> In 2008, the Department of Homeland Security (DHS) contacted Unspam Technologies, asking, "Do you have any idea how valuable the data you have is?" The DHS' email served as the impetus for Cloudflare, a technology company Prince co-founded with Holloway and fellow Harvard Business School graduate Michelle Zatlyn the following year.
Which sounds like the opposite of what we would want. Cloudflare being started because a three letter agency told him that harvesting internet data is valuable. Unless his take away was “they do that too? Better try to stop it!”
Is there something else you’re referring to?
This may be totally true, but it's extremely important to understand that it does not matter.
As a US-based company Cloudflare is subject to NSLs (https://en.wikipedia.org/wiki/National_security_letter) which will force them to reveal all traffic and never talk about it. There's nothing they can do to resist that, regardless of founder personality.
Combine this with the fact that Cloudflare terminates TLS traffic, so it's all in the clear within their infrastructure. It would be difficult to think of a more juicy target for intelligence agencies waving NSLs.
It'll all be classified so we'll never know (unless some future Snowden tell us). But it is logical and wise to assume all traffic passing through Cloudflare is siphoned off in cleartext to the TLAs.
I'm not saying your concern isn't valid, it's a great point. Only that if anyone was going to run a company like Cloudflare, we're lucky it's Matthew, he's not a dumbass.