In a recent episode of the podcast "You Should Know," Oyster founder and Executive Chairman Tony Jamous argues that fear-based leadership is quietly undermining modern companies. Jamous, speaking from Cyprus, contends that surveillance, reactivity, and command-and-control instincts are not strategic but are manifestations of fear, and they are increasingly incompatible with a distributed, global workforce.
The discussion, hosted by William Tincup and Ryan Leary, delved into the reasons behind the recent shift back to control-oriented leadership. Jamous noted that as interest rates rose and demand slowed, the pendulum between progressive and traditional leadership swung back toward control. However, he emphasizes that this approach is counterproductive, especially in remote work settings where trust is essential.
Oyster, a benefit corporation operating across more than 80 countries, uses remote work as a forcing function for trust. Jamous outlined a three-part method for shifting from control to trust: defaulting to best intent, practicing non-reactivity, and releasing the illusion of control. "You have 100% control by controlling your behavior at the top as a leader of the organization," he said. "You have to default to assuming best intent."
The conversation also covered the launch of Oyster's Global Payroll product and the company's Silver Lake-led funding round closed in Q3 of the prior year. Jamous was candid about the psychology driving executives into old habits. "One of the most damaging stories leaders tell themselves is that if they missed the quarter or the year, they're going to die," he said, framing Wall Street pressure as a wiring problem rather than a business reality.
Jamous, who was born in Lebanon and previously took an API software company public before it was acquired, described the personal shift between his first and second unicorn as "ego reduction." He credited leadership coach Pascal with a pivotal observation after the first exit: that the same outcome could have been reached by taxing himself and those around him less. Tincup and Leary connected that idea to hiring for ethics, with Jamous arguing that you build ethical environments, not screen for ethical people.
They also shared the story of an Oyster teammate in the Philippines who broke down when she realized she was trusted, illustrating the emotional impact of trust. The concept of a "clean company" vibrating at high trust was also discussed. Jamous revisited Oyster's mission to reverse brain drain and reduce wealth inequality by democratizing access to global job opportunities.
This episode of "You Should Know," which is part of the WRKdefined Podcast Network, is available now wherever podcasts are heard, and at wrkdefined.com. The show, reaching more than 3.9 million verified listeners each month, tackles pivotal leadership challenges, workforce dynamics, career mobility, and the impact of technology on hiring.
