Am I Bored With “Web 2.0”?
I read a comment on my “Looking For Inspiration” post this morning that suggested I was just getting bored with Web 2.0 like many others. It's something I've considered a lot lately. — I am certainly not bored with the investments we have made at Union Square Ventures …
Context & Ripple Effects
By mid-2008 the Web 2.0 label had become a liability as much as a brand. The fatigue narrative was already mainstream — Kleiner Perkins had reportedly halted Web 2.0 investments months earlier, and VC-bashing itself had become a recurring genre (Kedrosky asked in 2007 whether it was passe). Against that backdrop, Fred Wilson's denial that he is bored reads less like a defense of a buzzword and more like a defense of Union Square Ventures' portfolio and thesis. The debate echoes earlier cycles too: back in 2005 Mark Pincus was already asking where the love for Web 2.0 was, showing the hype-fatigue loop predates this moment.
First-order effects
- Wilson publicly re-commits USV to its existing Web 2.0 investments, signaling to founders and co-investors that the firm's early-stage thesis is unchanged despite sector-wide skepticism.
- The post forces a distinction between boredom with the 'Web 2.0' label and boredom with the underlying businesses — a framing other investors now have to answer for their own portfolios.
Second-order effects
- If marquee Web 2.0 VCs keep backing the category while firms like Kleiner Perkins pull back, capital consolidates around conviction investors, raising the bar for startups pitching trend-following funds.
- The label fatigue pushes the conversation from branding toward fundamentals — revenue models and distribution — consistent with contemporaneous arguments that startup income was being dismissed as 'noise.'
Third-order effects
- If the pattern holds, each hype cycle ends not when the technology stalls but when the vocabulary does — investors quietly drop the banner term while continuing to fund the same behaviors under new names.
- Sustained commitment by thesis-driven firms through label fatigue could entrench a structural split between momentum-driven and conviction-driven venture capital, shaping which companies survive downturns.
The trend: This is one data point in the recurring cycle of tech-label exhaustion, where investor sentiment turns on the buzzword long before the underlying platform shift is finished.