Angel investors more likely to lose money than hit a six: Dinesh Pai

When it comes to startup investing, Dinesh Pai, head of investments at Rainmatter and VP at Zerodha, knows the odds.

- Alokesh Bhattacharyya

Most angel or seed bets don’t work out. For him, investing isn’t about chasing the next big trend but about backing founders who obsess over solving real problems.

At the Mint Money Festival in Bengaluru, Pai spoke about why execution matters more than ideas, how failure can be a lesson if founders are honest and persistent, and why backing the right founder is more important than backing a trending sector.

He explained that most of the angel or seed investments fail, making careful evaluation and protecting investor rights crucial. Pai also shared how Rainmatter monitors its portfolio of 150 companies, stepping in to help founders with hiring, PR, or distribution, but otherwise trusting them to run their businesses.

Pai also offered some lessons from his past failures, and shared a final advice for young founders navigating the high-risk world of startups.

It always comes down to the person. There’s no single “typical” background. What we really care about is the depth of thought and the time a founder has spent obsessing over a problem.

You can usually sense quickly if someone is chasing a buzzword, like AI, just because it's fashionable, or if they've truly lived the problem and can teach us things we didn’t know. Those conversations make us sit up. At the end of the day, you're betting on someone who will stick with their team through the ups and downs.