Block’s Mass Layoffs Put Jack Dorsey on the Hook for $68 Million Party

Reports reveal that Jack Dorsey’s September 2025 in-person company event cost a staggering $68.1 million, roughly equivalent to the annual payroll for 200 employees, only to be followed five months later by layoffs slashing 40% of Block’s workforce.

The sequence of events draws criticism, sparking a broader conversation about AI, corporate culture, and fiscal responsibility. The Twitter co-founder turned Block CEO remains in the headlines over corporate strategy in Silicon Valley.

Block’s $68 Million Party, 4,000 Layoffs, and the AI Excuse: Did Jack Dorsey Just Redraw Silicon Valley’s Playbook?

According to Dorsey, the choice was between a gradual reduction that could undermine morale and a decisive, single cut that would position Block to grow “on our own terms.”

He framed the layoffs as a forward-looking pivot toward AI and agentic workflows, claiming in a company-wide note: “100 people + AI = 1,000 people.” According to the Twitter co-founder, intelligence tools paired with smaller, flatter teams enable a new, accelerated model of operations.

Wall Street responded with immediate approval, with Block’s XYZ stock surging 20–23% within an hour, adding approximately $6 billion in market capitalization. This translates to roughly $1.5 million in enterprise value per eliminated role.

Block’s $68 Million Party Draws Criticism

Meanwhile, Jack Dorsey has sparked outrage and debate with a spectacle that many critics say redefines corporate norms.

In September 2025, the former Twitter CEO reportedly spent $68.1 million on a Block in-person event, an amount roughly equal to the annual payroll of 200 employees.

The three-day festival in downtown Oakland featured performances by Jay-Z, Anderson .Paak, T-Pain, and Soulja Boy, and brought 8,000 employees from around the globe.

The party, recorded in Block’s own earnings as a $68.1 million increase in general and administrative expenses, has drawn widespread criticism.

Social media users described it as “psycho” and “crazy,” with some pointing to the stark contrast between celebration and accountability, particularly in light of the layoffs that followed.

To some, the spectacle of the $68 million party followed by mass layoffs sends a troubling message about priorities and managerial judgment.

It highlights the dangers of pandemic-era overexpansion and executive indulgence, with some critics arguing that the layoffs were a correction of years of overhiring and mismanagement.

“Yes, we over-hired during COVID because I incorrectly built 2 separate company structures (Square & Cash App) rather than 1, which we corrected mid-2024. But this misses all the complexity we took on through lending, banking, and BNPL. And that we’re now targeting $2M+ gross profit per person, 4x our pre-COVID efficiency, which stayed flat at ~$500k from 2019 until 2024. We have and do run an efficient company… better than most,” Dorsey responded.

Meanwhile, others see the layoffs as AI-washing, a convenient cover for structural inefficiencies.

“Sam Altman previously stated that ‘some firms are attributing job cuts to AI, when in reality, those layoffs were already planned or would have occurred regardless.’ He describes this, along with other exaggerations of AI capabilities, as “AI washing”… a tactic aimed at masking business issues. Just saying,” noted Graham Stephan.

Notwithstanding, Coinbase’s first CTO, Balaji Srinivasan, suggests that it signals a broader shift in tech toward AI-driven productivity and smaller teams.

Block’s severance packages, including 20 weeks’ pay, six months of healthcare, equity, and $5,000 in transition support, were generous by tech standards.