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On July 20, 2011, American announced an order for 460 narrowbody jets including 260 Airbus A320s.[34] The order broke Boeing's monopoly with the airline and forced Boeing into the re-engined 737 MAX.[35] As this sale included a Most-Favoured-Customer Clause, the European airframer has to refund any difference to American if it sells to another airline at a lower price, so Airbus can't give a competitive price to competitor United Airlines, leaving it to a Boeing-skewed fleet.[36]

To help fund the site, the founders created special edition breakfast cereals, with presidential candidates Barack Obama and John McCain as the inspiration for "Obama O's" and "Cap'n McCains".[25] In two months, 800 boxes of cereal were sold at $40 each, which generated more than $30,000 for the company's incubation.[26][27] It also got the company noticed by computer programmer Paul Graham, who invited the founders to the January 2009 winter training session of his startup incubator, Y Combinator, which provided them with training and $20,000 in funding in exchange for a small interest in the company.[18][28][29] With the website already built, they used the $20,000 Y-Combinator investment to fly to New York City to meet users and promote the site.[30] They returned to San Francisco with a profitable business model to present to West Coast investors. By March 2009, the site had 10,000 users and 2,500 listings.[29]
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