GenZ, Dropout Nerds, and The Great Reorganization (What Cluely Taught Us)
Can we call it a Black Swan if it's plain to see what's coming?
The Signal We Can't Ignore
Earlier this year, two 21-year-olds who were suspended from Columbia for building an AI cheating tool launched a startup called Cluely. One of the founders, Roy Lee, also had an acceptance rescinded from Harvard for behavior the University found unbecoming. They raised $5.3 million in venture funding from firms like Abstract Ventures and Susa Ventures, creating a controversial "invisible assistant" that helps users during virtual exams, interviews, and sales calls through undetectable AI overlays. In the week they announced a subsequent $15 million investment from the good folks at Andreessen Horowitz.
Their hiring model is simple. You're either a world-class engineer or a creator with a six-figure audience or they’re not interested.
No middle managers.
No HR (for now).
No deadweight.
The team is lean. The energy is relentless. Employees live and work together. They care about mission alignment, speed, ownership, and precision. Other predominant companies llike Palantir and Perplexity operate from a similarly motivated playbook.
Cluely's specific application is ethically controversial; it's designed to help people cheat on interviews, at work, in school, anywhere and everywhere their overlay will help their customers know what they need to know to get the job, build the relationship, pass the class, appear to be something or know things they don’t.
Beyond the momentary controversy, you see something profound: two college dropouts built technology that universities and corporations are scrambling to detect and ban. They created a product and company in a matter of weeks with a fervent customer base and $15 million of Andreessen Horowitz’s capital (Interesting Note: Ben Horowitz is one of Columbia’s most celebrated alums.).
The media debate over cheating is irrelevant. The tech will win. The signal is that two very young people with generative tools can move faster than institutions with thousands of employees, and that attention and virality are new requirements for all the companies we are building (Gary Vaynerchuk is looking like quite the oracle, again).
I'm 44 years old and have been building my career for two decades. I studied economics at Harvard and the University of Chicago and spent my professional years operating, optimizing and growing companies. I've diligently built within the old operating system (Six Sigma, Lean systems, ISO 9001 compliance, OKRs, Agile, Scrum) and have a distinct fondness for the attributes of each.
But it’s time to be done.
The cost structures, cultural defaults, and professional ladders that once defined modern business are being quietly and permanently, dismantled. And for the well being of my family, I selfishly want to be on the right side of this transformation.
This has been a strange year, I've been walking away from clients, intentionally taking the smaller end of lucrative engagement opportunities, and have passed on a series of executive and director level roles with some incredible companies.
I’m not seeing enough urgency. The jobs still exist, for now. But the structures around them, the justifications, the hierarchies, the assumptions, are eroding. What replaces them will be something leaner, faster, more creative, more distributed. It will be powered by a mix of AI and human ingenuity that the old playbooks their running fail to address.
We’re watching the most overt Black Swan event in history.
The Old Dream Is Dying (Quietly)
For decades, we told ourselves a story: go to school, pick a profession, climb the ladder, stay in your lane, and security will follow.
But that dream relied on a few underlying truths that no longer hold: that coordination was expensive, that expertise was scarce, that repetitive labor couldn't be automated.
Many of us, myself included, have built careers doing work that existed only because computers couldn't do it yet.
All of that is dissapearing like strands of wet sand in the ocean’s current.
AI doesn't threaten the professions. It hollows them out from the inside.
In engineering, tools now write, refactor, and ship code. Salesforce has paused engineering hiring because its AI systems increased productivity by 30%. With a year’s worth of AI assisted training, and the benefit of all the updates that ship between now and then, I doubt I’ll need to ask engineering friends for assistance or help to build the software and applications I want to build, or to use the tools that will get me there. Twelve months from now entire tranches of engineering talent will no longer be needed. It’s not that we won’t need the most talented engineers, it’s that the most talented won’t need teams anywhere near the size they current require.
In law, generative AI handles legal research, summarization, document review, and even early-stage drafting. Goldman Sachs forecasts that 44% of legal work will be automated.
In accounting, reconciliation, audit prep, and tax strategy are increasingly being processed through intelligent platforms. The market for AI in accounting is growing at over 40% CAGR.
