Shekhar Kirani — The Don Valentine of Indian SaaS #JeenaIsiKaNaamHain

“How are you doing today?”

It is a conversation starter line that is admittedly quite common. But with most people, this comes across as a perfunctory rite — something that is needed simply out of courtesy to start a conversation.

But not with him.

This gentleman asks this question in a manner that is almost avuncular — a friendly tone, a tinge of familiarity, a whiff of genuine concern. What stands out is not the line itself but the way it is delivered — a way that makes you feel like really opening up and sharing your darkest fears and deeply-held feelings.

This gentleman is our next guest for #JeenaIsiKaNaamHain — Meet Shekhar Kirani.

As a partner at Accel, Shekhar was one of the first VCs in India to recognize the country’s potential as a SaaS powerhouse and has backed many marquee SaaS firms starting with Freshworks and Chargebee to BrowserStack and Zenoti. At last count, Shekhar has 5 SaaS unicorns in his portfolio — a record that is arguably unmatched by any other VC in India! In a sense, Shekhar is the Don Valentine of Indian SaaS.

But my first meeting with Shekhar was way back in 2011 — long before he was a VC, Shekhar was a long-time tech operator, one with a doctorate in Computer Science behind him, no less. Shekhar had recently moved back from the US to India as the VP/Country Head of Versign India and we had invited him to the NASSCOM EMERGE OUT conference in Chennai. We wanted him to moderate a session with Kris “Cheeka” Srikkanth, the veteran cricketer — I remember this distinctly because Shekhar could not moderate anything as Srikkanth decided to both ask the questions and provide the answers himself! The session was hilarious and the audience had a whale of a time laughing their guts out thanks to Chekka’s keen wit. But I also remember that session for Shekhar — not for what he did but for what he didn’t. Unlike many folks who would have been keen to hog the spotlight in a high-profile event, Shekhar simply receded to the sidelines and let Cheeka hog the limelight.

In the years that followed, Shekhar not only made the switch over to the “dark side” by moving from an operator role to becoming a VC at Accel, but also became an enthusiastic participant and contributor to the community efforts that I was a part of. When we started iSPIRT, Sharad Sharma and I traveled to the Accel office and explained our mission to Shekhar. From that point on, Shekhar was a regular at the Fellows’ Council and many other iSPIRT initiatives. So much so that I used to schedule many events and meetings based on Shekhar’s availability as he would add so much value with his thoughts and ideas. It wouldn’t be an exaggeration to say that Shekhar had a crucial role to play in shaping most of the entrepreneurial activities that we did for SaaS and the product ecosystem under the iSPIRT umbrella.

When the idea of starting SaaSX struck me in 2015, one of the first calls that I made was to Shekhar. He played an active role in building SaaSX and repeated the same with SaaSBOOMi where he urged us to think big and be far more ambitious than what we had originally intended to be. While Shekhar had grown to be an influential investor in this time, he continued to be as available and approachable as ever, often volunteering his time and services for various events. We still have not been able to replicate the Product Tear-down sessions that Shekhar used to conduct for the community — they were a class apart both for their incisive questions as well as the gently-offered insights and suggestions.

In fact, if there is one thing in which Shekhar has not changed at all over all these years, it is this. His gentlemanly demeanor and his extreme humility. In the earlier days, I remember Shekhar driving a Honda City Brio — can you imagine a VC and that too one as accomplished as this, driving a small hatchback car?! I also remember a weathered Tag Heuer watch that he used to wear — it was very loose and it would take some time to settle at its intended resting place drawing a lot of attention in the process. Shekhar had a basic feature phone for the longest time in addition to his smartphone, which had a really thick cover presumably to shield it from breaking if it fell down. All in all, I used to enjoy noticing all these quirks that made Shekhar into the affable person he is.

