Vibe Coding, Investing in Creators, and Summer "Out East."

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Brief programming update:

The reader / writer relationship can, and should, be a collaborative experience, and considering that I pay rent by doing my best to 1) write interesting things and 2) invest in people building interesting things, I want to open this newsletter up a bit.

Outside of my normal blog posts, I have other projects I’m working on, ideas I’m thinking about, investments I’m interested in, and content I’ve found compelling that I’d like to share and discuss with you more regularly, and crowding a bunch of links as footnotes below 2,000 word blog posts is hardly the most effective way to do that. So, each Monday going forward, I’ll send a weekly newsletter discussing an idea I’m particularly interested in (either from last week’s blog or a new idea I’ve been pondering), other content I published last week, side projects I’m working on, ideas I’m interested in learning more about, and content I’ve found particularly valuable.

If you’re interested in anything that I’m working on (and especially if you know a lot about a particular thing that I’m just starting to dig into), then I would love to hear from you. Shoot me a note or leave a comment.

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My Experience with Vibe Coding

The ability to create simple software tools without having an extensive coding background has been my favorite aspect of the AI boom. In an effort to get more familiar with these tools’ capabilities (and limitations), I’ve forced myself to build tools that make my life better as opportunities to do so emerge. Last week, I published a new blog discussing my experience “vibe coding” and how I built a Spanish translation tool for newsletters that hit my inbox.

A preview of that blog:

I think most “non-technical” people like myself find the idea of “coding” or “programming” to be intimidating. I certainly found it intimidating. Having failed to learn how to code when I was in college, I had told myself that it simply wasn’t for me, I wouldn’t get around to it, and it would just be a skillset that I would always lack. But “coding” is really just telling your computer to generate a specific output, and the barrier to at least experimenting with all of this stuff now is simply a couple of hours of free-time, a bit of curiosity, and the ability to ask a few good questions and follow directions.

And you learn so much more by doing the thing than simply reading about the thing.

I now have at least a novice understanding of how Vercel works, how web hooks work, how API calls work, and where the “prompt” that actually translates my emails to Spanish fits in my code base. It would only take me ~5 minutes to build this same tool to translate newsletters to French. Or Mandarin. Or Hebrew. Or Italian. The reason is that, by virtue of “doing the work,” I have a more thorough understanding of the logic underpinning the work.

And an underrated benefit of an exercise like this: it instilled confidence. Building any sort of “software,” even something as simple as a newsletter translation tool, makes “technical” things so much less intimidating.

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What I’m Working On:

1) Investing in creators.

I joined an early-stage venture fund, Slow Ventures, in January, and a few months back, we launched a dedicated fund to invest directly in “Creators” and “Creator-led businesses.”

While the last 15 years of “venture capital” has largely consisted of investors giving two giga-IQ MIT or Stanford dropouts millions of dollars to build software companies, venture capital, at its core, is supposed to fuel the growth of massive, important businesses. Great founders and compelling businesses take many different shapes and sizes, and our thesis is that creators with distribution and high-trust audiences that are building in high-value verticals are immaculately-positioned to build sick businesses.

The Stanford kids might build a cool product, but they still have to market and sell it. Sales is a bit easier when you have 1.7 million YouTube subscribers.

That being said, we’re not interested in “influencers.” We’re looking for entrepreneurs who want to build killer businesses (as opposed to leveraging their platforms as billboards for other brands), know their community well, have a cult-like following in their respective niche, and have, ideally, at least mid-six-figure follower counts and annual revenue. We want to catch these creators at their inflection points and provide capital for them to build businesses on top of their platforms.

I’m spending most of my summer focusing on our Creator Fund, so if you are (or if you know anyone who is) a creator that fits this description, I’d like to chat.

*For a more detailed description of the types of creators we’re looking to back, check out the four most recent “What We Look For” blog posts written by Megan Lightcap (Partner on Slow’s Creator Fund)

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2) If you’re in the Hamptons sometime this summer, let’s hang.

