This Angel Investor First Invested Rs 10 lakh in 2009, Now Stands To Make $20 Million After The Flipkart Walmart Deal


Way back in 1998, Ashish Gupta and his business partners sold their start-up—price comparison site Junglee—to Amazon for $240 million. And destiny today has made Gupta stand at a juncture where he is about to make roughly $20 million from a deal involving two bitter Amazon rivals—Walmart’s $16 billion buyouts of Flipkart. Gupta was the first angel investor in Flipkart who invested Rs 10 lakh in it in 2009. 

 Walmart Flipkart Deal

Gupta is the founder of venture capital firm Helion Ventures, which was dismantled in 2016 after a string of executives left to launch their own funds. Gupta is known to be one of the most successful angel investors in India.

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Gupta doesn’t make many angel investments but he has acquired a reputation of being a smart, low-key investor with a knack for picking winners. His track record as an angel is enviable.

Apart from Flipkart, Gupta has made several astute bets, including MuSigma and MakeMyTrip. At least three other investments in India have yielded big gains: cloud computing platform Minjar was bought by Nutanix this year, Merittrac was bought by Manipal in 2016 and IT services firm Daksh by IBM in 2004.

“Ashish has had a great track record as an angel investor and has made several smart bets that have paid off in a big way over the years. He’s had a knack of spotting and betting on smart ideas and founders,”

said Abhishek Goyal, founder of Tracxn

About Ashish Gupta

A US citizen, Gupta is a Ph.D. from Stanford University in California, and a computer science graduate from the Indian Institute of Technology, Kanpur. After selling Junglee, he worked at Amazon for a while. 


In 2000, Gupta and his wife Nita Goel, whom he met at Stanford, founded Tavant Technologies with two others. Gupta then did a Kauffman Fellows Programme to study the VC business. Two years on, he joined the Woodside Fund, an early stage VC firm in Silicon Valley. He then founded Helion in 2006.

In 2009, he wrote a cheque of Rs 10 lakh to Flipkart when it raised its first-ever round of capital from Accel Partners, which had agreed to invest $1 million in three tranches. In the first tranche that amounted to Rs 70 lakh, Gupta contributed Rs10 lakh. That bet will now yield $18-20 million. 

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Gupta stands to make an even bigger killing from his bet on software maker Mu Sigma in which he again made an angel investment, albeit a larger one than his Flipkart bet, and got an exit at roughly $50 million.

And even though Helion failed as a VC firm, Gupta is still respected and liked by entrepreneurs and investors alike.

“Ashish is one of the best investors I’ve ever met, both from an institutional and angel perspective. He’s usually 5-7 years ahead of the curve when it comes to betting on ideas. He likes to focus more on underlying trends than on what is happening right now. Most importantly, Ashish likes to genuinely help entrepreneurs and founders and work with them—and he doesn’t do it for money,”

said Rahul Chowdhri, a partner at Stellaris Venture Partners. Chowdhri was a colleague of Gupta’s at Helion. 

Other significant angel investors for Flipkart

Abhishek Goyal, who was an associate at venture capital firm Accel Partners, met the founders of Flipkart for the first time at a coffee club in Koramangala, the south Bengaluru suburb now dubbed as the country’s startup hub.

At the time, Flipkart was operating out of a two-storey house in the area and the hunt for investment was proving to be hard.

Goyal was impressed with the enthusiastic duo. He told them that if Accel did not end up investing, he would give them Rs 10 lakh from his own pocket.

It was Goyal who brought Ashish Gupta in the scenario.

Shekhar Kirani came on board as an angel investor after 2010. Kirani joined Accel in September 2011. 

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