Harsh Maskara Interview
Q. You went from investment banking to building Drip Project from your living room. What made you take that leap, and what were those first few months really like?
Investment banking taught me how businesses work, but I realised I wanted to be on the side actually building one. Drip Project started almost impulsively, from my living room, with very little structure and no playbook to follow. Those first few months were a mix of figuring things out, speaking directly to customers and doing everything ourselves. It was chaotic, but that closeness to the business taught me more than any classroom could.
Q. Drip Project grew nearly 400% year-on-year and was eventually acquired for $1 million. When did you first realise, “We’ve actually built something people are willing to pay serious money for”?
I don't think there was one dramatic moment where we suddenly knew we'd made it. It was seeing people come back, recommend us to friends and genuinely care about what we were building that gave us confidence. The growth numbers validated the business, but the stronger signal was that we had created something people had an emotional connection with. The acquisition was ultimately a validation of that work, rather than the starting point of it.
Q. You’ve built, scaled and exited one brand, and then started again with CHK. What is harder, the first company, or starting your second company when everyone already expects you to succeed?
The first company is harder because you're learning everything for the first time, but the second can be more psychologically demanding. You have experience now, but that also means people assume you know exactly what you're doing. The reality is that every category, consumer and company presents a different set of problems. With CHK, I've had to consciously stay comfortable with being a beginner again.
Q. With Drip Project, you turned jewellery into something accessible and aspirational for India’s hip-hop and Gen-Z audience. What did you understand about young Indian consumers that established brands were missing?
Young Indian consumers weren't necessarily looking for brands that told them what was cool; they wanted brands that understood the culture they were already part of. At Drip, we saw that jewellery could be an extension of identity rather than simply an accessory. Accessibility mattered, but so did having a distinct point of view and speaking to people in a way that felt native to them. That combination helped us build relevance without trying to manufacture it.
Q. You’ve worked with celebrities, investors and major personalities. What’s the difference between a celebrity endorsement that genuinely builds a brand and one that is simply an expensive Instagram post?
The biggest difference is whether the person has a credible relationship with what you're selling. A celebrity can give you reach overnight, but reach alone doesn't necessarily create brand value. The strongest partnerships feel like a natural extension of the person's identity and give the audience a reason to believe the association. If the only takeaway is that someone famous wore the product once, you've probably bought attention, not built a brand.
Q. If you were 20 again with no money, no network and only your current knowledge, what would you build and what would you do differently?
I'd still start with a consumer problem rather than trying to come up with a clever business idea. I'd spend far more time talking to customers before building anything and get to a real product much faster. I also wouldn't wait for the perfect network or resources because you can build those along the way. The biggest thing I'd do differently is trust the process sooner and spend less time worrying about whether I was ready.
BIO
Harsh Maskara is the CEO and Co-Founder of CHK.

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