If you are in for a rabbit-hole of parallels between the Internet and Railroads, definitely check out the publications of Andrew Odlyzko [1]. For a mathematician, he has accumulated some of the most fascinating history surrounding the Internet Bubble and Railway Mania. He's written several papers on Railway Mania, but one in particular [2] has so many interesting anecodotes and analyses of the failures of investors during the time that it deserves to be found bound in leather on the top of the desks of VC partners everywhere. Also to be found: critiques of Metcalf's law, contributions to the solution to Fermat's Last Theorem, as well as some interesting analysis and work on cryptography and cryptocurrency.
[1] http://www.dtc.umn.edu/~odlyzko/
[2] http://www.dtc.umn.edu/~odlyzko/doc/hallucinations.pdf