From Dotcom Era to AI Boom — How Did Deep Kalra Keep MakeMyTrip Ahead of Every Trend?

Few Indian entrepreneurs have witnessed — and shaped — the evolution of India’s internet economy as closely as Deep Kalra, the founder of MakeMyTrip. From building a travel-tech startup when mobile phones weren’t even mainstream to leading a company that now integrates AI across operations, Kalra’s journey is a masterclass in navigating change.

In a brief but insightful conversation with TICE, Kalra reflected on how MakeMyTrip has continuously adapted through eras — from the early days of the internet to the age of artificial intelligence — and what it takes for a startup to survive through crises.

From the Web to the World of AI

“When we started, forget AI — we didn’t even have mobile phones,” Kalra smiles, looking back at a 25-year journey that parallels the growth of India’s tech ecosystem. “We are as old as TiEcon today,” he says, referring to the global entrepreneurship conference.

What kept MakeMyTrip relevant across technological waves, from the dotcom era to AI, Kalra explains, was a founder’s instinct to “keep your ears close to the ground.”

“Like the Red Indians used to do — putting their ear to the ground to hear the enemy coming — entrepreneurs must pick up signals early,” he says. “You have to sense whether a trend is just a fad or something that will shape the future. If you believe in it, you must realign your resources quickly.”

That philosophy has guided MakeMyTrip through every inflection point. When the app revolution began, most companies tried balancing between web and mobile. MakeMyTrip took a bold call — it stopped all web development and went all-in on mobile apps. “It was a big, bold bet — and thankfully, it paid off,” Kalra recalls.

Today, the company is making a similar leap of faith — this time into artificial intelligence.

In August this year, MakeMyTrip launched a vernacular conversational AI assistant, “Myra”, which Kalra says is already handling over 25,000 conversations a day at higher conversion rates than non-conversational transactions. “People love using it to discover, plan, book, and even manage post-sales queries,” he adds.

AI, however, is not just customer-facing at MakeMyTrip. “We are using AI in HR for resume screening and interview scoring, on the product side for summarizing thousands of hotel reviews in a few lines, and even in our release cycles — our agility and quality checks have significantly improved,” he shares.

The message is clear: for MakeMyTrip, AI is not a buzzword — it’s a core business enabler driving productivity, user experience, and efficiency.

The Startup Playbook for Surviving Crises

Having weathered multiple storms — from the dotcom bust to the COVID-19 pandemic — Kalra knows what crisis leadership demands.

“There’s almost a crisis playbook now,” he says. “Our toughest time was during the dotcom bust — from 2001 to 2005, it was an existential crisis. We sometimes had money for just two months of salaries and rent. What kept us going was conviction — belief in the idea, and a team that believed in you.”

Fast forward two decades, the pandemic posed a different kind of challenge. “It was the worst of times for travel. This time, we had money — but we had to hold on to our people,” Kalra recalls. “Our team members were anxious, some wanted to move, and we had to focus on retention — on staying calm and doing the right things, not panicking when you don’t need to.”

That sense of composure, Kalra believes, defines great leadership — especially in uncertain times. “Every crisis teaches you something,” he adds. “It’s about holding your nerve, taking care of your people, and keeping faith in the long game.”

As MakeMyTrip celebrates 25 years, Kalra’s focus remains unshaken — stay curious, stay adaptable, and stay close to the customer. Whether it was betting on mobile before India went mobile-first or now embracing AI before it’s mainstream, his entrepreneurial compass continues to point toward evolution.

In an age where startups rise and fall at lightning speed, Deep Kalra’s story stands as a reminder that resilience, reinvention, and readiness to pivot are timeless traits of lasting entrepreneurship.