What remains in each of these fields is not the middle, it's the top talent that handles the last mile and the hardest problems. It is not the Harvards, Columbias, and MITs of the world that will be eliminated; it’s all those who perform the work that we consider technical today, but will quickly become administrative. Imagine the leverage the top talent, institutions and firms will have when they have deployed GenAI at scale and can service that many more customers, students and governments. Imagine how many profit dollars they will accumulate.
The same holds for the management consulting space, if McKinsey and BCG, are willing to set their egos and cultural aires aside and build products proliferate down market.
Judgment, synthesis, and creative problem-solving are the capacities future generations will popularly build for, not mathematical acumen, coding capacity, or the fast-twitch memory of accounting rules and legal precedent white collar professions have rewarded. Everything else is being handled by software. And when we need to go deep, we will rely on our trusty new generative assistants.
The Creator Is the New Company
While the old world compresses from the inside, a new economy is flourishing at the edges, while being laughed at by all the ladder climbers in skyscrapers with unfinished, vacant floors. Isn’t this precisely the state of play Clayton Christensen warned established companies against in The Innovator’s Dillema?
Goldman Sachs projects the creator economy will nearly double from its current $250 billion valuation to $480 billion by 2027, representing a compound annual growth rate of 10-20% driven by over 50 million active creators worldwide.
Scale is becoming the more manageable part of the equation, influence and attention are the variables to solve for now. Goldman Sachs notes that 61% of consumers trust creator recommendations more than traditional advertising, particularly among Gen Z and millennials.
The financial infrastructure is already adapting, with fintech companies like Karat and Willa emerging specifically to handle creators' irregular income streams and cross-border payment complexities. In the last 24 hours as I was constructing this article, Robinhood made a series of announcements, including the ability of their application to now offer investment into private markets, and expanded crypto access.
Goldman Sachs is documenting the emergence of a new economic model where individual humans, augmented by AI tools, can operate with the reach and revenue that once required entire corporations.
Between 2018 and 2020, a convergence of infrastructure made this possible: cloud costs dropped, payment rails matured, and social platforms shifted toward interest-based discovery. Anyone with skill and signal could suddenly participate at scale.
Call it the creator economy, but forget the implied cheap cultural innuendos. These aren't just content creators. These are individuals who own distribution, monetize attention, and operate with the scale and speed of teams that used to take dozens to match. The best creators today are founders, operators, and media companies rolled into one. The models they are originating will become standard operating procedure across the professional world of the future. Companies like Cluely and firms like A16Z are taking these models as directional for how they will build and scale the next corporate behemoths.
Gen Z Isn't Lazy. They're Just Early.
To many in the corporate world, Gen Z looks like a problem. They don't follow the old rules. They don't want to be in the office. They won't tolerate bad management. They leave quickly. They build on the side.
This is rational behavior on their part.
Gen Z came of age during a period of economic instability, rapid automation, and the mass disillusionment of "safe" jobs that manifested over COVID and then led into the layoffs we’ve seen since across the tech and financial sectors. They are betting on flexibility, purpose, autonomy, and leverage, not hierarchy, titles and the brands of the S&P 500.
They're not avoiding the ladder.
They've just realized there's no longer going to be much room at the top.
Metrics Can't See What's Happening
One of the reasons this transition feels "invisible" to many is that the systems we use to measure economic activity are outdated. GDP doesn't capture solo entrepreneurs making six figures through online products and affiliate sales. Employment statistics can't track AI-assisted microbusinesses built in Notion, Airtable, Cursor and ChatGPT.
If you're a 28-year-old running a six-figure business out of a browser, the government might still consider you underemployed.
We are reorganizing how value is created, but the data hasn't caught up.
From the Social Graph to the Interest Graph
The old world of distribution was based on who you knew.
The new world is based on what people care about.
Platforms like TikTok, Instagram Reels, and YouTube Shorts don't care who you are. They care what you make. And if it hits, it spreads fast. Cluely is emblematic of this truth. TikTok is leading with ads that show the small business success stories proliferating across its platform.
The shift from social graphs to interest graphs has made virality meritocratic. Anyone can win. And status doesn't accumulate; it has to be re-earned daily through cultural resonance. This means small creators can compete with ad-buys of large corporate marketing departments.
See Andrew Chen’s new piece:
Corpospeak: Why you still sound like a faceless corporate entity
You don't need a pedigree.
You need your humanity and creativity.
And in the algorithmic economy, your proof lives in your output.
