Trail, Trial & Magic
For Hari Ganapathy, the transition from ‘Thor’ to ‘Morpheus’ was nothing less than a trial by fire. Though a rugged journey for over a decade, which was punctuated by a devastating pandemic, Pickyourtrail found its ‘magic’ as the cofounder stayed with his unwavering conviction to pick the bag, drop the baggage, and continue with the journey!
“Are you scamming me,” the interviewee got alarmed. It was just a few minutes into the prologue, Hari Ganapathy was getting into the groove to hunt for his maiden tech guy, and the cofounder of Pickyourtrail had only shot two innocuous and clichéd questions. Well, this is the best the non-techie could have done. He did his homework, Googled ‘five questions to ask in PHP,’ and diligently followed the script. Though questions like “what is the difference between a static and dynamic website,” and “what is PHP most used for” were sure to make even a tech amateur cringe, Hari was doing his best to judge a senior tech talent for a role he never had in his startup, which was started in 2013, and remained bootstrapped for the first five years.
The job applicant, meanwhile, was terrified. “I mean, who asks such questions,” the candidate continued with his outpouring of immense disbelief. “Do you guys even know anything in tech,” he grilled the interviewer with his searing questions, abruptly stood up, and scurried out of the room. The meeting was over. “I literally ran and stopped him at the door,” recalls Hari who was feeling embarrassed. “Please don’t get us wrong,” he implored. “We are genuine. I was just trying to understand the tech stuff and chat,” he tried hard to explain his point. “We were not scamming,” he said.
A few years later, sometime in 2019, the tables turned. “Are we getting scammed,” wondered Hari. The first-generation entrepreneur was intensely gripped with a distressing emotion. “What’s happening? This can’t be real,” he said to himself. Five years of bootstrapped journey, and now Hari and his team were looking for some strategic backers. There was one promising backer, and somebody referred Hari to the potential funder. The second name sounded familiar, but there was not much info about the guy. “I Googled and tried to look for Kumar Vembu,” he recalls. There were some YouTube videos, bits and pieces of information, and the guy was for real.
Clap, Clap, Clap
Finally, the pitch started. A few minutes later, something unusual happened. “Kumar started clapping. He just kept clapping,” says Hari. Though Kumar liked the idea, vision and the business, and it was normal for him to get impressed with a bunch of youngsters charting a differentiated path, Hari found his ‘clapping’ unnerving. Reason was obvious. The founder had made umpteen pitches to VCs, many liked the idea, but nobody ever got so excited. “We don’t know if we’re getting scammed. We don’t know what’s happening,” wondered Hari, who was bugged with a few more vexing thoughts. “Is he trolling us? Is he making fun of us,” he wondered.
The trail of unanswered questions continued. “Why is he not grilling us on how the business would scale? What did he find so exciting…Hari was still hunting for answers. There were none.
The same day, in the evening, the founder got a call from Kumar Vembu’s team informing him about the decision to invest. “We were almost convinced it was surreal,” he says. One meeting, and decision to invest didn’t make sense. Well, when individuals added up, it made more than sense. In February 2019, Kumar Vembu, co-founder of GoFrugal, Shyam Sekhar, founder of iThought, and Freshdesk’s cofounder Girish Mathrubootham backed the travel tech venture. Pickyourtrail’s funded journey made a hefty start.
A year later, pandemic came knocking and took the winds out of the sail. It was March 2020, it was the same room, it was the same funding pitch, and Hari was pitching to the same set of backers. Over the last twelve months, Pickyourtrail travelled at a furious pace. The headcount increased from 50 to around 250, and revenue jumped from Rs 4 crore to Rs 12 crore. For a startup which managed to touch Rs 4-crore mark in five years, 300% growth was staggering. Given the heady growth, and the need to build a war chest to fight the uncertainties of the pandemic, Hari was dead sure to get the funding.
