Deepak Ravindran, Founder & CEO, Lookup

‘There is a 99 per cent chance that a startup will fail. Plan for the 1 per cent’ Deepak Ravindran is wrapping up a Monday morning call with an investor when I arrive at the office of his latest venture, hyperlocal store discovery app Lookup, situated in the heart of India’s startup capital in Koramangala, south Bengaluru. A young, all-woman call centre team occupying a section of the modest office space busies itself ringing several vendors to find the best price for a kilo of bananas—lamba wala. Lookup uses chat to put customers directly in touch with offline stores nearby, but when they cannot find an item in stock, or if the store won’t respond to their queries within minutes, the call centre kicks into action to find the next best solution. Stores can either drop off the products themselves, or rely on Lookup’s logistics partners to ensure delivery at the earliest. “We see traffic to the tune of 100,000 messages and facilitate 300 transactions every day. We have about 1.1 million users and are integrating a payment wallet into the app,” says Ravindran.

He wears a serious look that seems at odds with the spiked hair, tattooed forearm and slight, almost collegiate, frame. The standard-issue entrepreneurial armour of black t-shirt and jeans and the discreet luxury watch give him away. Then there is his remarkable network of mentors and investors, including Infosys co-founder Kris Gopalakrishnan, Twitter co-founder Biz Stone, Silicon Valley businessman Vinod Khosla, and a handful of European VCs. The 27-year-old is no greenhorn. A serial entrepreneur, Ravindran has walked through the wreckage of his nest twice, and learned from his mistakes. Both times, he picked up a piece from the rubble, and enshrined it within a new idea. This burnished nugget is his abiding faith in the value of bridging the online-offline gap, and of helping people find answers.

Ravindran earned his entrepreneurial stripes at Innoz, an SMS-based search engine he founded in 2008 as an engineering student in Kasaragod, Kerala. Unknown to his parents— government employees from Thrissur who thought their son was well on his way to a cushy software job—he dropped out of college along with three others. They each pooled in Rs 30,000, got a seed loan from Technopark in Thiruvananthapuram, and made sure the local magazines gave them good press. The boys did not become millionaires overnight, but they did become local celebrities, especially after their selection for a two-month- long incubation programme at IIM-Ahmedabad.

Renting a few servers in the US, the Innoz team built a solution for people who did not have internet on their phones. If you were looking for information from Wikipedia, or cricket scores, weather updates or movie reviews, you could simply text your question to Innoz’s ‘SMSGyan’ search engine and you would receive a text with the answer. Innoz was gaining traction, but after two years, it was yet to start making money. A telecom partnership was imminent for survival, but it seemed like a far-off dream. “So in 2010, I packed my bags and went to Delhi, staying put there until I could strike a deal with Airtel and eventually other telcos,” Ravindran says.

“He pretty much hustled it,” says Sanjay Vijaykumar, founder and CEO of MobME Wireless Solutions, a Kerala-based mobile and internet company. “Back then, telecom operators did not entertain small players. But Deepak was relentless.” The story goes that when Ravindran’s mother read an article about MobME in the Malayalam magazine Vanitha, she mocked him for dozing away while Malayalees who were only a couple of years older worked hard and got featured in the media. “Deepak read the article and got on a train from Thrissur to Trivandrum to understand what we were doing. He was curious,” says Vijaykumar, who is also chairman, Startup Village, a public-private incubator in Kochi whose board Ravindran would later sit on.

At its peak, Innoz saw traffic from 130 million people across 15 geographies. It was making a few crore rupees in revenues every month and according to Ravindran, generating many times as much for telecom operators, who were charging a rupee for every query. “We had moved to Bangalore and were living the dream. There was a lot of cash flowing in and it felt good,” he says. A 10,000-sqft office building in Koramangala, which had a basement with a gym and an entertainment area, became the site of much merriment. “We had a chef from Kerala and a rooftop kitchen. There were parties and sometimes we invited celebrities,” says Mohammed Hisamuddin, a co-founder at Innoz who now runs entri.me, a Kochi-based test preparation platform. “We made mistakes,” says Ravindran. “It was a sobering experience when smartphones and changing regulations edged us out.”

When the good times ended, Ravindran lost many friends and found himself looking inward for answers. “When you are that young, you think money can replace a lot of things. But you eventually realise it is the value you create with the money that matters,” he says. The four founders made a neat packet—about a million dollars—and they paid back their investors in full. They also made Innoz open source before they started up again. Soon, Ravindran and Hisam were back on their feet and they decided to move to Silicon Valley to launch a location-based app called Quest that aimed to get people to answer one another’s questions in real time. Ravindran invested Rs 60 lakh in the venture and lost all of it. Upon his return to India, while he was still coming to terms with failure, a call from Kris Gopalakrishnan, offering him Rs 1 crore to go start something, cheered him up and steered him towards founding Lookup.

Lookup recently raised $2.5 million in Series A funding from Vinod Khosla and others in order to hit 10 cities by the end of 2015. A lean startup, with all of 50 people onboarding 75,000 vendors, it does not need a lot of cash, says Ravindran. “I may make mistakes, but I won’t make the same mistake twice.” Unlike some of the competition— hyperlocal is the buzzword in startup circles this year— Lookup does not come with a finite list of products on its app, making it light and flexible. “This is my third attempt. And this time, I want to build something that lasts. I am not thinking of an exit at all,” he says.

He enjoys travel—he has visited 15 or so countries—and drives a Mercedes-Benz CLA that he bought last year. But for a few uncertain months, these luxuries had seemed out of reach. More than one good thing came out of Innoz, though. Ravindran met his fiancée Shilpa Thakur when he needed to file a patent for the company three years ago. She is a global technology attorney with Inventus Law, based in California. The two are getting married in Kovalam in December.

Ravindran gives a Rs 1 lakh grant to students who want to explore ideas—“When I had no money to travel to the US to attend a conference, it was Kris who gave me one lakh rupees”. He has also set aside Rs 1 crore that he will extend as advance to 20 local stores to help them buy raw materials for products they can sell through Lookup. The reason he is here running a company, he says, is because someone had faith in him. And he wants to return the favour.

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