Listen to them in order, oldest to newest. I would not recommend starting with the most recent "Jad and Robert: The Early Years" which is mainly about the hosts.
And if you want to cherrypick one show to start with try: Musical Language.
As it relates to business: the show is a veritable collection of case studies revolving around people, culture, and science. Myself: I'd recommend the Space episode.
Great interviews with entrepreneurs, and they're each about an hour long -- perfect for road trips.
Complete list here: http://www.venturevoice.com/library.html
If you're into sci-fi try the old BBC radio series Journey into Space, Operation Luna (the first in the series).
Also, it is just fascinating to listen to accounts from pre-Christian times. The characters share many common human traits with us, but are also deeply different. It will make you question what it means to be human.
2. "Predictably Irrational" by Dan Ariely
3. "The Search" by John Battelle
4. "Made to Stick" by Chip Heath and Dan Heath
5. "The Tipping Point" by Malcolm Gladwell
That should cover your trip. I've listened to all of them and really liked all of them. "Blink" by Gladwell is also good, but not as business related.
I would love to hear any other suggestions people have in this category.
"The Paradox of Choice" by Barry Schwartz was a great read.
It'll only take about forty minutes to finish.
If you go with a Teaching Company course I highly recommend their "Great Minds" series (though without a library it is a bit spendy): http://www.teach12.com/ttcx/coursedesclong2.aspx?cid=470&;
The Teaching Company has "The Great Ideas of Philosophy/Psychology" series and courses in economics I'd recommend.
The above titles can all be found at audible.com, and probably through itunes too.
Will and Ariel Durant: The Lessons of History A great synthesis by two lifelong historians on what can be learned from a study of history. Covers human nature, society, culture/morals and many other important topics and takes as objective a view as possible.
You can listen to it over and over and get some great insights. Dense, but easy to listen to. There is one small section that is slightly dated and shows that they were writers in their own time but most of it is timeless.
I highly recommend this. It will really give you insight into our world.
(it's nominally about running a manufacturing plant, but I think a lot of the takeaways apply just as well to startups)
Atlas Shrugged by Ayn Rand
Much of what makes an audiobook great is the reader's grasp of the material. Both of these books are great works of literature, but the skill of the reader makes them even better as audiobooks.
I really liked Cannery Row too.
Look for Parsec award winners or Hugo award winners.
http://www.amazon.com/Behind-French-Revised-Complete-Illustr...
Coincidentally, I'm leaving soon on a car trip to Morocco and was just preparing to sync the free Michigan Modern Standard Arabic and the Pimsleur Egyptian Arabic audio courses to my iPod.