Little did he know that the trail was about to enter into a zone of trial. “We don’t want to be bad parents,” said Shyam Sekhar of iThought, who nipped all the funding talks. “I am not giving any money,” he said. Other investors too declined. Hari was stunned. The entrepreneur had worked on three possible scenarios, and presented it to the backers. The calculation was based on the assumption that the pandemic would last for six months. “We made Plan A, B and C,” recalls Hari. Plan A, he tells us, was to keep the team size of 250 intact, and no salary cuts. Plan B was to have a lean and mean team of 30, which meant massive downsizing, and less financial support to survive. And Plan C was to have a team size of 100. The funding amount to support all the three plans were elaborately thrashed out.
‘Bad’ Parents, ‘Good’ Upbringing
The backers, interestingly, had a different plan which was not part of any plan made by Hari. “We don’t want to be bad parents,” Shyam Sekhar reiterated, and expressed his confidence. “I am sure you guys will figure it out,” he said, adding a rejoinder. “Please ensure that the cash you have lasts for 10 months,” he said. Pickyourtrail had plunged into the biggest crisis of its life. Though the magnitude of the hardship was unprecedented for everybody, especially those in the travel and hospitality segments, the stark co-relation of the flip side of being in the business vacation and entrepreneurship never came out so brutally and vividly. “There are many moving parts in a vacation,” says Hari. “And you don’t control any of the moving parts,” he says.
There are indeed endless moving parts in a vacation. You can’t control the hotel. You don’t have control over the flight. You can’t control the activities, and you can’t control rain even though you can predict and plan. There are more things that you can’t control: volcanoes, and disruption of holiday plans; pilot strikes and disruption of flight plans…Now contrast it with a long list of things that an entrepreneur can’t control. Let’s start with funding. Now who could have predicted the magnitude of the funding winter or a generous funding spring? Next is policies. Crypto and fantasy games…both have turned from darling to pariahs. There are too many moving parts, too many variables, and too many ‘what ifs.’
For a good part of his life, though, Hari — who had a superhero nickname of THOR — had done his best to have things under control. An aggressive go-getter, he had been wired to have a crack at things during his corporate stints at Britannia, Reckitt and InMobi. “In some sense, Thor is always hustling through muscle,” says Hari, adding that hustle in his case was to muscle his way through any crisis, sticky situation or tough task. As an employee, Hari excelled. “I was known to get things done,” he says. And as a founder, what made things slightly easier for the hustler was the absence of formidable challenges during the formative years of his entrepreneurial journey.
Pickyourtrail had a passionate beginning. The cofounders — Hari Ganapathy and Srinath Shankarnarayanan — loved to travel, the entry barriers in the travel industry were low, and the duo eventually decided to make business out of their love. Hari explains why it was easy to start. “When we started, a lot of people knew that we loved to travel,” he says. So getting the first set of customers was easy. A lot of their friends were getting married, and consequently the first 100-odd customers wanted to travel for their honeymoon. Though the start was word-of-the-mouth and the customer experience, the cofounders were clear that they were not going to build a lifestyle business.
Over the next few quarters, the friends discovered the not-so-easy side of the vacation business. The big question was: how do you scale? Foreign travel was not a repeat and high frequency thing. “It’s neither Swiggy nor Uber,” says Hari. Non-repetitive and non-recurring is the toughest part of the venture. The business or the bane of our business, explains Hari, is that every month you start from zero! If attracting talent and hiring emerged as big challenges, then getting hold of supplies was equally daunting. Pickyourtrail started as a marketplace but ground realities made it pivot. “We realised that the pain point not one part of the vacation, but the entire vacation,” he says.
There was an irritating blip in the journey, though. Hari talks about the bummer. While looking for strategic backers, the cofounders got involved with one of the potential funders. The talks went well, data was exchanged and all business information was shared in a transparent manner. After a few months, Hari got to know that his prospective investor had bought a rival startup of Pickyourtrail. “I was so frustrated. It was quite unfair,” he says. The journey, though, continued. THOR kept hustling.
