As far as I can tell, he has a general reputation of being a bit of a loudmouth quasi-contrarian, but with some basic credibility behind him. He seems, for example, to be on the right side of climate change, arguing that the potential for disastrous temperature rise really means that action should be taken, and those to the contrary bear the burden of proving their do-nothing position.
And on economics, I have the feeling he might be more or less right (if you ignore the personal sledging of Obama) that the economic problems are not really solved:
Oh, absolutely! The last crisis  hasn’t ended yet because they just delayed it. [Barack] Obama is an actor. He looks good, he raises good children, he is respectable. But he didn’t fix the economic system, he put novocaine [local anaesthetic] in the system. He delayed the problem by working with the bankers whom he should have prosecuted. And now we have double the deficit, adjusted for GDP, to create six million jobs, with a massive debt and the system isn’t cured. We retained zero interest rates, and that hasn’t helped. Basically we shifted the problem from the private corporates to the government in the U.S. So, the system remains very fragile.So, he worries about "massive debt". But things start looking wonky in the second part, when he is asked how the Trump administration can address this:
Of course. The whole mandate he got was because he understood the economic problems. People don’t realise that Obama created inequalities when he distorted the system. You can only get rich if you have assets. What Trump is doing is put some kind of business sense in the system. You don’t have to be a genius to see what’s wrong. Instead of Trump being elected, if you went to the local souk [bazaar] in Aleppo and brought one of the retail shop owners, he would do the same thing Trump is doing. Like making a call to Boeing and asking why are we paying so much.OK, he's stop making any sense. So, Taleb is giving Trump for being a non-expert who talks at a level people can understand. The problem is - he's ignoring Trump's actual, and plain to see, ignorance on a swathe of economic and other problems, and on those matters where you can tell his general direction, Trump's approach (lower taxes, big infrastructure spend, Mexican wall, the EPA) is only going to make matters Taleb complains about ("massive debt", climate change) worse. Not to mention that the path Trump is taking is to decrease banking regulation - no sense of a banker punishment there; quite the opposite.
As for Trump putting "business sense" into the system - Trump proudly pays no tax and brags about using debt to his advantage, and the string of litigation against his business conduct is embarrassing.
So yeah, sorry, but I have trouble taking Taleb seriously.