Caldwell was born in El Paso, Texas, and graduated from Stanford University in 2003 with a B.S. in symbolic systems and a B.A. in psychology.[1]
After graduation, Caldwell worked briefly for VA Linux (where he had previously worked as a summer intern) before founding Imeem in late 2003 with Stanford classmate (and ex-Napster engineer) Jan Jannink.[2] Imeem was eventually bought by MySpace.[3]
Caldwell founded Mixed Media Labs in 2010. Its first product was picplz, a photo broadcasting application for phones.[4]
In October 2010, Caldwell spoke at Y Combinator’s Startup School event at Stanford University about the failures of Imeem and of the challenges still facing the music industry. [5][6]
Caldwell started App.net, through Mixed Media Labs, as a social network similar to Twitter, but with no advertising, instead relying on user and developer subscriptions.[7][8][9]
On May 6, 2014, Caldwell announced the service has not seen sufficient subscriptions to support any full-time employees and that it would remain online but without plans for enhancements or improvements.[10]