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Blake Mycoskie visited Argentina in 2002 while competing in the second season of The Amazing Race with his sister. He returned on vacation in January 2006, and noticed that the local polo players were wearing alpargatas, a simple canvas slip-on shoe that he began to wear himself and which are the model for the original line of Toms Shoes. They are made from canvas or cotton fabric with rope soles, but Toms makes theirs with rubber soles. Mycoskie said that when he was doing volunteer work in the outskirts of Buenos Aires, he noticed that many of the children were running through the streets with no shoes on. He decided to develop a type of alpargata for the North American market, with the goal to provide a new pair of shoes free of charge to youth of Argentina and other developing nations for every pair sold. According to Mycoskie, Bill Gates encouraged him by saying that the lack of shoes was a major contributor to diseases in children.
In June 2014, the company announced that Mycoskie was looking to sell part of his stake in the company to help it grow faster and meet its long-term goals. On August 20, 2014 Bain Capital acquired 50% of Toms. Reuters reported that the transaction valued the company at $625 million; Mycoskie's personal wealth following the deal was reported at $300 million. Mycoskie retained 50% ownership of Toms, as well as his role as "Chief Shoe Giver". Mycoskie said he would use half of the proceeds from the sale to start a new fund to support socially minded entrepreneurship, and Bain would match his investment and continue the company's one-for-one policy.
A story by LA Weekly priced the manufacturing cost of a pair of Toms Shoes at $3.50-$5.00 in U.S. dollars, and noted that the children's shoes given out by the company were among the cheapest to make, which is not necessarily apparent to consumers. According to garment-industry author Kelsey Timmerman, many people he spoke to in Ethiopia were critical of the company, saying that they felt it exploited the idea of Ethiopian poverty as a marketing tool. An Argentina-based shoemaker agreed, saying that the imagery used by the company was manipulative.