A VC: Musings of a VC in NYC

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Sleep

A VC: Musings of a VC in NYC

I got an Oura ring a couple of years ago and have been working on improving my sleep and sleep habits ever since. For much of my adult life, I have been a poor sleeper. I have always been able to fall asleep quickly, but I have been plagued by two sleep issues. The first is waking up in the middle of the night and not being able to get back to sleep.

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CEO 360s

A VC: Musings of a VC in NYC

I’ve written about this topic before. It is an important topic and I want to raise it again. Boards often discuss CEO performance without really knowing how things work inside the company. And CEOs often have very little visibility to how they are doing and what the board thinks about their performance. When you work for one person, your boss, it is typical that you will have regular catchups and at least an annual review of your performance (ideally more frequent).

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How This Ends (Part Three)

A VC: Musings of a VC in NYC

The venture capital sector has been in a sustained downturn for almost eighteen months. How does this downturn end? Well, it may have already ended, but let’s see about that. We will know for sure in a few quarters. The NASDAQ peaked at roughly 16,000 in November 2021. By June 2022, it was down 33%. It stayed down for all of 2022 and ended the year at roughly 10,500.

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Voice Input

A VC: Musings of a VC in NYC

Smartphones have had voice input for over a decade now and yet I don’t know that many people who use voice input regularly. I would guess that maybe 10 to 20% of smartphone users are using voice input regularly. That’s a guess based on absolutely no data other than observing friends, family, and colleagues. However, in the last week I have started to use voice input a lot more as a result of a friend encouraging me to do it.

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Fun Friday: Upside Pizza Club

A VC: Musings of a VC in NYC

This is the second post in a row where I am bringing back an old tradition. This time it is Fun Friday, something I haven’t done in about five years. Like last week, the catalyst is our portfolio company Blackbird Labs, which I posted about a few months ago. Blackbird is a platform for the restaurant industry to build loyalty/membership and related business models on.

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AIVC

A VC: Musings of a VC in NYC

I was approached by a company this week that has trained a large language model on all of the blog posts I have written here at AVC. There are 9059 of them for those that are counting. They wanted to offer me a chat bot called “ask Fred.” I told them no thanks. Let me explain. I am totally fine with anyone using all of the content I have produced here at AVC to train their AI models.

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Etsy Lens

A VC: Musings of a VC in NYC

I am the Chair of the Etsy Board and have been an investor and board member at Etsy since the mid-2000s. It is a company that I love and get great joy from being part of. Last year Etsy quietly launched a feature that has completely changed the way I use Etsy. It is called Etsy Lens. Etsy has millions of items for sale in its marketplace but shopping on Etsy is generally not intent-driven.

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