On turning 44…

Given how much I write about OpenAI these days, it’s easy to lose sight of just how truly great ChatGPT is as a product and service. Case in point: while thinking about my 44th birthday, I realized that because of daylight savings time ending this past weekend in the US, my birthday was technically one hour longer than a typical day. A 25-hour birthday!¹

This got me wondering if this has happened before on the day of my birth and while yes, I suppose I could have figured this out via Google Search, it’s just so much easier and convenient to do so via ChatGPT. And it led me down a bit of a rabbit hole, learning about how thanks to the Energy Policy Act of 2005, the end of DST shifted from the final Sunday in October to the first Sunday in November.

Should DST go away entirely? That’s an entirely different debate that basically everyone on the internet is always ready to have.

Anyway, yes, my birthday has been 25 hours long in the past, but only twice before: in 2008 and 2014, because before then, the shift happened earlier. And actually, I was writing about my birthday back in 2014, when I turned 33, but didn’t realize it was a 25-hour day. Undoubtedly, in part, because I was in Ireland at the time.²

So while we all debate the use of AI and how much money is flowing into creating these systems, it is worth taking a step back from time to time and realizing how much we actually use them now for basically every little query, all the time. At least I do. And if you don’t yet, you will. Even if it’s Gemini or some other flavor. This particular world has changed so fast. And clearly it will change even more so in the next year.³

Thoughts on: 43, 42, 41, 40, 39, 38, 37, 36, 35, 34, 33…

¹ Alright, fine, technically I’m in England right now where the time shifted back a week or so ago. But let me have my fun (and hour). I was born in the US and stayed up late watching US college football (Go Blue) and Game 7 of the World Series (my god, what a game).

² And I remember that well because I had just written up some thoughts about GV’s (then still formally Google Ventures) investment in Slack at the time.

³ Also, 25th Hour remains such a great film (and presumably book, which I sadly have not read). Sort of wild that it was written by David Benioff, who most people will know as a showrunner of Game of Thrones, but yes, is related to Marc Benioff (cousins). Who acquired Slack.

The below post was originally published on February 21, 2024 on Spyglass.

If you start me up
If you start me up, I’ll never stop.

The Rolling Stones song, incidentally the one used to launch Windows 95, is stuck in my head. Because it’s what I keep thinking about while trying to start using the Vision Pro. And I do mean “trying” because it’s really sort of a chore.

I know, I know. Play me the world’s smallest violin.¹ But that doesn’t mean I’m wrong. And it’s the thought I keep coming back to while using the device: it’s really quite inconvenient. To be clear, there is a lot to like about it. And I have a lot more to write about such things — once it is started up, I often don’t want to stop using it (hence the song in my head). But this is my daily struggle with it right now, for better or worse, a week+ in to using the device.

I went ahead and timed it. It takes roughly 90 seconds to go from having the Vision Pro in its case to actually putting it on and being able to use the thing. In there, a number of steps are required:

• First, if you bought the official carrying case, which I did,² and store the Vision Pro in it, which I do, just opening up the $200 puffy giant Easter Egg is a bit of a challenge. The zippers are shrouded under the fabric and go veeerrrry slowly around the oval.
• Once you get the case open, you have to remove the battery pack from its holster and then plug the cable into the Vision Pro itself. This is easier said than done as the connector cable isn’t super intuitive to connect without looking at the thing and trying to align some dots. The first few days I was trying to do this in the dark and was very frustrated by the experience as I couldn’t see the dots. I’m better at it now, but it’s still not great.
• Then you put the device on, which depending on your head strap, requires pulling and/or tightening the strap. I have yet to nail this either. And I feel like I’m constantly shifting the device to make it more comfortable on my head.
• Then you remove the screen cover — must protect the EyeSight feature at all literal cost. And then you wait about 30 seconds for the device to boot up. At first, it’s just black and you’re not sure anything is happening. There should probably be some sort of sound here. Apple invented the computer startup sound. Come on, guys.
• You’re then asked via an on-screen tutorial to calibrate your eye positioning by holding down the digital crown.
• Finally, an Apple logo appears. And a few seconds later, the room you’re in appears, followed by a prompt to enter your device passcode. This is easier done by reaching out and poking the numbers versus trying to do so with your eyes, in my experience.
• Only then do your apps come into focus, and the device is finally ready to use.

90 seconds may not sound like a lot of time, but in our age of always-on/instant computers, it’s a lot of time. The iPad sort of broke all of us in this regard. Because while the iPhone itself is instantly on, the iPad is the device that many “regular” folks (like my mother, for example) use as a main computer. And it’s ready to roll in like a second.

Sure, it’s not an entirely fair comparison, since what I’m describing with the Vision Pro is a cold start, while the iPad/iPhone is almost always a hot one (meaning, the device is already on). But even from being powered down, the iPad takes about 10 to 15 seconds to start. Not 90.

Also, I think it’s a more fair comparison than it may seem because it’s how I actually use each device. When I’m done using an iPad, I just set it somewhere, or put it in my bag. When I’m done using the Vision Pro, it’s back to the case. Could I, say, put it on a table? Sure, but I have two little kids. This thing cost $3,500. You do the math.

Also, even if I just sat it down, it will undoubtedly need to charge soon because the battery life is only around 3 hours of usage time. Compare that to a full day for pretty much every other device at this point, including MacBooks. So my only real option if I want a faster boot up is to leave it somewhere where it’s constantly plugged in to the wall. And again, this just isn’t convenient.

Fine, fine, fine. Just to get ahead of this argument, I’ll go ahead and just boot it from a sleep state (as opposed to being completely off). This still takes around 15 seconds — not bad, but not instant — after you put it on, take off the protector, and let the software unlock via your eye scan. You can add another 20–30 seconds if you want to say, connect the device to your MacBook to use as your screen (which is what I’m doing right now).

