Why a Good Investor is an Annoying Curmudgeon When You Pitch

This is your chance to convince us why we shouldn’t be concerned about the issues we see

Photo by ella alpert on Unsplash

When I first started investing in startups back in 2009, I was a nice guy. Yes, really.

I came to angel investing because I wanted to help other founders. I was building my second startup in Los Angeles, which didn’t have much of a startup scene in those days. I wanted to foster a supportive local community to help other founders succeed.

So I listened to a lot of pitches. Most sounded great. I would ask some softball questions to dig into the product and use cases. If I liked it, I invested. Most of them failed.

As more failed, my pattern recognition got better. Market too small. Entrenched competition. No startup experience. No industry knowledge. Takes too much money. Takes too much time. Lack of founder commitment. All the usual reasons startups fail.

I’m a product person, and a former engineer who gets excited about technology and problem solving. So I kept asking the same questions, digging into the product and technology as if I were a collaborator. But when it came time to decide whether to invest or not, I started considering all the likely failure modes and passing on most of the…