His main point? "Once they have that reputation as being awesome it will stick around no matter how badly they perform after their initial success"
And I totally agree. In fact, after a success the odds are more in your favor. So if you can't succeed again, it calls into question your 'true' level of talent.
The vast majority of these silicon-valley companies are built with investors' money (typically from Venture Capital firms). The VC business model generates outsized returns on a few successful companies which pay for all the failures. Careers and entire funds can swing to success based on the outcome of one company so if you're a founder you deserve that credit. It also means you've returned tons of extra money to investors that pays for all your subsequent losses.
Kevin Rose specifically is an interesting case because Digg was not a success for his investors, but her personally did well.
To me, this all sounds like the Fundamental Attribution Error. Kevin Rose is thought to have some special talent, when really all he did was get lucky, and really, not even lucky enough to get his investors paid. His subsequent failures would seem to support this.
However, we must have our stars and Time coverboys. I would say that the reason he keeps getting biz is directly related to his fame, and not so much his business acumen or skills. Call it Calcanis Syndrome.