The Flattening Firm
This is a Substack about operating companies, so back to the operating before we end: Inside companies, AI is not just replacing individual tasks it's erasing entire layers of coordination. Dashboards have replaced (and will continue replacing where they haven’t) middle managers. AI copilots are replacing project trackers. Internal comms is becoming a prompt template. Research departments are being compressed into a browser plugin and single lead researcher to synthesize all the output.
By 2026, 20% of companies are expected to eliminate half their middle management. Not because of cost-cutting, simply because they can.
Coordination is no longer expensive. It's becoming automatic.
And that changes everything about the design of our companies, the unit economics of their goods and services, and the structure of the markets within which they operate.
Here are just a few of the frameworks and systems AI is quietly rendering irrelevant:
Six Sigma — The model has already optimized the funnel
Agile — Standups? Your AI has already shipped the update
Scrum — Your burn-down chart is now a real-time dashboard
OKRs — The model adjusts KPIs in seconds
Gantt Charts — Pretty. Slow. Obsolete.
SWOT Analysis — ChatGPT simulated 500 scenarios while you brainstormed "Threats"
Balanced Scorecards — Your dashboard just ate your strategy deck
PMP — Project management, meet prompt engineering
Certifications are beginning to hold the value of the CD collection you forgot to take to the used record shop to sell in 2005.
If You’re Mid-Career This Should Feel Threatening
If you're reading this in your 40s or 50s and feel concerned or skeptical, I get it. You should feel those things. You've built expertise, climbed ladders, and invested decades in mastering systems that worked.
A quick story:
Last summer I had a college intern who arrived on day one of his work having never opened an Excel spreadsheet. I gave him a ChatGPT membership and assigned a group of analytical and data-cleansing tasks to be completed in Excel or Google Sheets (I didn’t care either way). Within 36 hours he had completed the first set of tasks with ease and within the first seven working days he was performing tasks with ease that had taken me 15 years to master. All of the work was done with ChatGPT and Google Script Editor. He didn’t write one equation into one cell, didn’t concern himself with Macros, and created output that was more flexible than anything I had anticipated receiving. He wasn’t a computer science major. I’m still trying to convince him to build his personal brand.
The choice isn't between the old way and chaos. It's between adapting now or being forced to adapt later, when you have less control over the terms.
The people who will thrive aren't necessarily the youngest or the most technical. They're the ones who recognize that collaboration with AI, building an online reputation, and testing ideas at speed are essential to the path forward.
You may still have the title, the team, and the salary, but if you're not learning to do every component of your work with these new tools, you're becoming obsolete. Experimenting with writing a few prompts isn’t enough. Delete Google search from your phone. Use Perplexity or Chat Search instead. Stop writing in a Google Doc and start writing in collaboration with Chat or Claude in one of their completely collaborative canvases. If you’re not making these changes you better be actively reducing your cost of living and making some sound investment decisions.
This Is Your Invitation
The shift I’m describing is as inevitable as ESPN talking about the Yankees, Lakers and Cowboys during losing seasons. You may not have language for it yet, but I know you see that the old maps are fading, and the new ones are being drawn by people with the kind of irreverence I’ve been describing.
That's why I stepped away from traditional roles.
That's why I'm writing this.
That's why I'm betting everything on this moment,
Start building, friends. Connect with others doing the same. The infrastructure is already here. The only question is whether you'll use it.
⸻
Do. Fail. Learn. Grow. Win.
Repeat. Forever.
- John -
John Brewton documents the history and future of operating companies at Operating by John Brewton. After selling his family’s B2B industrial distribution company in 2021, he has been helping business owners, founders and investors optimize their operations ever since. His frameworks have generated over $500M in enterprise value. He is the founder of 6A East Partners, a research and advisory firm asking the question: What is the future of companies? He still cringes at his early LinkedIn posts.
John, I enjoy reading your articles.
"The signal is that two very young people with generative tools can move faster than institutions with thousands of employees"
The signal is right. That's what we call adaptation. The new generation has adapted to the technology at a fast pace, like we did with PCs. won't call it a Black Swan event, it's 'just' a paradigm shift. It only feels different because we haven't transitioned from the old models to the newer ones yet. We are in the process.
I'd say that these young creators and entrepreneurs are quite Agile, because Agile and Scrum aren't about process or an event like stand up; instead, they are about moving fast to create and deliver value.