My point is that we’ve been spoiled in our age of instant, always-on computers. I recall very well the many minutes I used to have to wait to start up my old PC. I would leave the room and come back while… the… dots… loaded… Or to wake up the laptops of yesteryear. Cue those fans. A 90-second start time might seem reasonable in comparison. But that’s not the comparison here. It’s no longer 1984 or 1994. It’s 2024. And this computer is on my face!

Sure, the Apple Watch was a bit rough in those early days, but it was always on (when it had a charge) on your wrist. This is quite different as it’s something you have to pick up and physically put on each and every time you want to use it.

We haven’t even talked about the consideration that it’s going to mess up your hair each time you put it on. And potentially leave red marks on your face depending on how tight you wear it (Apple will undoubtedly say that if it’s leaving marks on your face, y̶o̶u̶'̶r̶e̶ ̶h̶o̶l̶d̶i̶n̶g̶ ̶i̶t̶ ̶w̶r̶o̶n̶g̶ wearing it too tight, but tight to me is far more comfortable than loose). It’s hard to drink certain drinks while wearing it. Like a glass of wine. Beer bottles FTW. Also straws. If there’s a big future for this device, there’s going to be a big future for straws.

Practically speaking, what I’m saying is that there’s a large hurdle in my head which I have to overcome each time I think about using the Vision Pro. It’s not looking dumb — mainly because I’m not going to take it anywhere beyond my home. It’s just always going to be faster to grab my MacBook or iPad (or yes, iPhone). And so I have to purposefully want to do something in the Vision Pro. Writing in it, which again, I’m doing right now while connected to my Mac is nice. But no nicer than doing it on the actual MacBook screen. In some ways, it’s slightly worse. So it’s really only going to be the handful of things that you either only can do on the Vision Pro (immersive content) or are better on it (watching movies). There needs to be a lot more of such activities if this device is going to work, long term. Or the device is going to need to get a lot smaller and quicker, fast.

It will, of course. But it will also take time. And so for now, the other devices in your life are going to be more convenient to use. And so you’re going to use them a lot more than you do the Vision Pro. That’s just the reality of the situation right now. No point in not being honest about it. An inconvenient truth, quite literally.

The above post was originally published on February 21, 2024 on Spyglass.

¹ Actually, that would be a pretty good Vision Pro app. Though perhaps complicated given the use of your index finger and thumb to make such a gesture…

² I’ve seen a lot of folks polk fun at the look of the case, but I actually quite like it. It’s sort of like something an astronaut might carry while walking towards their shuttle to space. It could certainly be more svelte, but the Vision Pro definitely seems like it will be safe in there. Perhaps even if dropped from space. Putting it into a laptop bag is another matter…

Vision Pro’s Inconvenient Truth was originally published in 500ish on Medium, where people are continuing the conversation by highlighting and responding to this story.

The below post was originally published on February 21, 2024 on Spyglass.

San Francisco is back! In 3 to 5 years it will be over again. And then back again. Anyone who has been around long enough has seen this story go round and round at least two or three or four times at this point. It’s perhaps the most clear example of the “build them up to knock them down” idea in reporting,¹ because unlike companies or people, San Francisco never actually dies or fades away.

Here’s my (rather boring and very obvious) take on this: San Francisco will never stop being the key tech hub. Certainly not in the lifetime of anyone reading this.² Instead, there will be a natural diffusion of the centralized power of the region over time. And not because of San Francisco falling, but because of other areas rising with spreading diasporas of people from successful companies as tech continues to permeate every and all industry.³

But the Bay Area will remain the main wellspring for what’s next and what’s new, as we’re now seeing with AI. That’s largely because of legacy but also because of sheer proximity. People who haven’t lived there forget, but San Francisco is tiny. Famously, 7 miles by 7 miles. That’s both a weakness (for development and diversification) but also a massive strength (for land value and clustering).⁴ There’s a level of serendipity of chance encounters that happens in San Francisco (and the Bay Area in general) that’s unlike anywhere else. Again, this is largely by design. Mother Nature’s design.

Much is said (and written) about the importance of Stanford (and Cal) and all the VCs being in one place. But again, this is all related to the above. The Bay Area is tech’s natural hothouse.

At the same time, the monoculture that’s the byproduct of all of this is a problem. New technology can help dissipate such issues, but it’s only temporary. And this is also getting worse with time, in my view. And tangential but related to this is the always rising backlash against that culture from various factions outside of it.

All of this plays into the ebbing and flowing of the region, which is real but also overplayed by the media (shocker). The pandemic was the latest and most extreme catalyst of all this, but it will not be the last.⁵

I write all this as someone who, yes, left San Francisco. After a dozen years living in the city (my wife even longer), it just felt like it was time. Yes, some of the very real problems (see: above) fueled some of the decision.⁶ At the same time, now almost a year removed, I think I’m gaining the perspective to say that it remains a magical place, in many ways (see: above).

I don’t expect I shall return. In fact I mean not to.⁷ But others will.

The above post was originally published on February 21, 2024 on Spyglass.

¹ That is, the notion that after you build something up with enough stories, it’s far more interesting to then write about its downfall. Which then also becomes boring, and so the stories of resurrection begin!

² Even an inevitable earthquake will likely only rally support for the region after years of being dragged in the press (see: above).

³ Some of this diaspora, by the way, is caused by taxes. That is, California’s very high tax rate naturally leads some successful people to leave and settle elsewhere. Like the wind spreading seeds from a plant in bloom.

⁴ The political situation in the city seems untenable and needs to be fixed. But I have to believe will be, at some point. (Update July 2025: It seemingly has been!)

