Some investors write cheques, while others transform ecosystems. Shailendra Singh belongs firmly in the second category.
I am writing this on the flight back from the US. As the lights dim, I am reflecting on my very eventful trip. We hosted the electrifying Vertical Velocity (link to the blog here) and our flagship US event: Caravan. I’ve had so many coffee meetings, I’ve forgotten more than I can remember, but the chat my colleague Keerthi and I had with Shailendra was unique.
The 90-minute conversation felt less like a meeting and more like a masterclass in understanding how great venture capital actually works. Here was someone who had built Peak XV into a powerhouse with hundreds of large companies, and a quick AI-powered search tells me there are over a dozen IPOs and a few more on the horizon. Yet the discussion ranged from the nuts and bolts of the Indian startup ecosystem to audacious visions for what SaaSBoomi could accomplish in the US.
As I sat chair in a quiet cafe, I was struck by how he carries himself. When we first met, his warm hug was a display of affection reserved for close friends. Mind you, this was the first time we had met. And during the meeting, he leaned forward to listen to us, his words carefully chosen, and his mannerisms relaxed. He exuded confidence not just in himself but, strangely enough, even in SaaSBoomi. His intuitive understanding of how SaaSBoomi operates was astounding, and without us asking, he offered to help.
“Look, I’m there to support SaaSBoomi in any way I can. And if, as a firm, we are not able to lend support, I will write a personal cheque for you,” he said over our second cup of coffee.
His readiness to support our cause to build a product nation demonstrated his unconditional backing of all our efforts.
I’ll be honest, I wasn’t surprised. I had heard that the way Shailendra operates is unique, and I had witnessed it first-hand many years ago when he had pledged to support Nasscom within minutes of being asked. Back then, it wasn’t about the amount; it was about the signal it sent: he backs people building an ecosystem, not just companies generating returns.
From his roots in Kanpur to building programs like Surge that democratise access to venture capital, Shailendra has spent nearly two decades proving he is one of the best investors in the world. He takes calls at odd hours and shows up when founders need him. He even takes coffee meetings with a motley crew trying to empower SaaS and AI founders.
While this plane shudders, I am reminded of a comment from a founder who once worked with Shailendra.
“He can spot patterns before anyone else can,” he told me in confidence.
And how right he was. Shailendra’s pattern-spotting ability is visible across his early investments, but the big one that stays in my mind is the one in Gojek and Tokopedia. The two Indonesian companies merged to form GoTo, which resulted in one of the largest IPOs in the region’s history.
The story goes that Shailendra spotted Tokopedia in October 2014. He saw something no one else did and backed the company. A year later, he backed Gojek when it was a small motorcycle ride-hailing app. Where others saw two companies, he spotted a superapp.
When the combined entity went public, it listed at a valuation of $28 billion. Peak XV’s exit from this investment has not been publicly announced, but a founder friend told me the cash out was substantial.
This is precisely the kind of pattern Shailendra Singh has built a career recognising. The ability to see something others miss. To back people when the metrics don’t yet exist. To understand that the greatest companies don’t look like great companies at the beginning. They look like risks that most investors won’t take.
As the conversation meandered to its end, we moved from the coffee shop to a Thai restaurant next door for an unplanned lunch. And I did something I rarely do: I asked for a selfie. I try as hard as I can to not show up in photos, but this time I couldn’t give up the opportunity.
“I’m just a regular person,” he said.
Perhaps. But regular people don’t build what he’s built. They don’t see what he sees. And they certainly don’t show up the way he shows up.
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.
