Riding a trend is definitely a sensible thing to do, it reminds me of a lesson that's quite common in fighting sports is to use an opponents momentum to your own advantage.
That said, you can get lucky and happen to work on one of the trends or you can try to spot one and ride it consciously.
There's a factor that doesn't change though, you need to be able to execute and I think Ryan is giving himself way too little credit for being good at execution.
In particular he had already garnered a significant following with carsonified conferences and his blog before thinkvitamin (now treehouse) took off at the time.
There's always the cautionary tale of friendster, who could have been Facebook if they had been better at product management.
That said, you can get lucky and happen to work on one of the trends or you can try to spot one and ride it consciously. There's a factor that doesn't change though, you need to be able to execute and I think Ryan is giving himself way too little credit for being good at execution.
In particular he had already garnered a significant following with carsonified conferences and his blog before thinkvitamin (now treehouse) took off at the time.
There's always the cautionary tale of friendster, who could have been Facebook if they had been better at product management.