This first-person narrative is drawn from an extensive conversation with Sid Masson, a 37-year-old entrepreneur and the visionary founder behind Wokelo AI. The dialogue has been thoughtfully edited and refined to ensure both conciseness and clarity, distilling his reflections into a narrative that captures the essence of his professional journey and insights.
After dedicating roughly three years to his role as a consultant at Deloitte, Sid found himself struggling with a growing sense of emptiness and detachment. Consulting, by its very nature, involves rapid cycles of intense engagement—analyzing problems, formulating strategic recommendations, and then swiftly moving on to the next client or project. This constant turnover left him unable to witness the tangible results of his work. The projects he contributed to would often continue evolving without his presence, and although his strategic insights were appreciated, he never had the opportunity to see their real-world implementation. Over time, this created a void—a feeling that despite his professional accomplishments, something fundamental was missing from his career satisfaction and sense of purpose.
Recognizing this disconnect, Sid made a pivotal decision to transition into the technology industry, seeking a domain where he could directly influence outcomes and build lasting impact. In 2021, when he was in his mid-thirties, he made a life-changing move from India, his home country, to Seattle in the United States to pursue a master’s degree in business analytics at the University of Washington. This marked his second relocation to the US; he had first moved there in 2015 while working at Deloitte before returning to India in 2019. The decision to go back demonstrated both his commitment to personal growth and his awareness of the rapidly expanding opportunities within the data and technology sectors.
During his graduate studies, Sid immersed himself in the evolving field of artificial intelligence–driven analytics, a specialization that offered deep insight into how technology could enhance decision-making and efficiency. It was during this period that he encountered the early wave of generative AI technologies—a revelation that shifted his entire professional perspective. He began to understand how such innovations could fundamentally transform the knowledge economy. Specifically, he realized that the kinds of repetitive and analytical tasks he had performed as a consultant, such as conducting market research, creating detailed PowerPoint presentations, or synthesizing large amounts of client data, could be largely automated through AI. Beyond consulting, he could envision similar benefits for professionals in other intellectually demanding industries, including investment banking, business analysis, and market intelligence. This understanding became the foundation for his entrepreneurial vision.
In 2023, approximately a year after completing his master’s degree, Sid co-founded Wokelo AI—a company devoted to using artificial intelligence to streamline knowledge work and enhance productivity. Together with his cofounder, who had also come from a consulting background, they decided on a hybrid operational model that bridged two innovation ecosystems: the United States and India. Sid, based in Seattle, assumed the role of CEO, while his cofounder, located in India, took on the responsibilities of CTO. Their decision to anchor the company across two continents was both strategic and pragmatic—they aimed to leverage the rich technological talent pool in India while maintaining access to the business networks and investment opportunities in the US.
Operating a company that spans time zones and continents proved to be a demanding yet rewarding endeavor. The inherent challenge of coordinating teams across such vast distances was counterbalanced by the tremendous benefits that came with it. By hiring staff in both regions, they created an operational rhythm that allowed continuous productivity—essentially enabling Wokelo AI to function around the clock. Initially, they bootstrapped the company with their own resources. Only after developing and rigorously testing their first product—a web-based application—did they begin seeking external funding. Their cautious, product-first approach paid off: the startup successfully raised a total of $5.5 million across two funding rounds.
Their first major milestone came in June 2023, when they secured $1.5 million during their initial fundraising effort. At that point, financial constraints meant they could not afford to offer employees extravagant salaries, yet they remained focused on recruiting driven professionals who shared their vision. Sid concentrated on growing the sales and customer-facing teams in the United States, while his cofounder hired product developers and technical staff in Bengaluru, widely regarded as India’s equivalent of Silicon Valley.
Although it might have been simpler to build a US-based team from Seattle or the Bay Area, choosing Bengaluru proved advantageous for several compelling reasons. The city boasts a thriving startup ecosystem, world-class developers, and a culture deeply rooted in technological innovation. More importantly, the cost of hiring skilled personnel there was significantly lower than in American markets, allowing Wokelo AI to scale more efficiently. The result was a business model that not only optimized operational expenses but also ensured that productivity and innovation never stopped. Thanks to the overlapping time zones—India aligning with the Middle East and Southeast Asia, and the US syncing partially with Europe—their team could maintain continuous momentum without demanding unsustainable hours from any one region.
