Nicholas Rudder is the co-founder and CEO of Sphere, an AI-powered cross-border tax compliance platform that helps businesses navigate international sales tax, VAT, and GST regulations. After pivoting from a failed EdTech marketplace and losing his technical co-founder, Nicholas just raised $21M in Series A funding from Andreessen Horowitz—a remarkable comeback story that includes selling his first five contracts using only a Figma prototype.
What you'll learn:
- How Sphere is becoming the "Deel of revenue compliance" for global businesses
- Why Nicholas pivoted from EdTech after 18 months and what made him choose tax compliance
- The strategy of selling contracts with a high-fidelity Figma prototype before building the product
- How to convince investors to back a pivot when your co-founder has left
- Why businesses struggle with international tax compliance and how AI solves it
- The importance of hiring an internal recruiter once you raise significant funding
- Why San Francisco remains the best place to build a startup despite the challenges
- How YC's network helped navigate a critical health insurance crisis
- The advantage of being a solo founder when recruiting high-quality founding engineers
- Why raising from a position of strength creates better fundraising dynamics
In this episode, we cover:
(00:00) Introduction to Nicholas Rudder and Sphere
(01:10) The EdTech marketplace that didn't work
(03:08) Why EdTech is such a difficult market
(09:16) The hard pivot to tax compliance
(10:56) Selling five contracts with a Figma prototype
(13:10) When the co-founder left and twins arrived early
(21:58) Why international tax compliance is broken
(27:10) Sphere's vision as the "Deel of revenue compliance"
(31:34) The unintentional path to Andreessen Horowitz
(38:54) Why VCs all know when you're raising
(41:37) Building Sphere in SF vs. the UK or Australia
(46:23) Immad's advice on hiring internal recruiters
(51:14) Rapid fire: Founder inspirations and lessons learned
