Automattic closed a new funding round of $288M in February and recently completed a $250M share buyback aimed at current and ex-employees at a $7.5B valuation
I don't think he was even old enough to drink. Now, he runs a $7.5 billion company https://twitter.com/... Matt Mullenweg / @photomatt : Some belated news and some timely news, on the latest with @automattic: https://ma.tt/... Dan Primack / @danprimack : Per @photomatt: Automattic raises $288 million in new funding, plus did a $250 million secondary deal (mostly for employees) at a $7.5 billion valuation. https://ma.tt/... @jasonlk : Actually seems cheap to me at $7.5B for 40% of the web https://twitter.com/... Peter Pham / @peterpham : gotta love @photomatt , just out there building up and to the right. https://twitter.com/...
Context & Ripple Effects
Two years after its $300M Series D from Salesforce Ventures priced it at $3B post-money, Automattic has repriced itself at $7.5B — and paired the raise with something unusual for a private company: a $250M secondary buyback that puts cash directly into current and former employees' hands rather than only onto the balance sheet.
Mullenweg's interview with Protocol frames the deal as two moves at once: primary capital for the business, and an internal liquidity market for staff. For a company whose headcount had grown large enough that early shares were illiquid paper, the secondary is as much a retention instrument as a financing event.
First-order effects
- Current and ex-employees holding Automattic stock can now sell roughly $250M of it at $7.5B per share pricing, converting years of illiquid equity into cash while staying private.
Second-order effects
- A 2.5x markup over the 2019 Series D resets the bar for any future Automattic raise or acquirer, and makes employee secondaries a live template other late-stage private companies will be pressured to copy.
Third-order effects
- If the pattern holds, big private companies will routinely run internal liquidity markets alongside raises — but the corpus also shows the downside tail: the same company later offered staff buyouts and cut 16% of headcount, so secondary-fueled valuations can outlast the headcount that justified them.
The trend: Late-stage private companies are closing the valuation–liquidity gap with employee share buybacks, decoupling paper valuations from both public markets and long-term staffing plans.