If you want to read from an insider's perspective, read this book from a Keyhole PM (I just finished).

Very interesting to see how Keyhole struggled with cash flow needs and long sales cycles in the post-dot.com bubble just as the average startup struggles now.

Also, In-Q-Tel was just an investor at the company, and many were wary about why Google (who didn't have any mapping product) would go that route.

https://www.goodreads.com/book/show/35820393-never-lost-agai...