Nothing is ever as risky as you think it is
unschooled.org
unschooled.org
Also: A lot of what makes it hard to be a founder is not the shame of failure, but knowledge of lost time. If my company goes under, I'm not as disappointed in my lack of success as I'm disappointed in time not spent more productively elsewhere. There's a subtle distinction there.
You're right that there are objective downsides to startups (e.g., time sunk into something that doesn't pan out), but the lower bound is known and, to me at least, not that bad. Working on a startup that fails isn't like shorting stocks (which has a theoretically unlimited downside). In fact, I'd argue the worst case is many times better than working two years at Microsoft or Google, at least in terms of personal growth and development.
It doesn't have to be an either/or. There's plenty of time to both fail at a startup and work a couple years at Google.
A related trick is to keep the scope of your experiments small so you can feed that information back into the development of future experiments very quickly. (cf. Col. John Boyd's "Patterns of Conflict")
Spent 2 years as an online poker player, you learn that your short term productivity is an illusion. What is most important is a type of effort that produces long term gains. With that perspective you become better at prioritizing and understanding what both you and those around you (customers, investors) want. So the only way to be "unproductive" is to not follow through thoroughly on what you are doing now.
But you need to be smart enough to get out when the long term is, as we say in poker, -EV (http://en.wikipedia.org/wiki/Expected_value)
Talking to a woman at the supermarket has the inherent "risk" of being ridiculed, while having the obvious objective upside that it might get you laid - or at least makes you a more confident person. In the same way (now regarding business), pouring time and money into a startup has the inherent risk of said startup going under (and losing some past time and/or money), while the obvious objective upside that if the company makes it big, you're a billionaire. Hell even if it doesn't you've earned experience you can apply in your future endeavors, and you didn't have to listen to 7am lectures at the local college for four years to get to not learn even a tenth of what you learn failing at building a startup.
Also (for many drugs) not as risky as most people think.
There's a human (irrational) bias to be risk averse, but that doesn't mean it's always safer than we think. We also have selection bias as a counterpoint. There are plenty of similar posts with the opposing view based on the later bias, too.
Instead, let's try to be more rational and understand probability:
Probability Theory: The Logic of Science http://bayes.wustl.edu/etj/prob/book.pdf (draft)
http://www.amazon.com/Probability-Theory-Logic-Science-Vol/d...
he's totally right in how he contrasts asking someone out vs riding a motorcycle without helmet. and yes, starting a company has little physical downside (if crafted with reasonable caution, by doing things like minimizing expenses early until business model proven, etc) but a huge potential physical upside (great wealth and freedom).
Similarly, "Nothing is as risky, or as safe, as it first seems."
Also, I disagree with his dismissal of subjective risk. If taking a particular action feels bad to you, then it feels bad. A better course than trying to deny that would be to learn to accept your feelings but to go on in spite of them. Feelings are much easier to change over the longer term, usually by short term acceptance - your unconscious will eventually realize that the feelings are overblown (if they are) and you will come to react less strongly with repetition, over time.
"There was no use worrying about the possible difficulties to come, they always loom very large and terrible in the distance, but when one arrives at the foot of a wall there is always some foothold that enables one to climb it."