I have spent the past 10 years working with startups. Among the most rewarding parts of this journey has been advising early-stage entrepreneurs on day zero—pre-idea, pre-incorporation and pre-pitch deck. My biggest misses have also come from my failure to ask these entrepreneurs to take my money as a pre-angel check.
In 2010, Ankit Gupta and Akshay Kothari were post-graduate students at Stanford. Ankit, my junior at IIT-Bombay, along with Akshay, came up with the idea for Pulse—a news reading app for iPad. Those were early days in the app ecosystem. The first iPad had only been launched in April that year. Three months into advising Pulse, Akshay asked me how I would like to be involved. I should have answered, “I’d like to put in $10,000". But I did not. Angel investing was not something regular folk considered doing back then.
Pulse was among the most downloaded apps on iPad and won Apple’s design award in 2010. The company raised a $1 million seed round soon after, a $9 million Series A in 2011, and was acquired by LinkedIn in 2013 for $90 million. At the time, the app had grown to over 30 million users worldwide. The team then spent four years building LinkedIn’s content platform (the re-imagined feed we can’t seem to get enough of).
Even though I couldn’t invest in Pulse, I’ve been fortunate to be able to invest in several other enterprises with Ankit over the past four years. We helped create Curie Collective, a syndicate of former and current startup founders who write pre-angel cheques and work with entrepreneurs towards their first fundraise. Our first pre-seed investment, TravelTriangle, netted us a 10x return.
The lesson here is simple. If you have the privilege of advising super smart entrepreneurs in their very early days, remember to ask if they’ll take a small cheque from you.
A section where investors talk about missed opportunities in startup investments
