"The Wright Brothers" by David McCullough - Shows how Orville and Wilbur surpassed the leading researchers of the day to be the first to achieve controlled, powered flight. Does a great job of describing their work ethic and research process.

"The Myths of Innovation" by Scott Berkun - Not exactly about how hard things got done, but it discusses some of the misconceptions and assumptions we make about current technology and the process of inventing new tech.