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Nicholas Rudder: CEO & Founder, Sphere
Overview
Published 28th January, 2026.
Episode #241 features Nicholas Rudder, Founder & CEO of Sphere — which recently raised a US$21M Series A led by Andreessen Horowitz (a16z), to help some of the world’s fastest-growing companies, including Lovable, Linktree and Deel, navigate complex cross-border tax compliance using AI.
Nick shares the defining crucible of his journey: Growing up in Europe and Australia, then moving to the US chasing a dream, losing a co-founder, rebuilding as a solo founder, navigating a high-risk twin pregnancy that forced his family out of the US, and holding conviction when belief and momentum collapsed.
He breaks down how deep CFO discovery led to Sphere’s model of using AI as a junior analyst to interpret global tax rules, the magic behind zero-churn customer retention, motivating engineers and more— offering rare insight into building a durable company in a high-stakes, regulated industry.
Enjoy!
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The High Flyers Podcast features in-depth interviews with the world’s most influential figures in business, tech, finance, government and sport. Launched in 2020, it has ranked in the global top ten for past three years, with listeners in 27 countries and over 200+ episodes released, and featured in Forbes, Daily Telegraph, and at SXSW.
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