On Conan & Cynicism: Reflections on the Road Less Taken

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In the midst of aimless time-suck instagramming the other day, I came across a post with Conan O’Brien’s words overlaid on a pixelated screenshot. The post itself was worth sub-10 likes, but the snippet made me curious enough to search for the full quote online.

“All I ask is one thing, and I’m asking this particularly of young people: please don’t be cynical. I hate cynicism, for the record, it’s my least favorite quality and it doesn’t lead anywhere. Nobody in life gets exactly what they thought they were going to get. But if you work really hard and you’re kind, amazing things will happen.”

Turns out, Conan said these words after his acrimonious split with NBC in 2010. The context is relevant but not crucial to appreciating its universality; apparently it resonates with a lot of people.

I am expanding on this quote because throughout the course of my journey as an entrepreneur, it has been incredibly easy to become jaded. By default, my personality errs towards the cynical side, so I have to be extra careful about not slipping into a dark place of no return. Besides, people who are always happy can get annoying. I used to deem it a “healthy” dose of skepticism, one serving dually as a protective barrier and a source of humor for people who “got it”. As shitstorm after shitstorm hit though, I found myself conscientiously shifting towards a more optimistic worldview in order to survive. This sometimes came back to bite me, but more often than not, maintaining a positive attitude resulted in things working out for the best. For example, when first setting up ZAOZAO, no payment provider was willing to take a risk on a crowdfunding platform – what was this foreign concept of accepting credit card information before physical exchange of goods happened? Three lawyers, two crooks, and a threatened lawsuit later, we managed to narrowly escape an extortion case at the cost of delaying our site launch six weeks! If we had given up then, there may never have been a ZAOZAO. And that was just the beginning.

There were the letdowns from application rejections and red tape encountered because of systematic inefficiencies, being led astray by male “investors” who turned out to be sleaze bags, witnessing nepotism in action on a more frequent basis than expected. Let’s not forget when someone you’re paying and who is supposed to be on YOUR side turns out to be a handful, or worse, the opposite: unresponsive and unaccountable. Eventually you learn how these things work, and the next time a similar situation comes up, you have an idea of how to handle it better than the last time around.

These days, I get approached a lot for advice by business school students and college-aged aspiring entrepreneurs alike. Previously, in public interviews and conferences I would have given lame, cliché answers: “Do what you love” or “Prepare to sacrifice a lot”. While both of these platitudes hold true, they are also painfully stock standard as far as the entrepreneurial narrative goes. Ramen dieting, couch surfing, look at me suffer in pursuit of my dream…whatever.

I recall when I first started out on the other side of the table, seeking the wisdom of seasoned veterans. By and large, most were friendly. Some gave the same namby-pamby answers I gave on record, and a select few thought they were doing me favors by being “real”. In the latter category fell the cynics: those who had clearly been burnt along their own journeys who then felt entitled to vehemently discourage the pursuit of mine. I appreciated their soul-crushing “realness” at the time and rationalized this tough love approach, but in retrospect, they were just plain mean. There is no need to tear down the dreams of some bright-eyed youngun with (maybe) delusional dreams of achieving his or her goals. Sure, a reality check is sometimes warranted. But so much of that delusion is what keeps us going, and it is what ends up driving us for a long time to come. It’s the magic that could turn into the game changer.

As I advise the upcoming generation of inventors and hustlers and dreamers, I realize that I now have a better answer to give. Cynicism helps no one. Hard work is a given. Being generous is a difficult thing to do in times of struggle, financially and emotionally. At the apex of my selfishness as an entrepreneur, I valued my time so highly that I would count every minute spent not on my startup as an opportunity cost. Don’t be that person who refuses coffee with someone because they’re a nobody, or worse, one who ignores a vetted introduction. That’s just a dick move. Be kind.

Conan’s words just enabled me synthesize from a jumble thoughts that have been swimming around my head for 3 years these clear takeaways. I already had the answers. They were simply hidden in various reminders of my experiences…that in spite of unexpected detours along the journey, amazing things do and will happen.

They certainly have for me.

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Laid Back Fridays

Met with the co-founder & CEO of e27 this afternoon.

Only one meeting on today’s agenda. #laidbackfridays

Was connected with the co-founder & CEO of e27 a few weeks ago after meeting with one of INSEAD’s faculty members. Have been meaning to sit down with him to give him a sneak peek of our new site and introduce the new features, but because of my utterly manic travel and work schedule, it only happened today.

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Back to the Grind

My McQueen umbrella doubles as a weapon. Wearing Edge of Ember, Carrie K & Cartier rings.

My McQueen umbrella doubles as a weapon/arm weight. Wearing Edge of Ember, Carrie K & Cartier rings.

It’s rainy season over here in Singapore so my 100lb umbrella goes everywhere with me. Relieved the areas I had meetings at today were not affected by the flash floods. Never thought rain boots would be a necessity in Singapore, but then again the weather is so neurotic that I’ve seen some people go from wearing tiny tanks to piling on knitted cardigans and scarves in the span of a few hours… and we are right next to the equator.

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Heat Wave

Hong Kong

Nothing like dark gloomy skies and humidity to welcome me back home.

Been up since 3am this morning and am falling asleep as I type this entry. Have an investor meeting in an hour and am downing caffeine like open bar is closing. Hope I don’t fall asleep narcoleptic style. The next three weeks are going to be packed with designer meetings- I’m talking 6-8 back to back meetings each day! Will be working with our freelance photographer and videographer as well. Our new site (launching in a few weeks time) will be very visually stimulating. Expect a completely different look, feel and concept from what’s live now.

- Ling

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