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Chronicles

The story behind the story

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Yahoo takes a ~25% stake in Taboola and plans to use Taboola's ad tech as part of a 30-year exclusive deal expected to generate $1B+ in annual revenue

Yahoo's chief executive sees the deal as a long-term bet on digital advertising.  The companies estimate that their ad partnership will generate $1 billion annually.

New York Times

Context & Ripple Effects

Taboola spent 2019 consolidating its corner of native advertising by buying rival Outbrain for $250M in cash and 30% equity, leaving one dominant content-recommendation platform. Yahoo, meanwhile, has a track record of large media acquisitions aging badly — it wrote down Tumblr by $230M after paying $1.1B for it.

The 2022 move reads as a lesson learned from both histories: rather than buying an ad business outright, Yahoo takes a ~25% stake and rents the technology exclusively for 30 years, while CEO Jim Lanzone rebuilds Yahoo around owned distribution — an AI search engine, original sports video and podcasts, and plans for a retail stock trading service on Yahoo Finance.

First-order effects

  • Yahoo locks up Taboola's recommendation and native ad stack exclusively for three decades, converting its pageview inventory into an estimated $1B+ annual revenue stream without integrating an acquired company.
  • Taboola gains a marquee anchor client plus a strategic shareholder holding roughly a quarter of its equity, de-risking demand for its network.

Second-order effects

  • Rival ad networks and SSPs are shut out of Yahoo's inventory for 30 years, pushing them toward other large portals and intensifying competition for remaining open web supply.
  • The deal gives Taboola the scale and balance-sheet credibility to keep signing platform-level exclusives — a playbook it later extended with the Apple News and Apple Stocks native advertising deal, which moved TBLA shares up ~5%.

Third-order effects

  • If long-duration exclusives become the norm, native advertising structurally consolidates around a few scaled platforms, and mid-size publishers' monetization options narrow to renting those stacks rather than operating their own ad tech.
  • For Yahoo, the pattern points to a post-acquisition model: own audience and distribution, partner for infrastructure, and take equity instead of control — the inverse of the Tumblr-era buy-and-integrate approach.

The trend: Large media companies are shifting from acquiring ad-tech capabilities to locking decades-long exclusive rental deals with consolidated platforms, taking equity stakes as the hedge.

Discussion

  • @benmullin Ben Mullin on x
    Scoop w/ @LaurenSHirsch: Yahoo has taken a ~25% stake in Taboola as part of a 30-year ads partnership https://www.nytimes.com/...