Learn From Your Customers with Robert Levin

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In this episode of Time to Press Pause, host Ellen Williams interviews Rob Levin, a long-time friend and business colleague, about the pivotal moments in his entrepreneurial journey that stemmed from deliberately taking time to pause and reflect.

Rob shares two main “press pause” stories:

1. New York Enterprise Report: Rob launched this media venture in 2003, featuring a magazine and business events for small business owners. Although it gained reputable national advertisers and high-profile features (including two stars from Shark Tank), it never became financially robust. After a decade of grinding, he finally paused to evaluate the magazine’s actual viability. This reflection led to his decision to sell the business—a move that, while not lucrative, allowed him to pivot and pursue more sustainable opportunities.
2. Work Better Now: In 2018, Rob co-founded a company providing remote executive assistants from Latin America to U.S. businesses. Initially focused solely on placing assistants, a client’s unexpected success with multiple hires prompted Rob to pause and rethink the broader possibilities. Realizing the talent’s varied skill sets, Work Better Now expanded from offering just EAs to filling 40+ different roles. This pivot required retooling the entire business model but proved far more impactful for clients and for the company’s growth.

Throughout the conversation, Rob emphasizes the importance of pausing—whether to determine when to exit a struggling venture or to glean deeper insights from client feedback. He credits meditation, intentional journaling, and delegating administrative tasks (by having his own assistant) as crucial ways to create mental and strategic space. Both Ellen and Rob underscore how reflective time helps entrepreneurs distinguish between customer suggestions worth pursuing and those best set aside. Ultimately, Rob’s experience illustrates that methodical pauses and openness to feedback can catalyze stronger, more resilient business models and leadership approaches.