Winnie Chiu (pictured left), president and executive director of Dorsett Hospitality International, opened the day with some pretty honest relevations about herself, her place in the family business started by her father and her relationship with money.

Chiu represents the new generation of hoteliers that’s entering hospitality in Asia, determined to run them differently and to take the Asia Factor to the world stage.

She first cut her teeth in banking (Credit Suisse) – always a good place to start and learn about how to make money – and then went into retail where she bought and ran shopping centres – a good place to learn about real estate.

She didn’t have problems getting herself taken seriously and being accepted by her father’s peers, her own peers and staff when she stepped into the top role – when you meet her, you know why. Chiu exudes confidence, she is clearly smart, she thinks fast on her feet and she’s carved her own path and identity.

I can well imagine the trepidation she may strike in the hearts of those who work for her, and who may not be able to keep up with her pace and her vision although she says she likes people who challenge her and she likes to see people grow.

Born into money, Chiu knows she is privileged not to have to worry about not having any and she sees it as a means to an end. On stage, she jested about how she’ll try not to lose the family fortune since it is said of family businesses that the first generation makes it, the second builds it and the third loses it.

She certainly has an acumen for making it and she believes in value creation and the need to recycle capital. Some examples –after she sold The Mercer (with sales proceeds of HK$289 million), she bought Dorsett London. When she sold Dorsett Regency Hong Kong (with sales proceeds of HK$800 million), she bought The Matrix London the very same day.

To grow Dorsett, she wants to tap into the Chinese wallet, recognising this as the future consuming class. Her advantage is that she is of the same generation weaned on digital, and she knows how important social media is in influencing Chinese travellers’ decisions – even though she confesses she is not a heavy user herself – and let’s not forget, social media also now has a big influence on the value of real estate – more buzz, more bucks.

And she intends to bring all her skills, knowledge and insights to bear as she fans her brands outwards in tandem with the travel aspirations of a new generation of Asians.

So in many ways, you could say that, like her grandfather and father before her, Chiu is a pioneer in her own way, forging a new era in Asian hospitality and building a brand that she says will blend the best of East and West.

In his talk, Stephan Ekbergh (pictured left), CEO of Travelstart, South Africa who has taken his brand to the Middle East with Asia his next frontier, said pioneers have to dare to be different – to be a rebel, to be creative and to have passion, determination and grit.

He acknowledges the power and influence of the Asia Factor – “God loves you, there are so many of you”, he quipped – but what he feels could hold Asia back is – what he’s observed from his numerous visits to the region – the striving for perfection.

“You don’t have to be perfect all the time,” he said.

I was reminded of his message and Chiu’s comments – about needing to carve your own path – last weekend when I was at the Singapore Management University judging the final round of the WIT Developer & Designer Challenge.

Three teams had answered the challenge by Brand Karma and WIT to design the 21st century hotel website using Trisara, the luxury resort in Phuket, as a template.

Among the teams was Team Currency, the all-girl team (pictured right), which won our first Challenge and it was good to see how they and the other two teams had fleshed out their ideas.

There were some common elements in the three designs – heavy use of visuals – Pinterest and Instagram-like feel, prominence given to reviews, strong social elements and, of course, mobile optimization.

One team suggested an on-site Companion App which would work as check-in, room key and concierge.

The scores on this project contribute up to 40% of their term marks and so you can see the amount of work that went into it.

The two other projects were from STA Travel – a rebranding proposition – and from Over The Rainbow, a not-for-profit organisation whose aim is to spread awareness of stress and depression among youths, and to build community support around this mostly urban affliction.

It was interesting listening to the teams talk about how their eyes were opened to the subject – youth depression was not something that had come up on their radar before.

Yet after doing the project, which involved putting together a five-minute video on the subject and how travel could be one of the outlets used to shift perspectives, many said they realized they faced many common issues that lead to stress and depression.

The number one factor – living up to expectations particularly that of family, followed by society and friends.

“I feel I have to be perfect all the time,” said one when he related how doing the project actually helped him get over a tough patch in his life.

I grew up in an education system which did not encourage me to ask questions, to think critically and different, let alone be a rebel. Yes, I know times have changed – kids are smarter, more informed, more connected these days and the whole web is now a massive classroom and chatroom – but sitting in that class last weekend, I asked myself, how much has really changed?

These are the brightest and best of students in Singapore – yet I sensed some restraint and conformity in the presentations and answers.

This is the one element I believe we in Asia have to conquer if we are to truly deliver on the full promise of The Asia Factor.