“I dropped off my son to school this morning and thought to myself, ‘He’s going to be a cool kid,’ which is the total opposite of me. I was super chubby, short and got bullied a lot. I think I became social later in life by default,” he jokes.

Poon and I are sitting in the newly opened Woaw Gallery in Wan Chai, the fifth outpost of the contemporary art gallery concept and “passion project” he founded during the pandemic. It’s one of many ventures – or “side hustles” as he likes to call them – that has seen climb the ranks among the city’s most pioneering and creative entrepreneurs.

Listing them would take up a big chunk of this article, but highlights include streetwear brand Clot and retail store Juice, independent coffee roaster Elephant Grounds and hip hospitality venues like Margo. The latest, Cardinal Point, which he calls a food and beverage “concept within a concept”, boasts a sleek outdoor bar, an arts club, and Chinese, Japanese and French restaurants.

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“Being entrepreneurial was my idea of freedom and allowed me to break free from relying on people. I didn’t come from mega generational wealth, so I was always trying to take care of my mother,” says Poon.

“Everything I’ve done comes from a personal need, or from a consumer’s point of view. I’m always curious and looking to try new things so I’ve managed to tap into this collective consciousness of people who are on my wavelength and who want to do cool things. We bounce ideas off each other and that’s how many of these projects happen. I just go with the flow.”

Poon’s background is testament to the fact that success is a combination of ambition, hard work, determination and of course being at the right place at the right time. Born in Hong Kong, he spent much of his childhood and teens bouncing between the city, Canada and the US, where his father worked for American tractor manufacturer, Caterpillar.

It wasn’t long before he become engrossed in subcultures like basketball and hip-hop, which led him to secure an internship with Universal Music. On his first day of work the company went bankrupt so he ended up at “urban” label Interscope Records, where he did everything from picking up phones to rearranging filing cabinets.

“My dad always told me that if I can’t do a small thing correctly, no one would take me seriously, which is why I did everything to my utmost best. Eventually I landed a job out of college with a well-known manager who handled the likes of 50 Cent and Shaggy,” remembers Poon. “Unfortunately, I got fired and so I ended up back in Hong Kong in 2003.”

It was then that Poon and Chen – then a rising film star – decided to join forces and open Juice, a clothing store inspired by their love of basketball and streetwear. Although Poon modestly refers to himself as the “sidekick” and Chen as the “visionary”, there’s no doubt that he played a key role in the company’s trajectory as it transitioned from a small retail operation into an empire that includes covetable brand Clot. It also firmly positioned both founders – and the city – on the global streetwear map.

“Everything is a learning process. The more you learn, the more you realise that you don’t know anything. It taught me the importance of hard work, work ethic and the realisation that nothing happens overnight. Now we are celebrating 20 years and it has gone by so quickly,” he says.

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While fashion projects took up a large portion of his twenties and early thirties, Poon “shyperactive” mind and innate curiosity led him to branch out into different fields, although success wasn’t always guaranteed. While Elephant Grounds hit gold with their ice cream sandwiches, others like the Blohk Party music festival and defunct Top-Fit boutique gym fell flat. Although much of what he does is driven by his instincts, he acknowledges the role of not just a great team and support system, but also the open environment in Hong Kong, which has allowed him to thrive creatively.

“I think that every generation experiences different challenges. If you have a great idea Hong Kong is the best place to execute it, but the rents are also tough. If you find a good concept then 100 competitors pop up, but for the most part Hong Kong is still a very good place to do business,” he says.

“It’s also important to tap into younger people to come up with ideas. At the same time, this generation needs to realise that success doesn’t come for free. Kids today always ask what’s in it for me. That mentality does not foster growth. Everything works full circle. The reward of good work is more work.”

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It’s clear that Poon’s outlook has also changed dramatically since he turned 40 and got married. The birth of his son two years ago has also meant that his priorities have changed. He’s swapped late nights for early mornings, school drop-offs and meditation, while his latest passion is reading and learning as much as he can about the next digital wave, including AI. Being a father has also made him think more about creating a more lasting impact and giving back to others.

“The next important thing for me is education. As I get older want to see how I can be a resource to younger kids, especially as I just became a father. I see a lot of potential with Woaw Gallery so launching a residency would be my dream,” he explains.

“Many artists come to Hong Kong and realise how amazing it is. I’d love to give them the opportunity to move here, absorb the culture and paint for six months. I’m still figuring out what it looks like, but it would be a non-profit organisation. I sometimes like to put it out there in the universe to see if something catches on.”

As for his next project, he has nothing in the works – although he is open to any possibility.

“I heard the Fringe Club is up for bid,” he says with a twinkle in his eye. Watch this space.