Camcorders are back, let's hang in SF, tune into my weekly livestreams?

August 4 weekly update.

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Make Analog Great Again

I had the pleasure of attending a FeedMe / Technology Brothers party at San Vicente in The Jane Hotel last Thursday. It was a very fun evening that included an eclectic crew of media personalities, startup founders, operators, at least a few dozen of my “Twitter friends,” and several other people whose faces I recognized but names I couldn’t recall. That’s becoming an increasingly annoying thing: recognizing someone’s face but not their name. I imagine that sooner or later we’ll all have AI wearable tech that can quickly recognize someone’s face and zap an instant “TLDR” about them to your brain via Elon Musk’s Neuralink, but until then, I need some better mnemonic tricks.

Anyway, the fact that this party was pulled together in around a week is quite impressive. Kudos to Emily, John, and Jordi for a party well-done.

Discussing the intersect of technology and art with my good friend Hunter.

One of the more interesting side plots of this evening was my friend Zach Pogrob walking around recording the party on a 2000s cam-corder. Zach has built a big following, particularly on Instagram, over the last few years, and a couple of weeks ago, he started recording day in the life vlogs on a 25-year-old camcorder. See below for a partial recording of last Thursday’s vlog (feat. me, among a few others).

(You can watch the full-length videos, with sound, on his X account.)

A few weeks ago, when I flew home for a post-book trip to see my family, my mom showed me a few tapes that she had recovered from when I was ~3. (Considering that I was born in 1997, they were probably recorded on the same camcorder Zach is using in 2025). When you’re watching your three-year-old self discuss, with a comically-strong southern drawl, what he wants to eat for lunch, the grainy quality of the video is part of the charm. The imperfections are the catalysts for nostalgia: they make the whole recording feel “real.”

That same phenomenon kicked in when I watched Zach’s recording from last Thursday’s party. The whole video felt more raw, and less performative, than most of the content I see online now. And that rawness was welcoming.

We live in a world today where you can “write” blog posts in minutes with ChatGPT, generate full-length videos using prompts with Google’s Veo3, and automatically remove every “like” and “um” from a podcast recording with AI transcription tools. Photos taken on your iPhone are automatically digitally-enhanced, and it’s safe to assume any “Instagram model” looks nothing like their profile in the real world because every image is edited beyond the point of recognition.

“Good” content is cheap and automatic, and thanks to the explosion in AI tools, it’s difficult to know what content is “real.” In fact, the more “perfect” that something is, the less likely it is to be “real” in 2025. The result? We now trust, desire, and appreciate the things that “look worse” because they feel authentic. That’s why polaroids at a wedding, handwritten letters with a few typos, or videos recorded on a 2000 camcorder are quietly becoming more appealing than digitally-enhanced iPhone photos or text messages and DMs. Even if you haven’t realized that you feel this way, I bet your intuition picks up on it. An example:

I grabbed dinner at Gurney’s in Montauk with a few friends last Saturday, and a couple of girls at the bar snapped a few photos of us. Look at these two photos below. Which is the “better” picture, meaning higher pixel count and image clarity, and which picture “feels” more real?

The second picture is, objectively, “better.” You can read the hour and minute hand on our watches and see the individual hairs on our heads. The clarity with which iPhones can now take photos is incredible. But the first photo feels more “real.” Like, the former is the actual memory, and the latter is like a digital manifestation of the memory. We like the “worse” photo more because it’s “real.”

As “perfect” content becomes easier and easier to create, I think we’re going to experience a collective wave of desire for simpler, less “perfect” outputs. I have a couple of reasons for this thesis:

First, technology is advancing at such a rapid pace right now (new tools and AI model improvements seem to roll out daily), that it’s just exhausting to keep up with everything. If your work even vaguely touches the tech world, I’m sure you’ve felt anxious to stay on top of new trends and developments, and if you don’t work in or around tech, you might feel hopelessly lost with no chance of catching up. When the current rate of change of technology is anxiety-inducing, “antiquated” techniques welcome us with a warm embrace that says, “It’s alright to not be on the cutting edge of everything.” They provide a much-needed escape from the our never-ending acceleration.

Second, because we can mass-produce “flawless” content, “flawless” content now feels cheap. It’s supply and demand: when you can generate 100s of blemish-free photos, podcast “recordings” without a single grammatical error, and detailed “research reports” in seconds, the value of these outputs drop to zero. AI made efficiency so simple that “efficiency” alone lost its value. Things that take time, that can’t be faked, have only grown scarcer in a world where everything is rushed, and that scarcity is valuable. You’re only going to get a couple of polaroid photos at a wedding, but I bet the wave of nostalgia that hits when you look at that one blurred print you keep in your wallet is a magnitude stronger than when you scroll through the 500 other pictures saved on your phone from the same weekend. The gravity of a handwritten letter, whether from an appreciative former student to his mentor or from an infatuated bachelor to his new love interest, carries 10x more weight in a world dominated by voice notes and ChatGPT-prompted messages. Higher friction = higher value when perfect = free.

