Founders in Arms Sphere's $21M Series A: Nicholas Rudder on Building Cross-Border Compliance
Nov 18, 2025
Nicholas Rudder, co-founder and CEO of Sphere, discusses his journey from a failed EdTech startup to raising $21M in Series A funding for his AI-driven cross-border compliance platform. He shares insights on validating demand using a Figma prototype, navigating the complexities of international tax, and the emotional challenges of losing a co-founder. Nicholas also emphasizes the significance of hiring an internal recruiter post-funding and compares the startup ecosystems of San Francisco, the UK, and Australia.
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Revenue Compliance Is Multi-Dimensional
- Sphere aims to be to revenue compliance what Deel is to payroll compliance.
- Cross-border selling brings many revenue compliance problems beyond indirect tax, including withholding, input tax, e-invoicing, and tariffs.
Pivot From EdTech To Tax Compliance
- Nicholas pivoted from an EdTech marketplace into an AI-powered cross-border tax compliance business.
- He raised $21M from Andreessen Horowitz after building Sphere from that pivot.
Found Pain From Firsthand Experience
- Marketplaces feel cross-border tax pain intensely because they are liable for platform GMV.
- Nicholas returned to his finance background to target a problem he had firsthand and validated with CFOs.