In 1997, Hastings worked on cryptographic protocols and tools free of U.S. cryptographic export restrictions with Vincent Cate, who started the International Conference on Financial Cryptography in Anguilla that same year.
Hastings founded HavenCo in 2000, originally incorporating in his country of residence, Anguilla, before a second incorporation in the Channel Islands. Hastings was the CEO; other co-founders included Ryan Lackey and Sameer Parekh. Immediately following its public launch, HavenCo was the subject of a great deal of press coverage, including Hastings' appearance, along with several cofounders and the "royal family" of Sealand, on the cover of Wired's July 2000 issue, before the company was entirely nationalised by the government of Sealand in 2002, after commercial failure and mounting tensions.
In 2002, Hastings began work on seasteading with Patri Friedman, a project aimed at building floating communities free from the restrictions of current governments. This collaboration continued through 2009, including a talk by Hastings at the Seasteading Institute's annual conference.