan says.

And that is how he became the director of Marc Straus, a boundary-pushing gallery in New York's Lower East Side.

It is another chapter in the very colourful life of an adventurous soul who has been, at various stages, a teen rebel, a tech whiz, a multimedia marketing agency owner and a restaurateur.

With his shaved head and colourful Japanese tattoo snaking up his left arm, Mr Tan cuts a trendy hipster figure.

The elder of two boys, with a grin, lets on that his parents are retired teachers. "My father was the vice-principal of a primary school; my mother taught at Marymount Convent, so it was a strict no-nonsense household," he says.

"I was the nerd who started wearing big spectacles in Primary 3 and came in first in class every year," adds the former pupil of St Michael's Primary.

Drawing and painting were his passions. "My dad was a big comic book collector, so I read a lot of comics, from Marvel to DC to all the indie labels, and I loved to draw superheroes."

In his teenage years, however, he went through a rebellious phase. "One of my really good friends started smoking at 13, and I picked it up too. I was hanging out with boys who were older and cooler. And when you have girls involved...," he says, voice trailing into laughter.

One vice, he says with a mock grimace, led to another, and before long, he was playing hookie, trading fists and making mischief in shopping centres.

"I tried to vandalise another school's signage and shoplifted at a bunch of places, and was caught stealing a wallet in an Orchard Road department store. Luckily, the store didn't report me to the police. They called my parents, who had to come and get me," he recalls.

The rebellion, he says, was not fuelled by anger.

"I think it was me trying to test limits. I'm the type who likes to see how far I could go," says Mr Tan, who went to St Joseph's Institution (SJI) for his secondary education.

His plummeting grades, together with his antics, could have got him expelled. "Brother Paul Rogers helped to pull me through when I was in Secondary 4," he says, referring to the former SJI principal.

Quite the academic revolutionary, Brother Paul told him to go to his office every day after school.

"He made me stay in his office every day until 5pm just so I would stay out of trouble," he says. "He talked to me many times, tried to figure out what was wrong with me and my motivation for doing the things that I did."

The sessions riled Mr Tan, but they did him a lot of good.

"This was before the mobile phone. There was nothing to do except wait in his office, so I reckoned I would just read my textbooks. And I turned around and studied non-stop," says Mr Tan, who obviously does not believe in doing things by half-measures.

Although he could have gone to a junior college after his O levels, he took up a friend's recommendation and enrolled in a multimedia computing course in Ngee Ann Polytechnic instead.

The decision had a huge impact on his life. To begin with, it introduced him to the computer in a way he had never imagined.

"Before that, I used a computer mostly to play games, but now I was learning how to actually make those games. I went deep into it."

He started devouring a lot of books, and was soon a self-taught Flash guru. Macromedia Flash is a multimedia and software platform used to create vector graphics, animation, browser games and other Internet applications. "I loved it because it appealed to both my left and right sides of the brain. It was very logical, but it also allowed me to be artistic and creative," he says.

The early 2000s saw an explosion of multimedia applications, and his technical wizardry soon got him gigs to build interactive websites for clients, including Singtel and M1.

"I was making about $5,000 a month just building websites," says Mr Tan, who freelanced throughout his three years in the polytechnic. "It dawned on me that all I needed was my two hands and a sharp mind, and I could take on life. It helped me to structure what was to come."

His skills also came in handy during his national service. He was posted to the signals unit and spent his NS working on websites.

After completing his national service, he wrote to a few creative agencies detailing the IT projects he had handled. A small progressive outfit called Mind Wasabi offered him an internship. One of its principals, Mr Shaun Martin, took him under his wing.

"He taught me proper design, including typography. It was like going to the best design school; he showed me how to do things right. He was a brilliant programmer and mathematician, and I learnt a lot from him."

Mr Martin's parting words to the young man after his three-month internship: "You either go to a place like New York to further your studies or you go and start your own agency."

The first was too expensive an option, so Mr Tan settled on the second. By then as a budding part-time deejay spinning at nightclubs, such as Zouk and The Butter Factory, he had become good friends with Mr Jonathan Nah, an advertising veteran and deejay.

"I asked him to join me. He had just left an agency, and he said, 'Let's go for it.' "

Ohplay started in 2004 in Mr Tan's bedroom, but within a couple of years it grew to a team of about six people occupying the second floor of a building in Joo Chiat.

Besides working for the likes of Nike, The National Museum and the Singapore Fashion Festival, they also worked with bigger agencies, such as Bates and M&C Saatchi, on digital concepts for clients, including Mitsubishi, Audi and Qatar Airways.

Mr Tan made a more-than-handsome income, and learnt a lot about being an entrepreneur.

"I was handling business development, liaising with vendors, managing numbers and the bottom line."

The good times, however, beat a retreat with the 2008 financial crisis. Agreeing that they had a good run, he and his partner decided to close shop and move on to the next chapter of their lives.

His next stop was with Bates in 2011, where he became its digital creative director. During his 21/2 years with the agency, he worked on accounts such as Disney and Singtel, and also won several awards, including an Effie for a Singapore Polytechnic campaign in 2012.

Mr Tan's next detour came unexpectedly. A friend bought a bar in Ann Siang and roped him in to help rebrand and run it.

He came on board The Establishment Group as a partner, founder and creative director, and over the next three years helped to conceptualise, brand and set the marketing direction for several food and beverage ventures: Gem Bar, Zui Hong Lou kitchen bar, Pluck bistro, and Wanton, Seng's Noodle Bar, all in the Club Street and Tanjong Pagar areas.

He found creating and branding products exhilarating. "I was involved in everything, from bar fittings and websites to branding and menus," he says.

The business expanded to include digital outfit Recess. Meanwhile, he also co-launched furniture lifestyle store Supplies & Co.

His enterprising ways explain why he could walk into Art Stage last year and drop so much money on each of those Santin pieces.

But Mr Tan had started to collect art several years earlier. It began when he built a website for British musician, deejay and record label boss James Lavelle, who had spun on several occasions at nightspots such as Zouk.

"I knew he was a big collector of street art, and I wanted something from his collection. I told him, 'I don't want your money but once we're done, send me a bunch ofimages and I'll pick something.' "

Mr Tan settled on a Pointman figure that had appeared on many of Lavelle's albums by famous street artist Futura. He did not realise its value until someone offered him $30,000 for it.

"It was a bug. I was 25 and I started thinking... okay, what do I want next?"

With his obsessive streak, he plunged into the world of contemporary art and started reading all the books he could lay his hands on.

"I just went crazy. I had to know everything, so I pored over art books, got to know all the European masters and then the contemporary artists. I started looking at auction results," says Mr Tan, who has amassed a collection of about 50 art pieces, including works by KazOshiro and Jeffrey Gibson. Most of them are stored in warehouses.

"Most of the artists are around my age group, some older, some slightly younger," he says. "It's good for me to know them and grow with them. It's like supporting a vision and pushing creativity forwards."

When Mr Straus offered him the job, he accepted it without thinking. "My parents are confused and wonder why I can't stick to one job," he says with a laugh. "But life is too short, so we have to try and experiment." He has been working in New York since August and loves it.

The gallery, he says, represents 16 artists. "I do everything, from admin to building strong relationships with clients and artists. I also look at branding and marketing," says Mr Tan, who lives in Brooklyn.

The chatty gallery director says he has enjoyed every turn his life has taken. "Everything has happened from out of the blue. First, it was about making lots of money. Then, it was starting my own company and running a team. Then, it was about winning some awards, and in F&B, it was seeing happy customers."

He wants to grow with the artists whose works he now markets in New York. "And this, I might do for a while," he says with a grin.