I love thinking about the future of, well, everything. I consume tons of blogs, books, and videos by thought leaders and seek out conversations with those who are way more informed than me. Often, though, I get my inspiration from Science Fiction.
I love science fiction that extrapolates current trends into the near future and focuses on the impact of technology on society; I'm talking about stories that strive for scientific accuracy and grapple with the implications of disrupting the complex systems and norms of our civilization (as opposed to stories using space as a backdrop for an old fashioned adventure).
The best scifi inspires me to explore new interplays between technology and human behavior and foster ambitious, contrarian dreams for my own entrepreneurial journey. Here are a few authors and books I highly recommend.
Doctorow was one of the first modern authors whose science fiction changed my thinking around technology and entrepreneurship. The two books I'd most recommend are Down and Out in the Magic Kingdom and Makers. The former is a novella that explores life under economic post-scarcity and introduces a fascinating reputation based currency: Whuffie. Makers explores the maker subculture and provides interesting speculation as to the future of innovation and collaboration. Both books are available for free (Woohoo, Creative Commons!) via the above links. His short stories tend to be amazing as well...
Suarez is behind the Daemon / Freedom two part series. It is an extremely interesting look at the future of collaboration and resilient communities as intermediated by technology. The first book is mostly set-up for the ideas in the second but you really should read both!
Stross is another modern scifi author; I thoroughly enjoyed his novel Accelerando (also free). The book examines the impact of accelerating technology on society (think: the singularity) by following a few characters in jumps over several decades. While the whole book is a fun ride, the early chapters (closest to the present) are most interesting for inspiring startup ideas.
Stephenson may be best known for Snow Crash, which had a very interesting take on the future of the internet, especially considering he wrote it in 1992. I actually recommend deferring that book in favor of The Diamond Age, which explores the impact of nanotechnology / nanoscale production on society. Two other good reads of his are Cryptonomicon, which includes a great primer on cryptography, and Reamde which feature an interesting online gaming world but is otherwise a more ordinary thriller.
Vinge originally coined the term "The Singularity" in reference to the struggles of speculating about the future. His book, Rainbows End examines a post-scarcity society and features many interesting product ideas and social conventions.
That's all the recommendations I have for now... what am I missing?