Since leaving my acquiring company, I’ve been having a Rip Van Winkle moment as I re-engage with the people, technology and culture of our industry. I didn’t realize how much I’d lost touch with what was happening during my 8+ years of building & growing a business. I’m sure at least part of this was the pandemic, where a 100% of my Google searches included the words “Covid-19”, “election”, or "comfortable sweatpants." But a larger part of it came from the unconscious disconnect I did with the external world to focus on my company.  So here are some random thoughts ruminating in my head this morning:

Miami Tech?

At first I thought this was a joke: a new tech hub in Miami. And then I saw a legit investor like Keith Rabois talking up the cause. I get the attraction: warm weather, cultural diversity, no income tax, and a tech-friendly mayor. I’m a fan of sipping mojitos on South Beach. But living in Miami? To that I say: hurricanes, global warming, heat, humidity, a nascent ecosystem, Florida politics, and... well, Florida.

Startup Valuations

What happened to startup valuations? I just looked at a deal for a company valued at $4B+ with recurring revenue of $40M+. I know my east coast roots are showing through here, but in what world does this make sense? When I hear these types of numbers, I can’t help but feel I'm in a dream scene of the movie Inception and the laws of physics no longer apply. Where is my lucky spinning top when I need it?


If I told you a few years ago I was setting up a public shell company with no commercial operations, no products, and no sales, and whose entire purpose is to raise money for an acquisition… I would expect you to report me to the SEC. Today if I told you this, you’d ask: how do I invest? When I hear people talk about SPACs, I can’t help but feel like one of the old man puppets in the balcony on The Muppet Show. Good news for me: there are early signs people are starting to listen to Statler and Waldorf.

Bill Gates

Bill Gates was having a pretty good pandemic. His early non-profit work in vaccines looked prophetic, he had established himself as a public health visionary, and he had become one of the most authoritative voices on Covid-19. And then the divorce happened. I like Pandemic Bill a lot more than Creepy Bill.


The suits versus pajama debate is heating up. I particularly liked the WeWork CEO’s gaslighting approach to the conversation. You want to work from home? Oh, you must be one of our “least engaged” employees? That said, I do believe innovation and culture are suffering working from home, and am not surprised to see companies looking to accelerate their return to the office. Spoiler alert for the pajama crowd: the future of work may look suspiciously like the past.

Twitter Subscription Service

I would totally pay Twitter $2.99 for using their service for the last 12 years. No brainer. Happy to do it. Can I pay in dogecoin? Wait, did you say $2.99 PER MONTH? Oh, no...


I believe digital assets have value. I also believe that establishing authoritative ownership is essential to this value. But I just don’t get NFTs. With 0.6% of the world’s energy consumption already going to Bitcoin mining, did we really need to solve ownership with another solution that promotes more wasteful energy consumption? Here is a wild idea: provide miners and validators crypto each time they take carbon out of the atmosphere. One tweet from Elon Musk and we can have both a new speculative asset and a long term solution to global warming.


Don’t ever say crime doesn’t pay. In return for infecting Colonial Pipeline with ransomware that encrypted all their data, DarkSide is reported to have received $5M in payment in order to release the data. It’s scary but this has been going on for years with very little action from governments. But do you know what four words scare me a lot more than “we’re low on gas“? “SCADA on Windows XP”.