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Pickyourtrail, the world’s only full-stack vacation startup, occupies a bustling office at the heart of Chennai. Founded by Hari Ganapathy and Srinath Sankar, this travel startup has gone from a 100-member team only 6 months ago, to more than 200 members today. This is their story of how they got here.

In 2012, Hari and Srinath went on a trip to Europe. Ardent travellers themselves, the duo had put in more than 2 months to fully plan and book their vacation. During their trip, they met other travellers who were on packaged tours, who all had one uniform complaint: their vacation didn’t have the flexibility nor the value that the duo’s plan had—they felt rushed between destinations and were unable to properly explore Europe.  

Once back home, Hari and Srinath were bombarded by friends asking for details on how they went about planning the entire trip. These interactions slowly multiplied and lead to an idea that would forever change their career roadmaps and the experiences of over 20,000 travellers. 

The bootstrapped beginning

A year after the Europe trip, Hari and Srinath opened up for business—they built a travel planning platform that not only allowed people to book flight tickets and hotels but also get manually made, customizable itineraries along with live support during their trip.

“Initially, it was hours and hours of work for every single customer. Not having a founder with a tech background, and being bootstrapped on top of that, was our biggest challenge. But it also helped us learn the basics and lay a strong foundation. We made and costed each itinerary according to the customer’s wishes, and though each one took almost 6 hours, it helped us reach where we are today.” – Hari Ganapathy, Founder, CEO.

By the time they hired a tech team, they had a clear product roadmap ready for them built on the basis of customer feedback. They eventually created a mobile app to provide live Travel Concierge service to their customers—which was previously done through Whatsapp and Telegram. The roles of the founders were also better defined. While Srinath gravitated to the tech backend and finance side of the organisation, Hari took on design, sales and marketing.

With the roles and roadmap sorted, it was time to scale. In the hyper-competitive travel industry, the initial successes were crucial for Pickyourtrail.

While their tech team was hard at work creating an algorithm that would bring down the time taken to generate a customised itinerary from 6 hours to under 5 minutes, Pickyourtrail was also investing in their sales and customer happiness teams. With almost no marketing budget, they’ve been profitable since day 1, doubled their revenues in their second year, and have kept up that trend to this day.

Funding and scaling

In 2018, Pickyourtrail raised $3million funding from a group of investors—Kumar Vembu (Co-founder, Zoho Corp), Girish Mathrubootham (CEO, Freshworks), Shyam Sekar (CEO, iThought) and Mr Rajgopal.

Though initially, the founders of Pickyourtrail were more inclined towards being bootstrapped rather than get VC funding, they were lucky to find a set of investors who were passionate about the product and gave the founders full operational freedom. “They appreciated what we had done to bring the company this far, and they trust us completely to take it further up the ladder,” Hari says.

This meant more freedom to experiment and hire the right resources, which directly translated to marketing spends and building their own digital acquisition channel. Along with this, they’ve further invested in technology, making sure that they remain on top of the innovation billboard.

Srinath, Founder and CEO of Pickyourtrail, says, “There is also a larger focus on taking this product global. End of the day there is a European going to the US  or an Australian going to Bali and the product is suitable even for them. We also want to try and understand what it takes to build traction in those markets.”

The funding also came just in time to fuel Pickyourtrail’s rapid employee growth—along with that came some unexpected policies, like making way for more furry companions in office. Pickyourtrail is perhaps Chennai’s only pet-friendly workspace. And its employees are overjoyed.

“I’ve been a pet owner for about 15 years and I can relate to people who have pets. When one of our employees was in talks with us, she laid down her precondition of bringing her pet to work. It was understandable. We thought that when we’ve found the right talent, such limitations shouldn’t be a showstopper and we agreed. Having pets around also helps reduce stress in the work environment, it’s a win-win,” says Srinath.

The road ahead

Pickyourtrail is now working on yet another trend-setter—Self-booking vacations online.

“To move forward at a faster pace, we need to make the process even faster, and that can only happen with self-service. We wanted to help customers book their vacation entirely online, without needing to talk to anyone. And it worked!’ says Hari.

Self-bookers now form a major chunk of Pickyourtrail’s customer basket. And they find more and more innovative ways to promote travel among their customers. One such example is their partnership with ICC for the upcoming T20 World Cup—Pickyourtrail is one among the only 10 travel partners chosen from India. They will now be providing their customers with Australia travel itineraries that come with tickets to the World Cup. This partnership is one of a kind, and Pickyourtrail is poised to make the most of it. This, combined with their other partnerships with brands like CRED will propel Pickyourtrail forward.

This travel startup is on an unstoppable journey, and it looks like they’re the complete package!

Speaking of journeys, wondering where to go for the New Year? The best vacations are ones where you can simply pack your bags and leave—no hassles. So here are 22 quick getaways that will make your New Year magical!