⁵ Again, just wait until there’s another literal earthquake.

⁶ Yes, crime and safety were a factor as well. This is where the angry pitchforks come out yelling about how much of that narrative is made up and to look at the data! All I can tell you is how we felt living on the ground there over all those years, especially in the latter years with small children: there was a growing unease and sense that things were getting worse, not better. Hopefully that changes as well.

⁷ Which is the quote from the movie, but not the actual quote from the book.

There and Back Again, a San Francisco Tale was originally published in 500ish on Medium, where people are continuing the conversation by highlighting and responding to this story.

Okay, I’ve had 24 hours to digest the latest edition of The Game. That is, the annual Michigan/Ohio State game. That is, the best rivalry in all of sports. You can argue with me about it, but you’re wrong.

I’ve been writing about this game for a long time. Coincidentally, I started blogging 20 years ago yesterday. Had I started 20 years and 10 days ago, when Michigan and Ohio State played in 2004, it would have been about The Game. Instead, there have been posts here and there over these past 20 years about that game. The Game.

Yesterday’s variant of The Game was one of the more wild ones I recall seeing. Unlike the last few years, where I felt varying degrees of good, this one was weird as I was somewhat at ease.

A few game have been closer at the very end — hello, 2016 — but only 2014 had a larger spread: 21 points in favor of Ohio State. They didn’t cover that spread, but won The Game, nonetheless. Yesterday’s spread landed at 20.5 points. Michigan, somehow, not only covered, they won The Game.

But the “somehow” also wasn’t rocket science. And it’s the real reason why Ohio State coach Ryan Day, unless he somehow wins the national championship this year, is probably going to be fired. And were it any other year before this year, with the new playoff, that loss would have meant Ohio State was out of the championship running, he would have probably been fired yesterday.

Trying to look at this objectively, Ohio State had one of the dumbest game plans in history. Rarely will you find a more obvious mismatch than Ohio State’s wide receivers versus Michigan’s secondary. It’s a testament to those receivers but also the fact that Michigan’s top CB — the best in the country and undoubtedly a Top 10 pick in the NFL draft — Will Johnson, missed the game with an injury. Again, this wasn’t hard to figure out.

And when Ohio State chose to spread it out and pass the ball, Michigan had basically no answers aside from a few pass interferences. If Ohio State had simply passed on every single down, they may have won by 3 or 4 touchdowns. That sounds like an exaggeration, but I don’t think it is. It’s a mismatch.

But Ryan Day had a different gameplan. One imagines that he was sick of hearing about how much “tougher” Michigan was than Ohio State. And so he was going to run. Run. Run. Run. Run. Run. This, despite the fact that one of the few true strengths of Michigan in their depleted state after last year’s championship run which saw half the team — and coach — jump to the NFL, is their D-line. Up front, Michigan is as solid as it gets. If Mason Graham and Kenneth Grant both aren’t also top 10 picks, both of them will go in the top 20. And they showed why yesterday. Ohio State could not and did not run the ball. In the 4th quarter they had 9 rushing yards. Nine.

In wanting to prove something with yesterday’s game plan, Ryan Day just proved he’s an idiot. And that Michigan is so far in his head that he may never beat them. If he couldn’t do it with the most expensive team ever assembled against a full-on transition year Michigan team post-Championship, why do we think this changes? It will never be easier than it should have been yesterday. Next year, Michigan has the number one prospect coming in to play quarterback.

Not the number one quarterback prospect. The number one overall prospect. Ohio State has the number two. And it’s why this rivalry is the best. But also, we have the number one.

Speaking of quarterbacks, Michigan’s current one, Davis Warren is an amazing story. The walk-on who beat cancer to start The Game. Does not get better than that. He showed a lot of heart in this game and season. But he also threw perhaps the worst throw in the history of Michigan football at the goal line in the 4th quarter. That ball was a few inches too low for an easy touchdown and instead was picked off. But Warren’s teammates picked him back up and made it so that no one will ever remember that throw. They’ll simply remember that Davis Warren beat Ohio State. I’m beyond happy about that.

Did I mention that Michigan was also playing without their best player on offense? With TE Colston Loveland — another likely first round pick — also missing the game due to injury, Michigan clearly had problems passing the ball — 62 total yards passing for the entire game. At the same time, I can’t help but wonder if not having Loveland helped Warren in a weird way. If he were in there during the normal obvious passing downs, Warren would have probably over-focused on him. And Ohio State may have been ready for that. Instead, Warren had to spread the ball around and while he wasn’t exactly lighting it up, he got the ball where it needed to go a number of times in The Game.

And this wasn’t exactly the first time Michigan played The Game without their best player and/or coach. This is somewhat of a tradition now, it seems. On paper, it’s bad. But again, you can’t help but wonder if it doesn’t loosen Michigan up a bit to just play.

And boy did they ever yesterday. They dragged Ohio State down in to the game they wanted. The one they could win. And they did. #GoBlue

Exactly 10 years ago, I was quite upset. What a difference a decade — and a championship — makes…

While I hinted at it last year, after upending (in a good way!) my personal life by moving the family to London,¹ this past year was all about doing so (in a good way!) on the professional side. Mainly, it was no secret that I had long aspired to get back to writing in a more robust way. I did the best I could keeping the muscle active during a dozen years as a VC, but as a creature of habit, it’s basically impossible to do that when your first (professional) duty is to portfolio companies and partners. And to email.

So. Much. Fucking. Email.

Oh yes, and family. Especially with two young children. There are only so many hours in a day and if 42 was about figuring out where I wanted to spend such time, 43 was about how. And so Spyglass was born and on my exact 11 year anniversary at Google — perhaps just to be able to make the ultimate dad joke that I went “to 11” — I left. At first, it’s very weird leaving behind a job where you’ve spent a significant portion of your adult life. But, as I found out, it quickly feels like you left that world behind years ago.

