From SIlicon Valley to Working In Lisbon: Greg Sherwin

Greg Sherwin merges tech and entrepreneurship in Portugal, inspired by his wife’s heritage. His journey from Silicon Valley highlights resilience and the benefits of cultural immersion.

1/14/20252 min read

Greg Sherwin represents a remarkable fusion of technology and entrepreneurship, making impactful contributions in Portugal through his innovative ideas and a deep appreciation for local culture. As the author of Connecting Online, Creating a Successful Image On The Internet, he shares his rich experiences in technology and networking. After over six years in Portugal, Greg has cultivated valuable insights into innovation and entrepreneurship, sculpted by a diverse career and cultural immersion.

His journey began with a fervent passion for math, science, and technology, leading him to nearly three decades of working in Silicon Valley. During this time, Greg collaborated with a variety of startups, gaining a treasure trove of experience as some triumphed while others encountered challenges.

While in Silicon Valley, Greg recognized the power of viewing challenges and opportunities through the lens of diverse cultures. His frequent visits to Portugal, influenced by his wife’s Portuguese heritage, unveiled the country's potential, particularly amidst its own economic challenges. Unlike Greece, which faced austerity, Portugal chose to invest in fostering entrepreneurship and tech startups, crafting an exciting landscape for Greg to engage with a revitalized economy.

Choosing to move to Portugal involved sacrifices, including a pay cut, but it was a decision fueled by more than monetary factors. It symbolized a chance for Greg to renew his perspective and immerse himself in a new cultural environment, reigniting his creativity in the process.

Greg’s connection to Portugal is deeply personal, as his wife is of Portuguese descent, intertwining the rich heritages of both Portugal and America. This blend resonates with many navigating multiple identities in our interconnected world. Moving abroad transformed his understanding of home and identity, a sentiment he has experienced firsthand.

As he settled into life in Portugal, Greg observed a compelling trend: many Portuguese expatriates were returning home, drawn by the burgeoning economic opportunities. He found himself at local gatherings alongside friends eager to bring their families back, contributing to a vibrant community that cherishes shared experiences. Greg envisions Portugal evolving into a melting pot, welcoming both immigrants and citizens from former Portuguese colonies, enriching its cultural fabric.

Over the years, Portugal’s culinary scene has undergone a stunning transformation. During Greg’s first visit two decades ago, options were limited, but now a vibrant mix of influences has emerged, with an increase in vegan restaurants rivaling those in San Francisco. This gastronomic evolution has created a space where diverse traditions can flourish.

In his latest professional chapter, Greg joined Portugal’s first unicorn startup, fully immersing himself in local customs and workplace practices. This role represented more than just career advancement; it allowed him to live fully and embrace the culture he loves. His journey illustrates the profound rewards of stepping outside one's comfort zone, facing challenges head-on, and celebrating the complexity of identity in our interconnected world.

Through Greg Sherwin’s experience, we are inspired by a narrative of resilience, adaptability, and the ongoing quest to find one’s place in a rapidly evolving environment. His story exemplifies how personal and professional growth can harmoniously coexist and how embracing new cultures can profoundly transform one's life and work.

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