23 years!


Rudyard Kipling was right!


“San Francisco has only one drawback — ’tis hard to leave.”

I thought I would be here for two years, maybe. And then go back to New York. And here I am, still here. The city has given me more than I have given it. The rush of a modern gold rush. Friendships. Little chance meetings that transformed who I am as a person. People have come, people have gone.

Booms. Busts. Booms. Busts. Booms.

Still here!

Charles Moore, School of Architecture, UCLA, said that “one of the basic human requirements is the need to dwell, and one of the central human acts is the act of inhabiting, of connecting ourselves, however temporarily, with a place on the planet which belongs to us and to which we belong.”

23 years later, it looks like I have found that place. I don’t yearn to leave.

23 years ago


More Magic Math from OpenAI?

When it comes to OpenAI, smart money is starting to do the math out loud. And something doesn’t add up. On surface, today’s news that OpenAI is offering 17.5% guaranteed returns to private equity firms looks like a shot at the Anthropic threat. Scratch the surface, and you start to see the story behind the story.

The PE deal is the kind of deal you do when you’ve borrowed against the future and the future is taking longer than expected.

Remember a few weeks ago when Nvidia CEO Jensen Huang (one of the backers of OpenAI) said that OpenAI was not a well-run business. Now Thoma Bravo founder Orlando Bravo is saying it out loud. Bravo walked away from the JV idea after questioning the long-term profit profile. It is not a coincidence that two smart money operators are arriving at the same conclusion. Just different words.

As I wrote


What To Read This Weekend

It has been a week of inference. I started the week writing about OpenClaw and its growing popularity. And I end the week with a recap of Nvidia’s GTC event. A lot has been written about the event, especially about Nvidia CEO Jensen Huang’s big claims of quadrupling his revenues to above a trillion dollars, the question that wasn’t asked, why?

Sure, we can dismiss this as a bluster of a bull-market darling, but in reality, if we believe that AI is going to be the new way of interacting with information (as I do) and will impact all sorts of industries, then you have to give his claim some thought.

As I explain in my breakdown of Nvidia GTC, Jensen’s Trillion Dollar Token Factory, for CrazyStupidTech, his boast makes sense for two reasons. First, this is indeed an inference inflection. What that means is that AI goes from being


Why Fraud Is The Boring Problem

Michael Smith used AI to create music, and then used AI to create bots to get the “plays” and took the smartest technology companies, including Spotify and Amazon, who should know better, for about $8 million. He is going to jail for his crimes. It is easy to dismiss this as one-and-done fraud. It is anything but. It is an early warning of how AI will disrupt the systems that power our digital society: how culture gets discovered, how commerce gets directed, and how conversations get shaped.

At present, most of our digital society is powered by tech that is, generically speaking, recommendation algorithms. Spotify’s Discover Weekly, YouTube’s suggestion engine, TikTok’s For You page, Amazon’s product feed, Facebook’s news feed. All of it runs on signals of human behavior. Stream counts, completion rates, saves, shares, playlist adds, clicks, purchases. These represent people making choices. The only way to fake that


How Not to Interview (Interesting People)

As a photographer who is primarily a writer, I like reading about photography so I can learn from those who create. I do that by reading photo magazines and listening to podcasts. One such magazine is Aperture. They take me out of the noise and bring me right into the core of the work. Photographers I don’t follow, or don’t know. Always a pleasant surprise.

In a recent issue they ran an interview with Christophe Lemaire and Sarah-Linh Tran. I have followed Lemaire since his time at Hermès, so I was genuinely excited to read about how he and Tran think about creating. Lemaire is one of the few fashion brands that earns the word “philosophy.” These are people who think in multiple planes: fabric, cinema, sociology, memory.

The initial excitement soon turned into disappointment. Not with the subjects but with the actual interview, and more specifically with the person


OpenAI Has New Focus (on the IPO)

The Wall Street Journal recently reported that leadership wants OpenAI, the company, to focus. Seems like a plain old business strategy story. Nope!

First, in more prosaic terms, the all-hands and what was said was indicative of need for focus and urgency. I read it as mild panic stations. Second, step back enough and a clear and complete image should emerge. It reveals the real game being played. It is the grand hand at the big AI poker table. The IPO. Who gets there first, who sets the rules. And who really wins.

The IPO is not about one company. Instead it is about three American AI companies — Anthropic, OpenAI, and SpaceX, which owns xAI. It is about the scale of money to be raised from the market. It is also the urgency to do so. The Economist notes that if all three offer 15 percent of their shares,


Lobster Boil

I had coffee this weekend with my good friend Michael Galpert, father to my godchildren. Too much coffee. We talked too much Claw. OpenClaw that is.

Michael has been running around the country organizing ClawCons. New York, Austin, Tokyo next. Not industry conferences. In the halcyon days of Web 2.0, we called them meetups and un-conferences. Sponsors are falling over themselves to get them attached to this new new thing, that borders on madness and hope.

Just people showing up in rooms because they want to talk about what OpenClaw makes possible. Developers, yes. But also small business owners, retirees, students, people who have never attended a tech event in their lives. The energy in those rooms, Michael says, is unlike anything he has seen in years.

I have known Michael long enough to know when he is genuinely excited about something versus just being hyperactive for a second. He


What To Read This Weekend

As I sit here on Sunday morning, reflecting on what has been one of the most hectic writing weeks in a long time, I can’t help but ask, why?

Of course, there was a lot of news and action. Not that any of that matters to me, but still, there were new Apple products that were up for review. I have had iPad Air and MacBook Neo in my hands, and ended up writing about them. Neo got me philosophical and took me on a different tangent from a regular review.

And there was that great story in the Financial Times about Softbank and its founder playing with fire (aka OpenAI). Something about it compelled me to write about it. That and a tweet by Stripe CEO led to me writing about Symbolic Capital, and as if to make my point, former Uber CEO Travis Kalanick emerged from shadows to


The Return of Travis Kalanick: Fact & Fluff!

Travis is back. It was only a matter of time.

Given his old compadres Emil Michael and Shervin Pishevar are back in the news, how could he, the king pooh-ba, stay in the shadows?

To a lot of us who have been in the know, Travis Kalanick has never really gone away. He has always been doing his thing, away from the limelight which ultimately became his undoing. For eight years, he was busy building Cloud Kitchens. I heard second-hand stories of progress and stories of challenges. That’s life and that’s business. And that’s startup life.

Still, the return of Travis as a spectacle has been amazing to watch. It has been worthy of putting some popcorn, firing up the (MacBook) Neo, and sitting down and consuming it all. The return says as much about him as it does about the new hype machine, aka whatever passes for media right