Upside

Upside magazine (1989–2002) chronicled Silicon Valley’s explosive growth while becoming a lightning rod for debates about tech culture. At its peak, the publication reached over 300,000 readers with investigative reporting and incendiary commentary, most notoriously its 1990 “Pussification of Silicon Valley” manifesto. This definitive account traces Upside’s journey from scrappy startup to cultural provocateur to dot-com casualty, examining its lasting impact on tech journalism and Valley ethos.

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”. Key claims:

• 40% funding drop for “aggressive” founders since 1987
• HR departments mandating “namby-pamby” management seminars
• Diversity hires creating “neutered corporate cultures” The article particularly mocked “new-age males” who “whine about burnout” and “apologize for success”. While claiming to support women in tech, it framed inclusion efforts as “risk-aversion disguised as progress.”

Shockwaves Through Tech

Reactions revealed Silicon Valley’s cultural fault lines: Supporters

• Oracle’s Larry Ellison called it “the only honest journalism left”
• Sequoia Capital’s Don Valentine hosted private luncheons with authors Critics
• NAACP and NOW organized advertiser boycotts
• Rev. Jesse Jackson condemned it as “Mein Kampf for tech bros” at Stanford
• Circulation surged 22% as copies circulated nationally Staff Exodus 30% of female employees resigned within a year, including rising star Kara Swisher (later of Recode). Advertisers like HP and IBM paused campaigns, costing $1.2 million in revenue.

Expansion and Innovation (1996–2000)

Bunnell’s Ambitious Reinvention

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

1. UpsideToday A pioneering web portal led by Bunnell’s son Aaron, featuring:
   • Real-time VC funding tracker
   • “Dot-Com Graveyard” monitoring failed startups
   • Traffic-sharing deals with Yahoo and Excite@Home
2. Upside Conferences High-priced executive summits featuring Bill Gates and Steve Jobs
3. UpsideFN (2001) $5 million radio network with CNBC veterans that folded post-9/11 By 2000, Upside employed 110 staff across print/digital – triple its 1995 size.

Notable Content Beyond Controversy

Investigative Triumphs

While remembered for provocation, Upside produced groundbreaking reporting:

• 1991 Microsoft Exposé Revealed anti-competitive tactics against DR-DOS, foreshadowing antitrust cases
• 1998 Amazon Analysis Predicted e-commerce consolidation 18 months before Pets.com’s collapse
• Dot-Com Graveyard Chronicled 327 failed startups (1998–2001) with darkly humorous post-mortems

Personal Tragedies

The human cost of Upside’s growth:

• Aaron Bunnell’s Death (2000) The 32-year-old digital chief died from drug-related causes in a New York hotel, later linked to 100-hour work weeks. Colleagues described him “chain-smoking through server migrations” to maintain Yahoo traffic deals.

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% as readers shifted online
• Last Gasp A 2001 $2M funding round failed to revive UpsideToday’s traffic, then down 65% post-Aaron’s death.

Final Chapter

The magazine filed Chapter 11 in 2002. Technology publisher Eric Lundquist bought residual assets for $850,000, shutting down operations to focus on Upside’s web archives.

Legacy and Lasting Influence

Cultural Touchstone

The “Pussification” article became a rhetorical blueprint:

• 1994 – Cited during Apple CTO Ellen Hancock’s ouster
• 1999 – Quoted in PayPal’s resistance to sensitivity training
• 2004 – Referenced in Google’s “Brotopia” manifesto
• 2025 – Still invoked in Elon Musk’s “Woke AI” debates

Media DNA

Upside alumni reshaped tech journalism:

• Rich Karlgaard – Forbes publisher
• Anthony Perkins – Founded rival Red Herring
• Chris Nolan – Pioneered political blogging with Spot-On

Modern Parallels

Upside’s spirit persists through:

• The Daily Upside Newsletter – Focuses on undercovered tech hubs
• Upside Today Podcast – Analyzes VC power dynamics
• Startup Skepticism – Prefigured critiques of WeWork/FTX eras Archival issues now trade for $300+ among Silicon Valley historians – a testament to Upside’s role as both chronicler and cautionary tale of tech’s original sin: conflating disruption with destruction.