George Packer has a thought-provoking comparison at The New Yorker:
[Peter] Thiel and Kachel [a homeless fan of Rachel Maddow] embody what could be called the politics of dissolution. In different, almost antithetical ways, they represent a political experience that would have made little sense fifty or sixty years ago. Each in his own way is alienated from the established order. Neither has any faith in traditional American institutions and élites. Thiel isn’t part of the corporate establishment, and he’s moved away from the Republican party. Kachel has no connections to organized labor; his main political affiliation is his devotion to the Rachel Maddow show. Neither of them puts much store in elections, or conventional politics generally. (For example, the subject of the 2012 Presidential race rarely came up in conversation with either of the two.) Both of them have a fundamental sense that things in America are not working. Both of them entertain fantasies of an alternative polity where things might work better: for Thiel, a floating city-state on the high seas where the long arm of national and international government can’t reach (he’s the largest supporter of the libertarian Seasteading Institute); for Kachel, a park in lower Manhattan where, for two months, a self-organizing community took root.
Since Tocqueville, conservative educators of liberalism (as Harvey Mansfield has called them) have cautioned that the particular dystopia toward which a free people are prone in a democratic age is (cue our own Paul Rahe) soft despotism. Government, we are warned, will become ever more distant yet ever more intimately involved in the details of everyday life, helping to deprive political life of human greatness and (as Allan Bloom put it) flatten out the soul. With only a slight shift of analytical perspective, we find ourselves on the road to serfdom.
Packer's careful musings suggest strongly what thinkers like Peter Lawler have proposed: that, paradoxically, we live in a regime where people are, in some important ways, more on their own than ever. Neither Thiel nor Kachel much resemble serfs. They're unique individuals, of course, but they shed light on who we find on the side of what often looks like the road to soft-despotic serfdom. What's more, they suggest how it is that others like them will wind up there.
Packer doesn't give the real distinction between Thiel and Kachel its due (Thiel wants to turn our metaphorical souls away from politics; Kachel wants us to attend to questions of justice even more deeply). But Packer does make what strikes me as the essential point --
Something about the turbulence of this age, the deep sense of dissatisfaction with things as they are, prompts people to discard the stale verities and invent new ones. Which, after all, is a very old way to respond to distress in this country. Whatever you think of their ideas and causes, both Thiel and Kachel represent something of the restlessness, the openness to the future, that has gotten America through other troubled times.
-- a suitably conservative lesson for our despairing acolytes of progress.