Deepak Gopalakrishnan

An engineer turned into a marketing ace

Folks, we're asking you to be candid — did it ever occur to you that some of the most creative folks often begin without a concrete plan? A leap of faith or a journey into the unknown isn't everyone's cup of tea, but a handful of creators willingly take that plunge — to create and be more. Whether it's the appetite for curiosity or storytelling, nearly all creators walk the less-trodden path hoping to steer a shift with their craft.


A cartoonist, comic creator, and writer — Deepak Gopalakrishnan is someone you can have an immersive conversation with over coffee or beer. He's a freelance content and marketing professional with bylines in prominent publications such as Arre, The Hard Copy, etc. He also runs an agency, Rough Paper Creative, with his wife, and they have a combined experience of over 20 years in advertising and events. While he thinks his friends introduce him as the guy who squandered a promising chemical engineering career to do something on the internet, his friends actually introduce him as a freelancer and writer in the digital marketing space.

Deepak hosts three podcasts: Simblified, Getting Meta, and The Origin of Things. With an established course on digital marketing, he has taught over 300 students; a conversation with him illustrates he isn't keen on being only a creator — he also wants to enjoy his creations, make them meaningful and lead a life he intends to. And oh, did we mention? He enjoys rock and metal music and loves PG Wodehouse.


Deepak grew up in the Gulf on a healthy diet of Archie Comics, Tinkle, and famous local magazines. As someone with a funny bone, he'd narrate jokes at school, write and make cartoons. But that didn't restrict him to comics and writing only — he also won several drawing competitions. But he declares that his childhood was boring, which pushed him to explore multiple things later in life. Even till engineering, he played by the book but keenly observed his surroundings. Obviously, that kept him in a creative periphery! 

"I'd look at my dad spending an outrageous amount of time parking our car backward, and I used to wonder why. Later, I realized he wanted to simplify his life when driving out. Surely, he isn't the only one with such a parking habit, but it somehow impacted me to plan better, making me understand that a shortcut now might only complicate life later."

Deepak's words found abode in diverse publications; he also won regional competitions, yet there was dismay. The fact that he gained not much exposure while growing up bothered him.

"I didn't explore much as I lived in a sheltered childhood. It's not like I was an obedient kid, but when you live in a country as humid, with houses far away from each other and deficient public transport, you never nurture hobbies. I didn't play cricket or have the typical childhood memories like that of a standard Indian kid. I only had books and TV."

The Formative Years

Then came engineering.

He was only comfortable in English, and the lack of speaking Indian languages made him cocoon into books and music. But, here's a twist in the tale — in college, they had a Poor Joke competition held in Malayalam to ease the first years, which Deepak ended up acing. In Malayalam, a PJ is called challi (meaning mud), which also signified the frolicking spirit of the event. However, competition is treated like one, and his seniors would maintain a leaderboard and proper format.

Deepak on why he’s called Chuck Gopal

Following the norm, Deepak joined MICA for his MBA right after his engineering. He cleared the entrance exam on his second attempt, and despite a profound interest in studying there, he admits to not making the most of his opportunities. 

"When you have free time and that too in abundance, you don't treat it with respect. But when you have only two hours, you want to make the most of it."

Entry Into Comics & All Good Stuff

It’s not just today, but even years ago, you were able to discover the most obscure yet phenomenal artists on Twitter. That element of discovery was what introduced us to diverse artists, and in a way, we were all a fragment of their growth story. Fly You Fools by Saad Akhtar was an iconic webcomic on Twitter, which Deepak admired. To the extent that whenever Saad hosted online competitions, he'd participate. 

"While my entry didn't win, I was one of the finalists; Saad chose the other entry, but the comments section was overwhelmingly in my favor. Around that time, a friend working with Pagal Guy approached me as they wanted to launch a comic series."

At Pagalguy, Deepak created plenty of comics that struck a chord with pretty much everyone who was preparing for an MBA or its entrance exams. He started experimenting and making cartoons, but he admits they weren't great. Since he'd take pictures on a DSLR and edit them, they didn't have the effect that digital comics had. However, things began to look up when he got a Wacom. By then, Deepak moved to Mumbai and regularly attended gigs — as a matter of fact, that's how he landed a job at OML.

"I cartooned by day and wrote in the night and that's how I balanced my entire day. I think that was a significant turning point in the overall scheme of things — they may look like little blips, but my journey would've been entirely different otherwise. I don't think it would have been a romantic story."

