Today I’m excited to announce that I’ve officially joined PJC as a General Partner. I’ve thought about becoming a VC for a long time. In fact, back in 2011 I was talking to my head of Sales at Backupify and we were discussing “doing what you love.” I talked about how what I really loved […]
Author Archives: robmay
Mistakes That VCs Cause Founders To Make
VCs get a bad rap, but I’ve always enjoyed talking with them. They see a lot of stuff, so, they are great sources of market information. It’s true that they sometimes screw up companies, but I don’t think it is in the way most people assume. It’s rarely that they are greedy, forcing you to […]
Synthetic Social Media Via AI
One of the favorite parts of modern video games, for many people, is designing their avatars. I’ve been thinking about this because I’m looking for AI to create an area I call “synthetic social media.” But so far I haven’t seen any companies in this space. Since it doesn’t exist, I don’t know exactly what shape […]
Does Customer Development Really Matter For Startups?
I was chatting with someone the other day about customer development and I asked a simple question. Now that customer development has become so common among venture backed tech startups, has it moved the needle at all on outcomes? I don’t have any hard data but, it seems to me that just as many startups […]
The Coming Rise of Synthetic Data in AI
More and more often, I am hearing startups talk about “synthetic data.” I’ve seen my existing startup investments start to use it, and I have seen entire companies formed around it. So, what is it? Put simply, it is data created by a machine. Now, why would we do that? Imagine that you want to […]
What Ethan Zuckerman Could Teach Googlers About Debate Culture
When I read recently about Google’s attempts to corral internal debates, I thought the way Ethan Zuckerman handled his leaving the MIT Media Lab was a very good model for how to handle debate in general. I’ve met Ethan twice while sitting on panels together and have always been impressed with how he handled himself. […]
Hiring, Reputations, and Why Backupify Was Really Successful
I remember doing reference calls on the very first executive I tried to hire at Backupify. I was 31 years old, a first time CEO, and had never hired a senior executive before. I had a candidate, and I mined LinkedIn for 3 people that had worked with him before to do reference checks. The […]
What Horses, Watches, And Bookstores Can Teach Us About Why Automation Won’t Kill Jobs
A few months ago I spoke on a panel, and I was asked a question that I am always asked about AI and automation – will it kill jobs? And if so, what do we do? The answer I gave surprised many people who said they had never heard an answer like this before so […]
The Half Court Ventures Story: What I’ve Learned From 4 Years of Angel Investing
Backupify was acquired in December of 2014. In June of 2015 I made my first angel investment. Along the way, I started a fund with my friend Todd Earwood, and learned a lot about investing. This post chronicles that path. Deciding To Angel Invest The first thing I did post exit was talk to lots […]
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 […]