Popagandhi

Dear (your name here),

Imagine for a second that the year is 2000.

Holding hands with your girlfriend in public is either an act of defiance or shame.

The world is years away from The L Word: nobody knows yet that it sucks, that lesbian life does not have to be "like that". (Bette Porter is bad for you; Jenny is worse.) No one has ever met a married queer couple. The idea did not exist. You're supposed to aspire to cohabitation, no kids, and two sets of power suits. But you don't.

You are never going to meet the woman of your dreams at the smoking section of the weekly queer party. Definitely not on the dance floor. They can't hear a single word you're saying, and they don't care. They don't care that you've found your major and the internship of your dreams. They won't even remember your name after they've fucked you (badly).

But it's not 2000, and no one really cares who you hold hands with anymore. Kinda. Sorta. We've made a ton of progress-there are now women married to each other! And you know them, because they write about it on Facebook! Ha!-yet for all the progress in the world, the music never improves at these parties. One day, maybe in 2040, we will have driverless cars and queer clubs which play jazz. I'm putting all my money on the driverless cars.

I just want to tell you that it's ok if you're badly dressed, somewhat awkward, and a bag of nerves. That your nerdy hair cut is OK, too. The makeup you don't have-you can always YouTube it later. Or not. Someone out there likes badly dressed nerdy girls who don't know how to put on makeup. They'll even listen to you talk about linguistics or Burmese history or app development, too. You'll meet her.

It's ok to screw up. It's ok to be messy. Nobody expects you to "grow up" any faster than you should. Your friends who are so 'sorted out'? They're all pretending.

That older woman you love is going to break your heart.

You're going to let her. Often.

That's okay, too. We learn.

Drink good whisky. Toss the vodka orange shit. If you have to drink rum and coke, make sure it's good rum. One day you'll learn that drinking is fun only when it tastes good, and you might even learn to stop just before you are no longer in control of your body, or your thoughts. Two is a good place to start taking stock. Zero if you are driving.

If the booze makes you want to call or text your ex / the love of your life (who doesn't feel the same way anymore, or ever), give your phone to your friends and tell them to never give it back to you until two hours after a sausage McMuffin.

It's okay to use an alias until you're comfortable that the girl you're talking to isn't an axe murderer. With girls, that can take anything from two minutes to never.

Don't stay over unless you want to see her again. Or unless she lives near a cool breakfast place, and it opens early.

One night stands are boring. But if you have to, and there are seasons for that kind of thing, you need to be ok with learning to ask and to answer uncomfortable but important questions. It's the right thing to do.

Avoid hyphenated relationships you're not really involved in, like the bubonic plague. They're worse than that. For example, avoid dating your ex-girlfriend's ex-girlfriend. Also avoid accidents: do not sleep with your ex-ex girlfriend's on-off girlfriend. Hyphens are trouble. There are hot, single women out there. You just have to look outside your phone book. No hyphens. No exceptions.

Eventually, you'll learn to identify the toxic ones before they even come close to you, and your heart won't be needlessly broken anymore.

Is there a type you're drawn to? Do they break your heart? Maybe it's the hapless artist whose broken spirit you want to save. You need to let her know she's not going to set your life on fire, just for the heck of it, ever again. Perhaps it's the stoic, powerful women in your life who don't appreciate your struggle for parity. It's ok-you're going to be more powerful than them someday. Without stoicism.

They're going to make you think that it's your fault. It's your fault that you're a slut. It's your fault that there's a string of broken hearts. Sometimes, it is your fault. Own up to them when you can. It might take years before you are sorry enough for everybody. But you tried. And no one cares.

Quite often, you will meet women who want you to travel halfway around the world to prove that you are really into them. They don't mean it. Don't go, unless you have other things to do there. Or unless you have a fire for her which isn't just in your loins.

If she wants to marry him, and still see you on the side, leave.

The world tells you it gets better. It does, and then it doesn't.

People-and this can be family, insurance companies, government bodies-are not going to take your love seriously. Especially if you are a woman who loves another woman. If you are feminine enough, nobody will like your 'rejection' of masculinity. If you are not, nobody will like your 'attempt' to threaten theirs, a threat which you've made just by merely existing. If you are a woman who loves a woman who was not born one, it's going to be that much harder for you. You will not be invisible for much longer.

Your family is much more resilient and loving than you imagine.

Love them back.

Be young. Be queer. Be the nerd that you are. When you get older, it's the algorithms that will get you laid.

