Several years ago I read the book “Logic of Failure.” The book is about how poorly humans deal with complex systems. To give you a simple example, when I was in college I had a roommate who didn’t understand how a thermostat worked. There is a time delay between changing the thermostat and changing the […]
Author Archives: robmay
Startup Marketing In 2020
I’ve done two enterprise software startups, and the biggest change between them was the shift in the customer acquisition landscape. In the early days of Backupify (2009 – 2011), if you were a company doing SEO, lots of content marketing, re-targeting, and social media marketing, you were cutting edge and not everyone did those things. […]
Defining The Services-As-Software Business Model For AI
My angel investment in Botkeeper has been one of the most influential in my thinking on how AI strategy is evolving. When new high impact technologies come along, they often shake up status quo business models and because no one understands what business models might emerge on the other side, it’s a wonderful time to […]
Why I Became a VC and Joined PJC
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 […]
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 […]