Doesn't raising this kind of money scream that you're eventually going to start to monetize the data flowing through your network (e.g. telecoms selling location data to bounty hunters)?
To go into more detail: no. We make our money by selling our service to our customers.
I'm a fan of your registrar service. I started experimenting with it not long ago and have begun moving most of my domains over. I understand it's still early days there. Any chance you could build up & clean up the billing reporting and controls for domains (separating it out better, making it easier to view just domain billing information & renewal info)? It's a bit haphazard currently. It would also be very nice to be able to register domains further out than a year (right now it's just a basic one year autorenewal on/off) - even if that offering cost extra per year to push the duration out. I'd guess the issue on wholesaling and allowing longer renewals, is that if the price goes up on you in the meantime, you can't pass that along (no buffer / profit margin built-in); so throw a reasonable fee on top for pushing the renewal out. As it is, I've been adding years on my existing registrar, before I move domains over to Cloudflare. Why do I want the longer duration? Peace of mind, instead of renewing every year. Not having to worry about domains expiring is a mental positive.
Telecoms also generate their revenue by just keeping the power turned on with their existing infrastructure (yes it does require maintenance and monitoring), but that didn't stop them from trying to find additional revenue streams by further exploiting their already paying costumers.
I do use Cloudflare on their free tier, and I don't think they are spying on everyone and selling ads against some profile they have built up. We'll just have to be vigilant because the status quo right now is to be big brother and sell targeted advertising.
I would strongly suggest that you reconsider your choice of metallic headgear.
Cell carriers have been selling location data, despite making plenty of profit off selling a service. It's quite clear "we could be making more money" is a (potentially) compelling argument for large organizations sitting on lots of consumer data.
But a place that is making a healthy profit on customers, and have no way to monetize a secondary stream at anywhere near the same amount of profit, have several incentives to not to deal with it. One is something that a lot of people have trouble wrapping their mind around, but as a business grows, it gets to a point where it isn't necessarily worth grabbing every penny, because while the business is exerting the effort to grab that penny it's missing a dollar. (This is one of the reasons why there's no chance that Google will simply one day be the entire software industry, or why Amazon still has parters in AWS providing services that you'd think Amazon could just provide.) Another is the risk of exposure or pissing off your profitable customers when they find out about your secondary monetization; if 98% of your possible profit is the business profit and 2% the secondary monetization, then it doesn't take much perceived risk before that's a bad plan.
(One of the reasons not to get too upset when some companies make a decent profit; it helps keep them from scrabbling about for ways to extract every last penny from you, which is when they start getting really destructive. You're often better off when companies are not motivated to do that, rather than trying to starve them too hard. I really wish Google and Facebook had found more productive ways to make a profit; we'd all be better off for it.)
Some stuff I'm just not sure why it's not on a free plan, or even just on an Enterprise plan. I'd love to be able to send a custom 502 for instance, but instead I just remap it to 500 in nginx now... because my choice is between customization or sending the semantically correct status code. (Hey I know you browse HN CF staff, I'd drop $20 in a heartbeat to get stuff like this that's low cost to you across my account)
Argo is really cool, but enabling it on my Mastodon instance would add about $200 for traffic to my bill...