>I am far more disturbed by someone who claims to be in the opposition but rather than publicly opposing continues to give every sign of being in fact a quiet supporter of the administration. Why should I have to worry that that's true?
You're stating you believe Sam is a Trump administration supporter?
The evidence would suggest he's more a supporter of the style of populist authoritarianism embodied by Trump, but a dissenter from the policy goals which Trump is using that to advance.
"He’s an outsider. He took on a system he thought was broken and then disregarded the rules, he got to know his users well and tested his product early and iterated rapidly."
An outsider who disregards the rules is the polar opposite of an authoritarian. Rather, I think he's admiring Trump's bias toward action and disregard for conventional wisdom, as well as for people who have a vested interest in the conventional wisdom.
They're hardly outsiders once they've become the leader of the country.
Trump is in a similar position now: he was an outsider during the campaign, but now that he's won, he's the consummate insider. The same phenomena applies to successful Silicon Valley startups: Google, Facebook, and Uber were all scrappy little startups until they became huge, at which point they became giant multinationals which need to be feared and resisted.
This I think illustrates the paradox in Sam's quote: in my read, Altman is referring to candidate Trump, while your outrage is devoted towards President Trump. As Obama said in one of his farewell addresses, "campaigning is very different from governing". Tactics that can be very effective (even necessary) on the campaign trail can become dangerous threats to democracy within the government.
> They're hardly outsiders once they've become the leader of the country.
A formal position of authority doesn't stop you from being an outsider in an institution; that's one of the reasons that purges happen: to recast institutions in which the leader is an outsider into ones in which he is not.
What I'm trying to highlight is the distinction between the struggle for power and the exercise of power. Campaigning for election is a struggle for power. So is purging your political opponents within the government. So is founding a startup.
Governing is the exercise of power. Deporting all immigrants and closing the borders is the exercise of power. "Grab 'em by the pussy" is the exercise of power. Leveraging a monopoly is the exercise of power.
Power struggles are usually looked at favorably by those whose interests align with the ascendant power structure, and unfavorably by those whose interests are entrenched. The naked exercise of power is usually looked at with distrust by everyone, on the theory that if they bully someone else, they could bully you next. There's a fairly wide grey area in-between; for example, I've categorized Trump's immigration orders as the exercise of power (which probably both you and tptacek would agree with), but someone who just lost his job to an immigrant would probably categorize it as a power struggle where Trump is fighting the immigrants oppressing him. And similarly, not everyone would buy your claim that a dictator committing a purge is an "outsider" in his government. The key point though is the relative power differential between parties: it's a struggle for power when the active party is the underdog, and the exercise of power when the active party is dominant.
The way I read Altman's quote, he's casting Trump's campaign in the same terms as the struggle for power that all startups have to go through. He's specifically not endorsing what Trump has done with that power once he attained it.
> What I'm trying to highlight is the distinction between the struggle for power and the exercise of power.
I'm not sure there is the kind of distinction here you are trying to draw; a struggle for (future) power is one context in which (present) power is exercised, they aren't opposing or conflicting concepts.
> An outsider who disregards the rules is the polar opposite of an authoritarian
Revolutionary authoritarians are, almost without exception, outsiders who disregard the pre-existing rules, both formal rules and merely conventional ones. The very few exceptions are insiders who disregard rules in the same way. Lenin, Hitler, and Napoleon, among others, were many things, but followers-of-rules-set-by-others wasn't high on the list for any of them.
I think you are confusing being the opposite of a willing subject of authoritarianism with being the opposite of an authoritarian.
You're stating you believe Sam is a Trump administration supporter?