Philosophy Mondays: Human-AI Collaboration
Today's Philosophy Monday is an important interlude. I want to reveal that I have not been writing the posts in this series entirely by myself. Instead I have been working with Claude, not just for the graphic illustrations, but also for the text. My method has been to write a rough draft and then ask Claude for improvement suggestions. I will expand this collaboration to other intelligences going forward, including open source models such as Llama and DeepSeek. I will also explore other moda...

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Web3/Crypto: Why Bother?
One thing that keeps surprising me is how quite a few people see absolutely nothing redeeming in web3 (née crypto). Maybe this is their genuine belief. Maybe it is a reaction to the extreme boosterism of some proponents who present web3 as bringing about a libertarian nirvana. From early on I have tried to provide a more rounded perspective, pointing to both the good and the bad that can come from it as in my talks at the Blockstack Summits. Today, however, I want to attempt to provide a coge...
Philosophy Mondays: Human-AI Collaboration
Today's Philosophy Monday is an important interlude. I want to reveal that I have not been writing the posts in this series entirely by myself. Instead I have been working with Claude, not just for the graphic illustrations, but also for the text. My method has been to write a rough draft and then ask Claude for improvement suggestions. I will expand this collaboration to other intelligences going forward, including open source models such as Llama and DeepSeek. I will also explore other moda...

Intent-based Collaboration Environments
AI Native IDEs for Code, Engineering, Science
Web3/Crypto: Why Bother?
One thing that keeps surprising me is how quite a few people see absolutely nothing redeeming in web3 (née crypto). Maybe this is their genuine belief. Maybe it is a reaction to the extreme boosterism of some proponents who present web3 as bringing about a libertarian nirvana. From early on I have tried to provide a more rounded perspective, pointing to both the good and the bad that can come from it as in my talks at the Blockstack Summits. Today, however, I want to attempt to provide a coge...
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Today one of our portfolio companies is holding their internal management training in our offices. They have asked me to talk a little bit about my own experience with the challenge of going from being an individual contributor to being a manager. I remember this being a very rough transition for me and it took me quite a long time to get comfortable as a manager. I went from individual contributor to founder and didn’t have the benefit of management training!
Looking back the biggest insight for me has been that your calendar doesn’t lie (about your priorities that is). It is way too easy to convince oneself that one is investing time in recruiting, motivating, communicating and all the other things that go into managing when in fact one isn’t. So go ahead and actually schedule time for all aspects of managing on your calendar as a way to force yourself to spend time on them.
The second biggest insight was that managing is like strategy. You can’t just pick random pieces and expect them to form a coherent whole. Just like you have to be the lowest cost producer if you want to win on price, you have to actually be disciplined if you want to lead by example. Too many times people will look at management books or hear from friends about some technique that works really well and immediately want to start using that without reflecting on whether that technique makes any sense as a part of their own approach.
And a corollary to that insight is that whatever approach you take to managing has to work for you as a person. Some people do great with St. Crispin’s day speeches and others would fall totally flat. That doesn’t mean the latter can’t be great managers (in fact the reverse may be true), it just means that they have to pick a different approach. Which leads me to a final thought: it is perfectly OK to come to the conclusion that you want to go back to being an individual contributor instead.

Today one of our portfolio companies is holding their internal management training in our offices. They have asked me to talk a little bit about my own experience with the challenge of going from being an individual contributor to being a manager. I remember this being a very rough transition for me and it took me quite a long time to get comfortable as a manager. I went from individual contributor to founder and didn’t have the benefit of management training!
Looking back the biggest insight for me has been that your calendar doesn’t lie (about your priorities that is). It is way too easy to convince oneself that one is investing time in recruiting, motivating, communicating and all the other things that go into managing when in fact one isn’t. So go ahead and actually schedule time for all aspects of managing on your calendar as a way to force yourself to spend time on them.
The second biggest insight was that managing is like strategy. You can’t just pick random pieces and expect them to form a coherent whole. Just like you have to be the lowest cost producer if you want to win on price, you have to actually be disciplined if you want to lead by example. Too many times people will look at management books or hear from friends about some technique that works really well and immediately want to start using that without reflecting on whether that technique makes any sense as a part of their own approach.
And a corollary to that insight is that whatever approach you take to managing has to work for you as a person. Some people do great with St. Crispin’s day speeches and others would fall totally flat. That doesn’t mean the latter can’t be great managers (in fact the reverse may be true), it just means that they have to pick a different approach. Which leads me to a final thought: it is perfectly OK to come to the conclusion that you want to go back to being an individual contributor instead.

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