The First Tycoon: The Epic Life of Cornelius Vanderbilt

When he died, Cornelius Vanderbilt net worth was more than 10% of the total money in circulation in the United States. He made the money himself through a serious of business ventures primarily in transportation. He lived relatively modestly, despite his significant wealth. (His descendants would use their inheritance to build great mansions.) He did not set out to build great monuments to himself. He did provide money to endow the university that now bears his name. However, he never set foot there, and didn't even ask for his name. (He thought the northern wealth should help support the south after the civil war.)
The book paints a very laudatory picture of his business dealings. He carries out his activities out of principle. He is constantly doing the moral thing and helping to increase the value of companies rather than simply extract money. The book seems to portray him in almost too positive of a light. He is seen as the humble businessman who only monopolized industries to help people out (or to exact revenge on bad actors.) There may be some truth to it, but it does feel like too much of a deification. Perhaps his moral compass is what enabled him to succeed where others failed. He wasn't after the graft. He wanted a big successful company. He started working on steamships. He was able to move boats around and make money where it was needed. He was involved in the pre-Panama-Canal route through Nicaragua. It was faster, but ended up dying due to politics, including "filibusters" who try to claim foreign land for America. He gradually ended up more involved with railroads, taking over the poor performing Harlem line and helping it to succeed, before taking over other New York Lines.
It is interesting to think that when he was alive and building his fortunes, places like Seattle barely even existed. The times also saw a conversion from individualists to large corporation. Boats could be bought and run by an individual. Only through government interference and "gentleman's agreements" were monopolies created. It was very easy for one boat to move to a new location. Horses and carriages were also individualistic. They could go just about anywhere, though not super fast. A good road would help (and thus some toll roads were created). However, these tended to be shorter distance turnpikes. Railroads started in this framework before changing everything. First they were similar to the toll roads. They were small rail lines serving local traffic. They were also quite dangerous. Then the railroads grew larger and larger. They needed to maintain the tracks, the cars and the engines. The expenses necessitated much more capital and large corporations. Long distance traffic involved traveling over a large number of different lines. There were often switches involved. This was costly and time consuming. Consolidation helped freight and passengers move faster. However, there were still plenty of opportunities for graft in the structure. After the experience with railroads, America turned to a more socialist transportation structure. Highways were built on the public dime, and open to everyone with an automobile. Airports were similarly often built with public funds and open to private airplanes. This seemed to appeal the individuality of users. (Anybody could be an operator on the transportation system with a minimum of capital), in spite of the large expense needed for infrastructure and maintenance. Even the railroads have become partially under the pervue of the government.
Vanderbilt would not recognize what has become of his "empire" today. However, he would likely appreciate the significant changes that have occurred in society.