I'm the CEO of an AI company based in the US and India. Seattle and Bengaluru have pros and cons — here's how I make it work.

In the rapidly evolving tech landscape, choosing the right location for a startup can significantly influence its trajectory. Sid Masson, the CEO of Wokelo AI, shares insights from his experience managing a company that straddles two continents: the United States and India. After spending three years as a consultant at Deloitte, Masson felt unfulfilled by the transient nature of his work, which often left him disconnected from the outcomes of his recommendations. Seeking a change, he relocated to Seattle in 2021 to pursue a master's degree in business analytics at the University of Washington. This move was pivotal, as it immersed him in the burgeoning field of AI-driven analytics, where he recognized the potential of generative AI technologies to streamline the labor-intensive tasks he previously handled. Just a year after completing his degree, Masson launched Wokelo, an AI company aimed at revolutionizing business analytics. Partnering with a cofounder based in Bengaluru, India, they strategically chose to operate across both locations to tap into a diverse talent pool and cater to a wider client base. Masson serves as the CEO, while his cofounder takes on the role of CTO. This dual-location model, while challenging, offers substantial advantages, including around-the-clock operations. The initial phase of Wokelo was bootstrapped, focusing on product development before seeking external funding. To date, the company has successfully raised $5.5 million across two funding rounds, with $1.5 million secured in June 2023. Masson strategically hired sales personnel in the US while his cofounder recruited technical staff in Bengaluru, known for its competitive talent and lower costs compared to American markets. Leveraging the time zone differences allows Wokelo to maintain continuous operations that benefit from overlapping work hours in various regions, including the Middle East and Southeast Asia. Masson emphasizes that the team in Bengaluru is not merely an outsourcing solution; rather, they function as integral members of a unified company. Despite recent shifts in H-1B visa policies, Wokelo remains confident in its hiring strategy, focusing on local talent in the US while utilizing L-1 visas for transferring employees from India. Masson balances his time between the two locations, spending roughly eight to nine months in the US and visiting India several times a year, often combining work with family visits. Seattle, with its stunning natural landscapes and robust tech ecosystem, serves as Wokelo's headquarters. Masson appreciates the city's unique charm, often humorously noting that the cloudy weather encourages a strong work ethic. In contrast, Bengaluru boasts a vibrant startup scene and significant exposure to tech innovation, although it faces challenges like poor infrastructure and heavy traffic. As Wokelo continues to grow, Masson and his team are open to expanding their reach to other countries but recognize the importance of cultural understanding in global hiring. Their experience and connections within India remain a cornerstone of their talent acquisition strategy. Ultimately, Masson believes that the key to a successful startup lies in finding the right environment that aligns with one's vision and operational needs.