OP #297: The Web is Dead—Long Live the AI Web

Author

Darren Herman
June 03, 2025

Welcome to Operating Partner #297

I was down and out for two weeks with the flu but it’s good to be back and human again. I appreciated all of your notes from last week’s OP - turns out some of the watch content hit a chord with the community. Lots of collectors and admirers here. I will not be adding watch content to each OP but will include from time to time. With that said, here’s a vintage Omega beauty that I’ve had my eye on… crazy to think the watch is 45 years old.

A couple of weekends ago, I went to the Boston Calling music festival and got to see Tom Morello, Sublime, Public Enemy, Vampire Weekend and of course, the Dave Matthews Band. Was a special evening as not only was I with my buddy Ryan who came down from VT, and my brother-in-law, but my daughter Ava too. She came out in support and got to experience some awesome live music. I was most excited for her to see DMB live, as she’s always in camp when they tour around here. I think she enjoyed the Blackbird Doughnuts as much as the music, but we had a blast.

Continuing on the music note, I’ve been listening to The Fray recently. I really like piano driven rock and the self titled album from 2009 brings back great memories (as does their 2005 album).

To start us off, here are a few articles:

The last link - to the AI Accelerator from U of Digital, is a course that I’m signed up to take. I have no idea if it’s going to be good but I do hold U of Digital in high regard as a paying subscriber to their newsletter.

Congrats to my friend Ari Paparo for announcing his new book, Yield: How Google Bought, Built, and Bullied Their Way to Advertising Dominance. I’m excited to read this book ! Also, kudos to the Obviously NYC team for launching their new campaign and initiative (highlighted by Jesse Middleton).

Last, the Knicks. What a season. More on that in OP #298. 

Thanks again for subscribing.

Be well, do good.
Darren

The Web is Dead—Long Live the AI Web

I’ve been thinking a lot about the web lately. I know, it's a bit odd, but occasionally my brain wanders this way. I'm part of that unique generation that remembers life before the web, navigated life as it emerged, and might even experience life after it—more on that intriguing thought soon.

Web browsers hold a special place in my heart. Having spent a few formative years at one in the valley, I gained deep respect for the subtle complexities of the web's presentation layer. Unfortunately, outside giants like Google and Apple, there aren't many browser companies thriving today. One of the most exciting independent browser projects recently shuttered its web project, signaling a poignant shift.

Yet, despite these challenges, we find ourselves standing at the brink of the web’s next evolutionary leap. Whether you call it Web 3.0, 4.0, 5.0, or simply "the Web + AI," it's clear we’re witnessing something fundamentally new.

Previously, AI sat atop the web—think those handy recommendation engines or chatbots popping up everywhere. But today, AI is embedding itself deep within the fabric of the web itself. My friend Brian O’Kelley seems to share this perspective, too.

If you run a web-based business, you've probably noticed your organic traffic declining. Let’s be honest—it's not fun. But here’s the intriguing flip side: if your brand is genuinely authoritative and stands for something meaningful, your "LLM traffic" (traffic driven by Large Language Models like ChatGPT) might be quietly rising. I’ve tested this with several of my portfolio companies, and visitor-for-visitor, this new LLM-driven audience is significantly more qualified and engaged.

So, what does this imply? Most brands will likely see less sheer volume of traffic from AI-driven queries, but what they lose in quantity, they gain in quality. This points to a web experience that's far more personalized, targeted, and valuable for both users and businesses.

It's no accident Nvidia’s stock is soaring—this AI-driven future demands massive computational power to deliver personalized web experiences rendered in real-time.

I get excited thinking about when our personal AI agents start seamlessly interacting with businesses’ AI agents. Imagine your own digital advocate negotiating on your behalf—this is when the web truly leaps forward, becoming not just smart, but actively intelligent. Welcome to the next chapter.

If you subscribe to the Operating Partner letter, this all probably matters a lot to your career.  Are you currently putting in the foundational work to ready yourself for the evolution?

Below are a few articles I came across this past week that I found interesting. While I may not agree with everything in each one, I think they're worth a read. If you stumble upon an article you think I or the Operating Partner community would enjoy, feel free to share it with me. Of course, I reserve the right to decide what gets featured in the OP.

Thank you for reading and subscribing. I hope you enjoyed OP #297!

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