In its early issues, the publication published controversial articles on investment firms Kleiner Perkins Caufield & Byers and Hambrecht & Quist.
Upside quickly became widely read in the Silicon Valley tech community but burned through $3 million between 1989 and 1992 and was constantly trying to raise money.
The Washington Post Company said it selected Upside due to the magazine's tech news and connections in Silicon Valley.
He struck a crucial deal with Yahoo that doubled traffic and launched a popular feature called "Dot-Com graveyard."
[7] In January 2001, Upside launched UpsideFN, a New York-based online radio network headed by GM Scott Hunter and J.T.