John’s Blog

For the next few months I’m going to be very consumed merging two companies together into one tech stack. One of the key reasons we were acquired last year was to unify a technology stack that has helped our business grow and to bring the tools we created to the larger Puck enterprise.

Both legacy organizations are running completely independent technology at the moment, but my goal is to bring it all together. Puck’s business is primarily run on Wordpress, which is a lovely platform for basic CMS needs but not great for running a complex editorial business out of the box. Quite frankly, it’s capped the growth trajectory of the company and I’ll be fixing that very soon.

But before we even think about content and publishing, I need to unify the billing and subscription side of the business. Both companies are running separate billing systems, tax systems, and reporting back-ends. And, both are single tenant by nature: they were purposely creating to run a single business. So we’ve kicked off the work of creating a multi-tenant architecture that will house legacy Air Mail, legacy Puck, and any future acquisitions all in one place.

This effort has been a ton of fun, and the team seems to be enjoying the ability to develop on a new system with some greenfield requirements and shed some of our legacy baggage. I know I feel that way.

We’re just getting started but the effort is already moving along at a steady pace. I love starting fresh and designing the architecture for the next 5–10 years of this company.

Elsewhere

In sporting news, the NFL playoffs have been such a joy this year. It’s refreshing to not have a single rooting interest so I’m able to actually enjoy the games for face value and root for the best scenarios, instead of always scheming for my team’s success.

I’m delighted to see John Harbaugh agree to a 5-year deal with the Giants to become its next head coach. I’m also delighted he’s not in the AFC. I’ll be rooting for him for sure.

Anthropic announced its Claude Cowork features which bring the power of Claude Code to more non-technical users that don’t want (or know how) to live in a terminal window. Claude Code is my absolute favorite tool right now and I’m using it constantly, for coding and non-coding projects alike. Excited to give Cowork a spin, even though I know I’ll probably keep using Code for now.

Apple announced the Apple Creator Studio which brings together Final Cut Pro, Logic Pro, Pixelmator Pro, and a bunch of other tools into one purchase and one subscription. $12.99 per month or $129 per year seems like a great deal for these apps. Not that I need another Apple subscription, but this looks very attractive.

OpenAI explained its approach to ads within ChatGPT which has felt like an inevitability given how much money they are spending. The framing is thoughtful and coherent and seems to be well considered. I’m still more than happy to pay for an ad-free subscription because of the immense value I’m getting from ChatGPT, but I completely understand the desire to open up the market to even more users that are more price sensitive and don’t mind seeing ads in exchange for using the service.

Happy Sunday. Here’s to another great week ahead. 🏈

A week into the year and I figured it’s as good a time as any to pick back up with some light blogging. The last half of 2025 was a complete blur with so many emotional ups and downs it’s not worth recounting them all. Overall I’m incredibly thankful and grateful for the chapter of life that I’m in. In short, I’m stoked for the year ahead.

This morning I updated my LinkedIn for the first time in about 7 years. I don’t like it over there (and I hope to go another 7 years without returning) but I made the jump to “formally” add Puck to my profile.

Late last year, Puck completed its acquisition of our little media startup called Air Mail. I’ve joined Puck as its CTO and couldn’t be more excited to have started this new chapter. The great news is that Air Mail is still alive and thriving within Puck and I still get to work on it every day.

🎧 Speaking of Puck, our incredible CEO Sarah Personette joined The Rebooting podcast with Brian Morrissey and shared a ton of great info about our approach and where we’re heading this year. (A nice shoutout to yours truly towards the end was also very cool of her.) Listen on Apple Podcasts or Overcast.

As we begin the process of merging two completely different company technology stacks, I’m knee deep in modeling and understanding both businesses so we can unify everything this year. We’ll be using Air Mail’s technology as the basis but making some substantial upgrades and improvements as we go. More on that throughout the year.

One week down. Here we go, 2026…

Yesterday the news broke that the Ravens had fired coach John Harbaugh after 18 seasons with the team. For context: 18 seasons is an eternity in the NFL and it's a credit to him and the franchise that they have been able to have such stability and success over this era. Harbaugh is for sure a future hall of famer and he should be recognized for how great he has been, and will continue to be for wherever he goes next. I'm sad about this news, but that's the business of the NFL. It's time to move on, and we'll see what happens next.

Thanks for the run, coach. 🙏

🎉 Happy New Year! I'm excited for a clean slate and to get back to work building. 2025 was a long one, but we made it through. Onward!

