Khailee Ng — Conversation about Necker Island, Marriage and the Gig Economy

Khailee Ng is a managing partner of 500 Startups, a venture capital firm. He has led more than 180 startup investments, with a few “unicorn” successes such as Grab and Bukalapa.

Khailee has previously founded Groupsmore which got acquired by Groupon and Says.com, which got subsequently acquired by Media Prima, Malaysia’s largest online media company.

BUT, even if you have zero interest in startups, this episode is well worth the time. This is really about the habits and beliefs of a successful (and fun) person.

Enjoy this conversation with a curious character!

In this conversation, we spoke about:

  • Lesson learnt at Richard’s Branson Necker Island
  • How does Khailee study and prepare for marriage
  • Principal to a kick-ass pitch
  • and much much more…
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Click “continue reading” for the link and show notes…

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How to Find Your Values

A series of fortunate event, I have achieved everything on my bucket list. It was disorientating.

I looked up at an old list of ‘fun-to-do’ projects, not knowing how to choose what’s next. I was paralysed. Then bored. Then, agitated by my boredom.

Inspired by my friend, JR Hinds, I took a month off in Taiwan and went searching for my values. In hopes that it will be the compass for the next chapter of my life (and it did). It helped me get unstuck and excited for life.

First things first, definition are important as we are building the truth. And this is how I define values:


A set of ideas, rules and principles that I’ve looked at very carefully about myself and have deliberately chosen. This is a habit. This is a way of life. I’m going to stay this way forever. I’m not going to compromise on it. I don’t want to live life any other way. I don’t need to prove it to others. It shouldn’t change much over time. It shouldn’t be profitable or easy. If they were, then no one would write books on it.

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“What other people think of you is none of your business. But isn’t it important to get business.”

Almost the opposite. We must care and even obsess about the people you want to help.

But… Who are these people? And what kind of business are you building?

To own a thriving business, you don’t need everyone. Just someone.

The goal is not to pander to the masses and undo the very things that made you special. The goal is to be special to the right someone.

Who are these people and how you are special is entirely up to you.

Trying to make everyone happy is a sure path to unhappiness and bankruptcy.

Shun the non-believer and make things better for the people to miss you when you were gone.

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The photo was taken in a funky little Airbnb in Kaohsiung, Taiwan while travelling with Paul.

Compass for Sacrifices

We can argue that law is written by logic. But not really, it’s written by values.

A set of standards written by someone on how we should live our lives as a town, as a city, as a country. A set of priorities that are incentivised and enforced through the laws, grants and fines.

And the foundation of value start with the individual.

What are yours and can you articulate them?

It is the compass for how we want to operate in the world and what is worth sacrificing for. It is the reason behind the law. The logic behind the rules.

We are surprised when someone arrives early and show up day after day without fail. Someone who figures out a way to have a healthy lifestyle while running 3 non-profit companies, as they sit on the board for another two companies. We are shocked when someone uses the early morning to write their articles, one article a day for 10 years straight, even on the weekends and public holidays.

There are a few good books on keeping your values. Fewer still on finding them. It’s hard to think of a more essential thing to learn.

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The photo is taken at Portland, Oregon.

The Cost of Changing the World

A thought experiment.

You are going to the movies needs to be there by 7 pm. Everyone got in the car and you take the usual route. There is an accident on the road that causes bad traffic. So, you missed the movies.

Well, too bad. That’s life. Imagine another scenario.

This time when you are met with traffic, you suggest a new route. A shorter route. Unluckily for you, there is also an accident that causes bad traffic and everyone missed the movies.

Two scenarios, same outcome. However, this time it feels that everyone is blaming you for that stupid shortcut. And by everyone, I’m also including you.

So, why do we allow for luck to be the explanation in one case? But not the other. Why is it that when you challenge the status quo by taking a new route you feel more responsible for the way things turn out?

It is uncertainty. It is because we are afraid of the uncertainty. We are afraid of not knowing how things might turn out. It is because if we change course and things do not work out – It would be our fault.

Even if the certainty is that the route you are on is slower. There is comfort in the feeling that you know how things will go. We would rather stick with what we know even when we know it is not making us happy or fulfilled.

It is the reason why people don’t want to make change. It is why it is so hard to change course once we have started down a path. Changing course means trading that feeling of certainty for the possibility to make things better.

While the uncertainty of a new path might lead to failure. It is also that same uncertainty that allows for breakthroughs, for new discoveries and for success.

We can’t be certain how the future might turn out. We can never. But perhaps the best way to know the future is not to sit around with certainty – It is to dance with uncertainty and create the future you want.

That’s the cost of changing the world. The decision to take a chance.


(Hat tips to Annie Duke for pointing out the decision bias.)

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The photo was taken in Portland, Oregon at a hot air ballon festival.

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