Two Pairs of Pants

I've been selling and hustling for much of my young life. I've learned loads from each part of it, no matter how small or insignificant it may have been at the time. I sold cable car tickets. iPod cases. DVDs. Button badges. Most things, really. In hindsight, they've come together to define what I do today. It's amusing to think of it, really.


In my teenage years, I spent most of my vacation months hanging out in the Central Business District. Each day, I would sell (under the 34 deg C sun and extreme Singapore humidity) various items, ostensibly for a charitable organization that worked with destitute elderly people in Singapore.

I was 15. It seemed like a great way to spend my days{, and I made them between $10 000 and $15 000 a day, selling bookmarks to disgruntled bankers and lawyers (I was very good at it). Years later, we found out that the founder bought fast cars with the cash, which is why I now have a bullet point in my own charitable organization (we send girls to school in India)-"we travel by bus, train and economy class, and the only people who get paid are the people who work on the field".

Lessons learned: it was the first time I learned to sell the hell out of anything, and if you stand in the heat and sweat long enough (12 hours), eventually people will buy stuff from you.

Button Badges

With my brother Adrian Tan's help, I designed and made button badges. We ordered a button badge machine from eBay. We had different themes (his was punk music), I specialized in ironic and weird businessy/political/tech buttons.

People in Kansas seemed to like my buttons. A lot.

Lessons learned: there is great value in making. I wish I did more of that, and I will be trying to do more of it. Making something with your hands was the best experience ever for a kid of 15, and eBay at the time was revolutionary. It opened up a world of global commerce to me.

Etsy before Etsy

Whenever we went on family vacations, I would convince my parents to loan me a small sum ($100?) so that I could buy a bunch of 'craft' items from Bali, Bangkok etc.

I sold them on eBay for ungodly amounts of money because I would write beautiful copy about "handmade" and "artisan". In 2000. I truly believed it at the time.

I still have some of those photo frames, notebooks and paintings in my parents' house. When I discovered at the tender age of 16 that all of this stuff was mass produced, I felt I could not see them anymore.

Lessons Learned: having a product that people want is basic, but having a product people want and can easily access, is essential. eBay and PayPal opened that window, but good old copywriting was the secret sauce, and it continues to be for me in most of my businesses.


At 17, I came to terms with the fact that I am indisputably queer. I did not panic. I did not freak out too much. I was not bullied. But I also had no idea what it meant to be a queer adult: I did not know any such people, and I did not see them on TV or in movies. It was 2002. I ran a "DVD ring" which distributed queer video content (not pornography!) to other teens who wanted to see people like us on screen. There was no Tumblr. The idea that queer people existed on screen was something that saved my life.

The movies were horrible, and I don't believe that queer movies have improved since. It was something I needed to do at the time.

Lessons learned: I cannot do the things that I don't love. I don't love queer movies, and I don't love incremental tech that aims to solve first world or Silicon Valley problems.

iPod skins and cases

In the first year of college (2004), I imported iPod skins and cases. I was loads cheaper than anything available on the market-I seemed to know what people wanted, and built the connections to make that happen.

Emboldened by my marginal success as a 19 year old, I wrote to Waterfield Bags telling them I would like to be their sole Singapore distributor. I had no capital, of course. They wrote back with a very encouraging note and walked me through the process of what I should have if I wanted to do that. I of course, could not garner the resources. But it was the first time that someone had ever spoken to me like an adult. As a young Singaporean kid at the time, most of my life experiences (outside of the home, which was a very progressive environment for me in every way) had been about the things I could never ever do because I am a kid and I am a girl and not rich. 10 years on, just a year ago, I would get on a motorbike and travel a distance to a tiny office in a Jakarta suburb, to bug somebody to give me the rights to sell rather hard to get. He would say yes, and it would become the basis of all of the work I am doing today.

Lessons learned: Don't pre-judge yourself. You are not weak, inferior, poor, or incapable because someone of where you come from or what you are. Action, like the act of reaching out and saying I will do this, does.


In 2004, I started selling Macs at one of the Apple retailers, and did so well I was featured in Cult of Mac and Scoble's blog, which brought me a certain degree of international / tech 'fame'. There are many people I know, still talk to, or have met, especially in the US and in Europe, because of these early international tech links. In many ways, every aspect of my adult life has changed because of the years I put in selling computers and iPods. That I run around doing crazy businesses, Steve Jobs 2005 Stanford commencement speech. Learning to sell the shit out of anything, standing on my feet for 8 hours a day. And I mean anything.