Personal idiosyncrasies apart, Shekhar has a keen mind, shaped in part to his time at the prestigious Indian Institute of Science, Bangalore. He is well-read on most topics and if you ask him for advice on anything, Shekhar will inevitably respond with a thoughtful and deliberate thesis around the subject, in most cases coming up with some unique perspective of his own. While he has never prefixed his name with the “Dr.” tag that his Phd degree permitted him to do, Shekhar was extremely passionate about academics in general and was particularly keen to contribute back to his alma mater IISc in any way possible — he helped the institute in a number of ways and as usual did all this discreetly without any fanfare or publicity.

Speaking for myself, Shekhar played a big part in my jump from the world of communities to the world of venture capital. After exiting iSPIRT, I was looking for a new opportunity and reached out to Girish Mathrubootham of Freshworks. Girish advised me to speak with Shekhar about joining Accel and he was kind enough to make a warm intro and recommendation. While I had many doubts about entering the world of startup investment, it turned out to be an amazing experience and working with Shekhar was a major reason why this turned out to be this good. He not only went out of his way to help me onboard Accel, he constantly guided me on how I should be contributing internally and externally.

With some of his best friends :)

During my time at Accel, I got to observe Shekhar from close quarters and there were three aspects that I would particularly like to highlight.

Shekhar never fails to ask the founders who met him one simple question — “Who is your customer?”. He would analyze the response to that question to assess how well you understand the lay of your business. The next question would usually be “Why would a customer buy your product?” — the answer to this would help him figure out the value proposition and levers that drives the startup. In fact, Shekhar was in general a big fan of asking the “Why”. Any time, I would go to him with an idea, he would always encourage me to think about the “why”. It might seem like a simple question but it was a deep one and I learnt some of my biggest life lessons by picking up this philosophy.

The second aspect of Shekhar’s that stands out is his amazing storytelling skills. In particular, I remember his mountain analogy for startups. Drawing parallels between the journey of a founder and that of a mountain climber aiming to reach the peak, Shekhar used to say, “Most founders pick the mountain they see first and start climbing before thinking about whether this is the right mountain to climb and whether they are well prepared to climb. It takes the same amount of effort, time, energy and hard work, whether you climb a small mountain or a large one. So think about which mountain you want to climb before you start climbing.” Shekhar’s point was that often founders get stuck on the “wrong mountain” and realize this only when they are halfway through their journey, which makes it very tough to abandon the mountain they’re climbing to go after a new larger opportunity.

The final aspect that I want to talk about is Shekhar’s quality of giving 100% attention while listening to you. It is one thing to be smart and a good storyteller but if you are not a good listener, all the communication will only be in one direction. Shekhar is one of those rare souls who makes sure to always listen to you patiently and understand the context before offering guidance. I know so many founders who are not even funded by Accel and have received good advice from Shekhar. I felt that Shekhar is particularly good with 2nd-time founders who are planning to start up again as he can have really detailed two-way conversations with such founders — he also has a framework that he helps founders with what they should be doing next. And all this starts with a simple question — “How are you doing today?”!

A proud moment for Shekhar when Freshworks went public

All these facets make Shekhar a great teacher — I get the feeling that he loves to teach and share his knowledge with others and he loves it when he is helping other founders and they are using these lessons to make a big difference. That is a good trait of a teacher and I have this idea of School of Entrepreneurship which I am hoping that Shekhar would start some day. I have also been telling Shekhar to write a book around entrepreneurship but am yet to convince him — hopefully, someday he will agree to do this for the community.

I happen to be good friends with the founders of many of Shekhar’s portfolio companies and they all talk glowingly on how he spends a lot of time with them every week and is always there for them personally or professionally. Despite being very busy, Shekhar regularly helps out founders who are not part of his portfolio in so many ways. I also know how much the SaaS ecosystem admires Shekhar and how grateful we are for his contributions.

We wish Shekhar all the best and we hope he continues to contribute to the Indian entrepreneurial ecosystem. I am sure history will remember Shekhar not just for his professional contributions in taking Indian SaaS to global heights but also for being a gem of a person in his personal interactions with the broad community.

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