To be clear, I didn’t fully leave investing behind.² I just felt like I needed some time dedicated to ramping back up on the writing side, getting my sea legs back, as it were. And experimenting with where I want to take Spyglass. And roughly nine months into it, I’m quite close.

To me, writing has always been just as much about helping me to clarify my own thoughts. And after all these months, I truly feel like I have a clarity of thought on various topics that I haven’t had in quite some time. It’s really refreshing, honestly. It’s amazing how your brain awakens when most of your writing time isn’t spent on email.

Well, except, of course, the newsletter. Which I’m back to doing daily on weekdays. But that’s essentially just my real-time notebook for what I’m reading, writing, and thinking about. Again, just the process of taking those notes is beyond useful to me, so I appreciate everyone who is following along in that process.

A few more tweaks to Spyglass are coming, but then, I suspect, it will feel pretty feature complete. Of course, just v1. You always have to be evolving.³ Which feels good at the ripe old age of 43.

Published on November 2, 2024 📆
Sent from Oxford, England 🗺
Written on a 14-inch 2023 M3 Max MacBook Pro 💻
Enjoying a Braybrooke Helles Lager 🍻
Listening to “Things Behind Things Behind Things” by Bon Iver

¹ Not to mention my wife and I welcoming our second child! She’s great, by the way! And she brought good fortune with her: a 15–0 season by the Michigan Wolverines that literally kicked off right after she was born and ended with a national title. Tonight seems decidedly less promising: a visit from the current #1 team in the country to face a clearly rebuilding (after losing roughly half of their team to the NFL, including, of course, their coach, post-championship) Wolverines team in Ann Arbor. Too much to ask for a birthday present, guys? #GoBlue

² And I’m quite happy with my timing given the sheer insanity that is investing in the AI space right now. There’s far too much chaos and noise for my taste. It’s exciting and largely real, but anyone on the investing side who says they’ve cracked any sort of code yet is lying. The code is simply still shifting too quickly. It will slow.

³ Which someone should tell the United States, as I simply cannot believe we’re close to potentially returning to this utter madness. Hope?

Wow, I’ve been writing these for 10 years now…

• The Ultimate Question of Life, the Universe, and Everything
• Fourward
• The Essence of Time
• A November to Remember
• A Quiet Place
• A Different Kind of Ride…
• 36 Years In…
• A Farewell to 18–34
• Millennialism
• 33

The below post was originally published on February 8, 2024 on Spyglass. In it, I attempt to make sense of the then just-announced sports streaming bundle spearheaded by Disney (now officially called Venu — and now officially in limbo following a series of weird missteps, many of which are alluded to below).

If you’d like to sign up to get these updates in real-time, you can do so here.

Now that a couple days have passed since the seeming bombshell sports streaming announcement which would further blow up the cable bundle dropped, a slew of new little details have come along, as you might expect.

First and foremost, the timing of that announcement was pretty clearly to get ahead of Disney’s earnings the following day, where Bob Iger seemed to pull off a Michael Corleone baptism, executing (though in this case, not literally) a series of initiatives in concert that left his critics (and, importantly, Wall Street) in awe. More on this later today, but the key one for these purposes was the announcement that the long-awaited stand-alone ESPN streaming service would be coming in the fall of 2025.

In that light, the new sports streamer announcement feels like a rather brilliant way to bury bad news. 18 months from now may as well be 18 years from now in the fast-paced streaming environment.¹ If Iger had said nothing about the stand-alone ESPN service during earnings yesterday, he would have been asked. And so he either could have told the truth (that it was still 18 months away) or ducked the question, which would lead to more questions and annoyed analysts. By announcing the new sports streaming partnership — which is clearly so thrown together that not only does it not have a name yet, it doesn’t have a leader yet, nor is any of it built yet — Iger was able to bury the bad ESPN news.

And actually, even more brilliantly, the bad ESPN news almost looks like a positive now. Because there would have been some subset of would-be subscribers who would only want ESPN, versus this new bundle (which is still likely to be pretty expensive — more on that below), and so may have opted to wait for it. But they’re not going to wait over a year (presuming the new group can get the new service out the door in the next 6 months — which probably presumes it’s largely going to be built on Disney’s already in-place infrastructure for such services — I mean, might it just literally be Hulu with the other non-partner channels removed?!).

And so we finally have a streaming ESPN option (not including ESPN+, which of course is not actually ESPN, and is not only a part of this new bundle but presumably will be folded into the actual streaming ESPN service in the fall of 2025). But it’s not entirely un-messy either. From Peter Kafka at Business Insider:

And while the programmers behind the joint venture won’t say this out loud, they seem pretty aware that they’re going to get some blowback here.

Which may explain why, up until Tuesday, they hadn’t told any of the pay TV companies or sports leagues about their plans, industry executives tell me. (No one I talked to wanted to go on the record, yet. Though it’s possible we’ll hear from them in the coming days as they digest the announcement.)

This was the one big question I had upon first reading about all this: what would the leagues think of it? Surely, they can’t be huge fans given the potential ramifications of what it would mean for sports rights packages (i.e. why would these three companies still compete for those rights if this bundle gives them de-facto access, regardless of who wins said rights?). Such collusatory (I think I just made that word up) possibilities led many (including myself) to assume that of course these companies must have run this plan by the sports leagues first (since aside from bidding on new contracts, they all have existing contracts with the various leagues, which would be the key part of this new streaming service).

But assuming the above report is correct, Disney, Fox, and Warner did not let the leagues know ahead of this announcement.² I cannot wait to see what the response will be to that! Back to Kafka:

Another reason the “this is just another pay TV service” argument is important is that programmers want to tell the leagues that they’re not losing anything here, and may be gaining something.

