AT A GLANCE

Cloudflare
Magic AI
2009
Founded
2022
San Francisco, California
HQ
San Francisco, USA
$332 million
Total Raised
$465 million
Matthew Prince, Michelle Zatlyn, Lee Holloway
Founder
Eric Steinberger and Sebastian De Ro
Cybersecurity
Type
AI
Public (NYSE: NET)
Status
Private

FUNDING HISTORY

Cloudflare

Seed2009
$2M raised
Series A2011
$20M raised
Series B2012
$50M raised
Series C2014
$50M raised
Series D2015
$110M raised$3.2B val.
IPO2019
$525M raised$4.4B val.

Magic AI

Seed2022
$5M raised
Series A2023
$23M raised
Venture Round2024
$117M raised
Venture Round2024
$320M raised

BUSINESS MODEL

Cloudflare

Cloudflare operates on a freemium model with usage-based pricing. The free tier provides basic CDN, DDoS protection, and SSL for any website — this is how millions of sites use Cloudflare without paying a cent.

Paid plans start at $20/month (Pro), $200/month (Business), and custom enterprise pricing for large organizations.

The free tier is the growth engine, not charity. Every free website that routes through Cloudflare adds data to the network — more traffic patterns to analyze, more attacks to learn from, more threat intelligence to feed the machine learning models.

Free users make the paid product better.

Enterprise contracts are where the real money lives. Large organizations pay six and seven figures annually for advanced security, performance, and compliance features.

Revenue reached $1.67 billion in 2024 and kept compounding at roughly 28% a year. The company has been approaching profitability with improving margins.

Magic AI

Magic is building an AI that works like a software engineer, not a chatbot. The goal is a model you can hand a whole code base and a task, and it writes, reviews, and debugs like a teammate.

Their edge is memory. In 2024 they showed off LTM-2-mini, a model with a 100 million token context window.

To put that in perspective, that is about 10 million lines of code the model can look at in one shot, by far the biggest of any model at the time. The plan is to sell this as an AI coworker to companies that write a lot of software.

As of the 2024 rounds, the product was still not for sale.

HOW THEY STARTED

Cloudflare

The origin story starts with Project Honey Pot, a free open-source project that Matthew Prince created in 2004 to track online spammers and hackers. The project grew to track millions of malicious IP addresses, and the Department of Homeland Security started using the data.

But Prince noticed something: he had all this threat intelligence and no good way to help website owners actually use it.

At Harvard Business School in 2009, Prince teamed up with Michelle Zatlyn for a class project exploring how to turn that threat data into a product. Their professor gave them a B — which Prince has jokingly called the most expensive B in HBS history, given what the company became.

They brought in Lee Holloway, a brilliant but unconventional systems programmer Prince had worked with previously, as the third co-founder and technical architect.

Cloudflare launched publicly at TechCrunch Disrupt in September 2010 with a bold pitch: sign up for free, change your DNS, and Cloudflare will make your website faster and more secure. No hardware to install.

No software to configure. Just a DNS change.

In the first day, thousands of websites signed up. The simplicity was the product — in an industry where security meant expensive appliances and complex configurations, Cloudflare said "just point your domain at us and we'll handle it."

Magic AI

Eric Steinberger and Sebastian De Ro started Magic in 2022. Steinberger is an AI researcher who became convinced that the missing piece for a true AI software engineer was memory.

Chatbots forget what you told them a few thousand words ago. He wanted a model that could read your entire code base and remember all of it.

They raised a small seed in 2022, then a $23 million Series A in early 2023 led by Alphabet's growth fund CapitalG. From day one the pitch was not a chatbot.

It was an AI colleague that could handle real engineering work.

HOW THEY GREW

Cloudflare

Cloudflare grew by being free. The free tier removed every barrier to adoption.

A blogger in India and a Fortune 500 company could both sign up in five minutes. This created a massive installed base that generates word-of-mouth, training data, and upsell opportunities.

The developer community became the second growth engine. Cloudflare Workers turned the company from a security vendor into a cloud computing platform.

Developers build entire applications on Cloudflare's edge network, which creates deep technical lock-in. Once your application runs on Workers, migrating to AWS Lambda is a significant engineering effort.

Strategic pricing warfare accelerated commercial adoption. When Cloudflare launched R2 storage with zero egress fees, it directly attacked Amazon S3's most hated pricing model.

