What went wrong for Yahoo

Missed acquisitions & counterfactuals

• Many argue that if Yahoo had bought Google or Facebook, those companies would not be trillion‑dollar giants today; Yahoo historically suffocated acquisitions rather than scaling them.
• Examples cited: Flickr, Tumblr, del.icio.us, Broadcast.com, Astrid – all seen as diminished or killed post‑acquisition.
• Some see a Yahoo acquisition of Facebook/Google as potentially positive for society (less dominant platforms, different political climate), but others think some Facebook‑like network was inevitable.
• Debate over how much a board could have forced early Facebook’s founder to sell given voting control; conclusion: legally complex, power dynamics matter, but not as simple as “board can force it.”

Acquisitions, patents, and short‑termism

• Overture is framed as Yahoo’s “best” deal: its patents yielded ~8% of Google pre‑IPO, but Yahoo allegedly sold/settled cheaply and enabled Google’s keyword‑auction ad model, “buying its own gravestone.”
• LICRA v. Yahoo is recalled as another strategically poor, high‑profile decision.
• Commenters describe Yahoo leadership as relentlessly focused on quarterly metrics and traffic numbers, not on building new growth loops or transformative products.

Leadership, culture, and identity crisis

• Recurrent theme: too many CEOs, no coherent long‑term strategy, and an internal culture of risk‑avoidance and mediocrity (“wait for paycheck, stay under radar”).
• Several ex‑employees say Yahoo never decided if it was a media company or a technology company; it tried to be both and did neither well.
• Senior leadership is portrayed as spreadsheet‑driven media/MBAs without deep technical vision; they gave up competing in search rather than rallying engineers to fight Google.
• Later leadership is criticized for “throw spaghetti at the walls,” expensive but unintegrated bets, and driving the core business below the value of the Alibaba stake.

Technology bets and missed product opportunities

• Early strengths: Yahoo as “the most useful site on the web” (mail, finance, games, IM, directories, etc.), big FreeBSD contributions, Hadoop, ZooKeeper.
• But Yahoo repeatedly missed platform shifts: search (outsourced to others), browsers, cloud, mobile messaging, and social.
• Flickr could have been a base for YouTube or Instagram‑like products; Yahoo Games, Messenger, and Answers are remembered fondly but were not evolved into modern equivalents.
• Transition from FreeBSD to Linux is described as pragmatic (talent pool, SMP performance), not purely cultural.

Comparisons to Google and modern search

• Several contrast Yahoo’s “media portal selling content to users” model with Google’s “tech company selling users to advertisers.”
• Some argue Google is now repeating Yahoo’s mistakes: over‑monetizing search, allowing SEO spam, and relying on aging paradigms while LLMs increasingly answer “what function does X do Y in Z”‑style queries.
• Others push back, citing Google’s sustained AI output and vertical integration, but acknowledge user frustration with search quality.

Legacy and what remains

• Despite the decline narrative, Yahoo still ranks among the most visited sites globally and is strong in Japan (via a separate corporate entity).
• Yahoo Finance and some news usage persist; Yahoo Mail and legacy email domains (Verizon/SBC/etc.) continue to cause friction for less technical users.
• Overall consensus: Yahoo had huge assets and traffic, but decades of misaligned incentives, weak vision, and acquisition mismanagement squandered its position.