Exclusive: Sahil Gupta on Content, Corporate Life and Creating His Own Path

Sahil Gupta's journey has been anything but conventional. From finding confidence through theatre in college to building a career across tech, content creation, and entrepreneurship, he has worn many hats. In this conversation, he talks about turning workplace experiences into relatable content, launching his own brand, sharing the stage with Akshay Kumar on *Wheel of Fortune*, and why he believes AI is something to embrace, not fear.

You are working as a full-time tech lead and still decided to start making content around corporate life. What made you actually start, and what are your days like?

I was always creative as a child, but I didn't get the right platform in school to showcase that creativity. Because of that, I lost a lot of confidence and faith in my ability to do something artistic. However, when I went to college, things changed a lot. Somehow, I found the courage to audition for dramatics, and I was actually selected. I saw that people genuinely appreciated my talent, and from that point on, things started building up.

As for how my days go, I have a notebook where I write a to-do list every night before going to sleep. I wake up at 6:30 a.m., and based on my schedule and to-dos, I plan how and when to work on my content, startup, and office work.

You were just nine years old when you used to run imaginary game shows. When did that stop feeling like a childhood habit and start feeling like something you actually wanted to pursue?

It all changed in college when I won the first award of my life for drama, which was also my first performance ever. Until then, the principal of my school had made me believe that I had no talent and was never worthy of being selected for anything. But college changed everything. I started gaining confidence in my talent, and slowly but surely, I realized that I was capable of achieving bigger things in life.

I started YouTube in college, but that didn't work out. The same happened with Musical.ly and TikTok. However, I never looked at those experiences as failures. Instead, I saw them as learning lessons, opportunities to grow, improve, and prepare myself to do even better in the future.

Where did The 9 to 5 Show and the clothing brand come from? Was there a moment at work, something you felt or lived through, that made you think this needs to exist?

When I started getting recognized for my corporate content, I realized that a large part of my audience was Gen Z. I also noticed that in many workplaces, Gen Z was stepping into leadership roles, and across startups and companies, mandatory formal attire was gradually becoming less common. At that time, there was no brand focused on funky corporate clothing.

I had an audience, I identified a gap in the market, and I thought, why not create something that truly represents me? That's when I decided to start this brand, and I did. I had no idea the response would be so incredible.

How did it feel when you got the call for Wheel of Fortune? And take us to the moment Akshay Kumar actually walked onto that set. What were your thoughts? How was your experience?

When I first received a message from the casting director on Instagram, I honestly thought it was a scam. So, I asked my team to verify it, and when they did, it turned out to be real. I was actually being invited to appear on a TV show with Akshay Kumar. I had imagined a moment like this so many times in my life that I couldn't even process that it was actually happening.

When I went to the set, I surprisingly felt quite normal, which was shocking because I'm usually very nervous and anxious in situations like these. I had an amazing time on set and got to learn how production works, something I had always wanted to experience. And honestly, Akshay sir is incredibly funny in real life.

Even when the show was televised, I still couldn't fully process what had happened. Everyone around me was shocked and celebrating. My parents, family, and friends were overjoyed. But I think it took me about a week to truly realize that I had actually been on TV.

You built a whole platform around the 9 to 5 life, and now Gen Z is actively pushing back on that idea. Having seen both sides, where do you personally stand?

The irony is that my entire content revolves around exposing toxic workplace culture, but through comedy. I genuinely believe humor can heal a lot of things. It's a form of therapy that we all need in life.

People often tell me, “I was so stressed about something that happened at work, but after watching your video, I realized this happens to everyone, and sometimes the best way to deal with it is to take things lightly and not let it consume you.”

Hearing that makes me realize that I'm working from both sides. I'm highlighting the problems in workplace culture while also helping people cope with them through humor.

Everyone talks about "passion over paycheck," but you've lived both. Honest answer: can you actually have both, or is that just content?

I think it's different for everyone. In my case, I've been fortunate because content creation, my job, and my business are all things I'm deeply passionate about. They're like my babies. Luckily, they also make me money.

So, I might actually be the wrong person to answer whether “passion over paycheck” is better because, for me, my passion comes with a paycheck. The difference is that I never work just for money. I work because I genuinely enjoy doing what I do.

There have been times when I've turned down brand deals worth ₹3–4 lakhs because they didn't align with my content style or values.

Even in business, I haven't spent a single rupee of the profit I've made on myself. I reinvest it back into the business because I believe in building something bigger.

For me, money has always been a by-product of doing what I love, not the reason I do it.

AI is coming for tech jobs faster than anyone expected. As someone in the industry, does that scare you or excite you?

I'm actually very excited about AI in tech jobs. I believe that, with time, we have to accept that new technologies and tools will always emerge to make human life easier and more efficient. That has been the story of progress throughout history.

Take the invention of the wheel, for example. It was created to help humans travel and transport things more comfortably over long distances. Beyond that, it opened up entirely new possibilities. Moving food, water, goods, and resources became far more efficient, which ultimately created more opportunities and transformed how society functioned.

That's how evolution works. Every major technological shift looks scary in the beginning because it changes what people are used to. But change is inevitable, and more often than not, it pushes humanity forward.

So instead of fearing AI, I think we should be excited about how we can use these tools to improve our work, solve bigger problems, and become even more technologically advanced. The people who learn to work with AI rather than against it will be the ones who thrive.

If you could go back and talk to the younger version of yourself, still figuring things out, what would you tell him?

I would tell my younger self two things.

First, never quit, no matter what phase of life you are in. Good things take time, and everything happens for a reason. There will be moments of doubt, failure, and disappointment, but do not let those moments define your journey. Keep going.

Second, whenever something does not go as planned or you face failure, do not just ask, “Why did this happen to me?” Instead, ask, “What is this trying to teach me?” Learn from every mistake, understand the reason behind every setback, and use those lessons to grow.

Every failure carries a message. Find that message, learn from it, and keep moving forward.