My first interaction with Ashwin Ramasamy was brief yet intense. “Get in, I’ll drop you,” he said, offering me a ride. I got in his car, and for the next 30 minutes, Ashwin asked me precise and purposeful questions about volunteering and curating a community. I answered all his questions with a straight bat. His questions and the follow-ups to my answers weren’t tactical but considered. To each answer, he would dive deeper, unpacking each word to understand my motivations and philosophies.
I was unnerved for the first few minutes of the conversation. My friend Vinod often talks about user manuals for people, frequently espousing the ideas he used at CloudCherry. In that car, without realising it, I was learning Ashwin’s user manual.
It was 2013 when Ashwin asked me to hop into his car and grilled me for the better half hour. Back then, things were gentler, our lives were slower, and we weren’t as easily accessible, but we still managed to establish deep connections. Ashwin was one such connection I made in that sepia-tinted pre-high-speed internet world, and I am grateful for it. I wouldn’t have been able to understand and empathise with Ashwin with the innumerable notifications and social media elbowing aside real human connections.
Ashwin has made a long journey in the time I have known him. When I first met him, we were finding ourselves. I was at iSpirt, and Ashwin was running his company, Contract IQ, and curating a few Chennai-based communities. While his analytical mind remains as sharp as ever, the lens through which he views the world has widened. However, I noticed an intensity towards his work reflected in his fierce ownership of activities. His ambition of curating his communities told me that he was someone who would make a great volunteer.
And my gamble paid off.
I’ll narrate a short story that makes me laugh. A few months ago, we organized a 101 session for SaaS founders who want to access the US market. One of the threads in that session was setting up your company in the US. Ashwin was the volunteer assigned to this thread. His task was to get experts, arrange logistics, and establish a basic understanding of the subject so he could help founders navigate the talk. At the end of the session, we typically ask founders to rate their experience. Most founders gave the session 9 out of 10 points. Except one. That one said 3. You always get outliers, but this one was different. It sounded like an expert who found this session too basic.
We dug deeper and realised that the rating was given by Ashwin. To help him organise this session, Ashwin had spent three weeks in the weeds of opening companies in the US, the nuances, the edge cases, and regulatory hurdles. Most of these challenges are easily overcome by hiring lawyers and professionals, but not for Ashwin. He had given his session a lousy rating.
This is Ashwin. Only a few can match his intensity and focus. His commitment to excellence is exacting even for himself. And it is these standards that have helped him redefine himself as a founder. One of the reasons Ashwin is adored across our community is how he discovered true value in SGX. He was part of one of the first cohorts at SGX and had taken on Varun Shoor as his mentor. After a few months of working with Varun, Ashwin reimagined his second company, PipeCandy, which grew, found new customers, and ultimately managed to exit. Now, with Moative, he’s back in the saddle.
What was heartening was Ashwin’s generosity. He quickly grew into Varun’s shoes and began paying it forward by showcasing his learnings to other young entrepreneurs nationwide. He would patiently help founders find new avenues of growth in his own analytical, focused way.
Outside of work, Ashwin has, let’s just call it, a unique sense of humour. The punchlines are too nuanced sometimes, but his heart is in the right place. He steps up during times of need and loves his history. I once described him as a quintessential Chennai intellectual. He’s as interested in culture, history, and mythology as in products, toplines, and CAC. Often, he takes founders on heritage tours of temples with lunch and coffee breaks at the most unique restaurants and cafes in Tamil Nadu.
Not that I would know; Ashwin hasn’t offered to show me around yet. But probably after this post, there should be an invite coming. 😉
Thank you for your intense support, Ashwin. This wouldn’t have been fun without you.
From the Author:
SaaSBoomi began in 2015 as a small gathering of ~50 founders, and today, with over 500 events across three countries and countless lives touched, we’ve only just scratched the surface.
None of this would have been possible without the unrelenting passion of our 125+ volunteers — the lifeblood of SaaSBoomi.
Their contributions go beyond effort; they’ve built a community bound by camaraderie, empathy, and a shared vision for a Product Nation.
Pay it FWD is my tribute to every pay-it-forward champion I’ve encountered on this incredible journey.
Their contributions to SaaSBoomi and the broader ecosystem have been immeasurable, yet there remains a story left to be told — one that echoes the impact they continue to create.
