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.
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.
Mycoskie sold his online driver education company for $500,000 to finance Toms shoes. The company name is derived from the word "tomorrow", and evolved from the original concept, "Shoes for Tomorrow Project". Mycoskie initially commissioned Argentine shoe manufacturers to make 250 pairs of shoes. Sales officially began in May 2006. After an article ran in the Los Angeles Times, the company received order requests for nine times the available stock online, and 10,000 pairs were sold in the first year. The first batch of 10,000 free shoes were distributed in October 2006 to Argentine children.