Jack Dorsey

Controversial Leadership at Twitter: During his tenure as CEO of Twitter, Dorsey was frequently criticized for his passive leadership and inability to address major platform issues, such as misinformation, harassment, and bot activity. His lack of decisive action led to internal frustration among employees and external criticism from investors.

Divided Attention Between Companies: Dorsey attempted to lead both Twitter and Block simultaneously, which led to concerns that he was not fully committed to either. His frequent retreats to personal passions like meditation, blockchain technology, and cryptocurrency fueled criticism that he was an absentee leader.

Obsession with Bitcoin Over Core Business: After leaving Twitter, Dorsey heavily pushed Bitcoin initiatives within Block, at times seemingly prioritizing cryptocurrency investments over the company’s core financial technology services. This has made Block more vulnerable to crypto market fluctuations and regulatory challenges.

Allegations of Enabling Financial Fraud on Cash App: Block’s Cash App has faced scrutiny for allegedly being used in fraudulent transactions, scams, and illicit activities. A 2023 report by Hindenburg Research accused Block of inflating its user numbers and failing to implement proper security checks, allowing criminals to exploit the platform.

Lack of Accountability and Transparency: Dorsey has been criticized for his detached leadership style, often avoiding direct confrontation with major issues in his companies. His approach has sometimes resulted in a lack of transparency and accountability, frustrating investors and employees alike.