Through my time walking the fertile grounds of Mac stores selling thousands of dollars of hardware a day, often to the extent of forgetting to eat, I developed a loyal clientele of high net worth individuals to whom I became their personal technician. That put me through 4 years of relentless backpacking throughout and after college. I encrypted emails for mining tycoons. I backed up data (there was no 'cloud' back then!), retrieved data from corrupted hard disks, ran around with bootable flash disks with installable OSes and data retrieval utilities in my wallet. I had a FireWire cable in my pocket most of the time. I took apart hardware, put it together, and somehow never had enough screwdrivers. They paid me well for it, and they taught me about charging for what clients should think I am worth, rather than what I thought I was worth, which at the time was, not very much. I got to see every single Southeast Asian market extensively, traveling on $200 for a month (how did I do that?), learning to stretch my dollar. Being a part of the Jobesian / Apple meteoric rise and return in that period changed everything about my professional and personal trajectories.

Lessons Learned: hustle hard, and do it well; people in general will not take advantage of you. "How much will it cost for the 7 hours you just spent taking stuff apart for me and saving my data?" "Maybe $100?" (Remember, I was 19…) They would laugh and say, here you go. And hand me $1000. It taught me that when I am in a position to reward a young hustler, either financially or in terms of opportunities given, I most definitely will to pay it forward.

When I was in the middle of all of that, people constantly asked: why? What good does it do? Why are you travelling around India or Indonesia for weeks and months and living like a hobo, instead of taking multiple prestigious bank internships?

Somehow, I had the weird feeling that it would all make sense. It has only just started to (and it's not like I did shabbily in the time before). I quite simply chose a different path, not because I had so much conviction and talent, but because to me those paths were the only ones open to me.

I'm so excited to see what the next 10 years will bring. I've spent the last 6 months living in Jakarta, building Wobe and getting to learn every single day about the wonderful place that is Indonesia. What I have now, which I did not have before in my formative entrepreneurial years making buttons and selling DVDs, is a team of hugely amazing, talented, and most importantly, good people, who I have the privilege to lead. Teams are everything.

I've come to see that these insane plans of mine did not come out from a vacuum. I did not just sit in an office one day and decide, "I should get into (insert generic type of) business". They came from sitting in a 36 hour bus rides talking to people in languages I don't understand (Turkish and Arabic, for example), building and making all kinds of crazy products with all types of crazy people (I once built a website for a West African airline, but they never flew because their leader was deposed to Burkina Faso).

They came from being told several times a day that I could not have something because I am a girl, a foreigner, or just plain unlucky. A train, a bus, a business opportunity, but having to figure it out anyway because sometimes… you just have to.

One morning in 2010 I got out of a train from Aleppo, and found myself in Gaziantep, a border town between Syria and Turkey. The problem, as I soon found, was that I had no euros or Turkish lira. I did not have any money except worthless Syrian money. There was no ATM at the train station. I was, in short, screwed. Experiences like that have been far more difficult than anything hard about the hard in "it's so hard to do business in Asia".

(I managed to barter a ride to the next city.. I think I traded a Turkish kid some notes and coins 'from the Far East' so that he would buy me a $1 bus ticket!)

Experiences shape you. My formative entrepreneurship taught me about payments, exchange rates, marketing, making, selling and most importantly, customer service.

The time I had to sleep on the dust outside Trichy airport (long story), when the auto-rickshaw I was driving around South India broke down on an unlit hill. The many times on the road in which I've had to deftly worm my way out of extreme sexual harassment. All of those experiences are starting to make sense to me now.

I probably spent less on all of that over the past decade than I did on getting a degree. As a child, the stuffy classrooms in Singapore that I sat in and the theoretical problems I worked on, may have formed the foundation for many other things. I learned about hard work, and I also learned about dogged persistence there. But if you told me that all of my childhood dreams, inside those classrooms, looking out into the world and dreaming of a life on the road, doing things in the world, outside of a four-walled environment, that all of it would come true and that reality would be even better, I would not have believed you.

Thank you to all the crazy ones who believed in me enough, some of you even enough to come along on the ride with me. I pack snacks and biscuits, and two pairs of pants.

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