What an Unusual Week

It has been a week, that at best can be described as deliciously weird. I have neither been inspired to write, nor to indulge my passion for photography. Apart from necessary work, I have been out walking, and doing a lot of reading. And making notes for future writing projects. My brain is percolating, trying to find a clear thread to weave many disjointed trends, technologies, and behaviors that are emerging as a shift to the new software, aka, AI. Walking helps me think.

I have been making copious amounts of notes in my journal with a prototype fountain pen. I am hoping to write about it soon. The journal gives me an opportunity to doodle with pens that use a couple of flexible nibs. It is a wonderful therapeutic activity and helps the mind clear. They, the pen nerds, say that if you are experimenting with nibs, then your pen journey is complete. It is time to start paring back your collection. And I might be doing that soon.

All this is my long-winded way of explaining the lack of any activity on the old digital homestead. It is not the blog, but I have been ignoring social media. Apart from occasional stops to check direct messages, the focus has been on working on a few big pieces. Plus, work.

This past Wednesday, however, I got an alert from Jason Knit, who I have known from my days as a media entrepreneur. We are both dyed-in-wool members of the Tony Haile fan club. Jason tracks the shenanigans of large platforms (read: Facebook and Google) closely. And he noticed that during the Facebook’s anti-trust hearing, Mark Hansen, Facebook’s lawyer, was talking shit about two media people — me and Kara Swisher. (The Verge has a good summary.)

During the cross-examination of FTC’s key economic expert, Scott Hemphill, Hansen called me “a blogger from a failed blog” and Kara “a Vanity Fair reporter.” Kara last wrote for Vanity Fair in 2015, and now she is a certified powerhouse. But accuracy isn’t part of court proceedings, is it? Hansen went on to ask Hemphill, “If Om Malik is a failed blogger, correct?” And he went on to pick a line (and a footnote) from one of my blog posts, where I talk about being trapped in the Zuck’s Hell. What Hansen was trying to do was undermine Hemphill’s credibility but also dragging me and Kara through the mud. (Kara did a good job of giving Meta hell on her podcast’s latest episode.)

It is funny to see yourself being raked over coals as part of a court hearing. If you are going to give it, you also gotta take it. If anything, the dust-up got me thinking about Facebook and the glory days of social networking one more time. It made me think of the days that I was a blogger, when I hosted the Open Compute launch event at Facebook. I was disappointed that Hansen didn’t cite one or more of my better, in-depth articles about Facebook and its shenanigans, around privacy and data abuses.

I have had no qualms in pointing out the nefarious and amoral ways of Facebook’s master and his acolytes. Whether it was Beacon (back in 2008) or the disinformation campaigns in 2016, I have not been shy about writing about Facebook’s true intentions. Mark Zuckerberg’s world is a shape-shifting whirligig of what he thinks is reality.

Facebook’s trial kerfuffle got me back on social media, where I learned that Airbnb had launched a brand-new strategy. They were launching a new “experiences” push that would help the company expand into new directions. Everyone from Sam Altman to Patrick Collison was praising Brian Chesky’s bold new strategy and his onstage presentation. I am not surprised. I have been a fan of Brian ever since I met him when Airbnb was three guys and an air mattress.

This new strategy makes perfect sense. I said as much five years ago. The world was in lockdown. Travel was canceled. Hotels were empty. Airbnb was done. I didn’t buy the panic. Why? Because companies that survive existential crises do by remembering who they are and what they mean to the people who use them. I said as much in my “contrarian” view on Airbnb. That was on April 9, 2020.

To me, it was clear as day that Airbnb was never about travel. “Travel is not really about leaving our homes, but leaving our habits,” Pico Iyer, one of my favorite writers, once wrote. I translated that as a “chance to experience new places, cultures, food, and ideas. Airbnb has to help enable that idea of experience, even if it means doing it from the confines of our homes.”

This past week, Airbnb took another step toward embracing that identity. Airbnb is saying what it should have said all along: We’re not here to rent you a room. We’re here to help you feel something. That’s a subtle but important shift. The internet has flattened everything and turned everything into a transaction. Airbnb, for all its flaws and missteps, understands that to matter in this new world, you have to offer meaning, not utility. Even if they failed in an earlier attempt, half a decade later, we are in a new world.

The emergence of Generative AI is fundamentally redefining how we interact with information. I have written about this shift previously. Over a year ago, OpenAI launched a facsimile of an App Store. It was an effort to get all sorts of services to use its chat-style interface and create a new way of engaging with information. Travel booking companies were a big part of that push.

Since then, using AI for travel has become a dominant trend. It means that there is an opportunity for someone to create a whole new “experience” around travel. And Airbnb has put its hand up.

I don’t know about you, but for me, Expedia or Booking.com are not brands that bring on the warm-and-fuzzies. They are a reminder of the old internet’s death trap. Airbnb, with its history and roots in identity, gives it an edge over others. It has customers’ “identity,” and it largely has their “trust” to become a starting point for all travel and related experiences. It has all the ingredients to transform itself into an AI-first company. The company has introduced a brand-new suite of services, including AI-assisted trip planning.

There is no doubt that the AI travel market is going to be a fiercely contested one. One or more of the incumbents are going to be chewed up. Airbnb’s secret advantage is the close relationship between Sam Altman and Chesky. But Airbnb’s trump card is the fact that it is led by a founder. Wired published a long article about this new transformation. It is illuminating and lays out Chesky’s grand ambition. I read the piece and walked away thinking that this strategy isn’t as baked as one might think. What comes next will be harder. Execution always is.

And all this while Airbnb and Chesky (and friends) were talking up their book, a different part of the technology world was having its own convulsion.

Charter and Cox were merging in a $34.5 billion deal. The cord-cutting and death of cable TV is behind the consolidation in the cable industry. The emergence of fixed wireless isn’t helping matters either. No one has been noticing it, because we are distracted by the shiny new thing — AI. The combined company is now bigger than Comcast and had a collective revenue of $69 billion. That is still less than what Apple makes in three months. Andy Abramson, an old compadre, did an analysis of the why of the Cox-Charter deal. You should go read it. Light Reading did a deep dive on the merger.

With the dust finally settling on the week, I am in writing mode. Though playing around with my fountain pens, inks, and new flex nibs is a good distraction.

May 17, 2025. San Francisco