[lusr]

What you said is true if you're young and you don't have much data to assess yourself with, but even if you're not pg and don't have a model of success well backed with data, the fact is that if you're 30 or 40 years old there are plenty of objective third parties you will have encountered throughout life who have assessed you for free.

For example, if you've been through a demanding course of tertiary education and performed better than average that says something. Indeed any endeavour that required a fair amount of intelligence, skill, and commitment where you came out above average says something: starting other businesses and having done better than average comes to mind.

In addition to the flaw pg pointed out, the second mistake the article's analysis makes is to ignore the number of opportunities you have; it seems to assume you have a single opportunity. In reality, you can make some less than optimal choices in life and still sometimes do just as fine in the end.

If you're young I don't see what's wrong with gambling a bit: if you're 20 and have zero data about how well you will perform, I believe it's still completely rational to aim high. If you don't get the $100 million exit by 25, you can reconsider your options. After 5 years of aiming high you'll have more than enough data to assess whether it's time to change your aim or to keep going.