That is: If someone decides to stop paying Comcast and switches over to the new bundle instead, the sports leagues’ audience stays exactly the same. And maybe, the pitch goes, the bundle will attract a new audience that isn’t paying to watch this stuff, so the league’s reach increases. (This, by the way, is the same argument that Comcast and the NFL made when they put that playoff game on Peacock last month.)

Yes, this is one way the new company/service will try to calm the leagues down. “This is just like YouTube TV, but only for these handful of networks that will focus on sports.” But again, I suspect they’ll be far more worried about what it means for the potential bids on the next wave of rights versus actual viewership. Which Kafka finally gets to at the end of his piece:

And from the sports guys: “Wait. All three of you used to compete to buy TV rights from us. Now you’re all working together? How is that good for us?” Analyst Michael Nathanson flagged this Tuesday night in a research note he published on the announcement: “Will the new structure ensure that each competing stand-alone company is still incentivized to go as big on their next set of sports rights?

A big obvious test case for this question will be the upcoming deal for NBA rights, which are currently shared by ESPN and TNT/TBS for $2.7 billion a year. The league wants to jack that up to $7 billion or more. Do ESPN and TNT compete as hard as they did last time for that deal — as long as one of them gets it and puts it in the new thing?

I’m not sure this is explicitly why these three networks got together on this deal — and again, I think Disney had the most obvious rationale — but it certainly can’t hurt.³ They, of course, cannot say that. But something clearly had to change with regard to the ever-increasing sports rights and the new streaming reality we’re entering with the end of the cable bundle.

Also interesting:

Important caveat here: If you watch the NFL — the most popular programming on TV — this package won’t be a full replacement for the stuff you’re already paying for. That’s because the bundle doesn’t include CBS and NBC, which have big deals with the NFL, so you’ll be missing about half of the games you’d get with traditional pay TV.

Not only does this sports bundle not include those two key players in sports content (thanks to their NFL deals), their parent companies apparently weren’t even approached about joining this new venture. That’s all sorts of fascinating, but again perhaps speaks to Disney just wanting a stopgap measure of sorts. But also the fact that if they had gotten Comcast (which owns NBC) and Paramount (which owns CBS — at least for now) on board, the amount they would have had to charge consumers in order for this service to make sense for all the networks would have been probably pretty close to what you now pay for cable. Certainly what you’re paying for a “full” MVPD, like YouTube TV, which is about $75/month (and itself getting awfully close to what you’d pay for cable).

This also explains why the programmers have been floating a price point of $50 or so a month for the new bundle thing: They have to sell the programming to themselves at the same price they sell it to the cable guys and everyone else. (This was also described to me as the logic for not including NBC and CBS in the package — once you add in their fees, you’d end up with something that costs about the same as regular cable TV.)

$50/month versus $75/month is probably the minimum gap you could have to make this service make sense to some people — notably those who only want sports and don’t care about the rest of the cable bundle. (Though yes, the $50/month will undoubtedly come down a bit when bundled with one of the other parent company streaming services: so, say, Disney+ + “SportsStream” for $55/month versus the $58 it would be buying both stand-alone, etc).

Anyway, we now will have sports without needing to pay for cable. But not all sports. For that, you’ll need to get an antenna for the NBC/CBS games. And increasingly, subscribe to one of the “pure-play” streaming services, which are striking deals to stream games as well (Amazon, Peacock, etc).

One key to this new service, in my mind, is how the three co-owners actually make it look and feel. If it’s easy to navigate to the games/content you want, it may be worth it. For all the grief Hulu gets in hindsight, they actually got this element of the service quite right. The current sports streaming landscape is a mess — really, the entire streaming landscape is a mess when it comes to finding anything — so this may be an interesting way to test out some sort of unification.

A bundle, if you will.

I’m reminded of a similar general idea I had about a year ago — but for ESPN itself (which yes, was also an idea I had for Hulu back in 2015. I’m full of ideas!):

The way to square this circle might be to revisit an idea I wrote about back in 2015 — well before Hulu was offering live sports, let alone touting it as the main selling point in their advertising campaign (you’re welcome, Disney). Eight years ago, this was actually far less straightforward as Disney was just one (equal) partner in Hulu. But the aforementioned Fox acquisition made them the main partner. The RSNs were going to be a headache for this. That problem has now just about inverted (though dealing with a few major RSNs like the one owned by the Yankees will remain an issue). And now Hulu has a full over-the-top streaming cable service in the form of Hulu + Live TV. There may be a way to thread this needle.

All of the streaming cable replacement services are now more or less the same — and looking a lot more like traditional cable in price on down these days — so a focus on sports for Hulu’s service could remain a smart selling point and they should double-down on it. They should create a new UI that aggregates all the games you want to watch in a smart way. (Something which we’re all increasingly longing for in an era of increasing content fragmentation.) This is a natural place for ads, ads, ads, ads, ads, which Disney must appreciate. And they can upsell the other services that offers some sports, such as Amazon for some of their NFL games and Apple TV+ for their MLB and MLS games. Again, in the past this would have seemed impossible, but now it’s a standard business practice.

With Fox and Warner content, Disney now will be able to build a compelling experience around sports. Perhaps so much so that the other players have to get on board (again, similar to what happened with Hulu — as it was Disney who joined later!) It won’t be under the ESPN banner, but rather that content will be a part of the package. At least until the actual ESPN streaming service gets here in 18 months. Then all bets are off — or perhaps on, as it were.