Back in November, my two roommates and I decided that it was probably time to “grow up” and get our own apartments when our current lease ended. However, for one last hoorah of extended adolescence, we rented an Airbnb with four other friends for a month in East Hampton to close out the summer before embracing the post-roommate stage of life. Three days in, we’ve been having a blast. For anyone grasping onto the twilight of their adolescence, I would highly recommend embarking on a similar adventure before riding off into the sunset of your post-roommate life. Anyway, If you happen to be in the Hamptons over the next three weekends, and especially if you’re a creator or a startup founder working on anything particularly interesting, shoot me a note. $14 latte and/or adult beverage on me.

3) Rebuilding private markets one email at a time.

One of the projects I’ve been working on since joining Slow Ventures has been building an email list for facilitating private-to-private transactions between institutional investors. Private markets are highly fragmented across a dozens of private stock-trading platforms, and brokers run opaque processes for pairing parties (while charging fees along the way). So we launched a weekly email list for institutional investors to express interest in buying/selling different stock where we pair willing buyers and sellers. If you’re an investor at a VC/GE/PE fund and want to learn more / get involved, check out our site here.

4) Spanish lessons round 3.

Duolingo is a phenomenal business but a terrible way to actually learn a foreign language. I’m regularly practicing Spanish again, and in my humble (gringo) opinion, you pretty much have to speak with a native speaker regularly, with no English involved, to actually make notable improvements. I’ve been taking hourly lessons on italki for like $10 an hour. The TLDR with italki is that you can search for professors by country and language and pay for 1 on 1 lessons. It’s great. My professor Andrea is just lovely; she’s basically a Colombian aunt for me at this point. I’ve been taking “lessons” with her for like 2 years at this point, and these lessons are really just us riffing about life.

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Ideas I’m interested in:

• All things equestrian: If you nerd out on the equestrian world / know the horse competition market well, I’d love to chat.

• Weird, niche, conferences: If you’re particularly obsessed with a “thing” that a lot of people are obsessed with, like Dungeons and Dragons, and your “thing” has a conference, convention, or some other IRL gathering that you spend real money to attend, lmk. If it feels like a cult, even better.

• AI is making us stupid: The ability to generate an acceptable answer via AI overlord chat interface without having to do the hard work (read: thinking) to create that answer is going to make us stupider, no? Knowledge compounds, but answers =/= knowledge. The work of figuring out how to get to the answer, over time, builds a cerebral plumbing system that develops your intuition. It is, obviously, bad that we are increasingly outsourcing “thinking” for the sake of efficiency, and I’m curious what the work might look like after a generation of kids spend years using ChatGPT for literally everything. The folks who consistently “win” LLM search results are going to make so much money.

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What I’m reading / listening to:

• An inmate serving life in prison for selling drugs on the dark web has been working as a software engineer for database company Turso. Pretty cool to see someone getting a second chance, digitally, while behind bars. Given that inmates often struggle to adjust to labor markets when they re-enter society (leading to really high return to custody rates), the opportunity to work remote from prison seems like a huge net positive to society.

• Sam Lessin just turned 42 (happy belated, boss) and re-shared a reflection post from his 40th birthday on X. Some gems in here, particularly on navigating the pursuit of “option value” vs. identifying one’s Summum bonum.

• I thought this was a particularly interesting blog post about modern society’s increasing preference for taking outsized risks for the chance at hitting “jackpot,” regardless of the probability of that outcome, as “upward mobility” through hard work and “making an honest living” feels increasingly unachievable due to inflation, wage stagnation while asset prices boom, and technological disruptions of labor markets.

• This conversation between Patrick O’Shaughnessy and Adam Sandow on weird, high-leverage business models built on top of print media is just fantastic. TLDR: media is a broken business model, but the distribution that comes with media companies can be incredibly lucrative. (This pattern matches our creator investment thesis, FWIW).

- Jack

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