Upside

Founding Vision and Early Turbulence

The Insider’s Launchpad

Banker Anthony B. Perkins and technical writer Rich Karlgaard founded Upside in 1989 with $3 million from venture capitalist Tim Draper, Silicon Valley Bank’s Roger Smith, and Estée Lauder heir Gary Lauder. Their mission – "for Silicon Valley about Silicon Valley" – targeted an elite readership of investors and C-suite executives. Early managing publisher Jay Whitehead established the magazine’s combative tone with exposes on Kleiner Perkins and Hambrecht & Quist, revealing boardroom conflicts at these investment giants.

Leadership Coup

Internal power struggles mirrored the corporate battles Upside covered. In May 1992, Perkins was ousted as publisher after clashing with investors over spending $250,000/month on a 25-person newsroom. Karlgaard resigned weeks later to lead Forbes ASAP, abandoning a planned Forbes-Upside partnership. The turmoil left the magazine adrift until 1996, when PC Magazine founder David Bunnell acquired control through his investment group.

The "Pussification" Era (1990–1995)

Nuclear Cover Story

The November 1990 issue’s black cover screaming "HAS SILICON VALLEY GONE PUSSY?" in white block letters became tech media’s most controversial moment of the decade. The 12-page feature "The Pussification of Silicon Valley" accused venture firms of favoring "sensitive, consensus-driven leaders" over "alpha visionaries".

• 40% funding drop for "aggressive" founders since 1987
• HR departments mandating "namby-pamby" management seminars
• Diversity hires creating "neutered corporate cultures"

Expansion and Innovation (1996–2000)

New owner David Bunnell secured $4 million from The Washington Post Company in 1997, launching three ventures:

1. UpsideToday - A pioneering web portal
2. Upside Conferences - Executive summits featuring Bill Gates and Steve Jobs
3. UpsideFN (2001) - A $5 million radio network with CNBC veterans

Financial Collapse (2000–2002)

Dot-Com Dominoes

The NASDAQ crash eviscerated Upside’s ecosystem:

• Advertising - Tech ad revenue plunged 72% ($18M to $5M annually)
• Circulation - Paid subscriptions dropped 40%
• Last Gasp - A 2001 $2M funding round failed to revive traffic

Legacy and Lasting Influence

Cultural Touchstone

The "Pussification" article became a rhetorical blueprint referenced in various corporate and tech discussions.

Media DNA

Upside alumni reshaped tech journalism:

• Rich Karlgaard – Forbes publisher
• Anthony Perkins – Founded Red Herring
• Chris Nolan – Pioneered political blogging