Sid emphasizes that this global structure does not come at the expense of quality. The company deliberately avoids treating its Bengaluru office as an outsourcing hub. Instead, both offices operate as integral parts of a unified organization. Their employees across continents are collaborators rather than separate units, working toward common objectives with equal commitment and mutual respect.
When asked about potential challenges related to immigration regulations—particularly the evolving rules surrounding H-1B visa sponsorships—Sid expresses confidence in their approach. Their current employment strategy relies primarily on hiring local talent within the US who do not require sponsorship, while reserving L-1 visas for internal company transfers from India to the US. This method ensures flexibility without introducing unnecessary complications or disruptions to business operations.
However, maintaining effective communication and collaboration across time zones does require ongoing coordination and compromise. Since Sid’s mornings coincide with his cofounder’s evenings, their schedules often involve early morning or late-night meetings. Drawing on their consulting backgrounds, both are accustomed to long and irregular hours, so these time differences feel more like a continuation of their previous work rhythm than an obstacle. They maintain regular communication through video conferencing tools like Zoom and make a deliberate effort to meet in person every few months—alternating between visits to the US and India—to strengthen their personal and professional connection.
Sid typically spends eight to nine months each year in the United States, traveling to India two or three times annually. These trips often serve a dual purpose: combining business commitments with family visits, creating a balance between professional obligations and personal connections. For him, this blend of work and leisure adds joy and vitality to his demanding schedule.
Both Seattle and Bengaluru have earned a special place in Sid’s life and career, not only as business hubs but also as sources of inspiration. The company’s headquarters are situated in Seattle, where Sid resides in nearby Redmond. He describes the city as having an extraordinary fusion of natural beauty and technological vibrancy, a place where scenic hiking trails coexist with some of the world’s most influential tech companies. Despite often being overshadowed by cities like San Francisco, Seattle has fostered an underdog mentality that fuels innovation. Home to giants such as Amazon and Microsoft, it nurtures a culture of focus and determination—perhaps, as many local founders humorously suggest, aided by its characteristically cloudy weather that encourages productivity over distraction.
Bengaluru, on the other hand, pulses with entrepreneurial energy. The city hosts the Indian headquarters of numerous global technology companies and fosters a robust ecosystem for startups. In Sid’s view, its atmosphere closely mirrors that of California’s Bay Area, radiating a shared enthusiasm for innovation, artificial intelligence, and the future of digital transformation. The conversations, community events, and professional networks all echo a collective ambition to build the next wave of technology. Yet, this thriving ecosystem coexists with practical challenges: infrastructural inefficiencies, congested traffic, and less-than-ideal road conditions often complicate daily mobility. Despite these obstacles, the advantages of operating in Bengaluru far outweigh its inconveniences.
Sid’s reflections on geography extend into broader advice for entrepreneurs. He believes that every founder must carefully consider where their business will take root. While cost optimization is often important, hiring from other countries purely to reduce expenses can be risky without genuine cultural and professional familiarity. Understanding local labor laws, employment norms, and workplace expectations is vital for sustainable growth. The differences between India and the United States, for example, include varying notice periods, regulatory frameworks, and approaches to recruitment—all of which can meaningfully affect operations. For Wokelo AI, Sid’s and his cofounder’s personal and professional networks in India made it much easier to recruit high-caliber talent from both universities and tech startups.
Ultimately, Sid underscores that the success of a global startup depends on aligning your business model and cultural values with the ecosystem best suited to your mission. Selecting the right location is not merely a logistical decision—it’s strategic, shaping everything from innovation capacity to team cohesion. For Wokelo AI, maintaining dual anchors in the US and India continues to be the foundation of their global vision: to create technology that empowers knowledge workers everywhere while embodying the collaborative spirit that made the company possible in the first place.
Sourse: https://www.businessinsider.com/ceo-ai-company-seattle-bengaluru-compare-tech-india-silicon-valley-2025-11
