Back in 1998, Ashish Gupta and his business partners sold their start-up—price comparison site Junglee—to Amazon for $240 million. Exactly two decades later, Gupta stands to make roughly $20 million from a deal involving two bitter Amazon rivals—Walmart’s $16 billion buyout of Flipkart. Gupta was the first angel investor in Flipkart, investing Rs10 lakh in it in 2009.Gupta is founder of venture capital firm Helion Ventures, which was dismantled in 2016 after a string of executives left to launch their own funds. But what’s not known is Gupta is also one of the most successful angel investors in India.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. One venture capitalist, who is an old friend of Gupta, joked that his angel investments have been more successful than the bets Helion made.In any case, 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.Graphic: MintGupta could not be reached for comment.Gupta, a US citizen, is a PhD 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.Gupta continued to make angel investments. In 2009, he wrote a cheque of Rs10 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 Rs70 lakh, Gupta contributed Rs10 lakh. That bet will now yield $18-20 million.Gupta stands to make an even bigger killing from his bet on software maker MuSigma 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, partner at Stellaris Venture Partners. Chowdhri was a colleague of Gupta’s at Helion.