Guru Ji’s Playbook Stood the Test of Time — Ashish Gupta #JeenaIsiKaNaamHain

In 2007, I had gone to attend Proto, an IIT conference on technology. Back in those days, conferences were run very differently. Tech-led human interactions were making deep inroads and we could sense the massive change coming. It was a weekend, and the halls were packed, teeming with leaders and tech enthusiasts alike, caught in a web of deep engagement.

I saw a gentleman with a backpack, surrounded by 8–10 people listening to him with rapt attention. They stood like that for at least 45 to 60 minutes, engrossed. I couldn’t place him immediately but soon after, I realized he was Ashish Gupta of Helion Ventures. Earlier, he had been the co-founder of Junglee and during the dot com boom, he sold the company to Amazon for an unheard-of sum those days — 250 million dollars! I had been following the news and found it to be a spectacular development for the Indian tech ecosystem. This was a landmark moment in making the country’s tech presence felt in the global peerage. It was extremely rare those days — this kind of acquisition by a global company and for a staggering amount at that.

A year or so later, in 2009, Sharad Sharma and I invited him for an Unconference session at NASSCOM’s NILF and I remember how expertly he orchestrated and made it entertaining as well. The free-flowing thoughts were very impactful to the attendees and there were quick takeaways. He spoke engagingly and got people to think in a different direction. A gentle nudge from him but with great purpose — that’s been his trademark style. He connects with people exceedingly well and is a very patient listener. He does not jump into an advisory mode straightaway. He will listen to you with great concentration and only when you are done, he will share his insight and put it in the right context.

Now let me share an experience and you will also get an idea of what kind of a human being he is. It was during my iSPIRT days in 2013 and for the first time, the playbook roundtable format was introduced by Ashish Gupta along with Sharad Sharma, Vivek Subramanian, Aneesh Reddy, and Shankar Maruwada. It was a very new approach to engaging with founders and in the years to come it would catch on tremendously. Ashish Gupta was the one who introduced us to this format, and this particular session was to be held at their Helion office in Bangalore. The first session was facilitated by Shankar Maruwada who became a good friend and continues to help with many initiatives.

This is what happened.

After the session started, the office helpers came in with refreshments to be served. The room had more people than it could comfortably accommodate — as we had some last-minute conformations — and the boys were struggling to serve in a manner they were normally used to. I think one of them nearly tripped over but didn’t cause any real damage. Seeing his plight, Ashish Gupta rose from his seat and lent a helping hand, graciously serving all of us. I was immensely touched by his gesture — that a man of his stature could roll up his sleeves whenever required, and no work was “small” for him. That day, he led from the front and showed how much he cared for people, and he was always keen to help, be it through his supreme understanding of the industry or in a manner, as this. The imagery is still fresh. I can see him taking the cups and saucers from the boy in a kindly way and serving all the participants with such grace.

Tremendous learning!

Over the years, we became very close, and I always went to him for advice. He is lovingly called Guruji. He is one of the most well-read people that one gets to see, and his knowledge spans a huge range of topics. The advice that he gives is also very practical and contextual. He does not let his wide repertoire of knowledge come in the way of having a practical approach to problem-solving. Helion Ventures has spawned many entrepreneurs and has also inspired others to be VCs. Ashish Gupta has been the driving force behind this.

There’s Guru ji’s prasad — he has an answer to every question. If you go to him with a problem, he will try his best to address it. Helion Ventures was known for being a founder-friendly VC and possibly among the first of its kind.

He lives in the Bay Area now, so I don’t get to see him so often but whenever I do, I always tell him that he was one of the pioneers. People like him have taken startups to great heights. The Roundtable format is now a decade old and continues to be one of the most effective ways to engage with the community, and the industry will always be grateful to Ashish Gupta for having introduced it.

He is still a very humble person, but I am not sure if he still carries a backpack along. That imagery will always stay on.

Thank you, Guru ji, my dear friend. The ecosystem owes you a lot. I hope we have lived up to your expectations. Here’s wishing you great health and happiness.