He should look up Roald Coase - mid 20C who tried o answer the question of why have firms at all - big or small. The “market” ought to be able to supply services (secretary, welding etc) - but his “Theory of the firm” suggests that there are complex processes inside a firm that are pretty easy to employ someone and teach them, and pretty hard to write a contract for.
So there is a natural size of a firm that is a tug of war between savings of contracting out and the cost of contracting to the market
My still to be published magnum opus claims this is upended by software - that processes can be written and followed in software reducing the cost of hiring and changing the dynamics in favour of large companies.
But software literacy in all employees will enable smaller companies to outperform larger ones - we hope
Coase was a founder of the field sometimes called "New Institutional Economics" and I think Terry is basically independently reaching some of the conclusions that have already been published in that field, including some of Coase's.
I think North, Wallis, and Weingast's Violence and Social Orders is a little more directly on point to his posts, but I believe I share at least part of your point of view here — and would love to see a precis of the magnum opus!
Why would software be qualitatively different from all other forms of automation that came before? And suppose, for the sake of argument, that software is fully automated at some point--what then happens to the firm?
So there is a natural size of a firm that is a tug of war between savings of contracting out and the cost of contracting to the market
My still to be published magnum opus claims this is upended by software - that processes can be written and followed in software reducing the cost of hiring and changing the dynamics in favour of large companies.
But software literacy in all employees will enable smaller companies to outperform larger ones - we hope