Welcome To Coconut Headsets

I’ve been blogging since 2003, when I wrote the Businesspundit blog, which I sold in 2008. Then I moved to coconutheadsets.com, but in 2014 moved to Medium, feeling like it provided better distribution for my thoughts. I don’t really like it anymore so I’m moving back here as my primary source of writings. I’m also the same Rob May that writes the Inside AI newsletter. I run Talla as CEO, and am a partner at Half Court Ventures, the fund I started with Todd Earwood. We are the most active AI seed investors on the East Coast.

If you want to know what Coconut Headsets means, read up on cargo cults. I chose the name because in startups and investing, there are many erroneous ideas out there that follow a similar vein. I try to break those mindsets. I hope you can find something on this blog you disagree with, that challenges your thinking. Otherwise, I haven’t done my job.

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