Taleb does not draw any real conclusions. He opens his essay with a story showing the clear advantage of the employee over the individualist contractor, and he admits that a complex economy needs
Taleb is, at least here, himself a slave to capitalist ideological categories. The view of employees as merely slaves is, however, a capitalist idea. Employees are metaphysical slaves not because of some inherent Aristotelian slave nature, but because capitalism necessarily constructs the employee as a slave. Hence, I'm a revolutionary: socialism is not about some set of government policies, or even a different political regime; socialism is about a thoroughgoing transformation of all social relations, as thoroughgoing as the transformation from lord-subject relations to bourgeois-proletariat relations. A critical transformation is the elimination of the social relationship of the capitalist employee.
It's worth examining the story Taleb relates to open his essay. Taleb introduces the transportation entrepreneur who uses individualist contractors for all the tasks, including pilots. With a lucrative flight about to take off, his contractor pilot, having received a better offer, cancels his contract and pays the contracted penalty. Our entrepreneur is unable to find a replacement pilot and (presumably even with the pilot's penalty) faces financial ruin for not being able to actually make the trip. How much better, Taleb confidently asserts, if the pilot were an employee, with a reputation for reliability to maintain. An employee would never blythely abandon a task for a short-term financial gain. But Taleb poses a false dichotomy. Assuming that pilots really cannot be found at short notice, the obvious alternative to Taleb's contractor/employee dichotomy is to make the pilot a partner. Partners have "skin in the game" (presumably Taleb would thus approve) both financially and reputationally.
One transformation of socialism is thus to make most everyone a partner. Not disconnected individualists, maximizing their personal gain without a thought for others, and not employees, concerned only with pleasing or placating their