In mid-August, as Cloudflare was starting its ninth year, Prince became embroiled in the political controversy over President Donald Trump's remarks about a deadly rally in Charlottesville, Virginia.
The Daily Stormer, which espouses white-supremacist views, then praised Trump for citing violence on "many sides" — rather than singling out those who organized the event — and wrote "we are at now at war." The site also said it would help organize similar far-right rallies across the country.
Those writings came after one protester and two state troopers were killed during the Charlottesville rally, and prompted other internet service providers like Google and GoDaddy to cancel services they provided to the site, making it harder for Internet users to find.
Prince, however, hesitated to do the same.
That's because Cloudflare had a policy, stated on its own website, that it would not terminate a customer or take down content "due to political pressure."
The stance in favor of free speech put the company in the crosshairs of those who said it was being sympathetic to violent, right-wing groups.
"We were stuck. We had this problem, [and] were very alone," Prince told CNBC, as he sat on the rooftop of his company's headquarters in San Francisco during the company's annual Internet Summit in September.
But then comments from others forced the hand of Prince, who co-founded the company with COO Michelle Zatlyn in mid-2009.
First, another CEO "whom I admire," Prince said, tweeted that Cloudlare should boot the Daily Stormer off its services, as its rivals had done.
Prince called up the fellow executive, whom he declined to name, and during the discussion, this person made a "thoughtful, rational argument."
The Daily Stormer then raised the stakes with a claim that Cloudflare's management was supportive of its ultra-nationalist ideology.
Prince, in his blog post announcing the termination of service, called that assertion "the tipping point" in his decision.
The site disappeared from the internet for some time, but is now being hosted in Iceland and is once again accessible.
After canceling the Daily Stormer's service, Cloudflare faced criticism from free speech advocates, who worried it would set a dangerous precedent.
But Prince says he has no regrets.
"I would regret that as a policy, but it was just one instance. I don't regret the decision."