The "Bandwidth Alliance" partnered with cloud providers to eliminate data transfer fees. These moves positioned Cloudflare as the anti-AWS — the cloud company that doesn't nickel-and-dime you.

Magic AI

Magic's strategy is research first, product later, which is both unusual and expensive. Instead of shipping an app and iterating in public, they raised huge sums to chase a technical breakthrough in model memory.

The headline move was the 100 million token context claim, which got the whole AI world talking. They also cut a deal with Google Cloud in 2024 to build two supercomputers, called Magic-G4 and Magic-G5, using NVIDIA chips, to train bigger models.

Star backers like Eric Schmidt served as validation. The bet is that if the tech is far enough ahead, the product and the customers follow.

THE HARD PART

Cloudflare

AWS, Google Cloud, and Microsoft Azure are simultaneously partners and competitors. Cloudflare's network sits in front of these clouds, which makes the cloud providers uncomfortable.

As Cloudflare expands into compute (Workers), storage (R2), and databases (D1), the competitive overlap grows. The cloud providers could theoretically build or acquire similar capabilities and bundle them for free.

Profitability pressure is real. Cloudflare has prioritized growth over profits, spending aggressively on network expansion and R&D.

Operating margins have been negative for most of the company's public life, though they've been improving. Investors have tolerated this during growth-stock mania but patience may not last forever.

Content moderation controversies arise periodically. As a company that provides infrastructure to millions of websites, Cloudflare occasionally faces pressure to terminate service to controversial or harmful sites.

They removed 8chan after the El Paso shooting in 2019 and the Daily Stormer in 2017. Prince has described these decisions as uncomfortable, arguing that infrastructure providers shouldn't be arbiters of online speech but sometimes have no choice.

Magic AI

Magic has raised close to half a billion dollars and, years in, still has no product the public can buy. That is the whole problem in one sentence.

A giant context window is a great demo, but rivals like Cursor, GitHub Copilot, and Cognition's Devin already have real users and revenue. Magic has to prove that more memory actually makes a smarter engineer, not just a bigger number on a slide.

And it has to do that while burning enormous sums on compute against competitors who are already shipping. The clock and the cash both keep running.

THE PRODUCTS

Cloudflare

Cloudflare CDN — a content delivery network spanning 330+ cities in 120+ countries that caches and serves web content from the nearest location to each user, making websites dramatically faster. Cloudflare DDoS Protection — automatic detection and mitigation of distributed denial-of-service attacks.

Has blocked some of the largest DDoS attacks in internet history, including a 71 million requests-per-second attack in 2023. Cloudflare Workers — a serverless computing platform that lets developers deploy code to Cloudflare's edge network, running applications in 330+ locations worldwide with millisecond latency.

Cloudflare Zero Trust — a complete security platform replacing traditional VPNs and firewalls with identity-based access controls for remote workforces. Cloudflare R2 — object storage that competes with Amazon S3 but with zero egress fees, saving companies thousands on data transfer costs.

Magic AI

The centerpiece is Magic's LTM, or Long-Term Memory, model family. In 2024 they unveiled LTM-2-mini, a model with a 100 million token context window, pitched as the key to an AI that can understand an entire code base at once.

The broader product is an AI software engineer, or coworker, that can write and change code across a whole project. The company also announced Magic-G4 and Magic-G5, two supercomputers built with Google Cloud and NVIDIA to train these models.

Much of it is still research rather than a shipping product.

WHO BACKED THEM

Cloudflare

New Enterprise Associates (NEA) led the Series A. Venrock, Pelion Venture Partners, and Union Square Ventures invested early.

Fidelity, Microsoft, Google Capital (now CapitalG), and Baidu all invested in later rounds — notably both Google and Baidu investing in the same company. The September 2019 IPO raised $525 million at a $4.4 billion valuation.

The stock has since grown significantly.

Magic AI

Magic's backers are a murderers' row of AI insiders. It started with a $5 million seed round in 2022 and a $23 million Series A in early 2023 led by Alphabet's CapitalG.

Then in February 2024 came a $117 million round led by Nat Friedman and Daniel Gross, two of the most connected investors in AI. The blowout was August 2024.

Magic raised $320 million with checks from former Google CEO Eric Schmidt, CapitalG again, Atlassian, Jane Street, Sequoia, and Elad Gil. That pushed total funding to around $465 million, all for a company still building toward its first sellable product.

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