There's a wealth of literature out there about this, but it can never be said enough. Too many people work with assholes.

You see them everywhere.

The cafe owner that takes a shortcut by hiring an asshole barista? The barista plays shit music at your cafe and nobody wants to go there.

The startup founder who values talent over attitude? The asshole co-founder or top exec, no matter how good they are at their jobs, is going to screw you over.

Eventually you realize that you're losing money and that nobody wants to talk to you at industry events anymore. Or perhaps investors or future team members take you aside to say they want to be a part of your dream team, but… that guy is an asshole.

Assholes don't inspire trust.

Assholes can sometimes be nice, too.

People often make the mistake of assuming that the opposite of an asshole is a push-over. It is not. The opposite of an asshole is a decent business-person or partner who brings net positives to the table. An asshole, no matter how occasionally nice, perhaps to certain people, or to most people, has certain characteristics which breed mistrust and disdain.

At my first startup, I worked with a guy who was a really nice person, and very good at his job-to me.

I was new to the scene. I had no idea.

He had ideas, he got things done, he was a good person-to me.

But he was not a good person to people who could not give him something.

There will always be people like that.

I'm talking to a handful of investors at the moment and what I do for each one is to see who has worked with said people before. I call them, no matter how tenuous the link, and say: "What do you think of ____?"

You don't really have to get more specific than that.

You can, of course, to clarify some of the assumptions that people might have made, or to get more details on deals gone sour, etc, so that you can make up your own mind.

But I've found most often that if I am going to be met with silence or awkwardness or worse, with hemming and hawing which can seem unjustified, it's a red flag for me.

This applies to people I hire and to people I date, too.

You need to be sure that this person doesn't kick old ladies or torture pets when you're not looking. A good way is to see how they treat waiters and how they respond to the homeless or the poor.

I don't need you to be a bleeding heart old lady hugger (please don't), but life's too short for anything that isn't "fuck yes, yes and yes".

No amount of money is ever worth it. That's not idealistic-it's the most practical advice I was ever given.

Some time ago, some people (read: entrepreneurs) I follow on Twitter posed a seemingly innocuous question. What drives us, as so-called entrepreneurs, to do what we do? Is it hubris? Ego? Is it an out-sized and unrealistic view of one's abilities? For most of us, choosing this life also means the opportunity cost we left behind, often reluctantly: decently-paid jobs with career growth at startups, VC firms, tech companies, banks, even… bars. There has been no better time to be a tech exec. My friends, and I am sometimes envious of them, clearly smash through the income and lifestyle brackets in the top 1% of the cities they live in, even the world-what we do is such a upwardly mobile trajectory. The lifestyle, with the stock options in soon-to-IPO companies, global travel as part of international "launch teams" in the most successful tech startups, fuelled by the globalizing of venture capital and focus of said capital in my part of the world, is certainly tantalizing. No longer do you need to work in finance, it seems to say, with each job offer and recruitment mail, in order to eke out a nice life for yourself and your family. The stock options certainly don't hurt.

So what can it possibly be that some of us choose to do this? Even though it's easier than ever before to raise money and do your thing, the fact is no matter where in the world you do this, building a business is just terrible. It's fun, otherwise we wouldn't be drawn to it. It can also be rewarding, otherwise we wouldn't try. But. It's hard.

I'm torn:

Between the deluge of entrepreneur porn articles and this shit is hard articles (like this, but 10x more pity): I'm torn.

On the one hand, having the ability and the opportunity to start and run your own business, even to try, is a damn privilege. It really is.

On the other, there are so many moving parts. Skill sets you need to suddenly and abruptly become a ninja at. As a founder, from HR (super important) to project development to technical skills to payroll to accounting to taxes to… whatever challenges it throws at you, really.

The last couple of weeks have super hard.

Stressful.

Energizing.

Insane.

Gut-wrenching.

Incredibly amazing.

Many startup founders come across founder depression at some point, and I think it's a real risk you expose yourself to when you put so much of yourself on the line. No matter how well-adjusted you think you are, you need all the help you can get.

This is my second company. My first, right out of school, was a dev house that specialized in creating innovative marketing projects for advertising and FCMG companies through the then-new mobile and social platforms.

Pushing 30 this year, doing this at 30 is a world apart from how it was like to do this at 22. I'm sure there are many young startup founders who learn and grow on the job, or perhaps possess a certain self-awareness and ability which I did not have. But. I find myself, this week, making dozens of decisions daily-on the sorts of things which would have caused me a lot of grief, time, money or existential angst, back in the day.