Thor to Morpheus
Now back in Chennai, during the pandemic, the THOR found himself in a big spot of bother. There was nobody to fight. “I mean, what can you fight? You cannot fight the Pandemic. It’s not a person issue,” says Hari. It’s easy to fight a visible rival, but when the potent adversary is invisible, the fight becomes lopsided. “There’s nothing you can fight. There’s no way you could put planes on the runway, and get people to travel,” he says, explaining the predicament of the situation. Now with the backers declining to put in more money, Hari had no option but to bite the bullet. He went to his team, and shared the tricky situation. “Guys, if we need a runway of 10 months, then we need to take hard calls,” he explained his anguish.
It was a painful phase for the founder. “I’ve always prided myself in building teams. I’ve never had to lay people off,” he says. Now, during the pandemic, Hari was in the midst of difficult conversations. Hari narrates his trauma. “If your head gets chopped, you are dead. Right? But imagine you are bleeding slowly and dying,” he says. It was tough for founders and employees. The THOR was gradually making a transition to MORPHEUS. Hari explains. You can’t change the cards you have been dealt with. “What you can control is the way you play the game,” he says. From motivating his team that didn’t have much — or anything — to get charged up to starting Travel Café Series on Instagram where the founder talked about travel experiences in countries that were gradually opening up, Hari did all to spin motivation stories.
Though the task was difficult, it was made traumatic by another unforeseen event. In fact, Hari was thrown into a turmoil. His friend — who he had known for almost two decades — and cofounder expressed his desire to move out in 18 months. He felt he would not enjoy building large companies, and wanted to pursue his personal interests. (He finally left in December 2022). Pickyourtrail was entering into a painful phase of rebuilding, and the move by his friend meant that the journey became more challenging. “He confided in me as a friend,” says Hari. “It was a big challenge,” he says.
Though the forecast was gloomy, there was a silver lining. In fact, there were more than one. First was the candid approach of the backers who didn’t put in money. Hari explains why his love for investors didn’t diminish a bit, and why he considers them as ‘good parents.’ “Instead of pampering us with more cash, they asked us to figure it out for ourselves,” he says. “It is the best advice we could have got,” he says. Had it not been so, the team would not have been able to dip into grit and tide over the crisis. “Having them as investors is the best thing to happen to us,” he says. Second, the backers never pushed Hari to look for easy fixes like distress sell-out or do non-core things like delivering food or anything. Over the next two years, as the pandemic waned and travel was back with a bang, Pickyourtrail survived to tell its gritty story.
Ten years into the journey, has Hari also made some mistakes? He lists out the not-so-memorable ones. First, there was a phase when the startup tried to mimic a grown-up company. And it happened right after the funding. “We hired ahead of the curve,” says Hari. “We made that mistake of trying to become too big even before getting there,” he says. How can you have an over eight-member HR team when the headcount is around 250? Or how can you beef up the servers to handle too much load even when there was none? “When we started doing things slightly ahead of what we were, it became detrimental,” he says. Another issue was not having a clear title of CEO among the cofounders. Though to the best friends it never mattered a bit, the organisation needed that clarity.
Three years after the pandemic, is the journey on the right trajectory? Indeed, it is. There is one impediment, though. But it’s more of a mental issue. He explains. Hiring took a back seat during the Covid. “Due to this baggage, I am not hesitant to hire at a brisk pace,” he says. The magic, though, happens when the founder drops the baggage. During his college days, Hari was a theatre artist. After college, at 4 pm, when the rehearsals would start, the director would just make one announcement: drop your bag on the floor, and get rid of every baggage that you bring in. “On the stage, you’re a character. You can’t bring in your personal life, and baggage into the character,” he would scream.
Here’s wishing our Morpheus all the courage to pick the bag, drop the baggage, and continue his sensational journey!
