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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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.
Validate Before Hiring Engineers
- If you lack technical co-founders, validate with high-fidelity prototypes before hiring engineers.
- Use design partners and region-by-region rollouts to reduce risk and build only what's needed.
Native Integrations Beat Local Outsourcing
- Existing providers often outsource international tax to local partners, creating manual, costly experiences.
- Building native integrations to tax authorities can materially reduce third-party costs for customers.