Update: More on Disney’s Epic maneuver…

Disney's Epic Ambitions

¹ Again, presuming they can get this new streaming service off the ground much faster than 18 months, you do have to wonder what is taking Disney so long for stand-alone ESPN. Maybe it’s the gambling element? Or maybe they’re still just trying to slow roll it and wean off the cable teet ever so slowly…

² Aside: this is also undoubtedly why this news didn’t leak ahead of time, which is almost unheard of in this day and age given the players involved.

³ And, of course, you can’t discount the churn prevention benefits this streaming service will offer to Disney and Warner’s core streaming services, thanks to the strategic bundling each will offer. I don’t know what Fox is thinking/doing. Just getting some money to be in the car as the cable bundle finally rides off into the sunset, I suppose. Maybe they get to take this thing over when “real” streaming ESPN comes?

The above was originally published on February 8, 2024 on Spyglass. If you’d like to sign up, you can do so here.

The Stopgap Sports Bundle was originally published in 500ish on Medium, where people are continuing the conversation by highlighting and responding to this story.

The below post was originally published on February 6, 2024 on Spyglass. If you’d like to sign up, you can do so here.

Earlier tonight, I joked about Bluesky moving up in my social media power rankings. To position number 4 of the 17 sites and services that I now need to update in order to reach the audience that has now completely dispersed since Xitter shit the bed. This is actually not a joke. It’s a nightmare.

When launching this site last month, I tried to map out what the social media strategy would be.¹ Ultimately, I decided I would create dedicated feeds on Xitter and Threads. The former, mainly for legacy reasons and because that’s a known behavior — some people want to follow feeds of content there — the latter as sort of a “trying to skate to where the puck is going” situation. That is, the notion that Threads may very well be on its way to replacing Xitter. Not entirely, of course. But like 75% of the way there. Good enough.

The reality is that it’s not good enough. And, I suspect, nothing will be good enough. I think the social media distribution game is done — at least when it comes to links. It’s partially the (comically stupid) move Xitter made to deprecate links in their feed. It’s partially just the world moving on (to TikTok, Reels, and the like). But it’s all just way too complicated to manage now. My god, I forgot to post to LinkedIn tonight. Kill me.

All of this is part of the reason why I wanted Spyglass to be at least partially a link blog. I believe there’s still a subset of users who crave that link mineral. I just think they, like me, are not sure where to find it right now. And those holding said links have no idea where to share them. And don’t wish to spend an hour each day sharing them to those 17 different services.

Federation may alleviate some of this, but spoiler alert: not all of it.

Twitter basically recreating Nuzzel within Twitter was super-promising at first. Then Xitter made it laughably bad (and paywalled it). Artifact had some early promise, and then immediately committed seppuku. Flipboard, somehow, lingers. A few other sites of yesteryear do as well,² but nothing quite like Twitter pre-Xitter.³

That was fun. You shared links, people interacted with them. You talked about them. And then on to the next one. This is all a chore now. It enough to drive anyone back to RSS.⁴

¹ Which may be the filthiest sentence I’ve ever written, anywhere. Gross.

² Techmeme, the tech news link aggregator created long ago by my friend Gabe Rivera, remains king. Kudos for never even launching a mobile app in the face of immense ridicule. Just keep it simple. Links, links, and more links.

³ Might this new service help in some way?

⁴ I kid, I kid. Fun old takes aside, I’ve been using RSS the whole time. I’m a little worried that my beloved Reeder app on iOS and Mac hasn’t been updated in a few years. But they’ll pry it from my cold hands, just as they had to do with Google Reader back in the day. Perhaps the last time a company messed up content distribution to this extent.

The above was originally published on February 6, 2024 on Spyglass. If you’d like to sign up, you can do so here.

What a Mess was originally published in 500ish on Medium, where people are continuing the conversation by highlighting and responding to this story.

TechCrunch+ Termination - Lux Capital

With the unfortunate news of layoffs at TechCrunch last week, this post attempts to look at the why — and in particular, what went wrong with “TechCrunch+”, the site’s premium tier. With the large caveat that I was at TechCrunch a decade before Crichton, it all rings fairly true.

If you had asked me to extrapolate out where the site would be nearly 15 years after we sold to Aol (which itself went on to be acquired by Verizon, and then merged with Yahoo — Oath! — and finally sold to private equity, whew…) I honestly probably would have predicted roughly this trajectory. On one hand, it’s impressive that TechCrunch is still alive (again, especially given all the parental changes), on the other, this is basically what tends to happen as publications age and try to maintain growth while “remaining true to what they are”.

I was at TechCrunch through what many would consider to be the “heyday” — the 2008/2009 timeframe — but that was largely because the tech ecosystem was so much smaller then, and the tech publication ecosystem was much, much, much smaller. At one point, we still tried to cover every startup. Then every YC startup. Then it was just impossible to keep up. At the same time, many of those startups grew up — notably, Meta (née Facebook), which was right around the corner from our office in Palo Alto at one point.

And so coverage expanded to encapsulate more or less all of tech. I, of course, took on the Apple beat (which I had been doing previously at VentureBeat as well). And undoubtedly because tech itself began to permeate everything, and more people knew about the large companies versus the small startups, as Crichton notes, that coverage started to dominate site traffic. At the same time, there was a very concerted effort that startup coverage needed to remain the lifeblood of the site, as it were. TC founder Michael Arrington got this exactly right, even as the site scaled. Because again, the founder/entrepreneur ecosystem is what bestowed authority upon TechCrunch.

Writing up an article on the latest ravings of Elon Musk might take about 15 minutes (there usually wasn’t that much to say other than his statement, after all), but that one article could drive 100,000 page views or more. That was the secret treasure that funded the real in-depth reporting: cheap coverage of a big tech company coupled with the lucre of comparatively extraordinary ad revenue.

