OP #312: Culture in the Cloud (Tokyo Edition)

An abbreviated OP written while 39,000 feet traveling to Tokyo, Japan.

Author

Darren Herman
November 04, 2025

I’m on hour ten of a thirteen-hour flight to Tokyo. I’ve already done the three-hour hop through Minneapolis, and since I’m one of those people who can’t sleep on planes, I’ve run out of distractions. Two movies down. A handful of Mr. Beast episodes. Now, I’m here, writing this letter somewhere over the Pacific.

This trip is for business — a workshop to help one of our portfolio companies imagine the future with AI. But I came out a day early to wander Tokyo, visit a few stores I’ve been quietly following on Instagram and TikTok, and get re-inspired. The last time I was in Japan was 2014, during my Mozilla days, passing through Tokyo on my way back from Hong Kong. So, this feels overdue.

The workshop will be led by a friend I’ve known for two decades, which makes it even better. We’ll talk about AI by day and sushi by night. Not a bad setup.

It’s strange being thirteen hours in the future — literally. When I’m waking up, my family back in Boston is winding down. I travel a lot, but this one hits differently. It’s not the length of the trip; it’s the distance.

Anyway, enough about me and time zones.

Auren Hoffman recently published his November Reads newsletter — if you’re not subscribed, you should be. Auren, who founded LiveRamp, curates one of the sharpest monthly letters I read. It’s like the OP, but with his mind steering the ship.

One of the pieces he linked to explored the decline of print — and, by extension, the decline of reading. A sobering thought. I see it happening in real life: attention spans shrinking, depth giving way to dopamine.

He also touched on something I’ve been noticing too — the rise of AI-generated content creeping across YouTube, TikTok, and Instagram. Entire “podcasts” built in NotebookLM are being uploaded and passed off as the real thing. And honestly, more than half of listeners probably can’t tell the difference.

If we thought the world was digital before, buckle up. We’re entering a full-blown AI renaissance — unregulated, raw, and fast-moving. Someone once told me that legislation always follows innovation. That means we’re in the free-for-all phase, where creativity and chaos coexist. I’m both excited and uneasy about what’s ahead.

I’m part of a small watch photography chat on Instagram — twenty photographers (and one wannabe: me) swapping shots, gear, and editing tricks. Lately, AI has become part of that conversation too. My take? I love how AI can make workflows cleaner — remove dust from a dial, fix glare — but I don’t want it creating the whole image. Photography is craft. It’s human. I want to see the imperfections that make it real.

It’s ironic, though. Because in my day job, AI-generated content is the hottest topic across our portfolio companies. Every marketing survey mentions it. Every CMO wants to figure it out.

That’s what I’m wrestling with somewhere over the Pacific:
Where does the craft end and the code begin?

This is a modified OP due to travel and time zones. I hope you enjoy.

Happy Tuesday.
Darren

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 subscribing to the modified OP #312. I truly appreciate your time and attention each week.

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