I ran a short-lived experiment where I was writing time-boxed content on another site five months ago, and ultimately got busy with life.
I figured I should consolidate all my writing in one place.
So here are those varying pieces:
A Toast to Toasts
The Twitter Ouroboros
Adverse Incentives & Junior VCs
Spotif[AI] Between a Rock & a Hard Place
A Toast to Toasts - 1.17.25
Toasts aren't given enough anymore. Weddings mostly, sometimes birthdays, and once in a work party blue moon is a glass clinked and a pleasantry orated.
That's a shame. There's something special about a toast well wrought.
I'd argue that toasting is the real purpose for your high school public speaking class. Not the bullshit college powerpoints or myriad factoid vomits you will deliver your corporate overlords. The class failed you for the opportunities you'll have to warm a room and cheer your comrades. The perfect toast on a shimmering night can be romantic, it can be impactful.
I found myself toasting twice recently.
Ukrainian Dinner
The former was Ukrainian Dinner. My very dear friend has a hairbrained tradition-- Ukrainian Dinner. He's not Ukrainian. No one at the party was. No one at its founding was. But that's the theme. Between borscht and vodka, toasts are required of all who attend. Passed down from a friend of a friend, it's now an annual tradition, and it brings about toasts that only a half decade affair can.
As such, you can't come empty handed. Sure, a first timer can mumble through a tip to the host's good health. But a repeat offender appreciates the gravity. It's an occasion to be inventive in flattery of your friends; it's not often we publicly praise the people that enrich our lives. Everyone brings their 'A' game.
There's something magical about it. The room warm with laughs and familiar faces, a rotating cast around the core contingent. Between bouts of conversation, a chair will creak back and the next speech is at hand. It's a collective act of creativity that nurtures the wit we often neglect.
Beach Birthday
For my friends' fortieth birthday, they went all out. A trip to somewhere tropical with her best mates in tow. Amidst the preparations, her thoughtful husband asked the attendees to come with toasts in-hand, to be delivered throughout the course of the vacation. The results were tremendous.
Little riffs delivered from the heart. Some short. Some sweet. Some quick. Some long. People played with ideas and remixed the ask to their liking. Themes emerged over the first couple, and were played with by later toasters. Some made us laugh and some made us cry, with an authenticity that only small silly circles can create.
In our bland, flavorless world, it's a creative complement to the breaking of bread. I lament that these brief moments of human connection are so infrequent. And so I say, a toast to toasts, and adding a bit more spice to your life.
// 🍋
The Twitter Ouroboros - 1.15.25
"The internet introduces a world in which the importance and the difficulty of having principles is skyrocketed." - Ben Thompson
This quote comes from Ben's discussion breaking down Meta's recent content moderation changes. The internet pervades my life, and as I've leaned into social networks increasingly over the last twelve months, I've started to see the ouroboros cycle of self delusion that can emerge.
You read, you write, you chatter, you meme.
It's all fun and games as you banter back and forth. Yet... at some point you start to see just how narrow your feed becomes.
Twitter isn't as inherently recursive as a platform like TikTok, whose 'for you' lives to reinforce your slightest indulgences, yet it's very easy to find yourself within a homogeneous pool of thought. I meander through Crypto Twitter, then Tech Twitter, then American Dynamist central, and suddenly they've all got blurring views converging on groupthink.
The more you lean into a space like Twitter, contributing, conversing, and clashing with its inhabitants, the more you find yourself engulfed by its information stream. And realizing just how extremely that broad stream flows in only one direction. This is self-evident, but there are multiple layers at play: some amount of increased exposure (more consumption), some amount of increased engagement (more contribution), and some amount of psychological rationalization (more contemplation). The latter, I believe, is the more subtle.
We all view ourselves as being above the indoctrination of these platforms and their bedeviling algorithms, but therein lies the danger. Like your friend with a coke habit-- not perhaps outwardly acting as an addict, but always toting it along on any given outing and always at hand for their compulsive indulgence. It isn't a single Tweet that indoctrinates an addict, but the subtle slide of months engrossed in a singular point of view. The more you discuss and the more you contribute, the more likely your sense of investment is to rationalize and erode your original viewpoints in the slide toward your repetitive platform exposure.
Some of this is being dramatic. But it's important self-awareness.
So, this year I'm looking at my information diet, I'm reexamining my principles, and I'm trying to double down on refining my own voice.
This brain blast was prompted in part by Mario Gabrielle's resolution to cut his own social media exposure. I've paraphrased or bastardized a few of his ideas above, but I'll end with its relevance in a world of AI:
"Surrendering to that momentum by donating your attention is a step toward losing ownership of your mind. It is too easy to find yourself adopting opinions and preferences you haven’t thought through but that are part of the fabric of these networks.
It has always been useful to be inventive, but it is increasingly essential as AI continues to bolt knowledge work in great hungry gulps. If it has not happened already, very soon, our greatest advantage will simply be the ability to think as ourselves — to rely on our unique accumulated training data and apply our singular algorithm. The more your data and algorithm adhere to the dominant monoculture, the less you will have to offer.
