There have been three or four major misses that I can recall from my angel days before Orios—RedBus, Oyo, Capital Float and Freshdesk (now Freshworks). Each company had a story and, a reason for me to pass on, but in the process taught me a lot. First up on the list is RedBus, which I missed because the company had very little gross margin, and I was not comfortable with it.

The second was Oyo Rooms, in their earlier avatar as Oravel Stays. Ritesh was trying to bring in an Airbnb-like model (Airbnb is a community-based, two-sided online platform that facilitates the process of booking private living spaces for travellers). My concern with the Airbnb model was that people in India do not necessarily have good homes, so renting out a room to an outside guest and making money out of it did not seem like a compelling proposition.

Then I missed Freshdesk, as I like to be close to the companies that I invest in. Freshdesk being in Chennai, and I being an angel with a day career, it looked like a difficult bet to make, given that I would not be able to travel there frequently enough. The last was Capital Float. That is a slightly funny story.

I had met Shashank and Gaurav, the co-founders of Capital Float, briefly. Back then, fintech was just beginning to take off. It was not such a discovered venture capital space as it is now. However, I had to then make a trip to the US and I missed giving a more informed look at it. Then I came back and forgot about it, and only remembered after reading about their funding round in the papers.

The major lesson that I learnt from these misses is that when you have a great entrepreneur and, even if the business model is something that you are not fully convinced with, it is better to err on the side of risk and make the investment!

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