For the business side, TechCrunch’s focus on startups required second-order thinking. Startup-related articles got a fraction of the readership of an article on Apple, since no one is searching on Google for the name of a startup they have never heard of before. So why bother? Indeed, many of TechCrunch’s now-dead competitors didn’t bother. The key insight though is that these articles attract the startup CEOs and founders, and it is precisely this demographic that is so valuable for advertisers. Startup coverage was a form of service journalism, and one that happened to create a perpetual revenue machine.

And again, while most startups failed as is their nature, some would go on to become YouTube, Twitter (née Twttr née Odeo), Square (née Squirrel), Instagram (née Burbn), Uber (née UberCab!), etc. Having that historical context was incredibly important to the site’s credibility.

Subsequent editors would say (and even believe!) the right things about keeping true to that mentality. But it’s obviously much easier said than done. Both with growth and again, the game of hot potato the acquiring companies were playing. Even many of those large companies say the right things at times, but the incentives are never going to remain aligned. They’re just not.

And when an org becomes large enough, as TechCrunch did, there are even factions within the entity that necessarily have to battle, for resources and mindshare, if nothing else. As so a TechCrunch that’s covering startups, and large companies, and doing events all around the world, and doing ad sales, and doing a paid tier, and doing newsletters, and doing video… It’s just, a lot. A lot of pieces tacked on to a scaffolding that’s two decades old, built for a different world, in a different time.

The unique economics for TechCrunch around advertising and events funded the organization well, but they have an obvious flaw: they don’t really scale. There isn’t an infinite universe of big tech companies or venture-backed bubble companies willing to spend lavish sums on ad space. As for events, they rarely get better with ever more attendees, and it’s hard to replicate the scarce thrill of a flagship event multiple times per year. If TechCrunch’s business leverage was graphed as a parabola, it was holding steading at the optimal maximum for years — not growing, not shrinking, but as sustainable as a digital media company can be this century.

You either die a hero or live long enough to become CNET.¹

Also, every media entity in the world now covers and in many cases is dominated by technology coverage. And those technology companies are now the largest companies in the world. I recall doing by-the-minute coverage of Apple passing Exxon to become the most valuable company. In 2011, both had around $400 billion market caps. Today, Exxon still has a market cap of $400 billion. Apple has a market cap of $3 trillion. So does Microsoft. Alphabet (née Google) is at $1.8 trillion. So is Amazon. So is NVIDIA! Meta is at $1.2 trillion. Poor guys.

At the same time there are way too many startups that launch every week and month for any single site to possibly hope to cover. And technology publications are now either large and broad (i.e. The Verge, part of Vox Media) or they’ve broken into a thousand individual newsletters. A few players from the early TechCrunch days still exist, but almost all are owned and operated. A few, like TechCrunch, many times over. The rest are gone and dead.²

And yes, the individual economics trickled in…

What was missing, in the end, were the writers themselves, a sociological puzzle that took about two years for me to understand. Thanks to digital media economics the past two decades, business journalism had been wrecked by downsizing, limiting or outright ending the careers of thousands of reporters. A small proportion of them still thrived at major financial publications like Bloomberg or The Wall Street Journal or The Financial Times, but they were obviously unavailable to write for TechCrunch.

And worse, the younger, up-and-coming generation, those would would be best equipped to cover the industry, would often opt to work in it instead.

Even if you can find that talent, then the challenge becomes one of compensation. If someone understands the venture industry well enough, then they can almost certainly get a job at a VC firm and make a multiple of their media salary. Reporting on cloud infrastructure? They can triple their salary working at Amazon Web Services, without the daily doom of media layoffs looming over their overworked typing hands.

Crichton is now working at a VC firm. “TC-to-VC” became a thing. I left to become a VC a dozen years ago (to be fair, we did try to merge the worlds — an idea that now seems quaint — with CrunchFund, but that was quickly shot down by… yes, Aol).

¹ Still alive, and still for sale!

² Kudos to VentureBeat, where I worked before TechCrunch. Still alive — I just linked to them yesterday!

The above was originally published on February 6, 2024 on Spyglass. If you’d like to sign up, you can do so here.

The Crunch was originally published in 500ish on Medium, where people are continuing the conversation by highlighting and responding to this story.

The below post was originally published on February 5, 2024 on Spyglass. If you’d like to sign up, you can do so here.

The year is 2024, and I’ve just been kicked out of a cafe for using a laptop. Well, technically I wasn’t kicked out, but rather was asked to put my laptop away because with the new year, they’ve decided to implement a no-laptop-policy. So I was effectively kicked out. I simply had to leave because it’s a weekday. Even if I wanted to sit by myself for an hour or two and enjoy some coffee in silence, there’s work to be done.

That’s the thing. I wasn’t playing a game or scrolling through social media feeds. I was writing. That’s what I do. I suppose I could use a pen and paper to do that, as this cafe might prefer, but it strikes me as silly and decidedly less productive not to use the modern tools of one’s trade.

So here I am, writing this at a goddamn Starbucks, like an animal.¹ An animal with surprisingly good WiFi. And a laptop.

Look, I get it. You walk into any number of cafes around the world and it’s increasingly people behind screens, typing away, not being social. Worse, for the businesses, those people are often camped out for hours, taking up space. I even think it’s reasonable for that reason to implement rules during peak times. But again, that wasn’t this. There were a dozen empty seats in this cafe. It’s mid-morning. Also, I had not only just ordered a coffee, but a bite of food as well.

Anyway, every business can make rules as they please — “no shirt, no shoes, laptops, no business” — but this just strikes me as crazy in the modern world. As I put my laptop away and looked around, literally every single other person in the cafe was staring at their phone. Pop quiz, hot shot of espresso: is that better or worse? I can guaran-goddamn-tee those people are not writing anything on their phones. They’re scrolling feeds or playing Candy Crush. At best, they’re texting someone. Being “social” but not in the letter of this cafe’s law.

