I recorded this conversation with Anand Chandrasekar back in 2021. Listening to it again, I realised how many of the ideas still hold true today.
Anand is one of India’s most active angel investors, with investments across 100+ startups. But what struck me wasn’t his portfolio. It was his philosophy of working with founders—one built on generosity, honesty, and long-term conviction.
For those who don’t have an hour to listen to the full episode, here are the ideas that stayed with me.
1. Bet on product founders
One of Anand’s earliest influences was Rajeev Motwani, the Stanford professor and early Google investor.
Rajeev believed that he would invest into technical and product founders first, as they can also learn how to build great businesses. But it is much harder to teach someone how to build a great product.
That philosophy has shaped Anand’s investing journey.
In 2014, when Anand moved back to India, very few startups even had Chief Product Officers. Yet he believed that product would become the ultimate differentiator. Looking back, that seems obvious. At the time, it wasn’t.
2. Great startups solve low-NPS problems
Anand refers to Keith Rabois’s framework:
The market may look solved to outsiders. The customers often disagree.
The best founders obsess over these frustrating experiences and rebuild them from scratch.
Rupeek is one example Anand talks about. Gold loans existed for decades. The customer experience, however, belonged to another era. A better product created a much larger market than anyone had imagined.
3. Be loyal to the problem, not the solution
This was my favourite takeaway.
Founders often fall in love with their technology or their expertise. Great founders stay loyal to the problem.
As Anand puts it:
“My loyalty is to the problem statement. Whatever is the most elegant solution to that problem is what I’m going to pursue.”
That mindset gives founders the freedom to pivot without losing conviction.
The mission stays the same. The path evolves.
4. Thinking in bets
One book Anand recommends is Thinking in Bets.
The lesson is simple: if you truly believe in a trend, go all in.
His conviction was that India was building products for the next 100 million internet users. Companies like Khatabook, DealShare and OneCode were all different expressions of the same underlying thesis.
Rather than spreading himself thin across dozens of unrelated ideas, he doubled down on a few convictions and allowed power laws to work over time.
5. Indian founders have become extraordinarily ambitious
Anand made an observation that has only become more true now in 2026.
Today’s founders have ambition bordering on insanity.
And that’s a good thing. The role of early investors is not to pour cold water on those ambitions. It is to focus and amplify them.
The quality of founders in India continues to improve, and with it, the quality of companies being built.
6. Founder NPS is the only brand that matters
This line deserves to be framed.
“You make money from your successes, but you make your reputation from the really scary moments.”
The moments when things are not working. When founders need help. When difficult decisions have to be made.
That’s when your brand gets built. Not on social media. Not through content.
But through the stories founders tell about you years later.
Anand calls it “Founder NPS” (for those who don’t understand, this is Net Promoter Score used by companies to understand customer feedback)
I think that’s one of the simplest and most powerful definitions of reputation in venture capital.
7. Respond to cold emails
One of Anand’s investments in NoBroker started with a cold LinkedIn message.
His philosophy comes from Silicon Valley, where experienced operators generously gave their time to young founders.
If Steve Jobs could respond to a student asking for advice, Anand believes the least he can do is spend 15 minutes giving honest product feedback.
The lesson is simple:
Respond to cold emails. You never know where the next great founder comes from.
I must add here that I have made multiple investments responding to cold emails. As an investor, when I read an email, I always give the benefit of doubt to the founder. The question that comes up is “what if this founder eventually builds a valuable business? Would I regret not having responded?”
8. India has stopped being afraid of failure
Anand shared a story from Anupam Mittal. (he is now one of India’s best names on the entrepreneurship ecosystem, with him being one of the most popular Sharks on India Shark Tank)
Around 2016–17, the most searched keyword on Shaadi.com became:
Entrepreneur.
Something fundamental had changed. Being a founder had become socially acceptable. Failure was no longer permanent.
That cultural shift may be one of the most important reasons why this decade belongs to Indian entrepreneurs.
Books Anand Recommends
A few books that have influenced his thinking:
Atomic Habits by James Clear
Thinking in Bets by Annie Duke
Mindset by Carol Dweck
Nonviolent Communication by Marshall Rosenberg
The last one surprised me. Building companies is ultimately about navigating difficult conversations, stressful moments, and human relationships. Learning to communicate without creating conflict is an underrated founder skill.
People Worth Following
Keith Rabois, especially his writing on fragmented markets, product-led businesses, and full-stack companies.
One Question To Leave You With
If you had to optimise for just one thing as an angel investor, what would it be?
Returns? Access? Brand? Or founder NPS?
My answer after listening to Anand is becoming increasingly clear.
If you want to listen to the episode, refer to the attached link.
Have fun.
Shanti
