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.

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…

Enjoy this conversation with a curious character!

Links Mentioned

Connect with Khailee Ng:
Website | Facebook | Instagram

Necker Island By Khailee Ng
Chris Sacca
Yuri Wong
Hujan (band)
Teng Poh Si (theCICAK, Director)
Extreme Ownership by Jocko Willink and Leif Babin
Team of Teams by General Stanley McChrystal and
Bukalapa (company)
Protagonist (2007)
Joel on Software (Blog)
Present as yourself
The Pitch Effect: 5 Power Moves for 3 Minute Stage Pitching by Khailee
Le Hong Minh, VNG Corporation (Vietnam)
Leading remote team (MIT)
Patrick Grove
How to Love by Thich Nhat Hanh
The Seven Principles for Making Marriage Work by John Gottman
Getting the Love You Want by Harville Hendrix Ph.D.
The E-Myth Revisited by Michael E. Gerber
EarBuddyz 2.0 for AirPods

Show Notes

Lesson learnt at Richard’s Branson Necker Island [01:01]
Why was Khailee chosen for Necker Island? [06:11]
Pros and cons of VC funding and bank loans [10:13]
Khailee shares about Project Bazooka and Project Cicak [15:15]
Khailee discusses the impacts of a gig economy [32:15]
How does Khailee prepare his presentation? [01:03:21]
Elements of great pitch [01:08:30]
What did Khailee wish he had known earlier as a leader? [01:20:13]
Khailee on Tony Robbin’s Date with Destiny [01:45:15]
Why did Khailee re-think marriage and changed his thoughts on marriage [01:50:06]

Thanks for listening! 

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Special thanks to Shao Ning for the introduction.

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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