Is the age of AI-powered web browsers upon us? Another entry announced earlier this month is Perplexity’s Comet browser. Like Dia, it looks really nice and I’ll look forward to giving it a spin. (I’m on the waitlist, alas.)

The demo video from the announcement on X has a cool walk through.

Dan Goodin, writing for Ars Technica:

Authorities and researchers are sounding the alarm over the active mass exploitation of a high-severity vulnerability in Microsoft SharePoint Server that’s allowing attackers to make off with sensitive company data, including authentication tokens used to access systems inside networks. Researchers said anyone running an on-premises instance of SharePoint should assume their networks are breached.

The vulnerability, tracked as CVE-2025–53770, carries a severity rating of 9.8 out of a possible 10. It gives unauthenticated remote access to SharePoint Servers exposed to the Internet.

I worked on a few SharePoint projects in the early 2000s, and even back then it felt old and outdated. I was shocked that anyone would choose to use it for any purpose. And yet, here we are in 2025, and I have the same reaction anytime I see the word SharePoint crop up.

Last night’s Major League Baseball All Star Game was fantastic. The MLB has done a remarkable job taking this sport, which is rooted in century-old tradition, and modernizing it while making it entertaining. The other major leagues should be taking note of how baseball has improved and follow the lead.

Clayton Kershaw was mic’d up while pitching during the second inning and it was so much fun. “I’m gonna try and throw some cheese real quick hold on” he said as he thew a pitch. He even solicited the help of the commentators on which pitches to throw. Pure genius mic’ing Kershaw up during a game.

The league introduced the usage of ABS (Automated Balls and Strikes) that allowed either a batter, pitcher, or catcher to call for a review of an umpire’s ball or strike call. The players loved it, given their smiles while requesting its usage, and the system works: it correct a few incorrect calls.

The game technically would have ended in a tie, but the league had a great solution for avoiding that completely un-American result: a swing-off home run contest.

Watch the faces of the players competing in, and watching, the swing-off and tell me they all weren’t having a blast.

A fantastic night of entertainment. This is how you do it.

Kite is a fresh take on news consumption by the team at Kagi:

Kite reads public RSS feeds of thousands of (community-curated) world-wide news sources and distills them into one perfect daily briefing. You get every critical perspective and timeline in just 5 minutes. That’s it. No endless scrolling. No attention hijacking. Because we deserve better.

The public files for Kite are all open source on Github.

Kurt Wagner, for Bloomberg:

Meta Platforms Inc. Chief Executive Officer Mark Zuckerberg announced a major restructuring of the company’s artificial intelligence group, including a commitment to developing AI “superintelligence,” or systems that can complete tasks as well as or even better than humans.

Zuckerberg wrote Monday to employees that Meta’s AI efforts will fall under a new group called Meta Superintelligence Labs, or MSL, which will be led by Alexandr Wang, the former CEO of data-labeling startup Scale AI, according to an internal memo reviewed by Bloomberg. Wang, whom Zuckerberg called the “most impressive founder of his generation,” will serve as chief AI officer. […]

Meta will spend “hundreds of billions” on AI projects and research in the years to come, Zuckerberg has said, though the Facebook founder also expects that many firms will likely overspend on AI in an effort to avoid missing the wave.

CNBC has a copy of the memo from Zuckerberg, which begins with this:

As the pace of AI progress accelerates, developing superintelligence is coming into sight. I believe this will be the beginning of a new era for humanity, and I am fully committed to doing what it takes for Meta to lead the way. Today I want to share some details about how we’re organizing our AI efforts to build towards our vision: personal superintelligence for everyone.

Emphasis above is mine. What a bold statement.

Olivia Sophie Rafferty, for ai fray:

The Northern District of California has granted a summary judgment for Anthropic that the training use of the copyrighted books and the print-to-digital format change were both “fair use” […]

However, the court also found that the pirated library copies that Anthropic collected could not be deemed as training copies, and therefore, the use of this material was not “fair”. […]

This is a mixed ruling on fair use – a loss for both copyright holders and Anthropic, but potentially a big win for AI platforms in general. And, if upheld, the order would mean that AI firms using copyrighted material to train their LLMs may be allowed in the future. The only exception to this would be if the material has been pirated.

