Practicing Wisdom — Issue #6
1. What I Learned This Week
Theme: “From Platform Empires to Lonely Kings: A Map of Power, Connection, and Incentive Decay”
This week’s reading list tied together how scale reshapes meaning.
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Alphabet’s history is a case study in a company that stopped being a product and started being an infrastructure. In the span of a decade, Google went from “search company” to a civilization-scale operating system: email, maps, mobile OS, video, browser, cloud. Each product didn’t just succeed — it changed user expectations. Search taught us information should be free. Gmail taught us storage should be infinite. Android taught us open-source could outmaneuver closed gardens — if you had billions in ad revenue to subsidize it.
And yet, Alphabet’s success came with a cost: the collapse of narrative coherence. Are they an ad network? A research lab? An AI company? A holding company? Like many scaled entities, they now resemble a nation more than a business — and like nations, their internal contradictions are starting to surface.
One of those contradictions lives inside modern software itself.
In Stuff Costs Money, Benn Stancil takes aim at the romanticism of open source — not to mock it, but to mourn it. The story arc is familiar: build in public, go viral, raise money, feel guilty, commercialize, get yelled at. The soul-searching is sincere, but the outcome is almost always the same: eventually, free becomes too expensive to maintain. And the idealist becomes a capitalist — or a casualty.
Meanwhile, Scott Galloway’s Lonely Fans explores another system under strain: human connection. He argues that OnlyFans isn’t a sideshow; it’s a signal. It’s not just a business model — it’s the monetization of loneliness. When men stop dating and women stream to creator platforms, we aren’t just seeing a new economy emerge. We’re seeing an old one collapse: the relational economy of family, community, and analog intimacy.
I once read something by Carl Jung that acknowledged that any organization’s (call it a group, company, nation) morality is inversely proportional to the number of people involved. If you work at a company with five people and something immoral happens there is a low level of plausible deniability that you could not or should not have done something about it. But what if the company has 50,000 employees? At each level of scale it becomes more likely that you can point the finger at someone else and say “that person is more responsible for fixing the issue than I am” - whether that is true or not, it may be more plausible the larger the organization. That has worrisome implications when we talk about scale.
Google scaled until it became invisible. Software startups scaled until they had to shed their ideals. And intimacy itself is now scalable — but only as a service, not a relationship.
On a much more positive note, Alpha School is one of the most interesting stories I have come across in a long time.
Joe Liemandt’s experiment is a radical act of reconstruction: to take a 200-year-old institution and rebuild it from first principles. School, he argues, should be two things: (1) effective, and (2) loved by kids. That’s it. Using AI tutors, mastery-based progression, and compressed two-hour academic days, Alpha flips the entire model. The rest of the day is spent on life skills, projects, socialization — the stuff school was supposed to teach us, but never really did.
Let’s play with these ideas:
The internet gave us scale, but made us lonely.
The platforms gave us leverage, but take away soul.
And school, of all things, might now be the place where we learn how to be human again.
We’re living in the age of “platform decay.” What began as liberation now resembles entrapment. The most subversive act of this century may be returning scaled systems to their human scale.
Sources Referenced
“Building Alpha School and the Future of Education ” — Invest Like the Best Podcast (link)
“Stuff Costs Money” — Benn Stancil, Substack (link)
“Alphabet” - Acquired (link)
“Open Banking and Payments Competition” - Bits About Money (link)
Lonely Fans - No Mercy No Malice (link)
2. Key Distillations
“Scale always creates a second business: maintaining the narrative.” - Google was a search engine. Now it’s a nation-state with identity crisis.
“Schools don’t teach faster because they’re not allowed to teach differently.” - What looks like tradition is often just an outdated constraint masquerading as wisdom.
“‘Open’ isn’t a business model; it’s a phase.” - Every idealist eventually meets their margin.
“In payments, the interface hides the empire.” - Banks fear Open Banking not because of what users see — but because of what they might choose.
“You can’t out-market bad incentives.” - Whether it’s schools, banks, or startups — if the economics are broken, the story eventually breaks too.
“The longer an institution’s form goes unchallenged, the more we confuse it for function.”
3. One Contrarian Viewpoint
The modern SaaS stack is overfitted to yesterday’s problems.
Joe Liemandt’s boldest claim wasn’t about kids — it was about software. He believes traditional SaaS is entering an AI-driven extinction event. Not because SaaS is bad, but because it was optimized for a world of structured work and human-in-the-loop workflows. AI flips that. Now, the product is not the workflow — it's the output. If that’s true, then most SaaS companies today are selling training wheels for bikes that don’t need riders anymore.
4. One Investable Idea
AI tutors will create a new education stack — and make local schools obsolete as the default.
Liemandt’s Alpha School isn't just a private school. It’s a full-stack bet on the replacement of the public education format. The key insight is compression: if academics only need 2 hours a day, and outcomes are 2x better, then the remaining 6 hours can be optimized for everything else: leadership, teamwork, social-emotional growth. The business opportunity isn’t selling to schools — it’s replacing them. Look for platforms that offer AI tutoring + community + project-based social development — especially outside elite metros.
5. From the Archives: A Recall Highlight
“The most scalable tool in the world is a good default.”
— Issue #002
Still true. Especially in education and payments. The defaults are failing us — and redesigning them may be the most leverage-rich work of the next decade.
