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[ 3.4 ms ] story [ 18.1 ms ] thread
affluent man of means has much money, takes advantage of credit card (with possibly high credit limit) offers and rewards and leverages ability to acquire credit card rewards points through spend at price points above average consumer at a favorable points earning ratio - assuming selection of the "best" travel rewards card - which can buy you an airline ticket directly (revenue ticket) or can allow for strategic conversion of said points to airline miles that may get you even further on a point per mile v. cost per mile evaluation. Overall, from leveraging credit card reward points, brand loyalty (preferring an airline for travel, despite trip cost), airline's "First-Class product" promotional marketing, "mileage runs" all contribute to being able to fly for "free." Furthermore, review of aforementioned first-class product is possibly eligible for tax write-off as a business expense due to the airline industry marketing and "travel hacking" focus of his blog?
Good summary. Basically the trick is to be rich, and spend ridiculous amounts of money with the right credit cards.

It even says in the article that his brother was killed when he was young, so his parents felt guilty and bankrolled him.

spend it right, using the proper channels. The larger lesson is... make your money work for you / earn you money while you sleep.
There is more to the story around being banned from United than he states in the article. It wasn't about the lying, it was what he was doing after he received the certs.