The Story
Six chapters. One city that made me, one classroom that couldn't contain me, and everything that happened after.
Chapter 01
I grew up in the lanes of Ballygunge. Calcutta sheltered my parents before it sheltered me, so I did not just grow up in a city. I grew up in a story already several chapters old.
Satyajit Ray taught me that extraordinary stories hide inside ordinary lives. Pather Panchali, Charulata, Apur Sansar. Cinema as a way of seeing, not just watching. And Prosenjit Chatterjee, Bumba Da as the whole city calls him, showed me that you can carry a generation's emotions on your face and make it look effortless. I grew up watching his films and understanding that storytelling is the most powerful thing a human being can do.
There is nothing I love more than the monsoon in Calcutta. A walk around Rabindra Sarobar when the city slows down and everything feels like a scene from a film you cannot quite place. Daily life here feels like fiction. Not because it is unreal, but because it is so completely itself.
The love for business came naturally in a city where every lane has its own economy and everyone has a loud opinion. Calcutta gave me my taste, my curiosity, and my inability to do anything halfway.
Chapter 02
I passed out of Sri Sri Academy in 2017, part of the very first batch of that school. Christ University in Bangalore came next, BBA (Hons) with a Marketing specialisation, and with it a city that built me in ways Calcutta had not.
I worked through college. Mystery Junkies, an escape room company run by Rupert Piccardo and Sapna Gurukar, is where I learned how to actually talk to customers. Not pitch them. Talk to them. I set up rooms, managed reception, handled the cashbox, and made sure people left happy. Small work. Real lessons.
Bangalore also gave me Laila, a Bajaj Avenger Street 220, and my first real taste of the road. She lives with my friend Puru now, someone I met years later at Masters Union. Full circle, as these things tend to go.
I left with a degree, friends for life, and a dissertation on advertising and automobile sales that got applauded. The real education, as always, happened outside the classroom.
Chapter 03
Before Uncrowd there was PromotEdge, and before I could bet on myself I needed people who believed I was worth betting on. Gautam Saraswat, Rishi Jain, Avik Guha, Sayantan Guha, Saurav Agarwal. Each gave me something I still use.
Starting Uncrowd in late 2023 meant cold calls, no safety net, and a partner who handled what I could not. I handled everything client-facing. The pitches, the onboarding, the early weeks of every relationship. I built a team of eight, introduced SOPs, and made something that worked without me holding it up constantly. The most honest education in execution I have ever had.
Chapter 05
His name is Nawaab. Royal Enfield Meteor 350. Before him there was Laila, a Bajaj Avenger 220, and Bangalore roads that were just wide enough to get lost on.
The best birthday I have had was a solo trip to Tosh. No plan, just a road going up and mountains getting bigger. Mountains over beaches, always. Ladakh, Rajasthan, Wagah, Kasol-Tosh again. The list grows faster than I can ride through it.
Cars run just as deep. Audio builds, engine mods, the Baleno tuned exactly the way I want it. If you want to lose two hours talking about cars, I am your person.
Chapter 06
I taught myself to cook the way I learn most things: badly first, then less badly, then well enough to be proud of. I am not a recipe person. The goal is not to be home-cook good. The goal is to be actually good.
I had a cat. Bosco. He passed, and I will leave it at that. I am a cat person, always have been, though I love dogs too. There is something about a cat's complete indifference to your approval that I find deeply relatable.
The air rifle range is where I go when everything needs to slow down. Ten metres, a target, complete stillness. You cannot fake it. My father shot at national level. I come to it with that in the blood.
Boxing I do for the head more than the body. No strategy without discipline. Boxing teaches that faster than most things.
Chapter 07
One film, one book, every week. Not a goal. A rule.
Seedhe Maut. If you know, you know. If you do not, start with Nayaab and work your way through. Die-hard fan, not embarrassed about it. There is a directness to what they do that I find genuinely inspiring, not just as music but as a way of saying things that matter without dressing them up.
Kendrick, J. Cole, Nas. Bass-heavy everything. Music shapes a day the way good copy shapes a campaign, quietly and completely, without you noticing until it stops.
Coppola taught me that the best stories are about family, power, and loyalty. Taleb taught me to respect uncertainty. I am still working through the implications of both.
Want to know more?
Whether it's about work, a collab, or just the best route to Tosh, I'm always up for a good chat.
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Nishant Gupta
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