I have the opportunity, the right teams, and the business partnerships to push through with the sort of tech business I have always want to do: tech, finance and social good.

Now?

Now, we ship. And learn. And ship again. And learn again.

I love it. I hate it. I love it.

It was the best of times, it was the worst of times. It was a bit of both, really.

I'm not one for the mumbo-jumbo of the Myers-Briggs test, but I suppose it was striking that when I did it before my startup I rated very strongly as INFP, and yet now I'm very much on the ENTJ spectrum. It appears that having to do shit in a prompt, aggressive way does bring out very different approaches.

So, startups are hard. You already know that.

In my case, every attempt to think that through inevitably ends up being a little self-pitying.

How and why did I decide that leaving my family, and puppy, coming to a foreign place, to work on some problems involving the silos of payments, mobile, commerce and gender equity, was the best life and career decision of all?

Yet… I wouldn't have it any other way.

Yes, I know the rates of failure are high, in any startup. Not to mention one with foreign laws, language, culture, and way of life/business.

Yes, I know that there's only so much hustle can bring you. There's also the regulations and expectations of archaic industries and economies in certain countries.

But man, it's exhilarating. If shit hits the fan and nothing goes the way we intend despite the best laid plans of man (and woman), then at the least we can say that I now have very specific knowledge and connections in some fairly obscure Asian markets.

It was a brutal week.

I lost a kid in the community my foundation does a lot of work in. She was 14. She had dreams. She was vivacious. Perhaps, her undoing, in an unforgiving climate.

I lost a key team member. To the same brew of inexperience and lack of discipline and foresight. But team before product, and it's never going to be easy.

Also, some huge gains. Solved some massive business obstacles. Created some solid partnerships. Brought in many valuable individuals to build the team. Net-net, a good week, if a little brutal.

There's shit to do and a world of problems to solve. A glut of solutions we can create and design, and hopefully do so beautifully, with elegance, sensitivity and impact.

In late 2012 as I stood on a similar crossroad contemplating major life decisions, mostly relating to the geography and type of work I wanted to surround myself with, I found tremendous opportunities, but I also found my heart had already decided.

My 30s are to be spent in my backyard. In Asia. In the emerging markets of Asia. Doing as much insane and crazy shit as I can possibly throw at it. I feel honoured to even have a single shot at it.

I am.

It was the best of times, and the worst of times. Ask me again some weeks from now. Months. Years.

I think I will say that there's nothing else I would rather do, and nowhere else I would rather be, than here in the heart of Java, toiling for a dream.

I was just telling someone tonight: I force myself to meet a different stranger in Jakarta every single day that I'm here.

Even if I'm exhausted after work (which I usually am), I try to meet a new person, or eat a new food. Go to a new area.

The first time I lived outside of Singapore was when I moved to Dubai in 2007 right out of university. Then, without the metro or a usable public transport system, I was lost, angry and disoriented (I don't drive). I hear it's different now, but I'll never know.

Jakarta, despite the terrible traffic (and I don't think I'll ever stop saying that; I certainly haven't heard any locals stop complaining), works for me.

Between the ojek (motorbike taxi) and plentiful and good taxis, I'm pretty much covered.

I try to practise my Indonesian with total strangers, too.

Tonight's conversation went a little bit like this.

Cabbie: Why did you not get into the cab earlier! Is it because I am black?

Me: No!

Cabbie: Okay!

Me: How long have you lived in Jakarta!

Cabbie: 20 years! I'm from Timor! I play in a band! Check it out on YouTube! T-I-B-E-T B-A-N-D G-O-M-B-A-L

Me: Tay- ee- bay- aa- tay… fuck, what's this G in Indonesian?

Cabbie: Watch my videos! I'm singing! Let me put on some of my other music for you!

Me: (recognizes words like… cintamu, denganmu… JIWANG ALERT GOES UP)

Cabbie: Do you know about the galau?

Moments like these.

Rockstar cabbie in ridiculous YouTube video.

Nus Bany, is his name. He's the one in the insane costume. He also arranged and composed most of the music.

Nus Bany is now my regular taxi driver contact.

I intend to unleash him on all of my unsuspecting business visitors.

Yes, I know about the galau.

And it might be a sign that I'm moving further away from my Peninsular Southeast Asian roots when I now say galau over jiwang.

I love galau music. What's your fave?