The Freelance Plunge

For nearly seven years, Deepak worked in advertising for firms such as Ogilvy & Leo Burnett India before relinquishing that thriving job in 2016. He wasn't pleased with the work and felt it was a disillusion. Despite being good at his job, it wasn't a creative role but a strategy-oriented position, which didn't excite him.

"I was doing quite well and was an AVP; I was certain if I continued on this path, I'd become a VP. However, I was frustrated and didn't like how the agency handled pitches or the usual client work. I started to look out but wasn't keen on other agencies or managing clients as it would be similar work. I didn't want to take a pay cut to join someplace either. Magically, an opportunity at OML came my way and since I admired OML and what they were doing in that space, I took it up."

Deepak worked with OML for two years before moving on, but what triggered that decision? Well, he bumped into a friend at a standup comedy gig who thought Deepak should get back to teaching, standup, and mainly creating.

Deepak on why he chose freelancing

Content Creation

Deepak followed international podcasts and enjoyed The Bugle — to a point where he listened to all the 300 episodes. While it inspired him to start, he didn't really chalk out a concrete plan when he launched Simblified with his friend Naren in 2015. All he wanted was to keep Simblified as straightforward as possible and in his words, Simblified translates to breaking things down, which trickled into his later working years too.

"I had a few principles I decided not to deviate from — for instance, I wasn't keen on standard social media work. While I lacked clarity on clients or working style, I was particular about wanting to work with people I could have conversations with or gain something towards the end. I wanted to work on stuff I was proud of showing off. Thankfully, a lot of stuff ironed out in the first two and a half years — I’ve even put down my learnings through Twitter threads and online sessions."

Soon followed The Origin of Things (TOOT), which talks about the origin of diverse brands and startups. TOOT drops a new episode every Wednesday.

Listen to the latest episode of  The Origin of Things podcast

Pro Time Management

From the dawn of invention, farsightedness and sound management have played a major role. Whether it's time or resources — the kind of seamless convenience good time management offers is beyond rewarding. Even more so, for a freelancer or a content creator as they're usually on their own, which is a trade-off, but Deepak certainly nailed that area too. Quite organized and sorted — he strictly follows a calendar and plans his work, months in advance.

Deepak discusses his time management process as a freelancer

The Philosophy

From his conversations, it's abundantly evident that Deepak prefers working with principles and it largely influences his working style. He also says by remembering very little, he maintains a fine clarity on a few dots. 

"I don't want to remember a lot of things in haste. You have different principles for different clients in the advertising world, which wore me down. So, I like to approach things with honesty to keep it easy: one strain of thought everywhere. That's how I create content, too, by simplifying things for people to munch on easily."

Apart from keeping it simple, Deepak is also particular about his work and being organized. 

"I don't want to take projects just for money; instead, I'm keen on working with brands I can bring value to and drive projects I actually want to work on. This also allows me to be organized, and when someone asks me if I have the bandwidth to take more work, I know what my calendar looks like. When you're a freelancer, your instinct is to take on everything, but some projects end up consuming more time, so before starting, it's important to understand the time commitments."

Revenue Models

While Deepak hasn't monetized his podcasts as of yet, he charges about INR 300 a year for his newsletter, Things of Internet. 

"It's just an experiment to see if people would pay; I intended to offer more value as people who pay for content would end up consuming the information. I mean, why would anyone discard what they pay for?"

While most of his revenue arrives from the content and consulting gigs, he also runs a course on Digital Marketing that costs INR 4,000 upwards. Plus, he teaches at a university. But he is inclined to monetize various forms of his content — for instance, turning his podcasts into eBooks. All said and done, he accentuates the importance of creating noise around oneself when you're a freelancer. 

"Take Krish Ashok for example — Jalsa and Jilpa didn't make him money, but it got recognized enough for The Hindu to offer him work. So, in a way, all these non-monetary things end up building a brand for you."

The Way Forward

Deepak establishes the essence of managing his time and not overworking. As far as the old saying goes, it's all about quality over quantity. That said, he is keen on creating more body of work — whether it's blog posts, courses, or insightful tips for freelancers on Twitter. Recently, he has also started a Telegram channel, Frood For Thought, to help people on the internet develop a reading habit. In less than a week, it already has nearly 500 subscribers.

A creative bone with a dash of practicality and flair for puns, it’s needless to say, we'll get to see all that and more in his stories. Till then, if you're looking to break the ice with him, words are your weapon. Or you can send some hot sauce his way — a little birdie says it's his preferred choice of gift.

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