The mixed ruling in this case is potentially very interesting for the larger AI and LLM-based industry. The court here is establishing some precedent that training an LLM model is considered ‘transformative’ because it uses existing copyrighted works to create new outputs. This ruling sure seems to validate the approach of training LLMs on large datasets of copyrighted materials as acceptable, in the eyes of the court at least.

On the other hand, ‘pirating’ a bunch of books and content is obviously not fair use, and Anthropic will be on the hook for those damages in a future trial.

Hayden Field, for The Verge:

OpenAI has scrubbed mentions of io, the hardware startup co-founded by famous Apple designer Jony Ive, from its website and social media channels. The sudden change closely follows their recent announcement of OpenAI’s nearly $6.5 billion acquisition and plans to create dedicated AI hardware.

OpenAI tells The Verge the deal is still happening, but it scrubbed mentions due to a trademark lawsuit from Iyo, the hearing device startup spun out of Google’s moonshot factory.

Turns out that one of the hardest things in computer science still applies to our AI-driven world: naming things.

And really: “io” is such a common phrase in computing, it shouldn’t be able to be trademarked at all.

Matteo Wong, writing for The Atlantic, interviewed Claudio Cerasa, editor of the Italian newspaper Il Foglio about his use of AI tools and how they are evolving his paper:

With so many obvious pitfalls to using AI, I wanted to speak with Cerasa to understand more about his experiment. Over Zoom, he painted an unsettling, if optimistic, portrait of his experience with AI in journalism. Sure, the technology is flawed. It’s prone to fabrications; his staff has caught plenty of them, and has been taken to task for publishing some of those errors. But when used correctly, it writes well—at times more naturally, Cerasa told me, than even his human staff.

Still, there are limits. “Anyone who tries to use artificial intelligence to replace human intelligence ends up failing,” he told me when I asked about the “Heat Index” disaster. “AI is meant to integrate, not replace.” The technology can benefit journalism, he said, “only if it’s treated like a new colleague—one that needs to be looked after.”

The problem, perhaps, stems from using AI to substitute rather than augment. In journalism, “anyone who thinks AI is a way to save money is getting it wrong,” Cerasa said.

Dia, the new AI-focused browser by The Browser Company, is now available for use by Arc members. I'm not even sure what an "Arc member" is, but I've been a heavy Arc user for a few years now so I'm giving it a spin.

The interface is super clean and polished. It’s very tastefully designed. I haven’t quite figured out what I’ll use the AI chat sidebar for on a daily basis, but I’m giving it a shot.

The onboarding process was very useful as well—a rarity for browsers! Since I’m an Arc user, Dia imported all of my bookmarks, site preferences, and even my cookies and browsing data, so I haven’t had to sign-in to anything new and can just continue along my way like nothing has changed. Fancy!

I asked the chat interface to summarize the value proposition of Dia and its core features. Here’s what it said about itself:

Dia is a new AI-first browser from The Browser Company, designed to put artificial intelligence at the center of your web experience. Unlike traditional browsers, Dia features a deeply integrated AI assistant that’s always available in a sidebar, ready to help you summarize pages, answer questions, draft emails, or compare information across multiple tabs. Its minimalist, Chrome-like interface makes it approachable for everyday users, not just power users.

Dia streamlines everyday web tasks by making AI assistance seamless and ever-present. Whether you’re researching, writing, shopping, or planning, Dia reduces busywork and context-switching, helping you get more done in less time. Its focus on simplicity, personalization, and privacy aims to make the browser feel less like a tool and more like a helpful partner—one that adapts to your needs and grows smarter the more you use it.

M.G. Siegler:

Ever since the rise of Android to challenge the iPhone all those years ago, Apple and Google have stood atop the tech landscape when it comes to their big developer-focused events. And their temporal proximity to each other each calendar year have always highlighted the key similarities and differences. But never have they been more different than they were this year. Google I/O was AI, AI, AI, AI, AI, AI. Apple’s WWDC was UI, UI, UI, UI, UI, UI.

One felt like a company flexing. The other felt like a company hiding.

“Hiding” is a strong term. I think this was Apple focusing on what it does better than any other company out there and leaning into its strengths. And the same for Google. The dichotomy of these two conferences makes me wish the two companies got along better and could work together more.

This portion of the WWDC keynote yesterday was very tight and well presented. The design team at Apple is excellent at this type of update. Much like iOS 7, it instantly makes everything else on our devices feel outdated and stale. It will be interesting to see how quickly the rest of the industry attempts to copy this design language.