The High Flyers Podcast with Vidit Agarwal

#241 Startup collapse to $21M a16z raise: Sphere's Nick Rudder on Aussie Grit in the US, Selling to CFOs and Superhero wife

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Jan 27, 2026

Nicholas Rudder, founder and CEO of Sphere, who led a pivot and a US$21M Series A, shares gritty startup survival and leadership stories. He discusses selling to CFOs, building zero-churn retention, using AI as a junior analyst for global tax rules, hiring resilient engineers, and forging advisor partnerships to scale cross-border compliance.

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ANECDOTE

Wife As The Silent Cofounder

Nicholas Rudder credits his wife Anya as the reason Sphere exists and for supporting him through the lowest moments.
He describes partners of founders as “ghost founders” who deserve more recognition for emotional and operational support.

ADVICE

Validate Cofounders By Working Together

Do meaningful work trials together before committing to co‑founder relationships.
Build trust over time by working in the same team to surface complementary strengths and weaknesses.

ANECDOTE

Rebuilding Solo Amid A High‑Risk Pregnancy

After ScholarSight failed, Rudder faced a solo rebuild while managing a high-risk twin pregnancy and family relocation.
He says surviving that period taught him more about himself than anything else and strengthened his conviction to keep building.

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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.

It’s time to explore your curiosity — please 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.

Our guests include -- Malcolm Turnbull (Prime Minister of Australia), Anil Sabharwal (Global VP, Product at Google), Jason Collins (Head of BlackRock, Asia Pacific), Stevie Case (Chief Revenue Officer, Vanta), Brad Banducci (CEO, Woolworths), Jean-Michel Lemieux (CTO, Shopify + Atlassian), Sweta Mehra (EGM, NAB; ex CMO, ANZ), Bowen Pan (Creator, Facebook Marketplace), Sam Sicilia (Chief Investment Officer, Hostplus), Craig Tiley (CEO, Tennis Australia), John Haddock (CBO, Harvey), Niki Scevak (Co-Founder, Blackbird Ventures), Mike Schneider (CEO, Bunnings), Trent Cotchin (3x Premiership Winning Captain, Richmond FC), Peter Varghese (Secretary/Chief, Foreign Affairs, Australian Government), Jack Zhang (CEO, Airwallex), Matteo Franceschetti (CEO, Eight Sleep) and more.