Abhishek Gupta from Circles Life shares his journey from growing up in India to co-founding the world's first digital telco, which now operates in multiple global markets. Abhishek discusses the challenges of breaking into the telco industry, building a strong co-founding team, and navigating early fundraising struggles. With deep insights on startup culture, hiring, and decision-making, he emphasizes the power of first-principles thinking, resilience, and surrounding oneself with strong mentors. Looking ahead, Abhishek shares his plans to build in AI and expand into the U.S. This episode is a must-listen for founders navigating high-growth industries and global expansion.

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Abhishek’s journey into entrepreneurship began far from the startup world. Raised from a middle-class family in India, he was inspired early on by the idea of breaking conventional limits. He initially aspired to be an actor but soon realized it wasn’t his calling. Instead, he pursued engineering with a minor in business, which led him into consulting at McKinsey. Consulting gave him exposure to first-principles thinking and problem-solving at scale. He later transitioned into private equity, where he saw firsthand how business ownership worked—an experience that planted the seed for his eventual leap into startups.

The turning point came in Indonesia, where Abhishek worked on deals involving mid-sized companies led by self-made founders. Seeing people from similar backgrounds build impactful businesses convinced him that entrepreneurship was an achievable path. This realization led to the founding of Circles in 2014, with a mission to disrupt the telco industry and empower consumers.

Circles launched in Singapore with a digital-first approach, challenging traditional telcos by offering better customer experience and pricing transparency. However, the early days were far from easy. Abhishek and his co-founders struggled with raising capital, facing skepticism about entering such a heavily regulated and capital-intensive industry. Investors often misunderstood Circles as just another telco rather than a technology-driven platform. At one point, after 25 failed investor meetings, they shifted their approach, focusing on investors who deeply understood the telco space. The breakthrough came when one investor committed $10 million within 15 minutes of their pitch.

Beyond capital, one of the most critical decisions Abhishek made was in selecting co-founders and early hires. He emphasizes that trust and alignment in values are far more important than complementary skill sets. The startup journey is unpredictable, and having co-founders who can weather challenges together is crucial.

Circles’ expansion strategy was methodical, targeting markets with high smartphone penetration, strong demand for digital services, and dissatisfaction with existing telcos. They entered Australia and Taiwan as test markets before expanding further. Their business model evolved beyond just being a digital telco to offering SaaS solutions for other telcos globally. This shift allowed Circles to scale beyond consumer markets and position itself as an infrastructure provider.

Culture and incentives played a significant role in Circles’ success. Abhishek describes how they built a strong company culture through structured feedback loops, regular team bonding, and value-driven hiring. A key lesson from his leadership experience is that startup success isn’t just about great ideas—it’s about execution, resilience, and staying mission-driven.

Looking to the future, Abhishek is setting his sights on the AI revolution. After spending time in Silicon Valley, he’s convinced that AI will be the defining industry of the next decade. He plans to take another deep dive—this time, into the U.S. market—to build his next venture at the epicenter of AI innovation.

His final advice to founders: Success is a long-term game. Stay with the problem, adapt, and persevere—because in the end, prevailing is a choice.

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