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In this episode of the Remotely One podcast, co-hosts Rick Haney and Kaleem Clarkson sit down with Chicago-based entrepreneur Sam Rosen, co-founder of Deskpass, to explore his unconventional path to success and the future of coworking and flexible workspaces. Sam’s journey, full of twists and surprises, exemplifies resilience, innovation, and a sharp instinct for recognizing the shifting needs of the modern workforce.
Sam’s career didn’t follow a traditional route. His unique backstory as a "three-time college dropout" is a label he proudly embraces. Rather than viewing it as a setback, Sam sees it as an essential part of his identity as an entrepreneur. His success story proves that a college degree is not the only path to achievement—what really matters is passion, resilience, and adaptability.
Sam’s first major business venture was One Design Company, a digital design agency he founded from his spare bedroom in 2005. At a time when businesses were just beginning to navigate the digital space, Sam found himself in a unique position—acting as a translator between generations familiar with the internet and those who were not.
In 2008, Sam’s entrepreneurial instincts led him to co-found Chicago’s first coworking space, The Coop. At the time, the coworking movement was still in its infancy, with only about 300 spaces globally. His inspiration for The Coop came during a visit to Brooklyn, where he struggled to find reliable internet while working remotely from his girlfriend’s cramped apartment. After an unsuccessful attempt to work from a local café, Sam discovered coworking through a space called "The Change You Want to See." He was immediately drawn to the community-driven atmosphere and knew he wanted to bring this model back to Chicago.
As Sam’s career evolved, so did his business interests. By 2010, he had developed proprietary software to manage The Coop’s operations, including billing and scheduling. This software became the foundation for his next company, DeskTime, which he eventually sold. However, DeskTime was just a precursor to what would become his most successful venture to date: Deskpass.
Deskpass, the platform Sam currently helms, is designed to meet the growing demand for flexible workspaces. Remote and hybrid teams can use Deskpass to find coworking spaces across the globe, giving them the flexibility to work from various locations. Unlike traditional coworking companies like WeWork, which tie members to specific locations, Deskpass operates as a marketplace, offering a wide variety of workspaces without owning any real estate.
Today, Deskpass plays a pivotal role in the evolving landscape of remote work. The platform not only connects users with coworking spaces but also provides businesses with a way to offer remote and hybrid work options to their employees.
Sam’s story is a testament to the power of innovation, resilience, and the ability to forge one’s own path. His ventures—from One Design Company to Deskpass—highlight his forward-thinking approach to business and his deep understanding of the evolving needs of today’s workforce. As the world of work continues to shift, Sam remains at the forefront of the coworking and flexible workspace revolution, offering solutions that cater to both companies and individuals!
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