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
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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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Share Dialog
Share Dialog
One of the questions that I get asked a fair bit is what characteristics help a founder to be successful. I have often answered “being stubborn but not too stubborn.” I then elaborate stubborn as sticking to a vision even as others say it can’t be done and the inevitable setbacks occur, and not too stubborn as being able to take some input from others. It is a delicate balance. To this characteristic, I want to add a learnable skill: being a great communicator.
Yesterday we held our annual “investor day” — it is a day where we have some of our later stage companies present to a set of crossover investors. These are funds that invest in both private and public companies and are likely participants in a late stage, pre-IPO financing rounds. Each year I am struck by how good the founders and CEOs of these companies are at communicating. They speak clearly and freely, commanding the attention a large audience. They answer questions crisply and directly.
Communication is at the heart of the key roles of a founder. Attracting talent to a company, raising capital and setting the vision, mission and strategy all require clear communication. And while some people are better at it than others going in to founding a company, communicating clearly is a skill that can be honed through deliberate practice. As a founder you should actively seek feedback on the clarify of your communication and read up on how to speak and present. Having yourself taped and watching it, then comparing yourself to great communicators is also tremendously helpful.
If you have great resources for communication, please share them in the comments and I will pull these together in a subsequent post.
One of the questions that I get asked a fair bit is what characteristics help a founder to be successful. I have often answered “being stubborn but not too stubborn.” I then elaborate stubborn as sticking to a vision even as others say it can’t be done and the inevitable setbacks occur, and not too stubborn as being able to take some input from others. It is a delicate balance. To this characteristic, I want to add a learnable skill: being a great communicator.
Yesterday we held our annual “investor day” — it is a day where we have some of our later stage companies present to a set of crossover investors. These are funds that invest in both private and public companies and are likely participants in a late stage, pre-IPO financing rounds. Each year I am struck by how good the founders and CEOs of these companies are at communicating. They speak clearly and freely, commanding the attention a large audience. They answer questions crisply and directly.
Communication is at the heart of the key roles of a founder. Attracting talent to a company, raising capital and setting the vision, mission and strategy all require clear communication. And while some people are better at it than others going in to founding a company, communicating clearly is a skill that can be honed through deliberate practice. As a founder you should actively seek feedback on the clarify of your communication and read up on how to speak and present. Having yourself taped and watching it, then comparing yourself to great communicators is also tremendously helpful.
If you have great resources for communication, please share them in the comments and I will pull these together in a subsequent post.
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