I’m a tech entrepreneur and writer trying to make the technology world more thoughtful, creative and humane. You can read more about me here.
This is a blog about how culture is made, continuously updated since 1999. While you're here, check out my writing about tech , Prince , or the Best Of the first 25 years of this blog.
How I got pitched by Anna Delvey Many people will be familiar with Anna Sorokin, also known as Anna Delvey, who was one of the most high-profile of the wave of hipster grifters during the 2010s. Today, she's beginning to pivot into some kind of reality TV/competition game show...
23: What was 9/11? It’s hard to really take in, after all these years, that most people have no memory of the day. The majority of people in the world were either not born, or not old enough to be aware of what was going on, and then many who would recall are either...
How Oprah will screw up the AI story As I write this, we’ve just heard news that Oprah is planning to do a big broadcast special about AI and society. Despite the fact that it hasn’t aired, and I haven’t seen it or talked to anyone who’s seen it, we can reliably predict many of the...
Systems: How the Ultra-Wealthy Think About Money A lot of the ways that the ultra-wealthy think about, and act about, money seem almost incomprehensible to those outside of their orbit. Having had a chance to get some visibility into how a number of billionaires and centimillionaires think and...
Systems: Q&A about boards of directors Okay, previously we covered many of the most common things you'd want to know about a board of directors at an organization, including the basics like what a board actually does. Next up, I put out a prompt on my various social media channels to...
Systems: What does a board of directors do? Nearly every organization that is designed to have impact has a board of directors, whether that's a small non-profit, or a giant corporation, or anything in between. But having served on a number of boards across that entire range of institutions, I...
The New Alt Media and the Future of Publishing You might have noticed, it’s not a super fun time to be in the publishing industry, especially if you’re trying to do journalism. The years-long drumbeat of bad news issuing from nearly every newsroom has left people understandably despairing about...
Systems: The Purpose of a System is What It Does When trying to understand systems, one really eye-opening and fundamental insight is to realize that the machine is never broken. What I mean by this is, when observing the outcomes of a particular system or institution, it’s very useful to start...
Systems: What warms the heart? I have a lot of thoughts about systems and how they work, and how we can teach systems thinking to others. Maybe one good place we could start is by capturing this old tweet of mine, which probably deserves a permanent home since I don't use Twitter...
Prince, Letterman and Insufferability David Letterman (whose team is doing a wonderful job of presenting and narrating his formidable archives) recently posted an amusing anecdote about Prince's first appearance on his show, in December of 1994. It's a fascinating story, because it...
Make better documents. Whether it's resumes or reports, budgets or broadsides, I'm pretty regularly sent working documents from a wide range of people, and over the years I've noticed some consistent patterns that lead those documents to be less effective than they should...
“Wherever you get your podcasts” is a radical statement. You've heard the call to action at the end of nearly every podcast you've ever listened to: "Listen to us on your favorite podcast app", or in the phrasing of podcaster extraordinare Roman Mars, "...wherever you find podcasts"....
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