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

Kashmir was shut to the world for 30 years. From 1991-2021. When it reopened, I was fortunate to have gone there 3 times. All 3 different reasons.

Over the three trips across two years — I got to see three different faces of Kashmir:

• In 2022, as a tourist in a city just beginning to reopen after decades of isolation.

• In August 2024, as a trekker walking through its breathtaking, unspoiled Great Lakes.

• In November 2024, as a believer — meeting young founders building against all odds.

Each journey showed me something different. But one thread ran through all three:

Kashmir is a land that gives more than it takes.
Through its people, its mountains, its music, and its quiet courage.

This is that story. Of a place too often misunderstood.
And of why the greatest way to support Kashmir today is not pity and more social media posts, but participation.

A Tourist in a Reawakening City (2022)

When I first visited Srinagar in 2022, Kashmir was cautiously stepping out of three decades of isolation. The Shikharas floated again on Dal Lake. Tourists were back into its gardens and cafes. There was life. There was hope. But you could still sense the caution.

The military presence was visible, but the hospitality of the people was stronger — simple, kind, rooted in the land’s ancient traditions. There were eager shop owners trying to make a deal. One could see the beauty of handicrafts - From wooden artefacts, to beautiful handcrafted Pashminas. Their livelihoods depended on tourism, and you could sense the fragile new beginning everyone was trying to nurture.

A Trek Across Untamed Beauty (August 2024)

Two years later, I returned — not to the city, but to the mountains.
The Kashmir Great Lakes trek covers close to 87 kilometers across seven days, winding through high-altitude lakes, meadows, and passes close to the India-Pakistan border.

The week we trekked, the weather turned harsh — heavy rains, slippery trails, and the physical grind of long days. We were not alone. Over 1,000 trekkers were on the route that week, reminding me how fragile these landscapes are under the weight of tourism. (Yes, the number was 1000!)

At times, CRPF soldiers would quietly walk up to our group, checking on us, reminding us of the unseen tensions that still lace these mountains.
Tourism brings life — but it also brings responsibility, a fact we often forget.

Unlike other parts of the Himalayas, the Kashmir trail offers pure, untamed beauty.
There are no villages, no makeshift shops — only pastures, lakes, and valleys where sheep graze freely and the mountains guard their silence.

Through it all, the local mule men, porters, and guides worked tirelessly.
Hardworking, resilient, and quick to share a ‘shayari’ by the trail, they moved our supplies from camp to camp, their lives once again tied to the rhythms of tourism.

One thing struck me sharply: India has become fitter but Responsible tourism has yet to see adoption.

More people now undertake such treks. But alongside pride, there is thoughtlessness — trash left behind in a land that asks only for respect.

I also believe that as much as you can tour Kashmir, the real Kashmir beauty can be witnessed when you walk into the mountains.

We closed our trek with a soulful Sufi night, and I am grateful I had the opportunity to witness such pure art from Mohammad Noor Saheb and his group. Such experiences leave you wondering about how such pure love can be nourished in a terror torn state.

A Witness to Dreams (November 2024)

Later that year, I returned again — this time, as a believer in Kashmir’s future. As a startup founder, with my contribution to building Kashmir’s ecosystem.

I attended the launch of a new startup incubator in Srinagar, LaunchPad. We had about 50 founders, and many of the ecosystem enablers. The founders were young, ambitious, carrying invisible burdens that entrepreneurs elsewhere will never fully understand.

Building a startup is hard anywhere. In Kashmir, it demands something more: grit against uncertainty, isolation, and skepticism.

Investors are encouraging, but cautious.
Founders know that scaling in Kashmir isn’t easy.
And yet, when they startup and speak of ideas, of products, of dreams — there is hope.
Hope that refuses to die, even when circumstances are stacked against it.

But startups like Kashmir Box are changing that. They are building platforms that connect artisans to global buyers, using technology like geo-tagging to ensure fair trade and dignity.

Kashmir Box’s vision is to take Kashmir to the world!

I am also an investor in Kashmir Box, believing in their vision.

In the face of unrest, many wonder: What can we do for Kashmir?

The answer is simple:
Support its economy. Buy its crafts. Believe in its builders. Carry its stories forward.

Trade - dignified, fair trade — will build what terror so often breaks. We are now in 2025. We cannot respond to terror the same way we did in 1991. As a startup ecosystem that has created so much disruption, I am sure we will find ways to make this inclusive.

The next time you think of Kashmir, think beyond beauty.
Think about participation. If each of one can buy one product from Kashmir, we would have responded to the act of terror in a much better way. If you are a corporate, consider sourcing your gifting products from Kashmir.

Each of us can find small ways to support the economy — quietly, meaningfully, and consistently. The greatest rebellion against terror is not outrage. It is building bridges so strong that no act of violence can tear them down.

Kashmir has survived being broken, isolated, and forgotten.
Now, it deserves to be believed in — quietly, consistently, powerfully. By all of us.