Manifold Trilogy

Each novel contains the same or mostly similar characters, though these characters find themselves in wildly different circumstances in each story. In each of the three novels, the main character is a man named Reid Malenfant, a brash, ambitious entrepreneur and former astronaut who gets drawn up into the complexities of each novel's plot. Each novel starts off on Earth, in a relatively mundane near future, but eventually expands into the far future and deep space.