“She calls it as she sees it. There are no two ways about it,” Pankaj Mishra, the founder of FactorDaily, leaned forward as he told me about an enigmatic founder. “I can’t think of a better volunteer than her.”
We were sitting at a coffee shop in Indiranagar, Bangalore. And the subject of our meeting was Ashwini Asokan.
But before I called on Pankaj, I had been researching Ashwini for a year. I first heard of her in early 2017 when a colleague told me about this force-of-nature founder.
“She will call everyone out. Founders, investors, lawmakers. If she feels there’s something wrong, she will shine the light on it,” they told me.
I was intrigued. I started asking more questions.
Another friend shared her social media handle with me.
Her Twitter persona was fierce, fearless, and formidable. She pulled no punches.
I had found a line to connect with her. But I wasn’t convinced. I wanted to know more. So, I reached further into the ecosystem.
A well-known investor, whom she had met at an event, told me that she was one of the first in the country to run an AI startup. And he was highly impressed with the company’s trajectory.
“But who is she?” I asked.
He directed me to a podcast she had done with Pankaj.
“We don’t have enough women role models because we constantly bury the stories of women achieving…” she said on the podcast.
Her candour blew me away. I immediately reached out to Pankaj and arranged a meeting at the coffee shop.
At the meeting, he convinced me to tag along when he met her next. When the day came, I had butterflies in my stomach. I expected to meet a lioness, ready to roar. But she was one of the warmest people I’ve had the pleasure of meeting. She was witty, intelligent, and funny, but also sensitive to people’s discomfort. She made jokes, but never mocked.
I saw in her a leader who could be gentle and firm. She had the precision to teach and the humility to learn. I saw a SaaSBoomi volunteer. I knew she had the potential to transform our community, I just didn’t know how.
She eventually joined the community and hosted a few sessions.
We remained friendly but not friends. However, my relationship with her bloomed into a friendship only in 2023. She played a pivotal role in my life.
Over time, unknowingly, I have curated a few archetypes of friends.
- Mentors: People whom I turn to in times of need.
- Cheerleaders: People who encourage me irrespective of my decisions.
- Challengers: People who question my choices and force me to act rather than react.
- Listeners: People who hear me out, let me vent, and identify patterns.
- Do-ers: People who help me execute.
For instance, Krish would fit as a mentor, and Vinod as a listener; I am grateful to all those who fill these roles. Some people take up multiple roles in different situations. But Ashwini has been a challenger.
Now, here’s the caveat. A challenger doesn’t just disagree; they push, the nudge, they insist, they cajole. However, their objective is to expand the mind; they compel us to examine a problem and its solution from multiple perspectives. Ashwini has, many times, true to her founder mindset, insisted I take the more difficult path because she sees a larger payoff.
I’ll give you one example. When Ashwini first started to get deeper into SaaSBoomi in 2022, she asked me one question.
“Why have we geared the community towards the 0 to 1 journey and not the 1 to 100 or even 1 to 10?” she asked. “After all, we all need community.”
I don’t know if it was the isolation of the pandemic or the way she communicated that flicked a switch in my brain.
Soon after, she and I began brainstorming how we could expand SaaSBoomi, its reach, and, more importantly, its impact. Without needing to ask, she took on the mantle of being a curator and began to sign up scaled founders. In just three short years, we have 50 scaled founders across India who act not only as mentors to those earlier in their journey but also as a support network for one another. She helped us transform SaaSBoomi into the vibrant community it is today.
Ashwini has also been the driving force behind encouraging women founders to join our community. She hosted our first women-founders session in 2023. She has also helped us grow women’s participation from less than 3% to 15% at SaaSBoomi over the past few years.
Ashwini has also spotted patterns early and insisted that we start enabling our founders to think beyond SaaS and more into AI.
But more importantly, she has never let me rest on my laurels and has always pushed me to be better, not just as a community leader but also as a human being. Her advice is grounded in empathy and care.
Her relentless search for perfection has been infectious, which has led her to excel on the GC and helped us raise our standards.
But honestly, the best way to describe her is the lioness of our pride.
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.