Many places, of course, try to ban phones, but it never works. Because again, it’s 2024 and what if there’s a legitimate emergency? Also, the banning of phones is amazing in a time when millions of people have Apple Watches which are basically mini iPhones on your wrist. I’ve yet to see a watch ban, but if they start to happen, this cafe will be the first to implement one. Had they existed in the 1950s, newspapers would have been banned here. Books before that.

You know what I’m going to do? Next week, I’m coming back wearing an Apple Vision Pro. No laptop, you say? Wait until they get a load of this facetop! I’m just here, following the rules. Looking at you with a 100-foot screen playing Pulp Fiction over your head. And playing Doom on a 50-foot screen to your right. Don’t worry though, I’m not typing, as that’s damn near impossible to do on this device.

I kid, I kid. I’m not going to do that. But only because I’m not that guy (more on that guy in a minute). This Vision Pro isn’t leaving my basement office, let alone my home. But it is a particularly funny moment in time to think about a laptop ban in a modern cafe. We’re just about a decade removed from the “Glasshole” movement and already blowing up on social media are the so-called “Vision Bros”. In case that’s not self-explanatory, it’s the dumbasses who wear the new device while driving (self-driving or not). Or even just walking down the street. Or hanging out in yes, a cafe together. Daft Punk, eat your hearts out.

We absolutely are about to get the first wave of Vision Pro bans in cafes. And maybe in 50 years that will seem foolish as well.² But these new devices are going to make laptops look like quaint craftsman tools by comparison. And you know what? They are. It’s how we all work now, obviously. It’s literally counterproductive to deny this reality.

¹ Here’s an admission, I actually quite like Starbucks’ new Oleato™ drink. Yes, it’s coffee infused with extra virgin olive oil. Yes, that sounds disgusting. Or just European. It’s honestly interesting, a nice break from the bitter!

² Probably not. Because in 50 years, the Vision Pro will be a contact lens. So banning the current Vision Pro would be like banning a mainframe computer from a cafe in the 1950s. That feels reasonable.

The above post was originally published on February 5, 2024 on Spyglass.

If you’d like to sign up, you can do so here.

Laptop Ban? In 2024? What About My Facetop? was originally published in 500ish on Medium, where people are continuing the conversation by highlighting and responding to this story.

Hello! It has been a while. But with Spyglass, my new site, now firmly established, I thought I’d start to cross-post some content for this audience as well. Since I’m a firm believer in not letting content wither on the vine simply because it’s no longer “new”. The below post was originally published on January 23, 2024. If you’d like to sign up for Spyglass, you can do so here.

I said my second post would be another “meta” post, but I lied. The truth is that it’s late at night here in London and after a few hour delay launching this site earlier today, and during a “midnight feed” of a baby, I found myself thinking about the AirPods…¹

Specifically, how truly great the volume swiping mechanism is on the AirPods Pro. This must be my most-used gesture in life beyond perhaps swiping up to unlock my phone. I have AirPods in my ears a good percentage of the day and I’m constantly swiping up or down on the stems to raise or lower the volume of whatever I’m listening to. It’s so handy, literally. It’s done so casually now that it’s second-nature.

Yes, music and podcasts, but I also listen to nearly everything thanks to services like Matter.² And I also have the AirPods in right now, listening to things on my MacBook Air as I type this post. And I also increasingly have them in while watching TV at night — this is perhaps the single best feature of Apple TV, how easy it is to pair your AirPods — and they work brilliantly for that too. Is the movie or show too loud? Swipe, swipe, swipe. Do I want to pause it? Click.

It’s something so simple. And yes, I know other headphones do this. But Apple just absolutely nailed this little gesture in these little devices. I love the dial on the AirPods Max, but it’s almost the opposite of this — a grandiose gesture that’s trying to be just as clever (borrowing from the Apple Watch) as it is useful. It’s nice. But it’s not as functional as the swipes here.

I still vividly recall being a teenager carrying around a Sony Walkman (the cassette tape variety, not a Discman, for shame), and constantly having my hands wrapped around the thing to get ready to pause/rewind/fast-forward and yes, alter the volume. It was a pain that we couldn’t have known at the time. After all, we were walking around listening to music in our pocket — well, in our hands, or on our belt clips — how magical! Now we have literally every song in the world in our pockets which we listen to via these little earbuds that have high fidelity music beamed to them over thin air. It’s like performing some sort of magic spell to use your fingers to make it loud or to make it stop. Or to press and hold to hear the world better around you. Or to make it fade away. Technology really is incredible.

Anyway, seem like an appropriate type of ode ahead of the Vision Pro, where finger gestures are about to become even more of the thing.³ The main thing, in fact.

¹ I suspect I’ll be writing a number of these quick, late night posts. In part thanks to the aforementioned baby. But also because I have always just preferred writing at night. When the house is quiet. I’m a night owl who longs to return to my nest, but doesn’t long to be an empty-nester. And not to worry, I have something like a decade of early morning wake-up calls left to savor…

² Through GV, I’m an investor in Matter. Just because I’m biased, doesn’t mean I’m lying: it’s my most-used app. I use it to save and listen to nearly everything I read. It’s wonderful. And I’ve been doing this for years, well before Matter came along. It’s just better now.

³ There’s also the new-ish finger/hand controls for the Apple Watch. I like these gestures (finger taps) and use them at times where my broader hands are tied up. But it’s not quite as used day-to-day as I might have thought originally.

The above post was originally published on January 23, 2024.

If you’d like to sign up for Spyglass, you can do so here.

An Ode to the Volume Swipe was originally published in 500ish on Medium, where people are continuing the conversation by highlighting and responding to this story.