To be clear, I don’t think we’ll see most content revert to higher friction forms. In fact, I believe we’re in the early innings of an AI-content slopfest the likes of which the world has never seen. But our appreciation of higher-friction forms of communication and content creation will only increase as technology continues to push efficiency over everything. More camcorder videos, less Italian brainrot, please.

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What I’m Working On:

Dinners, drinks, and more in San Francisco

When I initially moved to San Francisco last February, I didn’t have a lot of free time outside of work to hang out with people as I spent most of Monday through Friday trying to learn how to be a VC, and most of my evenings and weekends trying to write a book. I’m flying back to San Francisco in two weeks, and this time around I’d like to actually hang out with some more interesting people in SF. I have personal and professional reasons for this: 1) I’m a fun-maximalist who thinks that spending time with fun people is the best possible use of one’s time. 2) I do work for a venture capital fund that gets paid for investing in particularly compelling folks, and I’d like to increase my surface area for meeting such folks. Some people say not to mix your personal life and professional life. I actually think that’s a pretty stupid outlook given that you spend at least half of your waking hours working, so if hanging out with interesting folks happens to benefit my career… good? I say all that to say that I’ll be hosting some official-ish dinners with different founders and generally interesting people this fall, and I would obviously love to have several non-official meals/drinks with folks in the area as well. So, hit me up, or tell your friends who are either 1) fun to chill with, 2) are crazy enough to start a company (and you actually think highly enough of them that you’d put your own money in to help fund it), or 3) both to hit me up as well.

Podcast-ish:

Megan and I have started recording weekly livestreams where we talk about all things “Creator Investing,” as well as whatever else we’re working on that week, on X and Linkedin (ideally I’ll add Substack or some other platforms as well soon). These are 1) just very fun in general and 2) a cool way to “go direct” with some of the stuff we’re working on at Slow. Tune in later this week and catch the next one.

Book Update:

I’m going to start working through my manuscript edits in a couple of weeks (it does seem like I’m just running back my spring 2025 playbook: spending all of my free time working on a book, though I’m confident the editing process will be far less intense than the writing process). Separately, I’m curious if anyone things I should record an audiobook. I quite like to talk, so it seems like a good idea. Anyway I should be done with all edits and such in less than two months, which is fantastic.

Ideas I’ve been thinking about:

• Consultants are the real AI winners: Last summer, I wrote an article discussing how Accenture was actually one of the biggest “AI winners” with higher annualized AI revenue than OpenAI in Q2 2024. The reason: companies are paying unlimited money to figure out how to “integrate” AI. I saw another example of this today, when my man Khe Hy, who spent his early career on Wall Street, tweeted that after he started documenting his journey down the AI rabbit hole, multiple buyside firms reached out for him to help their teams figure out how to implement AI. The result: Khe had a new career arc for him. If you have sector-specific knowledge in a particular field and you know AI pretty well (not, like, ML researcher-level well, but “here’s how you should use these tools in your work-level well), you could probably have a lucrative next few years. Something to think about.

• Our labor market is increasingly focused on keeping old people alive: Last week, Derek Thompson had a particularly funny tweet regarding recent labor market and GDP numbers:

  

  He’s not wrong. Per the most recent nonfarm payroll numbers, 73,000 new jobs were created… including 73,000 new jobs in health care and social assistance. This is obviously going to become more and more of a thing because young people aren’t getting married or having kids, old people are getting older and older without dying, and, for the first time in most of human history, old people also have most of the money, meaning they can afford to pay for specialized care. For most of history it wasn’t normal for the elderly to possess most of society’s wealth, but mass asset ownership + price appreciation combined with fixed income like social security has created a system where younger generations are increasingly “paying for” (both literally, via social security taxes, and implicitly, as consumers of goods that generate revenue for publicly traded companies whose stock prices go up) old people’s lives, and those old people are increasingly “hiring” young people to help them stay alive. Again, this is not “normal” in a historical context, but it is the way our world is structured now. It’s interesting to think about the longer-term economic and cultural impacts as this trend accelerates.

Things I enjoyed from the past week:

• I used to find Scott Galloway’s content to be a bit midwit, but I’ve since come around and really started enjoying his newsletter. He wrote an excellent piece last week on the importance of male friendships in adulthood.

• Ben Thompson’s last article on Figma and how it might be well-positioned as an AI winner due to it being the go-to collaborative design platform (the “platform” wins by integrating well with an ever-expanding list of tag-on tools) is very good.

• Since April, I’ve been using Sublime to bookmark and track any and all interesting content that I come across and want to read later, and I have found it quite, quite useful. Each week I save tweets, blogs, podcasts, etc to digest after work and on the weekend, and I also occasionally save in-line quotes that I might want to refer back to later. If you also have the problem of flagging a dozen “interesting articles” that you never actually circle back to read, I’d check it out.

Also, let me know what you think about this newsletter format. I think I enjoy it.

- Jack

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