June 9, 2026, held in New York hosted by Phil Winslow

1. Fireside Chat — Matthew Prince (CEO & Co-founder) with Phil Winslow

Framing device: Winslow brought the 2019 founder's letter as a "prop" and tested whether its theses still hold.

Key insights:

• Low-cost-to-serve as the moat, now amplified by agents. Prince (citing Clay Christensen's influence on him and co-founder Michelle Zatlyn) argues that agents, unlike humans, buy on rational fundamentals — cheapest, fastest, proven — not brand. He claims OpenAI built its latest platform on Cloudflare and points to a partnership with Anthropic.
• Mission may be "too small." Board member and former CTO John Graham-Cumming questioned whether "helping build a better internet" still captures the scope — a notable signal that management is contemplating a broader ambition.
• Security outlook (provocative): With AI models (he references "Mythos," ChatGPT 5.5) able to find vulnerabilities, Prince predicts a log4j-scale vulnerability roughly monthly/weekly for ~2 years — a boom for CrowdStrike, SentinelOne, Zscaler, Cloudflare — followed by a flip where software gets dramatically more secure and standalone security as a category fades into table stakes. Cloudflare's role: quietly virtual-patching the internet in partnership with model labs (early access to Anthropic's Mythos).
• Free tier → future business model of the internet. Bot traffic has already exceeded human traffic (ahead of their own H1 2027 forecast). Ads die because "bots don't click on ads." Prince floats: bot-targeted contextual content (an "AdSense for bots") and micropayments — of ~half a billion transactions/month on the network, 1–10% could carry a micropayment. Being the rails for this is why the free tier still matters.
• AI and internal velocity: A model trained on 10 years of incident data now gates every code release and config change; Jeremy (production engineering) saw incident rates "fall off a cliff." The dogfooding pattern (DDoS mitigation, registrar, Zero Trust, Workers all built for internal needs) continues — AI cost-control and security are the current internal pains turning into products. The two questions from every CTO/CIO: how do I do AI securely, and how do I not blow my budget?
• 20-year vision: Internet traffic 10–100x in five years; the most interesting question of the next five years is the internet's new business model — "not advertising, not subscriptions" — with Cloudflare positioned as the company everyone looks to for the answer.

2. Rita Kozlov — VP Product, Developer Platform ("Act 3")

Theme: agents need a new kind of cloud, and isolates are it.

• Scorecard on last year's predictions: (1) the shift to agents happened — open-source agent OpenClot/OpenClaw overnight surpassed React in popularity; (2) code creation exploding — Wrangler downloads up ~1,000% YoY; (3) Cloudflare as the AI build platform — 5.5M developers, plus the acquisition of VoidZero (company behind Vite), where Cloudflare's plugin is ~10% of total Vite downloads.
• Core technical argument — "agents must write code": Tool calling is artificial and LLMs are bad at it (she quotes Anthropic's Shakespeare-learning-Mandarin analogy). Context windows (~1M tokens) can't even hold Cloudflare's own API surface (2.5M tokens) — hence errors like her agent booking dinner at Le Mercerie on January 1, 2024. LLMs excel at code, so they need somewhere to execute it.
• The scaling math (the standout slide of the day): Powering one agent per US knowledge worker ≈ 10M CPUs (~20–30% of global server CPU production); globally, ~1 billion CPUs ≈ 20x global annual production. Containers/VMs cannot scale to per-task ephemeral code; isolates (the "big bold non-consensus bet" from nine years ago) are ~100x more efficient.
• Economics: Running 10k agent-generated apps ≈ 63% cheaper on Cloudflare; 1M agents ≈ ~75% cheaper (steady traditional apps can be ~15% more expensive — a candid caveat).
• Memorable analogies: fast-food franchise kitchens (old cloud) vs. pop-up kitchens (isolates); Andy Jassy was right about primitives, but the agentic era needs Durable Objects/Workers/Workflows, not S3/EC2/SQS.
• Customer voice: Mark Smith, head of infrastructure at Discord — "I know what hyperscalers will look like in 10 years... I'm looking to Cloudflare to define the next-generation cloud."