Long Slow SaaS Ramp of Death (Gail Goodman): http://businessofsoftware.org/2013/02/gail-goodman-constant-...
Wide-ranging; covers why SaaS companies are brutally difficult to build and how ConstantContact very gradually achieved escape velocity while on the titular long slow SaaS ramp of death and eventually got to the fabled hockeystick growth land.
Designing the Ideal Bootstrapped [Software] Business (Jason Cohen): https://vimeo.com/74338272 Jason presents a framework for how to find a product which will get you to $10k in monthly recurring revenue.
(If you liked these two talks and just want More Like That Please go to the Microconf video page and queue up every talk by Rob Walling, preferably in order.)
And, on an entirely different subject, Developers, Entrepreneurs, and Depression (Greg Baugues): http://businessofsoftware.org/2013/11/developers-entrepreneu...
And, as mentioned by keyanp, Randy Pausch's "Last Lecture". Vita brevis. Carpe diem.
And one of the most useful talks of all time for building organizations is by Ed Catmull (of Pixar)
I was so under-exposed to non C-family languages at the time that I asked the guy next to met whether the code used to demo the ideas "was Haskell or something else?" I felt embarrassed at the shocked look on his face; my grand exploration of Clojure (and other functional languages too!) began shortly thereafter. The previous evening, I'd accidentally had dinner with Dr. Gerald Sussman... what a conference, what an experience was Strange Loop 2011!
David Pearce on abolishing suffering 
Jurgen Schmidhuber "Universal AI and a formal theory of fun" 
Slavoj Žižek on "signs from the future" - also ties into  a bit because at one point he mentions how excess capital was found to actually reduce the efficiency of certain creative tasks 
A talk by Gary Bernhardt.
1. Contract document signed first before any work is done (even free work)
2. Never appeal to emotions
3. Kill Phase clause
Personally, I see "exaggerating for effect" as dishonest. Manipulating facts in order to generate a response is manipulation.
Honestly I'd rather have 5+ million people or whatever the view count get exposed to thinking which puts school structure into question than have a talk providing better solutions.
"Normal Considered Harmful" by Alan Kay: https://www.youtube.com/watch?v=FvmTSpJU-Xc
Probably the best, most eye opening talk on any topic, but especially on the roots of institutionalised racism, and perhaps the cause of a lot of issues today.
It is by "Akala", an English rapper, poet, and journalist at the Oxford Union and is is a shining example that you can gain a great amount of knowledge, if you are only willing to.
If you liked the Netflix documentary "13th" you will like this.
(All the recordings from "Intro to The Art of Doing Science and Engineering: Learning to Learn" are amazing)
Alan Kay: "OOPSLA 1997 - The computer revolution hasnt happened yet"
and +1 to anything by bret victor
and the paper that's the basis for it is also nice to have handy http://web.mit.edu/2.75/resources/random/How%20Complex%20Sys...
It's worth listening to if you're in a high pressure environment, or struggle with stress.
This really changes the way you look into your OOP code. Please watch even if you're not a Ruby programmer.
- Building the minimum Badass User (make your users awesome) by Kathy Sierra: https://vimeo.com/54469442
- Start with the Why? by Simon Sinek (then How? and finally What?): https://www.youtube.com/watch?v=IPYeCltXpxw
- Good design doesn't sell itself by Mike Monteiro: https://vimeo.com/121082134
Not an earth shattering talk or anything (and the title isn't super accurate) but the idea and message that is being presented is something I think people in our world need to be reminded of.
Jim reveals his depth in this talk. Here's one of the gems you'll hear:
"You can fail at what you don't want, so you might as well take a chance on doing what you love"
Wildly changed my worldview with regard to charities.
Talk by Dave Thomas which gives a interesting look at software engineering expertise.
Fantastic talk on both the biological-neurological and the psychological side.
I highly recommend Nothing is Something but all are great.
You know you want to know how it works ;)
Really good, no-nonsense talk. Good watch!