Because Jordan Peterson and Nassim Taleb have a large fan base overlap, use similar platforms for communication (Twitter), oppose political correctness, and both have contrarian tendencies, it’s understandable why one may be inclined to believe they share a similar philosophy; however, their philosophies are quite dissimilar.
I think Peterson is more ‘right wing’ than Taleb. Although Taleb opposes political correctness, contrarianism and opposition to political correctness are so commonplace that, ironically, supporting political correctness is more contrarian than not. Indeed, studies have shown that up to 80% of Americans oppose political correctness. And the popularity of South Park, Howard Stern, Saturday Night Live, and other popular programs that push the boundaries of ‘polite discourse,’ is evidence that opposition to political correctness is not exclusively of the domain of the ‘right’. Jordan Peterson frequently engages with the ‘culture war’ head-on, whereas Taleb tends to avoid those topics or is more oblique. Unlike Jordan Peterson, I have never seen Taleb speak out against single-mother parenting, the ills of feminism, the gender wage gap, out-of-wedlock births, etc.
Regarding facts, both engage in a fair share of hand-waving. Jordan Peterson’s humans-as-lobsters hierarchical system is not accepted by the scientific community, and Nasim Taleb similarity works outside of the bounds of academia. But I think Jordan Peterson’s ideas (such as about IQ and what he called ‘biological essentialism’) hold up better to scrutiny than Taleb’s attacks on GMOs. Taleb is much more critical of IQ and HBD research, and frequently targets the likes of Sam Harris and Steven Pinker, whereas Peterson shares Pinker’s ‘enlightenment values’ and agrees with Pinker’s overall positive assessment of society as it pertains to the decline of poverty and violence. Peterson’s certitude regarding human biology and its relationship to socioeconomic achievement and gender achievement gaps, is somewhat surprising considering Peterson’s themes of mysticism and mythology in his lectures and his wishy-washy definition of ‘truth’ in his debates against Sam Harris.
However, a key philosophical difference is that Jordan Peterson tends to hold experts in high regard and believes the individual can rise to the top of social hierarchies by being competent, whereas Taleb downplays the ability and knowledge of experts, which is why he constantly attacks economists, quants, and other academics. Although Peterson, like Taleb, is heterodox, he does not attack academia and experts with nearly the same vitriol as Taleb does, and seeks to use academia as a conduit rather than, as Taleb does, work completely outside of academia or attack it. Again, a central theme of Peterson’s lectures is the ‘centrality of competence,’ and competence is very important and determines one’s position/status in society, which is also very important, and a view Teleb disagrees with. As quoted by Taleb in The Bed of Procrustes: Philosophical and Practical Aphorisms “Contra the prevailing belief, ‘success’ isn’t being on top of a hierarchy, it is standing outside all hierarchies.” For Taleb, status and hierarchies are not as important ( much of his writing is about downplaying or tearing down such hierarchies), and unlike Peterson, status is not due to biology or other traits intrinsic to the individual such as IQ, but rather by exploiting the epistemological blind spots of experts (such as by taking advantage of ‘fat tails’ in the stock market and other Black Swan events).