Dear Reader,
Mitt Romney reportedly turned roughly $450,000 in retirement savings into as much as $100 million.
Peter Thiel reportedly transformed less than $2,000 inside a Roth IRA into approximately $5 billion, both in less than 2 decades.
Those are extraordinary outcomes – not typical ones – and I would never pretend otherwise.
But they reveal something important:
Wealthy investors often study the account structure and access mechanism before the investment becomes obvious to everyone else.
That lesson matters right now.
Because while ordinary investors chase the same crowded AI names, an enormous stream of capital is moving into the infrastructure beneath the entire industry.
It doesn’t need to invent the next chatbot.
It doesn’t need to replace Nvidia.
Its opportunity comes from the money pouring into the physical and financial foundation AI requires.
And President Trump reportedly recognized the setup early – investing as much as $25 million of his own money.
The danger is assuming you can wait until your employer adds something similar to its retirement menu… or until another AI headline finally makes the opportunity obvious.
By then, you may be trying to evaluate it alongside a much larger crowd.
I’d rather give you the evidence now, while you still have time to consider the complete case calmly.
Good investing,
Alexander Green
Chief Investment Strategist, The Oxford Club
P.S. The research behind this presentation connects the opportunity to a projected $216 trillion AI event. Watch the briefing to see how that figure fits into the investment case.
Cloudflare Wants to Bill Every AI Answer That Uses Your Content
The debate inside most investment committees about Cloudflare centers on the security and Zero Trust business. That is the wrong conversation to be having in November 2026.
The more consequential question is whether Cloudflare has quietly built the toll road for the AI economy and whether the market has any idea what that is worth.
What Changed This Year
Cloudflare has moved from blocking AI crawlers, to charging them, to paying publishers when content is used, and on September 15, 2026, it changed the defaults for how new sites treat AI traffic. That three-step evolution happened inside twelve months. Each step widened the company’s commercial surface area without requiring a single new data center.
Training-oriented crawling is now roughly half of AI-bot traffic on Cloudflare Radar, versus about a tenth classified as Search. That ratio is the starting point for understanding why the monetization bet is structurally large. The traffic is already there. The question is whether Cloudflare can price it.
Around July 1, 2026, Cloudflare announced a pivot from charging per crawl toward a pay-per-use model, where publishers can get paid when their content is actually used in downstream AI experiences such as a cited answer, with early partners including Ceramic.ai and You.com. The earlier pay-per-crawl model had an obvious flaw: a page could be fetched a thousand times and cited nowhere. Cloudflare argued in July 2026 that “crawling is a crude measure of value”: a page might be crawled once and cited thousands of times, or crawled repeatedly and never used. Pricing by use, rather than fetches alone, is the cleaner economic unit.
The Business Case Bears Are Ignoring
Cloudflare has been building out a monetization stack alongside access controls: the Monetization Gateway to help content providers charge for access behind Cloudflare, Cloudflare Wallets to support machine-to-machine payments for agents, and Pay Per Crawl. Rather than being caught reacting to AI disruption, Cloudflare is presenting itself as the infrastructure layer that arbitrates the relationship between publishers and AI companies, a position with recurring revenue potential if these products gain real adoption.
In January 2026, Cloudflare acquired Human Native, a UK-based AI data marketplace that helps publishers and developers turn unstructured content into something that can be licensed. This is a meaningful step: it brings a training-data licensing team into the company that already controls crawler access for its customers.
The acquisition logic mirrors a broader pattern in enterprise software. Salesforce has been making similar moves, folding AI-native acquisitions into a platform that existing customers are already expanding spend on.
The Core Business Is Accelerating Too
Third-quarter revenue totaled $782.0 million, representing an increase of 39% year-over-year, crossing $3 billion in annualized revenue. CEO Matthew Prince called it Cloudflare’s fastest revenue growth in nearly four years while expanding profitability. Dollar-based net retention reached 122%, up 3% year-over-year. The underlying security and connectivity business is not slowing while the AI monetization layer is being built. That is a rare combination.
What Investors Are Missing
The pay-per-use model is not yet a line item anyone can underwrite cleanly. What is changing is that Cloudflare has started describing early contributions from what it calls its Act IV products, while moving pieces like Pay Per Use and the Monetization Gateway into beta this fall. Wall Street is debating valuation on the security business while a structurally new revenue model sits in the footnotes.
Stocks to Watch
- Cloudflare (NET): Q4 revenue guidance of $845.0 million to $846.0 million represents projected year-over-year growth of 38%. The AI monetization layer is the option the current multiple does not reflect.
- News Corp (NWS): Among the largest content owners with the most to gain from usage-based compensation at scale, and among the most exposed if the model fails to gain AI company adoption.
- Alphabet (GOOGL): As both a Cloudflare customer and a major crawler operator, any framework that meters crawler access changes Alphabet’s cost structure for training and answer generation.
