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4rom Side Hustle To Full Time Gig (4 Years Of 5Why)

“Dear Dad, you always told me that an honest man has nothing to fear, so I’m trying my best not to be afraid. ” – Frank Abagnale [Leonardo DiCaprio], Catch Me If You Can

It’s a strange feeling, being told often that you’re apparently going to do well with your life. Then looking into your bank account and realising you’ve never been more broke. The sleepness nights are real, the doubt is more present than ever before, and even The Joker seems a laughable opponent in comparison with your own mind at 3am some mornings.

5Why jumped into its fourth year of physical existence in 2017, but less than a year’s milestone in terms of a physical business. We’ve gone from uni blog / side project to full-blown content and events business. And the past six to eight months have been the first months of the full time side.

It often feels like you’re running away from failure. He’s chasing you, and despite the odd dollar that comes in, great partnership or achievement – he’s still got you in his sights. Much like the film Catch Me If You Can (highly recommended), where Leonardo DiCaprio plays con artist Frank Abagnale, constantly on the run from Tom Hanks’ Carl Hanratty and the FBI. Abagnale is constantly being chased for fraud and con acts and is quite often lucky to escape.

Whether you’ve seen the film or not, boy there are mountains of luck at play. Lucky moments, lucky escapes, lucky results. But what actually is luck? Does it exist? Is it real? Is it just romantic probability? It’s something I’ve asked myself for years.

Do I believe in it? Sure. I’m a natural optimist, and luck is the Berocca for my glass half full of water. However – I also believe and feel like I’ve learnt that we all get our doses of luck, of opportunity, of promise. And it’s really up to us to seize that. Are you switched on enough to realise what that moment of luck is and how to take advantage of it?

Let me throw you back to circa 2013. A young, brash, Indian-Portuguese lad, studying journalism and PR at a private university; not exactly your poster boy. But much like Abagnale, I was trying to find my place in the world. And I realised that every university kid had his or her 15 cents (sometimes more like three dollars) of opinion. So I thought let’s maybe give these guys an outlet to share their stories and opinions. So 5Why was born, essentially a blog with a tongue in cheek, fun, yet political tone (is that even a plausible combination?)

One thing I realised a year or two in, as I approached the end of my degree and started to work in the corporate scene, was that for all of the opinions Gen Y and millennials had, we never really had much guidance as young people. I’d ask people if they would write for the site, and some would look at me and say “Gordo, I’d really love to write for 5Why, but I don’t know what the f*ck I’m doing with my own life! How can I write about my own opinion?”

Some people felt socially uncomfortable, people didn’t know how to fill out a Census form, how to apply for renting an apartment, how to speak to someone on a Tinder date, whether or not they should solo travel. The list goes on.

And eventually it came to a point where I thought, “is this going to just be a blog side project or am I going to have a real crack?” So based of that guidance learning, I pulled a team together and pitched it out.

As much as con artistry has it’s ‘perks’, I focused on what I knew well – content, strategy and marketing. And like Abagnale I was off on this journey, and similarly didn’t really know where I was going at times. We got some backing and have gone from 0 to 50,000 unique users on site a month in just over six months.

There are no guarantees in business, that’s for sure. And where we’ll end up with 5Why is still a mystery. But I have perspective and a vision that drives me and gives me confidence.

Some of you may be familiar with Suroosh Alvi, the Co-Founder of Vice. I was listening to an interview with him recently* and when he was thinking about launching his first magazine title and was unsure if it’d be successful, he got dished some epic advice.

Do it. If he did the magazine and it failed after a few editions, he has physical proof of a concept he worked on and launched that would get him jobs and plenty of career opportunities. And if successful, it could become a huge media platform.

Vice Media is now worth upwards of USD $4 Billion.

One of the biggest things I’ve learnt is that you have to be like Abagnale. You have to have the stamina to keep running, stutter, change direction and sometimes even get caught. Often Tom Hanks’ Hanratty will catch up to you, but like in the film, Abagnale ends up being offered a lucrative role to join the FBI given his experience in cons and fraud.

Be aware of your surroundings. Know when your moment of luck comes up, and be ready to grab that unicorn by the horn.

We all need to aspire to be the people in the movie, not the just the people paying $22.50 to watch it.


Big ups to the person who got me onto the How I Built This podcast, you know who you are! Also a very recommended series of podcasts.

Gordon D'Mello

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