As much as possible, I would like to ensure that I continue thinking like myself rather than running someone else’s program." - Mario Gabrielle, Monk Mode
It's about getting smarter with WynnGPT. Discerning training and careful curation for feeding my own wrinkled wetware a higher quality diet.
// 🍋
Note: Article.app pieces are time-boxed, stream of consciousness for the most part. Expect errors, warts, and fallacies.
Adverse Incentives & Junior VCs - 1.9.25
“Show me the incentives, I’ll show you the outcome.” - Charlie Munger
Adverse incentives abound in venture. From “Founder first!” VCs shackled by fiduciary duties to “Long term capital partners!” needing liquidity in 24mo, it can be a confounding headache for the uninformed.
I think this is particularly prevalent when founders meet with Junior VCs.
Analysts/Associates are often stuck between a rock and a hard place, and many toe the line of safety to the detriment of founders. “Too early!” or “Not right now!” are often coded for “We don’t think you’re the team” or “We think this is Tinder for Dogs”. Responses are often mushy pleasantries devoid of substance.
But what leads to this behavior?
A few things:
— Venture is a long term game, and the longer you’re here, the more surprises you see. Tinder for Dogs might pivot to the Dog Walking Unicorn. Every VC is balancing feedback with keeping the door open to future conversations…
— … and many founders do not like being told their baby is ugly, even if feedback could be productive. So, many Juniors fall victim to a flawed risk-reward calculus that fizzles down to “We’ll circle back!”
— Plus, many Juniors believe they have neither the bona fides (builder experience, track record) nor the platform (founder/partner/title) to speak authoritatively in a way that will find founders receptive. Khosla can torch your idea because he’s Khosla; the proof is in the pudding. Johnny Junior can torch his reputation with a bit of spicier feedback poorly communicated.
Counterintuitively though, in seeking safety, many Juniors do injury to themselves and their brands as non-committal, wish-washy, fake, or memetic (“How can I be helpful!”).
The best investors have brands of being honest and providing quick “No’s” with actionable advice. In fearing polarity, Juniors often relegate themselves to the milquetoast pack of mediocrity.
I’ve done this. I’m not proud of it.
As I’m in the space longer, I get more comfortable with my voice, my value add, and where I think I have room to impart something thoughtful and where I should really shut my dumb mouth. But it’s still a balancing act. We’re in a very human business.
As frustrating as it is, founders should be aware of the game they’re playing and the incentives across the table.
// 🍋
Spotif[AI] Between a Rock & a Hard Place - 1.3.25
Spotify has to be in such a strategically frustrating spot right now.
If they integrate UGC (AI-generated music) from subscribers natively, they'll likely get a revolt from the artists + labels.
So, they're stuck waiting for an AI music platform to start disrupting them, at which point they'll be forced to acquire it at an exorbitant premium once the market/zeitgeist attenuates to this type of content. By the time that it's possible (or even allowable) for Spotify to enter that race, it will (definitionally) be won.
In a perfect world, it seems logical to me that Spotify would leverage its huge distribution advantage and simply empower its deep user base to become creators. A kind of Roblox judo move that keeps the created content on their platform and embeds additional monetization opportunities (tokens for generation, improved sound design, new subscription tier).
The classic 'creative destruction', attempting to cannibalize one's core business in order to attack adjacencies and shimmy up the next j-curve.
Unfortunately, this seems to be impossible (or incredibly challenging, to say the least). Attempting this kind of product expansion would likely be armageddon for its core business as the company was threatened by myriad lawsuits, artist desertions, and copyright infringements (how was the AI trained? on what songs? etc.). It would slaughter the cash cow in a recursive fashion, destroying the viability of the AI product launch at the same time as the user-base's original value proposition collapsed.
I think that Spoitfy is stuck over a barrel. The legal inertia from their agreements with record labels (supplier power - Porter's 5 Forces) acts as a hard stop inhibiting Spotify from taking the necessary steps in order to truly leverage the AI revolution (at this point).
And we've seen this with the platform's lukewarm attempts to interweave AI so far:
AI DJ: a marginal improvement over the legacy Radio feature
AI Thumbnail Generation for Playlists: a nice to have, but minimally improving an audio-centric platform
Generative Playlists: text-to-playlist (type mood, theme, etc.). Seems to overindex on your likes/current playlists. Eh.
But perhaps this is a bit myopic, disregarding:
AI generated podcasts
Artists leveraging AI in creation, production, song-writing, audio-engineering, etc.
AI song generation platforms (Suno, et al)
Maybe AI in the music stack simply sits elsewhere than the DSPs, with value leaking from their walled gardens.
Then-again, they may simply go with a Second Mover strategy: sidestep the legal landmines and let some disruptive player navigate the headaches to establish a market, then either buy or build into it in classic Apple fashion.
This core business question could certainly be motivating (in part) their emphasis on introducing video as well as their rolling up of other audio content, namely podcasts and audiobooks which drive significantly higher margins.
All said, I'm a huge fan of the platform and optimistic for the future, and excited to see how larger brains than mine grapple with this conundrum in real time.
// 🍋
Maybe I’ll get my writing back on track. Maybe not.
We’ll see.
// 🍋