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In 1994, Gretchen Apgar and husband Mike opened a cybercafe in Seattle's Belltown neighborhood with Mike's brother Tyler.
The move toward DSL took place in 1998.
In late 1999, the company expanded to a national level, offering DSL services throughout the United States.
In 2001, in the face of the collapse of many ISPs as a possible result of the dot-com bust, Speakeasy had marketed a program to allow for simple transfer of accounts, starting with the announcement of the failure of Flashcom, a former DSL internet provider.
In September 2003, Bruce Chatterley was made CEO of the company.
In summer of 2004, the company announced simultaneously their entry into VOIP, and their Onelink package, which allowed a DSL subscriber to maintain an ADSL line without the requirement of a telco line.
In spring of 2006 Mike Apgar stepped down as chairman and moved on to a startup company Ookla that he created while at Speakeasy.
On March 27, 2007 press releases by both companies announced the acquisition of Speakeasy by Best Buy, a Fortune 100 retail chain operating in the US, Canada and China.
On June 10, 2010 Best Buy announced it was reducing its stake in Speakeasy, which would be merging with Covad Communications and MegaPath Corporation to form a new joint company.
On December 31, 2014, MegaPath Corporation sold certain of its network assets and direct internet access customers to GC Pivotal LLC dba Global Capacity, in order to raise cash to invest in its wholesale and managed services business.
On May 10, 2018 ISP Fusion Announces Definitive Agreement to Acquire MegaPath
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Speakeasy may also be known as or be related to Speakeasy, Speakeasy Inc, Speakeasy Inc., Speakeasy LLC and Speekeasy Inc.